WO2012029361A1 - Composition durcissable - Google Patents

Composition durcissable Download PDF

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Publication number
WO2012029361A1
WO2012029361A1 PCT/JP2011/061441 JP2011061441W WO2012029361A1 WO 2012029361 A1 WO2012029361 A1 WO 2012029361A1 JP 2011061441 W JP2011061441 W JP 2011061441W WO 2012029361 A1 WO2012029361 A1 WO 2012029361A1
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Prior art keywords
acrylate
parts
curable composition
meth
active energy
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PCT/JP2011/061441
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English (en)
Japanese (ja)
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中澤　淳
礼一朗 川瀬
大野　富久
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ナトコ 株式会社
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Priority to JP2011547100A priority Critical patent/JP4967076B2/ja
Publication of WO2012029361A1 publication Critical patent/WO2012029361A1/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
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • 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

Definitions

  • the present invention relates to a curable composition capable of forming a film having a high refractive index and excellent scratch resistance, which is used in applications such as a lens coating agent, a prism sheet, and an antireflection film.
  • the introduction of an aromatic ring is considered to increase the refractive index of the cured product obtained from the curable composition.
  • a curable composition containing a di (meth) acrylate having an aromatic ring and a compound other than the di (meth) acrylate having an ethylenically unsaturated group is known (see Patent Document 1).
  • Patent Document 1 a curable composition containing a di (meth) acrylate having an aromatic ring and a compound other than the di (meth) acrylate having an ethylenically unsaturated group.
  • the refractive index of the cured product is high, but the rigid component is introduced into the molecular chain, so that the flexibility of the cured product is lost, resulting in trouble during processing.
  • the cured product suffers from the disadvantage that it undergoes plastic deformation in response to external stress or the scratch resistance is reduced.
  • Patent Documents 2 and 3 it has also been attempted to introduce an elastic component into the molecular chain for the purpose of improving the scratch resistance of the cured product.
  • the lens sheet described in Patent Document 2 is formed from a cured product of an active energy ray-curable composition containing polycaprolactone-modified urethane (meth) acrylate and a monomer or oligomer having a (meth) acryloyl group.
  • this cured product has good scratch resistance, its refractive index is low.
  • Patent Document 3 contains urethane (meth) acrylate obtained from a high molecular weight diol compound, urethane (meth) acrylate obtained from a low molecular weight diol compound, monoacrylate having a phenyl ether group, and a photopolymerization initiator.
  • a resin composition for a sheet-like lens is described.
  • the cured product obtained from this composition cannot have a sufficiently high refractive index by introducing an elastic component, and the scratch resistance is not sufficient.
  • JP 2003-342329 A Japanese Patent No. 4142330 Japanese Patent No. 3979508
  • the present invention has been made by paying attention to the problems of the prior art as described above, and the object is to form a cured product that exhibits a high balance between high refractive index and excellent scratch resistance.
  • the object is to provide a curable composition.
  • a composition is provided.
  • the benzophenone derivative is, for example, a compound represented by the following chemical formula (1).
  • R 1 is hydrogen
  • R 2 is hydrogen, a methyl group, a carboxymethyl group, a functional group represented by a phenyl group or the following formula (2).
  • the curable compound is preferably an active energy ray curable compound, and the curing agent is preferably a photopolymerization initiator.
  • the active energy ray-curable compound preferably contains urethane (meth) acrylate or epoxy (meth) acrylate containing 30% by mass or more of an aromatic ring.
  • the active energy ray-curable compound preferably contains a polycaprolactone-modified urethane (meth) acrylate formed by a reaction between an organic isocyanate and a polycaprolactone-modified alkyl (meth) acrylate.
  • the curable composition of the present invention contains benzophenone or a derivative thereof, a curable compound and a curing agent, and the content of benzophenone or a derivative thereof is set to 13 to 40% by mass.
  • the content of benzophenone or a derivative thereof having two benzene rings in one molecule is increased, resulting in a curable composition.
  • the refractive index of the cured product formed from the product can be increased.
  • the scratch resistance of the cured product can be improved without causing poor curing of the curable composition.
  • the curable composition of the present invention it is possible to form a cured product exhibiting a high refractive index and excellent scratch resistance in a balanced manner.
  • the curable composition of this embodiment contains benzophenone or a derivative thereof, a curable compound, and a curing agent.
  • the content of benzophenone or its derivative is set to 13 to 40% by mass.
  • Benzophenone (C 6 H 5 COC 6 H 5 ) is a compound having two benzene rings, which are a kind of aromatic ring, in one molecule. Since this benzophenone has a high benzene ring content, it has a function of increasing the refractive index of the cured product of the curable composition and a function of improving physical properties such as scratch resistance.
  • benzophenone derivative a compound represented by the following chemical formula (1) can be used.
  • R 1 is hydrogen
  • R 2 is hydrogen, a methyl group, a carboxymethyl group, a functional group represented by a phenyl group or the following formula (2).
  • benzophenone derivatives include 4-methyl-benzophenone, 2,4,6-trimethylbenzophenone, methyl orthobenzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4′methyldiphenylsulfide, 4,4 '-Bis-4-dimethylaminobenzophenone, 4,4'-bis-4-diethylaminobenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-n-octoxybenzophenone, 2-hydroxy-4-chloro
  • Examples include benzophenone, 2-hydroxy-5-chlorobenzophenone, 2-hydroxy-4-methoxy-2′-carboxybenzophenone, 2,4-dihydroxybenzophenone, 2,2′-dihydroxy-4-methoxybenzophenone.
  • the content of benzophenone or its derivative in the curable composition is set to 13 to 40% by mass in order to effectively exhibit its function.
  • this content is less than 13% by mass, it is difficult to increase the refractive index of the cured product to a desired level, and it is also difficult to improve the scratch resistance.
  • content exceeds 40 mass%, the sclerosis
  • Curing compound a compound that is cured by active energy rays or a compound that is cured by heating can be used. However, the curing rate is high, the productivity of the cured product is improved, and the physical properties of the cured product are also improved.
  • Energy ray curable compounds are preferred.
  • the active energy ray-curable compound urethane (meth) acrylate, epoxy (meth) acrylate, or other monomer having an aromatic ring of 30% by mass or more can be preferably used. In this case, acrylate is preferred to methacrylate from the viewpoint of active energy ray curability. In the present specification, acrylate and methacrylate are collectively referred to as (meth) acrylate.
  • aromatic ring contained in the active energy ray-curable compound include a phenyl group, a phenylene group, and a naphthalene group.
  • the content of the aromatic ring is less than 30% by mass, it is difficult to sufficiently increase the refractive index of the cured product obtained from the curable composition, and the surface hardness of the cured product is increased to improve the scratch resistance. It is also difficult to let them.
  • polycaprolactone-modified urethane (meth) acrylate formed by reaction of organic isocyanate and polycaprolactone-modified alkyl (meth) acrylate can also be suitably used as the active energy ray-curable compound.
  • Urethane (meth) acrylate is obtained by reaction of organic isocyanate having a plurality of isocyanate groups in one molecule and (meth) acrylate having a hydroxyl group.
  • organic isocyanate having two isocyanate groups in one molecule include tolylene diisocyanate, naphthalene diisocyanate, diphenylmethane diisocyanate, isophorone diisocyanate, xylylene diisocyanate, hexamethylene diisocyanate, dicyclohexylmethane diisocyanate, 2,2,4- Examples thereof include trimethylhexamethylene diisocyanate, methyl-2,6-diisocyanate hexanoate, and norbornane diisocyanate.
  • organic isocyanate having three isocyanate groups in one molecule include a compound represented by the following chemical formula (3) in which diisocyanate is isocyanurate-modified, and a chemical formula (4) in which diisocyanate is adduct-modified. And a compound represented by the following chemical formula (5) obtained by biuret modification of diisocyanate, 2-isocyanatoethyl-2,6-diisocyanate caproate triaminononane triisocyanate, and the like.
  • the (meth) acrylate having a hydroxyl group examples include hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, hydroxybutyl (meth) acrylate, 2- (meth) acryloyloxyethyl-2-hydroxyethylphthalic acid 2-hydroxy-3-phenoxypropyl (meth) acrylate, o-phenylphenol glycidyl ether (meth) acrylate, pentaerythritol tri (meth) acrylate, and the like.
  • Epoxy (meth) acrylate is obtained by reaction of an epoxy resin and a carboxylic acid.
  • the epoxy resin examples include bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, bisphenol type epoxy resin, naphthalene type epoxy resin, biphenyl type epoxy resin, naphthol skeleton epoxy resin, alicyclic type
  • novolak epoxy resins such as epoxy resins, phenol novolac epoxy resins, and cresol novolac epoxy resins.
  • carboxylic acid examples include acrylic acid, methacrylic acid, 2- (meth) acryloyloxyethyl succinate, 2- (meth) acryloyloxyethyl maleate, 2- (meth) acryloyloxyethyl phthalate, hexahydrophthal Examples include acid 2- (meth) acryloyloxyethyl.
  • monofunctional (meth) acrylates As other monomers (diluted monomers), monofunctional (meth) acrylates, bifunctional (meth) acrylates, polyfunctional (meth) acrylates, and the like can be used.
  • the monofunctional (meth) acrylate examples include monohydroxyethyl (meth) acrylate, 2-ethoxyhexyl (meth) acrylate, phenoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, and 2-ethoxyethoxy Ethyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, polycaprolactone-modified hydroxyethyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, N-vinylpyrrolidone, acryloyl Morpholine, isobornyl (meth) acrylate, vinyl acetate, styrene, benzyl (meth) acrylate, o-phenylphenol ethoxy (meth) acrylate, nonylphenol (meth) Acrylate, tetra
  • bifunctional (meth) acrylate examples include neopentyl glycol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, and 1,4-butane Diol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, dipropylene glycol di (meth) acrylate, etc. Can be mentioned.
  • polyfunctional (meth) acrylate examples include trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, trimethylolpropane 3 mol propylene oxide adduct tri (meth) acrylate, trimethylolpropane
  • examples include tri (meth) acrylate of 6 mol ethylene oxide adduct, glycerin propoxytri (meth) acrylate, dipentaerythritol hexa (meth) acrylate, hexa (meth) acrylate of caprolactone adduct of dipentaerythritol, and the like.
  • Other monomers other than the above include bisphenol A type di (meth) acrylate, bisphenol F type di (meth) acrylate, bisphenol S type di (meth) acrylate, tricyclodecane dimethanol di (meth) acrylate, cyclohexane di Oligomers such as methanol di (meth) acrylate and 9,9-bis [4- (2- (meth) acryloyloxyethoxy) phenyl] fluorene can also be used.
  • the polycaprolactone-modified urethane (meth) acrylate is obtained by reacting an organic isocyanate with a polycaprolactone-modified alkyl (meth) acrylate represented by the following chemical formula (6).
  • organic isocyanate include the same as those mentioned above as specific examples of the organic isocyanate having 2 or 3 isocyanate groups in one molecule.
  • R is hydrogen or a methyl group
  • n is an integer of 1 to 10
  • m is an integer of 1 to 25.
  • polycaprolactone-modified alkyl (meth) acrylate examples include polycaprolactone-modified hydroxyethyl (meth) acrylate, polycaprolactone-modified hydroxypropyl (meth) acrylate, polycaprolactone-modified hydroxybutyl (meth) acrylate, and the like.
  • the curing agent serves to cure the curable compound.
  • a photopolymerization initiator is used.
  • the photopolymerization initiator include, for example, isopropyl benzoin ether, isobutyl benzoin ether, acetophenone, 2,4-diethylthioxanthone, 2-chlorothioxanthone, ethyl anthraquinone, isoamyl p-dimethylaminobenzoate, p-dimethylaminobenzoic acid.
  • the curable compound is a heat curable compound having a hydroxyl group
  • organic isocyanate is used as a curing agent.
  • the curable compound is a heat curable compound having an epoxy group, an amine compound, an acid anhydride, or the like is used as a curing agent.
  • the aforementioned curable composition can be cured by irradiation with active energy rays such as ultraviolet rays and electron beams, or by heating.
  • a coating can be formed by applying a curable composition to the lens surface or the substrate film surface and then irradiating an active energy ray or heating to cure the curable composition.
  • the normal heating condition is 70 to 90 ° C. for about 30 minutes to 1 hour.
  • a cured product obtained from the curable composition can be used as a prism sheet, an antireflection film, or the like which is a kind of lens sheet.
  • the prism sheet has a prism portion (lens portion) provided on a sheet-like base material.
  • a base material the thing made from synthetic resins, such as a polyethylene terephthalate (PET), an acrylic resin, a polycarbonate, can be used, for example, and the thing excellent in translucency is preferable.
  • PET polyethylene terephthalate
  • acrylic resin acrylic resin
  • polycarbonate polycarbonate
  • an active energy ray-curable composition or a heat-curable composition is injected into a predetermined mold, and after the base material is placed at a predetermined position of the mold, The curable composition is cured by irradiation or heating. In this way, a prism sheet having a prism portion provided on the substrate is obtained.
  • the active energy ray-curable composition When the active energy ray-curable composition is cured by irradiation with ultraviolet rays, it is desirable to irradiate ultraviolet rays with an integrated light quantity of 100 to 5000 mJ / cm 2 using, for example, a mercury lamp or a metal halide lamp. On the other hand, in the case of curing by irradiating with an electron beam, it is preferable that the irradiation amount is 1 to 20 Mrad at an acceleration voltage of 150 to 250 keV.
  • the antireflection film a layer formed from a curable composition is provided on a base film, and an antireflection layer is further provided thereon.
  • a synthetic resin film or sheet, a glass plate, or the like can be used as the base film. Among them, polyethylene terephthalate, acrylic resin, polycarbonate, or glass is preferable in terms of transparency.
  • the antireflection layer is a layer made of a material having a low refractive index, such as an amorphous fluoropolymer. Specific examples of the fluorine-containing polymer include those obtained by copolymerizing perfluoroalkyl (meth) acrylate, trifluoroethyl (meth) acrylate, and the like.
  • an active energy ray curable composition or a heat curable composition is applied to a base film, and after curing the curable composition by irradiation or heating with an active energy ray, Further, a material having a low refractive index such as an amorphous fluorine-containing polymer is applied and cured.
  • the active energy ray-curable composition is cured by irradiation with ultraviolet rays, it is desirable to irradiate ultraviolet rays with an integrated light quantity of 100 to 1000 mJ / cm 2 using, for example, a mercury lamp or a metal halide lamp.
  • the irradiation amount is 1 to 5 Mrad at an acceleration voltage of 150 to 250 keV.
  • the curable composition of this embodiment contains benzophenone or a derivative thereof, a curable compound, and a curing agent, and the content of benzophenone or a derivative thereof is set to 13 to 40% by mass.
  • the content of benzophenone or a derivative thereof having two benzene rings in one molecule is increased.
  • the refractive index can be increased.
  • the scratch resistance of the cured product can be improved without causing poor curing of the curable composition.
  • a cured product that exhibits a high refractive index and excellent scratch resistance in a well-balanced manner can be formed.
  • the benzophenone derivative the compound represented by the above-described chemical formula (1) can be used. Since this compound has a high aromatic ring content, it is useful for the purpose of increasing the refractive index of the cured product and improving the scratch resistance.
  • curable compound and the curing agent contained in the curable composition are an active energy ray curable compound and a photopolymerization initiator, respectively, the curing of the curable composition is accelerated, and the cured product is produced. It becomes the improvement of sex.
  • the active energy ray-curable compound contained in the curable composition contains urethane (meth) acrylate or epoxy (meth) acrylate containing 30% by mass or more of an aromatic ring, the fragrance of the curable composition As a result of the increased ring content, a cured product having a higher refractive index and better scratch resistance can be formed from the curable composition.
  • the active energy ray-curable compound contained in the curable composition contains a polycaprolactone-modified urethane (meth) acrylate formed by a reaction between an organic isocyanate and a polycaprolactone-modified alkyl (meth) acrylate
  • polycaprolactone-modified urethane (meth) acrylate improve the resilience of scratches on the surface of the cured product and improve the scratch resistance.
  • a part means a mass part and% means mass%.
  • Aromatic ring content (% by mass) in curable compound [(aromatic ring molecular weight ⁇ aromatic ring number) / molecular weight of curable compound] ⁇ 100
  • aromatic ring content in the urethane acrylate HUA-4 obtained in Synthesis Example 1 is calculated by this method as follows.
  • R-128H has a molecular weight of 222 and one aromatic ring (phenyl group).
  • MDI has a molecular weight of 250 and two aromatic rings (phenylene groups).
  • the molecular weight of the phenyl group is 77, and the molecular weight of the phenylene group is 76.
  • Example 1 Benzophenone [BASF Japan KK, DAROCURE BP] 15 parts, Trimethylolpropane EO modified triacrylate [Toagosei Co., Ltd., Aronix M-360, ethylene oxide total 6 mol addition] 85 parts and 1-hydroxy-cyclohexyl 4 parts of phenyl-ketone [manufactured by BASF Japan Ltd., Irgacure 184D] was mixed to obtain an active energy ray-curable composition.
  • the obtained active energy ray-curable composition was cured by irradiating it with ultraviolet rays having an integrated light amount of 400 mJ / cm 2 , and a prism portion made of the cured product was formed on a PET film to prepare a prism sheet.
  • Example 2 25 parts of benzophenone [BASF Japan KK, DAROCURE BP], 75 parts of urethane acrylate (HUA-3) obtained in Synthesis Example 6 and 1-hydroxy-cyclohexyl-phenyl-ketone [manufactured by BASF Japan KK, Irgacure 184D]
  • An active energy ray-curable composition was obtained by mixing 4 parts.
  • cured material of an active energy ray curable composition was formed on PET film like Example 1, and the prism sheet was produced.
  • Example 3 Benzophenone [BASF Japan KK, DAROCURE BP] 40 parts, bisphenol A type EO-modified diacrylate [Nippon Kayaku Co., Ltd., Kayarad R-551, ethylene oxide total 4 mol addition] 60 parts and 1-hydroxy- 4 parts of cyclohexyl-phenyl-ketone (manufactured by BASF Japan Ltd., Irgacure 184D) was mixed to obtain an active energy ray-curable composition. And the prism part which consists of hardened
  • Example 4 25 parts of 4-benzoyl-4'-methyldiphenylsulfide (SHUANG-BANG INDUSTRIALCORP, SB-PI 705), 158 parts of acrylic resin (AcB-1) obtained in Synthesis Example 3, and hexamethylene diisocyanate [Tokyo Chemical Industry Industrial Co., Ltd.] 4.9 parts was mixed to obtain a heat curable composition.
  • the solvent-dried heat-curable composition is poured into the mold and cured at 80 ° C. for 30 minutes, and a prism portion made of a cured product of the heat-curable composition is formed on the PET film.
  • a prism sheet was prepared.
  • the antireflection film was produced using this thermosetting composition. That is, this heat-curable composition was applied to a PET film as a base film, and cured at 80 ° C. for 30 minutes to form a layer (thickness 100 ⁇ m) made of the cured product. Subsequently, a coating agent comprising 100 parts of OPSTAR JM5010 (manufactured by JSR Corporation) and 0.3 part of 1-hydroxy-cyclohexyl-phenyl-ketone (manufactured by BASF Japan Co., Ltd., Irgacure 184D) is cured.
  • OPSTAR JM5010 manufactured by JSR Corporation
  • 1-hydroxy-cyclohexyl-phenyl-ketone manufactured by BASF Japan Co., Ltd., Irgacure 184D
  • Example 5 25 parts of 4-methylbenzophenone [Daido Kasei Kogyo Co., Ltd., DAIDO UV-CURE PMB], 75 parts of urethane acrylate (HUA-3) obtained in Synthesis Example 6 and 1-hydroxy-cyclohexyl-phenyl ketone [BASF Japan Co., Ltd., Irgacure 184D] was mixed to obtain an active energy ray-curable composition. And the prism part which consists of hardened
  • Example 6 Methyl orthobenzoylbenzoate (manufactured by SHUANG-BANG INDUSTRIALCORP, SB-PI 711), 75 parts of urethane acrylate (HUA-3) obtained in Synthesis Example 6 and 1-hydroxy-cyclohexyl-phenyl-ketone [BASF Japan ( Co., Ltd., Irgacure 184D] was mixed to obtain an active energy ray-curable composition. And the prism part which consists of hardened
  • Example 7 25 parts of 4-benzoyl-4′-methyldiphenylsulfide (SHUANG-BANG INDUSTRIALCORP, SB-PI 705), 75 parts of urethane acrylate (HUA-3) obtained in Synthesis Example 6 and 1-hydroxy-cyclohexyl- 4 parts of phenyl-ketone [manufactured by BASF Japan Ltd., Irgacure 184D] was mixed to obtain an active energy ray-curable composition. And the prism part which consists of hardened
  • Example 8 25 parts of benzophenone (BASF Japan KK, DAROCURE BP), 75 parts of epoxy acrylate (HEA-3) obtained in Synthesis Example 9 and 1-hydroxy-cyclohexyl-phenyl-ketone [BASF Japan KK, Irgacure 184D]
  • An active energy ray-curable composition was obtained by mixing 4 parts.
  • cured material of an active energy ray curable composition was formed on PET film like Example 1, and the prism sheet was produced.
  • Example 9 Benzophenone [BASF Japan Co., Ltd., DAROCURE BP] 15 parts, Dipentaerythritol hexaacrylate [Shin Nakamura Chemical Co., Ltd., NK Ester A-DPH] 25 parts, Acryloylmorpholine [Kotojin Co., Ltd., ACMO] 60 parts and 4 parts of 1-hydroxy-cyclohexyl-phenyl-ketone [BASF Japan KK, Irgacure 184D] were mixed to obtain an active energy ray-curable composition. And the prism part which consists of hardened
  • Example 10 25 parts of benzophenone (BASF Japan Co., Ltd., DAROCURE BP), 25 parts of epoxy acrylate (HEA-1) obtained in Synthesis Example 7, 50 parts of acryloylmorpholine (ACMO, manufactured by Kojin Co., Ltd.) and 1-hydroxy 4 parts of cyclohexyl-phenyl-ketone [BASF Japan Ltd., Irgacure 184D] was mixed to obtain an active energy ray-curable composition. And the prism part which consists of hardened
  • Example 11 40 parts of benzophenone [BASF Japan KK, DAROCURE BP], 25 parts of urethane acrylate (HUA-1) obtained in Synthesis Example 4, benzyl acrylate [manufactured by Hitachi Chemical Co., Ltd., FANCL FA-BZA] 35 And 4 parts of 1-hydroxy-cyclohexyl-phenyl-ketone [BASF Japan KK, Irgacure 184D] were mixed to obtain an active energy ray-curable composition. And the prism part which consists of hardened
  • Example 12 4-benzoyl-4'-methyldiphenylsulfide (SHUANG-BANG INDUSTRIALCORP, SB-PI 705) 25 parts, epoxy acrylate (HEA-2) 25 parts obtained in Synthesis Example 8, polyethylene glycol diacrylate [Kyoeisha Chemical energy, 50 parts of light acrylate 3EG-A, ethylene oxide repeating unit 3) and 4 parts of 1-hydroxy-cyclohexyl-phenyl-ketone [BASF Japan Ltd., Irgacure 184D] were mixed to obtain active energy. A linear curable composition was obtained. And the prism part which consists of hardened
  • the antireflection film was produced using this active energy ray curable composition. That is, this active energy ray-curable composition was applied to a PET film and cured by irradiating with an ultraviolet ray having an accumulated light amount of 300 mJ / cm 2 to form a layer (thickness: 100 ⁇ m) made of the cured product. Subsequently, a coating agent comprising 100 parts of OPSTAR JM5010 (manufactured by JSR Corporation) and 0.3 part of 1-hydroxy-cyclohexyl-phenyl-ketone (manufactured by BASF Japan Co., Ltd., Irgacure 184D) is cured.
  • OPSTAR JM5010 manufactured by JSR Corporation
  • 1-hydroxy-cyclohexyl-phenyl-ketone manufactured by BASF Japan Co., Ltd., Irgacure 184D
  • Example 13 25 parts of benzophenone [BASF Japan KK, DAROCURE BP], 25 parts of epoxy acrylate (HEA-2) obtained in Synthesis Example 8, phenoxypolyethylene glycol acrylate [manufactured by Shin-Nakamura Chemical Co., Ltd., NK ester AMP- 10 G, ethylene oxide repeating unit number 1] 50 parts and 1 part of 1-hydroxy-cyclohexyl-phenyl-ketone [manufactured by BASF Japan Ltd., Irgacure 184D] were mixed to obtain an active energy ray-curable composition. And the prism part which consists of hardened
  • Example 14 4-methylbenzophenone [Daido Kasei Kogyo Co., Ltd., DAIDO UV-CURE PMB] 25 parts, epoxy acrylate (HEA-2) 25 parts obtained in Synthesis Example 8, benzyl acrylate [manufactured by Hitachi Chemical Co., Ltd., 50 parts of FANCLIL FA-BZA] and 4 parts of 1-hydroxy-cyclohexyl-phenyl-ketone [manufactured by BASF Japan Ltd., Irgacure 184D] were mixed to obtain an active energy ray-curable composition. And the prism part which consists of hardened
  • Example 16 Benzophenone [BASF Japan Ltd., DAROCURE BP] 15 parts, epoxy acrylate (HEA-1) 60 parts obtained in Synthesis Example 7, polycaprolactone-modified urethane acrylate (UA-2) 25 obtained in Synthesis Example 12 And 4 parts of 1-hydroxy-cyclohexyl-phenyl-ketone [BASF Japan KK, Irgacure 184D] were mixed to obtain an active energy ray-curable composition. And the prism part which consists of hardened
  • Example 17 25 parts benzophenone [BAROC Japan BP DAROCURE BP], 50 parts urethane acrylate (HUA-3) obtained in Synthesis Example 6, 25 polycaprolactone-modified urethane acrylate (UA-1) obtained in Synthesis Example 2 And 4 parts of 1-hydroxy-cyclohexyl-phenyl-ketone [BASF Japan KK, Irgacure 184D] were mixed to obtain an active energy ray-curable composition. And the prism part which consists of hardened
  • the antireflection film was produced using this active energy ray curable composition. That is, the active energy ray-curable composition was applied to a PET film and cured by irradiating with an ultraviolet ray having an accumulated light amount of 300 mJ / cm 2 to form a layer (thickness: 100 ⁇ m) made of the cured product. Subsequently, a coating agent comprising 100 parts of OPSTAR JM5010 (manufactured by JSR Corporation) and 0.3 part of 1-hydroxy-cyclohexyl-phenyl-ketone (manufactured by BASF Japan Co., Ltd., Irgacure 184D) is cured.
  • OPSTAR JM5010 manufactured by JSR Corporation
  • 1-hydroxy-cyclohexyl-phenyl-ketone manufactured by BASF Japan Co., Ltd., Irgacure 184D
  • Example 18 Benzophenone [BASF Japan KK DAROCURE BP] 40 parts, epoxy acrylate (HEA-3) 35 parts obtained in Synthesis Example 9, polycaprolactone-modified urethane acrylate (UA-4) 25 obtained in Synthesis Example 14
  • An active energy ray-curable composition was obtained by mixing 4 parts of 1-hydroxy-cyclohexyl-phenyl-ketone [manufactured by BASF Japan Ltd., Irgacure 184D]. And the prism part which consists of hardened
  • Example 19 25 parts of 4-benzoyl-4′-methyldiphenylsulfide (SHUANG-BANG INDUSTRIALCORP, SB-PI 705), 50 parts of urethane acrylate (HUA-4) obtained in Synthesis Example 1, obtained in Synthesis Example 15 25 parts of polycaprolactone-modified urethane acrylate (UA-5) and 4 parts of 1-hydroxy-cyclohexyl-phenyl-ketone [manufactured by BASF Japan Ltd., Irgacure 184D] were mixed to obtain an active energy ray-curable composition. . And the prism part which consists of hardened
  • Example 20 Orthobenzoyl methyl benzoate (SHUANG-BANG INDUSTRIALCORP, SB-PI 711) 25 parts, urethane acrylate (HUA-2) 50 obtained in Synthesis Example 5, polycaprolactone-modified urethane acrylate (Synthesis Example 13) 25 parts of UA-3) and 4 parts of 1-hydroxy-cyclohexyl-phenyl-ketone [manufactured by BASF Japan Ltd., Irgacure 184D] were mixed to obtain an active energy ray-curable composition. And the prism part which consists of hardened
  • Example 21 Benzophenone [BASF Japan Ltd., DAROCURE BP] 15 parts, o-phenylphenol monoethoxyacrylate [Nippon Kayaku Co., Ltd., Kayarad OPP-1] 70 parts, polycaprolactone modified urethane obtained in Synthesis Example 12 15 parts of acrylate (UA-2) and 4 parts of 1-hydroxy-cyclohexyl-phenyl-ketone [manufactured by BASF Japan Ltd., Irgacure 184D] were mixed to obtain an active energy ray-curable composition. And the prism part which consists of hardened
  • Example 22 Obtained in 25 parts of benzophenone [BASF Japan Co., Ltd., DAROCURE BP], 60 parts of phenoxypolyethylene glycol acrylate [manufactured by Shin-Nakamura Chemical Co., Ltd., NK ester AMP-10G, ethylene oxide repeat unit number 1], Synthesis Example 2 15 parts of the resulting polycaprolactone-modified urethane acrylate (UA-1) and 4 parts of 1-hydroxy-cyclohexyl-phenyl-ketone [manufactured by BASF Japan Ltd., Irgacure 184D] are mixed to obtain an active energy ray-curable composition. It was. And the prism part which consists of hardened
  • the antireflection film was produced using this active energy ray curable composition. That is, the active energy ray-curable composition was applied to a PET film and cured by irradiating with an ultraviolet ray having an accumulated light amount of 300 mJ / cm 2 to form a layer (thickness: 100 ⁇ m) made of the cured product. Subsequently, a coating agent comprising 100 parts of OPSTAR JM5010 (manufactured by JSR Corporation) and 0.3 part of 1-hydroxy-cyclohexyl-phenyl-ketone (manufactured by BASF Japan Co., Ltd., Irgacure 184D) is cured.
  • OPSTAR JM5010 manufactured by JSR Corporation
  • 1-hydroxy-cyclohexyl-phenyl-ketone manufactured by BASF Japan Co., Ltd., Irgacure 184D
  • Example 23 40 parts of benzophenone [BASF Japan Ltd., DAROCURE BP], 45 parts of benzyl acrylate [manufactured by Hitachi Chemical Co., Ltd., funcryl FA-BZA], polycaprolactone-modified urethane acrylate (UA-) obtained in Synthesis Example 14 4) 15 parts and 4 parts of 1-hydroxy-cyclohexyl-phenyl-ketone [manufactured by BASF Japan Ltd., Irgacure 184D] were mixed to obtain an active energy ray-curable composition. And the prism part which consists of hardened
  • Example 24 4-benzoyl-4'-methyldiphenylsulfide (SHUANG-BANG INDUSTRIALCORP, SB-PI 705) 25 parts, o-phenylphenol monoethoxyacrylate (Nippon Kayaku Co., Ltd., Kayrad OPP-1) 60 parts Then, 15 parts of polycaprolactone-modified urethane acrylate (UA-3) obtained in Synthesis Example 13 and 4 parts of 1-hydroxy-cyclohexyl-phenyl-ketone [manufactured by BASF Japan Ltd., Irgacure 184D] were mixed to obtain an active energy ray. A curable composition was obtained. And the prism part which consists of hardened
  • Example 25 Benzophenone [BASF Japan Co., Ltd., DAROCURE BP] 15 parts, Bisphenol A type EO-modified diacrylate [Nippon Kayaku Co., Ltd., Kayarad R-551, ethylene oxide total 4 mol addition] 20 parts, Acryloylmorpholine [( Manufactured by Kojin Co., Ltd., ACMO] 45 parts, polycaprolactone-modified urethane acrylate (UA-3) 20 parts obtained in Synthesis Example 13, and 1-hydroxy-cyclohexyl-phenyl-ketone [manufactured by BASF Japan Ltd., Irgacure 184D 4 parts were mixed to obtain an active energy ray-curable composition. And the prism part which consists of hardened
  • Example 26 25 parts of benzophenone [BASF Japan KK, DAROCURE BP], 20 parts of urethane acrylate (HUA-3) obtained in Synthesis Example 6, phenoxypolyethylene glycol acrylate [manufactured by Shin-Nakamura Chemical Co., Ltd., NK ester AMP- 10G, ethylene oxide repeating unit number 1] 45 parts, polycaprolactone-modified urethane acrylate (UA-1) 10 parts obtained in Synthesis Example 2, and 1-hydroxy-cyclohexyl-phenyl-ketone [manufactured by BASF Japan Ltd., Irgacure 184D]
  • An active energy ray-curable composition was obtained by mixing 4 parts. And the prism part which consists of hardened
  • Example 27 40 parts of benzophenone [BASF Japan Co., Ltd., DAROCURE BP], 10 parts of urethane acrylate (HUA-4) obtained in Synthesis Example 1, benzyl acrylate [manufactured by Hitachi Chemical Co., Ltd., FANCL FA-BZA] 40 And 10 parts of polycaprolactone-modified urethane acrylate (UA-2) obtained in Synthesis Example 12 and 4 parts of 1-hydroxy-cyclohexyl-phenyl-ketone (manufactured by BASF Japan Ltd., Irgacure 184D) A linear curable composition was obtained. And the prism part which consists of hardened
  • Example 28 4-methylbenzophenone [DAIDO UV-CURE PMB, manufactured by Daido Kasei Kogyo Co., Ltd.] 25 parts, epoxy acrylate (HEA-2) 20 parts obtained in Synthesis Example 8, o-phenylphenol monoethoxy acrylate [Nippon Kayaku 45 parts Kaylad OPP-1], 10 parts polycaprolactone-modified urethane acrylate (UA-1) obtained in Synthesis Example 2, and 1-hydroxy-cyclohexyl-phenyl-ketone [BASF Japan Ltd., [Irgacure 184D] 4 parts were mixed to obtain an active energy ray-curable composition. And the prism part which consists of hardened
  • the antireflection film was produced using this active energy ray curable composition. That is, the active energy ray-curable composition was applied to a PET film and cured by irradiating with an ultraviolet ray having an accumulated light amount of 300 mJ / cm 2 to form a layer (thickness: 100 ⁇ m) made of the cured product. Subsequently, a coating agent comprising 100 parts of OPSTAR JM5010 (manufactured by JSR Corporation) and 0.3 part of 1-hydroxy-cyclohexyl-phenyl-ketone (manufactured by BASF Japan Co., Ltd., Irgacure 184D) is cured.
  • OPSTAR JM5010 manufactured by JSR Corporation
  • 1-hydroxy-cyclohexyl-phenyl-ketone manufactured by BASF Japan Co., Ltd., Irgacure 184D
  • the antireflection film was produced using this active energy ray curable composition. That is, the active energy ray-curable composition was applied to a PET film and cured by irradiating with an ultraviolet ray having an accumulated light amount of 300 mJ / cm 2 to form a layer (thickness: 100 ⁇ m) made of the cured product. Subsequently, a coating agent comprising 100 parts of OPSTAR JM5010 (manufactured by JSR Corporation) and 0.3 part of 1-hydroxy-cyclohexyl-phenyl-ketone (manufactured by BASF Japan Ltd., Irgacure 184D) is cured.
  • OPSTAR JM5010 manufactured by JSR Corporation
  • 1-hydroxy-cyclohexyl-phenyl-ketone manufactured by BASF Japan Ltd., Irgacure 184D
  • Example 30 25 parts of 4-benzoyl-4'-methyldiphenylsulfide (SHUANG-BANG INDUSTRIALCORP, SB-PI 705), 20 parts of urethane acrylate (HUA-4) obtained in Synthesis Example 1, o-phenylphenol monoethoxy 45 parts of acrylate [Nippon Kayaku Co., Ltd., Kayrad OPP-1], 10 parts of polycaprolactone-modified urethane acrylate (UA-5) obtained in Synthesis Example 15 and 1-hydroxy-cyclohexyl-phenyl-ketone [BASF Japan Co., Ltd., Irgacure 184D] was mixed to obtain an active energy ray-curable composition. And the prism part which consists of hardened
  • Example 31 25 parts of benzophenone [BASF Japan Co., Ltd., DAROCURE BP], 20 parts of epoxy methacrylate (HEA-5) obtained in Synthesis Example 11, o-phenylphenol monoethoxy acrylate [manufactured by Nippon Kayaku Co., Ltd., Kayarad OPP -1] 45 parts and 10 parts of polycaprolactone-modified urethane acrylate (UA-1) obtained in Synthesis Example 2 were mixed to obtain an active energy ray-curable composition.
  • benzophenone BASF Japan Co., Ltd., DAROCURE BP
  • EOA-5 epoxy methacrylate
  • o-phenylphenol monoethoxy acrylate manufactured by Nippon Kayaku Co., Ltd., Kayarad OPP -1
  • cured material obtained by irradiating an active energy ray curable composition to the electron beam of the irradiation amount of 5 Mrad with the acceleration voltage of 150 keV was formed on PET film, and the prism sheet was produced.
  • Tables 5 to 8 show the compositions of the curable compositions of Examples 1 to 31 and Comparative Examples 1 and 2, and the benzophenone content (% by mass) and the aromatic ring content (% by mass) in the curable compositions. Show.
  • BzPh Benzophenone [BASF Japan, DAROCURE BP] 4M-BzPh: 4-methylbenzophenone [Daido Chemical Industries, DAIDO UV-CURE PMB]
  • OBM Methyl orthobenzoylbenzoate (SHUANG-BANG INDUSTRIALCORP, SB-PI 711)
  • BMS 4-benzoyl-4'-methyldiphonyl sulfide (manufactured by SHUANG-BANG INDUSTRIALCORP, SB-PI 705)
  • BisA-DA Bisphenol A type EO-modified diacrylate [manufactured by Nippon Kayaku Co., Ltd., Kayarad R-551]
  • DPHA Dipentaerythritol hexaacrylate (manufactured by Shin-Nakamura Chemical Co., Ltd., NK ester A-DPH)
  • EO-TMPTA Trimethylolpropane EO-modified triacrylate (manu
  • ⁇ Test method> Productivity When the prism portion was formed, the time required for curing of the curable composition was evaluated as ⁇ when it was less than 1 minute, ⁇ when it was 1 minute or more, and ⁇ when it was not cured. did.
  • Coating film refractive index The refractive index of the cured coating film was measured with an Abbe refractometer.
  • Example 1 Comparative Example 2
  • Example 3 Comparative Example 1
  • Example 3 Comparative Example 1
  • Example 3 Comparative Example 1
  • the active energy ray-curable composition had better productivity than the heat-curable composition.
  • BMS 4-benzoyl-4′methyldiphonyl sulfide
  • Example 2 From comparison between Example 2 and Example 8, it was found that the scratch resistance was better for urethane acrylate than epoxy acrylate. From comparison of Examples 10 and 13 to 15, when the content of the aromatic ring in the curable compound is 30% by mass or more, the coating film refractive index is relatively high as 1.56 or more, especially benzyl acrylate and o- When phenylphenol monoethoxy acrylate was used, the coating film refractive index was found to be particularly high at 1.58 or more. Dilution monomers (PEG-DA3, ACMO, PPEG-A1, BZ-A, and OPP) were compared between Examples 1 to 8 and Examples 9 to 15 and Examples 16 to 20 and Examples 25 to 30. It became clear that the introduction of -A) improved the moldability.
  • Dilution monomers PEG-DA3, ACMO, PPEG-A1, BZ-A, and OPP
  • the coating film refractive index was relatively high at 1.57 or more.
  • ⁇ Evaluation items for antireflection film> (Average reflectance) The average reflectance (%) of light having a wavelength of 450 to 650 nm was measured using a spectrophotometer.
  • Coating film refractive index The refractive index of the cured coating film of the curable composition was measured with an Abbe refractometer.
  • the curable composition may be blended with a light stabilizer, an antioxidant, an antistatic agent, an adhesion improver, etc., if necessary.
  • a cured product obtained from the curable composition may be used as a Fresnel lens, a sheet-like lens, or the like.
  • the active energy ray-curable compound contains a monomer or an oligomer containing an aromatic ring of 30% by mass or more and having a (meth) acryloyl group.
  • the refractive index of the cured product can be further increased.
  • the refractive index of the cured product can be significantly increased.
  • a lens coating agent comprising the curable composition according to any one of claims 1 to 5, wherein the lens coating agent is used by being applied to a lens surface. According to this lens coating agent, it is easy to increase the refractive index of the lens and to improve the scratch resistance of the lens surface.
  • an antireflection film is formed on the cured film.
  • Antireflection film obtained by This antireflection film has a high refractive index and excellent scratch resistance.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Polymerisation Methods In General (AREA)

Abstract

La présente invention concerne une composition durcissable contenant du benzophénone ou un dérivé de celui-ci, un composé durcissable, et un agent de traitement, et la quantité de benzophénone ou du dérivé de celui-ci est établi entre 13 et 40% en poids. Le composé durcissable est, de préférence, un composé durcissable par rayons d'énergie active, et l'agent de traitement est, de préférence, un photo-initiateur. Le composé durcissable par rayons d'énergie active est, de préférence, un (méth)acrylate d'époxy ou un (méth)acrylate d'uréthane contenant au moins 30% en poids d'un noyau aromatique. En variante, le composé durcissable par rayons d'énergie active est, de préférence, un (méth)acrylate d'uréthane modifié par polycaprolactone formé par une réaction d'un isocyanate organique et d'un (méth)acrylate d'alkyle modifié par polycaprolactone.
PCT/JP2011/061441 2010-09-01 2011-05-18 Composition durcissable WO2012029361A1 (fr)

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JPWO2012099164A1 (ja) * 2011-01-19 2014-06-30 日産化学工業株式会社 ウレタン化合物を含む高耐擦傷性インプリント材料
JP2017088680A (ja) * 2015-11-05 2017-05-25 日油株式会社 活性エネルギー線硬化型樹脂組成物
WO2018174102A1 (fr) * 2017-03-23 2018-09-27 富士フイルム株式会社 Composition durcissable pour feuilles, produit durci et son procédé de production, feuille pour mise en forme tridimensionnelle, élément optique, feuille lenticulaire et structure tridimensionnelle

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CN110698642B (zh) * 2019-09-18 2021-06-04 江南大学 一种聚氨酯改性环氧丙烯酸酯树脂及其制备方法

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JPS594638A (ja) * 1982-06-30 1984-01-11 Mitsubishi Plastics Ind Ltd 低温収縮性ラベル用フイルム
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JP2010018797A (ja) * 2008-06-11 2010-01-28 Sekisui Chem Co Ltd 光学部品用硬化性組成物、光学部品用接着剤及び有機エレクトロルミネッセンス素子用封止剤
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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2012099164A1 (ja) * 2011-01-19 2014-06-30 日産化学工業株式会社 ウレタン化合物を含む高耐擦傷性インプリント材料
JP5884988B2 (ja) * 2011-01-19 2016-03-15 日産化学工業株式会社 ウレタン化合物を含む高耐擦傷性インプリント材料
JP2017088680A (ja) * 2015-11-05 2017-05-25 日油株式会社 活性エネルギー線硬化型樹脂組成物
WO2018174102A1 (fr) * 2017-03-23 2018-09-27 富士フイルム株式会社 Composition durcissable pour feuilles, produit durci et son procédé de production, feuille pour mise en forme tridimensionnelle, élément optique, feuille lenticulaire et structure tridimensionnelle
JPWO2018174102A1 (ja) * 2017-03-23 2019-11-07 富士フイルム株式会社 シート用硬化性組成物、硬化物及びその製造方法、立体成型用シート、光学部材、レンチキュラーシート、並びに３次元構造物

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