Classifications

• • 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
  • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K3/00—Use of inorganic substances as compounding ingredients
  • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
  • C08K3/20—Oxides; Hydroxides
  • C08K3/22—Oxides; Hydroxides of metals
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K9/00—Use of pretreated ingredients
  • C08K9/04—Ingredients treated with organic substances
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K9/00—Use of pretreated ingredients
  • C08K9/04—Ingredients treated with organic substances
  • C08K9/06—Ingredients treated with organic substances with silicon-containing compounds
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L101/00—Compositions of unspecified macromolecular compounds
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K2201/00—Specific properties of additives
  • C08K2201/002—Physical properties
  • C08K2201/003—Additives being defined by their diameter
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K2201/00—Specific properties of additives
  • C08K2201/002—Physical properties
  • C08K2201/005—Additives being defined by their particle size in general

Definitions

• the present invention relates to an active energy ray-curable composition and a cured product thereof.
• the object of the present invention is to provide an active energy ray-curable composition that provides a cured product having excellent transparency, light resistance, and transferability, and a high refractive index.
• the present invention relates to an active energy ray-curable composition
• an active energy ray-curable composition comprising: coated particles (A) in which at least a portion of the surface of inorganic particles (A0) containing a titanic acid compound represented by MTiO 3 (M is Ba and/or Sr) is coated with a surface treatment agent (B); a photopolymerizable compound (C); and a photopolymerization initiator (D), wherein the average particle size of the coated particles (A) is 10 nm to 40 nm, and the content of the surface treatment agent (B) in the coated particles (A) is 5 wt % to 20 wt % based on the weight of the inorganic particles (A0); and a cured product of the active energy ray-curable composition.
• coated particles (A) in which at least a portion of the surface of inorganic particles (A0) containing a titanic acid compound represented by MTiO 3 (M is Ba and/or Sr) is
• the present invention provides an active energy ray-curable composition that provides a cured product with excellent transparency, light resistance, and transferability, and a high refractive index.
• the active energy ray-curable composition of the present invention (hereinafter also referred to as “the curable composition of the present invention”) is an active energy ray-curable composition comprising: coated particles (A) in which at least a portion of the surface of inorganic particles (A0) containing a titanic acid compound represented by MTiO 3 (M is Ba and/or Sr) is coated with a surface treatment agent (B); a photopolymerizable compound (C); and a photopolymerization initiator (D), wherein the average particle size of the coated particles (A) is 10 nm to 40 nm, and the content of the surface treatment agent (B) in the coated particles (A) is 5 wt % to 20 wt % based on the weight of the inorganic particles (A0).
• coated particles (A) in which at least a portion of the surface of inorganic particles (A0) containing a titanic acid compound represented by MTiO 3 (M is Ba and/or Sr) is coated
• the coated particles (A) will be described below.
• the coated particles (A) contain inorganic particles (A0) at least a part of the surface of which is coated with a surface treatment agent (B).
• the inorganic particles (A0) contain a titanate compound represented by MTiO 3 (M is Ba and/or Sr).
• M in MTiO 3 may contain both Ba and Sr, in which case it can be represented as (Ba x Sr 1-x )TiO 3 (x is a number greater than 0 and less than 1).
• the inorganic particles (A0) contain at least one selected from the group consisting of barium titanate [BaTiO 3 ], strontium titanate [SrTiO 3 ], and barium strontium titanate [(Ba x Sr 1-x )TiO 3 , x is a number greater than 0 and less than 1].
• These compounds are generally known to be highly dielectric substances, but in the present invention, attention has been focused on the fact that these substances are transparent, have a high refractive index, and do not have the photocatalytic activity that titanium oxide has, and thus the application of these substances as new optical fillers with high transmittance and high refractive index has been attempted.
• strontium titanate [SrTiO 3 ] is preferred from the viewpoint of the refractive index of the particles.
• titanic acid compound represented by MTiO 3 (M is Ba and/or Sr)
• commercially available products can be used.
• it can be prepared by a known method utilizing a wet reaction between barium hydroxide or strontium hydroxide and titanium tetrachloride.
• the composition ratio of M to Ti in MTiO 3 (M is Ba and/or Sr) can be determined using a fluorescent X-ray analyzer.
• the inorganic particles (A0) preferably have an average particle size of 10 nm to 40 nm, and more preferably 10 nm to 30 nm.
• the average particle size of the inorganic particles (A0) is an average primary particle size measured from about 300 particles in a photograph (25k) observed with a transmission electron microscope [JEM-F200 manufactured by JEOL Ltd.].
• the average primary particle size is a particle size obtained by averaging the diameter of a circle having an area equivalent to the area determined from the photograph for each particle for all measured particles.
• the average particle size of the coated particles (A) is from 10 to 40 nm, and from the viewpoints of light transmittance and refractive index, it is preferably from 10 to 30 nm.
• the average particle size of the coated particles (A) is a value measured by a dynamic light scattering method. From the viewpoint of excellent control of dispersibility, one of the preferred embodiments of the coated particles (A) is one that is wet-synthesized.
• the surface treatment agent (B) coats at least a part of the surface of the inorganic particles (A0).
• “coating” means that the surface treatment agent (B) is chemically bonded to or physically attached to the inorganic particles (A0).
• the coated particles (A) can be dispersed in the curable composition without agglomeration, and a transparent cured product can be obtained.
• the surface treatment agent (B) is preferably a coupling agent (B1) and/or a surfactant (B2), and known ones can be used.
• the coupling agent (B1) is preferably at least one selected from the group consisting of a silane coupling agent, a titanate coupling agent, and an aluminate coupling agent
• the surfactant (B2) is preferably a surfactant having a hydroxy group, an ester group, a phosphoric acid group, a carboxy group, or an amino group.
• the surface treatment agent (B) may be used alone or in combination of two or more.
• the silane coupling agent includes a compound represented by the following general formula (1).
• R n SiX 4-n (1) (In the formula, R represents a non-reactive functional group or a group containing a reactive functional group, X represents a hydrolyzable group or a hydroxyl group, and n is an integer of 0 to 3. When n is 2 or more, R may be the same or different, and when (4-n) is 2 or more, X may be the same or different.)
• non-reactive functional group examples include hydrocarbon groups such as methyl group, ethyl group, butyl group, isobutyl group, hexyl group, octyl group, decyl group, phenyl group, fluorene group, 3,3,3-trifluoropropyl group, and perfluorooctyl group, and halogenated hydrocarbon groups.
• the reactive functional group examples include an amino group, a vinyl group, an epoxy group, a (meth)acryloyloxy group, and a mercapto group.
• Examples of the group containing a reactive functional group include an N-2-(aminoethyl)-3-aminopropyl group, a vinyl group, a ⁇ -(3,4-epoxycyclohexyl)ethyl group, a ⁇ -glycidoxymethyl group, a ⁇ -glycidoxyethyl group, a ⁇ -glycidoxypropyl group, a ⁇ -( ⁇ -glycidoxyethoxy)propyl group, a ⁇ -(meth)acryloyloxymethyl group, a ⁇ -(meth)acryloyloxyethyl group, a ⁇ -(meth)acryloyloxypropyl group, and a ⁇ -mercaptopropyl group.
• (meth)acryloyloxy means “acryloyloxy and/or methacryloyloxy”.
• hydrolyzable group include a chlorine atom and an alkoxy group (such as a methoxy group, an ethoxy group, and a propoxy group).
• non-reactive silane coupling agents having non-reactive functional groups include, for example, methyltrimethoxysilane, dimethyldimethoxysilane, phenyltrimethoxysilane, diphenyldimethoxysilane, methyltriethoxysilane, dimethyldiethoxysilane, phenyltriethoxysilane, diphenyldiethoxysilane, isobutyltrimethoxysilane, butyltrimethoxysilane, hexyltrimethoxysilane, decyltrimethoxysilane, butyltriethoxysilane, isobutyltriethoxysilane, hexyltriethoxysilane, octyltriethoxysilane, decyltriethoxysilane, 3,3,3-trifluoropropyltrimethoxysilane, methyl- ...
• silane examples include perfluoropropyldimethoxysilane, perfluorooctylethyltrimethoxysilane, perfluorooctylethyltriethoxysilane, perfluorooctylethyltriisopropoxysilane, trifluoropropyltrimethoxysilane, methyltrichlorosilane, and dimethylmethoxyhydroxysilane, 9H-fluorene-9,9-diylbis[(4,1-phenylene)oxy(3,1-propanediyl)thio(3,1-propanediyl)]bis(trimethoxysilane), bis[3-[3-(trimethoxysilyl)propylsulfanyl]propyl]phthalate, and bis[3-[3-(trimethoxysilyl)propylsulfanyl]propyl]hexahydrophthalate.
• reactive silane coupling agents having a group containing a reactive functional group include, for example, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris( ⁇ -methoxyethoxy)silane, ⁇ -(3,4-epoxycyclohexyl)ethyltrimethoxysilane, ⁇ -glycidoxymethyltrimethoxysilane, ⁇ -glycidoxymethyltriethoxysilane, ⁇ -glycidoxyethyltrimethoxysilane, ⁇ -glycidoxyethyltriethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -glycidoxypropyltrimethoxysi
• Titanate coupling agents include isopropyl triisostearoyl titanate, isopropyl tris(dioctyl pyrophosphate) titanate, bis(dioctyl pyrophosphate)oxyacetate titanate, isopropyl tri(N-aminoethyl aminoethyl) titanate, tris(dioctyl pyrophosphate)ethylene titanate, isopropyl dioctyl pyrophosphate titanate, isopropyl tris(dodecylbenzenesulfonyl) titanate, titanium tetra-normal butoxide, titanium tetra-2-ethylhexoxide, Examples include tetraisopropyl bis(dioctyl phosphite) titanate, tetraoctyl bis(ditridecyl phosphite) titanate, tetra(2,2-diallyloxymethyl
• aluminate coupling agents include acetoalkoxyaluminum diisopropylate, aluminum diisopropoxymonoethyl acetoacetate, aluminum trisethyl acetoacetate, and aluminum trisacetylacetonate.
• silane coupling agents from the viewpoint of compatibility with the photopolymerizable compound (C), preferred are silane coupling agents, more preferred are those having a functional group that easily reacts with the matrix for forming the coating (cured product).
• the matrix is an acrylic resin
• silane coupling agents in which R of the compound represented by general formula (1) contains a (meth)acryloyloxy group particularly preferred are ⁇ -methacryloyloxypropyltrimethoxysilane and ⁇ -acryloyloxypropyltrimethoxysilane.
• coupling agents from the viewpoint of refractive index and dispersibility, preferred are 9H-fluorene-9,9-diylbis[(4,1-phenylene)oxy(3,1-propanediyl)thio(3,1-propanediyl)]bis(trimethoxysilane), bis[3-[3-(trimethoxysilyl)propylsulfanyl]propyl]phthalate, bis[3-[3-(trimethoxysilyl)propylsulfanyl]propyl]hexahydrophthalate, and N-phenyl-3-aminopropyltrimethoxysilane.
• commercially available coupling agents may be used, such as OGSOL SC-001 and OGSOL SC-003 [both manufactured by Osaka Gas Chemicals Co., Ltd.].
• the solubility parameter (hereinafter also referred to as SP value) of the coupling agent (B1) is preferably from 7.0 (cal/cm 3 ) 1/2 to 9.3 (cal/cm 3 ) 1/2 from the viewpoint of dispersibility, more preferably from 7.5 (cal/cm 3 ) 1/2 to 9.2 (cal/cm 3 ) 1/2 , and particularly preferably from 7.9 (cal/cm 3 ) 1/2 to 9.2 (cal/cm 3 ) 1/2 .
• the SP value of the coupling agent (B1) is a weighted average of the SP values of each coupling agent based on the weight ratio of each coupling agent.
• the solubility parameter in the present invention is calculated by the method described in Polymer Engineering and Science, Vol. 14, pp. 147-154 (1974) by Robert F. Fedors et al. Specifically, it is a value calculated by the method described in formula (28) on page 153 of the document using the values (heat of vaporization and molar volume at 25°C of atoms or functional groups) described on page 152 (Table. 5) of the document, and more specifically, it can be calculated by applying the values of ⁇ e i and ⁇ v i described in Table 1 below, which are parameters of the Fedors method, to the following formula using the values corresponding to the types of atoms and atomic groups in the molecular structure.
• the surfactant (B2) preferably has a hydroxy group, an ester group, a phosphoric acid group (or a phosphoric acid ester skeleton), a carboxy group or an amino group, which have high affinity with the particle surface.
• surfactants having a hydroxy group examples include IONET S-80 (manufactured by Sanyo Chemical Industries, Ltd.) and EMANONE 1112 (manufactured by Kao Corporation).
• surfactants having an ester group examples include Sunflex EB-200 and EB-300 (both manufactured by Sanyo Chemical Industries, Ltd.).
• surfactants having a phosphoric acid group or a phosphoric acid ester skeleton include alkyl ether phosphate esters, etc.
• alkyl ether phosphate esters examples include IONET 1310R [manufactured by Sanyo Chemical Industries, Ltd.], NUCOLE 1000-FCP [manufactured by Nippon Nyukazai Co., Ltd.], ANTOX EHD-400 [manufactured by Nippon Nyukazai Co., Ltd.], TEGO (registered trademark) Dispers 651, 655 [manufactured by Evonik], Plysurf series [manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.], HIPLAAD (registered trademark), and ED-153 [manufactured by Kusumoto Chemicals Co., Ltd.].
• surfactants having a phosphate group other than alkyl ether phosphate esters include Light Acrylate P-1A [manufactured by Kyoeisha Chemical Co., Ltd.], Light Ester P-1M [manufactured by Kyoeisha Chemical Co., Ltd.], TEGO (registered trademark) Dispers 656 [manufactured by Evonik Chemical Co., Ltd.], KAYAMER PM-2, and KAYAMER PM-21 [all manufactured by Nippon Kayaku Co., Ltd.].
• surfactants having a carboxy group include alkyl ether carboxylic acids.
• alkyl ether carboxylic acids examples include Viewlite LCA-H and Viewlite LCA-25NH (both manufactured by Sanyo Chemical Industries, Ltd.).
• examples of surfactants having a carboxy group other than alkyl ether carboxylic acids include TEGO (registered trademark) Dispers 652 and 690 (both manufactured by Evonik Corporation) and Disparlon 2150 (manufactured by Kusumoto Chemical Industries, Ltd.).
• surfactants having an amino group include Disparlon DA-234 (manufactured by Kusumoto Chemicals Co., Ltd.) and Solsperse 32000 (manufactured by Lubrizol Corporation).
• surfactants (B2) those containing an acidic group such as a phosphoric acid group (or a phosphoric acid ester skeleton) or a carboxy group are more preferred from the viewpoint of dispersibility, and alkyl ether phosphoric acid esters or alkyl ether carboxylic acids are particularly preferred. This is because the acidic group can be chemically bonded to the inorganic particles or can be attached to the inorganic particles in the form of a carboxylic acid or phosphoric acid or in the form of a salt.
• an acidic group such as a phosphoric acid group (or a phosphoric acid ester skeleton) or a carboxy group
• alkyl ether phosphoric acid esters or alkyl ether carboxylic acids are particularly preferred. This is because the acidic group can be chemically bonded to the inorganic particles or can be attached to the inorganic particles in the form of a carboxylic acid or phosphoric acid or in the form of a salt.
• the content of the surface treatment agent (B) in the coated particles (A) is 5% by weight to 20% by weight based on the weight of the inorganic particles (A0), and from the viewpoint of dispersibility, is preferably 10% by weight to 20% by weight.
• the content of the surface treatment agent can also be calculated using a TG-DTA (thermogravimetric differential thermal analyzer).
• TG-DTA thermogravimetric differential thermal analyzer
• the coating of the inorganic particles (A0) with the surface treatment agent (B) can be carried out, for example, by dispersing the inorganic particles (A0) in a solvent at a predetermined temperature, adding a predetermined amount of the surface treatment agent (B) to the solvent, and mixing for a predetermined time. It is preferable to increase the dispersibility of the powder using a bead mill immediately before adding the surface treatment agent (B).
• the photopolymerizable compound (C) will be described below.
• the photopolymerizable compound (C) is not particularly limited as long as it is a compound that is cured by active energy rays. Specifically, (meth)acrylate (C1), (meth)acrylamide (C2) and N-vinyl compound ( C3) and the like.
• the photopolymerizable compound (C) may be used alone or in combination of two or more kinds.
• “(meth)acrylate” means “acrylate and/or methacrylate”
• “(meth)acrylic” means “acrylic and/or methacrylic”.
• Examples of (meth)acrylates (C1) include monofunctional (meth)acrylates having one (meth)acrylate group in the molecule, monofunctional urethane (meth)acrylates having one (meth)acrylate group in the molecule, polyfunctional (meth)acrylate compounds having two or more (meth)acrylate groups in the molecule, and polyfunctional urethane (meth)acrylates having two or more (meth)acrylate groups in the molecule.
• Monofunctional (meth)acrylates include n-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, n-pentyl (meth)acrylate, n-hexyl (meth)acrylate, n-octyl (meth)acrylate, isooctyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, glycidyl (meth)acrylate, morpholine (meth)acrylate, 2-hydroxyethyl (meth)acrylate, and 2-hydroxypropyl (meth)acrylate.
• Examples of the monofunctional urethane (meth)acrylate include a reaction product of a monofunctional (meth)acrylate having a hydroxyl group (a) and an organic monoisocyanate compound (b).
• Examples of the monofunctional (meth)acrylate (a) having a hydroxyl group include hydroxyalkyl (meth)acrylates (2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, and 1,4-cyclohexanedimethanol monoacrylate).
• the hydroxyl group-containing monofunctional (meth)acrylate (a) may be used alone or in combination of two or more kinds.
• the organic monoisocyanate compound (b) include an aliphatic monoisocyanate compound (b1), an alicyclic monoisocyanate compound (b2), and an aromatic monoisocyanate compound (b3).
• Examples of the aliphatic monoisocyanate compound (b1) include methyl isocyanate, ethyl isocyanate, propyl isocyanate, isopropyl isocyanate, butyl isocyanate, hexyl acrylate, octyl isocyanate, lauryl isocyanate, tetradecyl isocyanate, hexadecyl isocyanate, and octadecyl isocyanate.
• Examples of the alicyclic monoisocyanate compound (b2) include cyclohexyl isocyanate.
• Examples of the aromatic monoisocyanate compound (b3) include phenyl isocyanate and tolylene isocyanate.
• the organic monoisocyanate compound (b) may be used alone or in combination of two or more kinds.
• Monofunctional urethane (meth)acrylates can be obtained by subjecting a monofunctional (meth)acrylate having a hydroxyl group (a) and an organic monoisocyanate compound (b) to a urethane reaction by a known method.
• Commercially available products may also be used, and examples of commercially available products include Viscoat #216 [manufactured by Osaka Organic Chemical Industry Co., Ltd.], Etermer EM2080 [manufactured by Choko Materials Industry Co., Ltd.], and Genomer 1122 [manufactured by RAHN].
• polyfunctional (meth)acrylate compound examples include difunctional (meth)acrylates, trifunctional (meth)acrylates, tetrafunctional (meth)acrylates, pentafunctional (meth)acrylates, and hexafunctional or higher (meth)acrylates.
• bifunctional (meth)acrylate examples include di(meth)acrylates (ethoxylated bisphenol A diacrylate, etc.) of alkylene oxide (hereinafter, alkylene oxide may be abbreviated as "AO") adducts of dihydric phenol compounds [monocyclic phenols (catechol, resorcinol, hydroquinone, etc.), condensed polycyclic phenols (dihydroxynaphthalene, etc.), bisphenol compounds (bisphenol A, bisphenol F, bisphenol S, etc.)], acrylic modified bisphenoxyethanol fluorene, polyalkylene glycol di(meth)acrylates (polypropylene glycol diacrylates such as dipropylene glycol diacrylate, etc.), dimethylol-tricyclodecane di(meth)acrylate, 1,4-butanediol di(meth)acrylate, and 1,9-nonanediol di(meth)acrylate.
• AO alkylene oxide
• di(meth)acrylate of an AO adduct of a dihydric phenol compound examples include a di(meth)acrylate of an ethylene oxide (hereinafter, ethylene oxide may be abbreviated as "EO”) 4-mol adduct of resorcinol, a di(meth)acrylate of a propylene oxide (hereinafter, propylene oxide may be abbreviated as "PO”) 4-mol adduct of dihydroxynaphthalene, a di(meth)acrylate of an EO 4-mol adduct of bisphenol A, a di(meth)acrylate of an EO 10-mol adduct of bisphenol A, and a di(meth)acrylate of an EO 20-mol adduct of bisphenol A.
• EO ethylene oxide
• PO propylene oxide
• trifunctional (meth)acrylates include trimethylolpropane tri(meth)acrylate, tri(meth)acrylate of AO adduct of trimethylolpropane [trimethylolpropane with 6 moles of EO, 9 moles of EO, 15 moles of EO, 20 moles of EO, and 9 moles of PO, etc.], pentaerythritol tri(meth)acrylate, tri(meth)acrylate of AO adduct of pentaerythritol [pentaerythritol with 6 moles of EO, etc.], and tri(meth)acrylate of AO adduct of glycerin [glycerin with 6 moles of EO and 3 moles of PO, etc.].
• tetrafunctional (meth)acrylates include pentaerythritol tetra(meth)acrylate, tetra(meth)acrylate of AO adduct of pentaerythritol [pentaerythritol with 2 moles of EO, with 4 moles of EO, with 10 moles of EO, with 15 moles of EO, and with 35 moles of EO, etc.], and tetra(meth)acrylate of AO adduct of ditrimethylolpropane [ditrimethylolpropane with 10 moles of EO, etc.].
• pentafunctional (meth)acrylates include dipentaerythritol penta(meth)acrylate and penta(meth)acrylates of AO adducts of dipentaerythritol [dipentaerythritol with 2 moles of EO, 4 moles of EO, 10 moles of EO, and 15 moles of EO, etc.].
• Examples of (meth)acrylates having 6 or more functionalities include dipentaerythritol hexa(meth)acrylate, hexa(meth)acrylate of AO adduct of dipentaerythritol [dipentaerythritol with 2 moles of EO, 4 moles of EO, 10 moles of EO, and 15 moles of EO, etc.], and hexa(meth)acrylate of lactone adduct of dipentaerythritol ( ⁇ -butyrolactone, ⁇ -valerolactone, ⁇ -caprolactone, etc.) [dipentaerythritol with 3 moles of ⁇ -caprolactone, 6 moles of ⁇ -caprolactone, and 12 moles of ⁇ -caprolactone, etc.].
• polyfunctional urethane (meth)acrylate compound examples include difunctional urethane (meth)acrylates, trifunctional urethane (meth)acrylates, tetrafunctional urethane (meth)acrylates, pentafunctional urethane (meth)acrylates, and hexafunctional or higher urethane (meth)acrylates.
• polyfunctional urethane (meth)acrylate commercially available products may be used.
• Ebecryl 230 Ebecryl 8807, Ebecryl 9270, Ebecryl 8800, Ebecryl 4513, Ebecryl 680, Ebecryl 5129, KRM 8296, and KRM 8904 (all manufactured by Daicel Allnex Co., Ltd.).
• phenoxyethyl acrylate phenoxydiethylene glycol acrylate, o-phenoxyphenylethyl acrylate, m-phenoxybenzyl acrylate, benzyl acrylate, acrylic modified bisphenoxyethanol fluorene, 1,4-butanediol diacrylate, 1,9-nonanediol diacrylate, dipropylene glycol diacrylate, dimethylol-tricyclodecane diacrylate, ethoxylated bisphenol A diacrylate, meth ...
• Examples of the (meth)acrylamide (C2) include (meth)acrylamide, N-alkoxy(meth)acrylamide, N-alkyl(meth)acrylamide, N-alkoxyalkyl(meth)acrylamide, N-hydroxyalkyl(meth)acrylamide, N,N-dialkyl(meth)acrylamide, N-alkoxy-N-alkyl(meth)acrylamide, and cyclic amides having an N-(meth)acryloyl group.
• Examples of the N-alkoxy(meth)acrylamide include N-methoxy(meth)acrylamide, N-ethoxy(meth)acrylamide, N-propoxy(meth)acrylamide, and N-butoxy(meth)acrylamide.
• N-alkyl(meth)acrylamides examples include N-methyl(meth)acrylamide, N-ethyl(meth)acrylamide, N-isopropyl(meth)acrylamide, and N-butyl(meth)acrylamide.
• N-alkoxyalkyl(meth)acrylamides examples include Nn-butoxymethylacrylamide.
• N-hydroxyalkyl(meth)acrylamides examples include N-hydroxyethyl(meth)acrylamide.
• N,N-dialkyl(meth)acrylamide examples include N,N-dimethyl(meth)acrylamide, N,N-diethyl(meth)acrylamide, N,N-dipropyl(meth)acrylamide, N,N-diisopropyl(meth)acrylamide, N,N-dibutyl(meth)acrylamide, N,N-diisobutyl(meth)acrylamide, N,N-di-tert-butyl(meth)acrylamide, N,N-diheptyl(meth)acrylamide, N,N-dioctyl(meth)acrylamide, N,N-di-tert-octyl(meth)acrylamide, N,N-didodecyl(meth)acrylamide, and N,N-dioctadecyl(meth)acrylamide.
• N-alkoxy-N-alkyl(meth)acrylamide examples include N-n-butoxy-N-methyl(meth)acrylamide, N-methyl-N-methoxy(meth)acrylamide, N-methyl-N-ethoxy(meth)acrylamide, N-methyl-N-propoxy(meth)acrylamide, N-ethyl-N-methoxy(meth)acrylamide, N-ethyl-N-ethoxy(meth)acrylamide, N-ethyl-N-butoxy(meth)acrylamide, N-propyl-N-methoxy(meth)acrylamide, N-propyl-N-ethoxy(meth)acrylamide, N-butyl-N-methoxy(meth)acrylamide, and N-butyl-N-ethoxy(meth)acrylamide.
• Examples of cyclic amides having an N-(meth)acryloyl group include N-(meth)acryloylmorpholine, N-(meth)acryloylthiomorpholine, N-(meth)acryloylpiperidine, N-(meth)acryloylpyrrolidine, and N-(meth)acryloylpiperidine.
• N-alkoxyalkyl(meth)acrylamides N-hydroxyalkyl(meth)acrylamides, N,N-dialkyl(meth)acrylamides, N-alkoxy-N-alkyl(meth)acrylamides and cyclic amides having an N-(meth)acryloyl group are preferred, and N,N-dimethylacrylamide, N,N-diethylacrylamide, N-acryloylmorpholine, N-n-butoxymethylacrylamide and N-hydroxyethylacrylamide are more preferred.
• N-vinyl compound (C3) examples include N-vinyl-2-pyrrolidone, N-vinylcaprolactam, N-vinylimidazole, N-vinylacetamide, N-vinylformamide, 5-methyl-3-vinyl-2-oxazolidinone, N-vinylcarbazole, and N-vinylphthalimide.
• N-vinyl-2-pyrrolidone N-vinylcaprolactam
• N-vinylimidazole N-vinylacetamide
• N-vinylformamide N-vinylformamide
• 5-methyl-3-vinyl-2-oxazolidinone preferred are N-vinyl-2-pyrrolidone, N-vinylcaprolactam, N-vinylimidazole and 5-methyl-3-vinyl-2-oxazolidinone.
• the photopolymerizable compound (C) preferably has at least one aromatic ring, and more preferably has two or more aromatic rings.
• the refractive index of the photopolymerizable compound (C) is preferably 1.50 or more, more preferably 1.55 or more, and particularly preferably 1.60 or more.
• a photopolymerizable compound having a refractive index of less than 1.50 may be used in combination as long as it does not affect the decrease in the refractive index.
• the refractive index of the photopolymerizable compound (C) is a value measured at 25°C in an uncured state using the D line of a sodium spectrum with an Abbe refractometer [DR-M2 manufactured by Atago Co., Ltd., etc.] in accordance with JIS-K0062:1992.
• the refractive index is a value obtained by measuring the mixture under the above-mentioned conditions.
• the SP value of the photopolymerizable compound (C) is preferably 7.5 (cal/cm 3 ) 1/2 to 14.4 (cal/cm 3 ) 1/2 , more preferably 9.1 (cal/cm 3 ) 1/2 to 14.4 (cal/cm 3 ) 1/2 , and particularly preferably 9.2 (cal/cm 3 ) 1/2 to 12.0 (cal/cm 3 ) 1/2 .
• the photopolymerizable compound (C) is a mixture of two or more compounds
• its SP value is a weighted average of the SP values of each photopolymerizable compound based on the weight ratio of each photopolymerizable compound, similar to the SP value of the coupling agent (B1).
• the absolute value of the difference ( ⁇ SP value) between the solubility parameter of the photopolymerizable compound (C) and the solubility parameter of the coupling agent (B1) is, from the viewpoint of the wettability of the photopolymerizable compound (C) to the particles (A), preferably 0.5 (cal/cm 3 ) 1/2 to 4.0 (cal/cm 3 ) 1/2 , and more preferably 0.5 (cal/cm 3 ) 1/2 to 2.0 (cal/cm 3 ) 1/2 .
• the viscosity of the photopolymerizable compound (C) at 25°C is preferably 1300 mPa ⁇ s or less, more preferably 2 to 1300 mPa ⁇ s, and particularly preferably 2 to 700 mPa ⁇ s, from the viewpoint of transferability.
• the viscosity of the photopolymerizable compound (C) at 25°C can be adjusted by the types and composition ratio of the monomers constituting the photopolymerizable compound (C).
• the photopolymerizable compound (C) is a mixture of two or more compounds, the viscosity of the mixture measured at 25°C is used.
• the viscosity of the photopolymerizable compound (C) at 25° C. can be measured with an E-type viscosity measuring device (such as "VISCOMETER TV-25L" manufactured by Toki Sangyo Co., Ltd.) in accordance with JIS Z 8803.
• photopolymerization initiator (D) any of a photoradical polymerization initiator, a photoanionic polymerization initiator, and a photocationic polymerization initiator can be used.
• the photopolymerization initiator (D) include a benzoin compound (D1), an alkylphenone compound (D2), an anthraquinone compound (D3), a thioxanthone compound (D4), a ketal compound (D5), a benzophenone compound (D6), a phosphine oxide (D7), and an oxime ester compound (D8).
• Examples of the benzoin compound (D1) include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin propyl ether, and benzoin isobutyl ether.
• Examples of the alkylphenone compound (D2) include acetophenone, 2,2-diethoxy-2-phenylacetophenone, 2,2-diethoxy-2-phenylacetophenone, 1,1-dichloroacetophenone, 2-hydroxy-2-methyl-phenylpropan-1-one, diethoxyacetophenone, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]-1-butanone.
• Examples of the anthraquinone compound (D3) include 2-ethylanthraquinone, 2-t-butylanthraquinone, 2-chloroanthraquinone, and 2-amylanthraquinone.
• Examples of the thioxanthone compound (D4) include 2,4-diethylthioxanthone, 2-isopropylthioxanthone, and 2-chlorothioxanthone.
• Examples of the ketal compound (D5) include acetophenone dimethyl ketal and benzyl dimethyl ketal.
• Examples of the benzophenone compound (D6) include benzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, and 4,4'-bismethylaminobenzophenone.
• Examples of the phosphine oxide (D7) include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis-(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide, and bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide.
• Examples of the oxime ester compound (D8) include 1-[4-(phenylthio)phenyl]-1,2-octanedione 2-(O-benzoyloxime) and ethanone-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-1-(O-acetyloxime).
• photopolymerization initiators (D) 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis-(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide, and bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide are preferred from the viewpoint of curability.
• the photopolymerization initiator (D) may be used alone or in combination of two or more kinds.
• the active energy ray-curable composition of the present invention can be produced, for example, by uniformly mixing the coated particles (A), the photopolymerizable compound (C), the photopolymerization initiator (D), and other components as necessary, using a known mechanical mixing method (a method using a mechanical stirrer, a magnetic stirrer, or the like).
• the coated particles (A) may be dispersed in an organic solvent (such as ethylene glycol monomethyl ether, acetone, methyl ethyl ketone, methyl isobutyl ketone, and propylene glycol monomethyl ether acetate).
• an organic solvent such as ethylene glycol monomethyl ether, acetone, methyl ethyl ketone, methyl isobutyl ketone, and propylene glycol monomethyl ether acetate.
• the organic solvent may be distilled off under reduced pressure to adjust the content of each component.
• the curable composition may further contain a surface treatment agent (B).
• a surfactant (B2) is preferable.
• the total content of the surface treatment agent (B) contained in the curable composition is preferably 5% by weight to 20% by weight, and more preferably 10% by weight to 20% by weight, based on the weight of the inorganic particles (A0).
• the “total content of the surface treatment agent (B)” refers to the total of the amount of the surface treatment agent (B) contained in the coated particles (A) and the amount of the surface treatment agent (B) optionally added when preparing the curable composition.
• the content of the coated particles (A) is preferably 49% by weight to 96% by weight, more preferably 69% by weight to 95% by weight, based on the total weight of the inorganic particles (A0), the surface treatment agent (B), the photopolymerizable compound (C) and the photopolymerization initiator (D), from the viewpoints of the refractive index and adhesion of the cured product.
• the content of the photopolymerizable compound (C) is preferably 3% by weight to 50% by weight, and more preferably 4% by weight to 30% by weight, based on the total weight of the inorganic particles (A0), the surface treatment agent (B), the photopolymerizable compound (C) and the photopolymerization initiator (D), from the viewpoints of the refractive index and adhesion of the cured product.
• the content of the photopolymerization initiator (D) is, from the viewpoint of curability, preferably 0.1 to 10% by weight, more preferably 0.1 to 5% by weight, and particularly preferably 0.1 to 3% by weight, based on the total weight of the inorganic particles (A0), the surface treatment agent (B), the photopolymerizable compound (C), and the photopolymerization initiator (D).
• the curable composition of the present invention may be diluted with a leveling agent (F) as necessary within a range that does not impair the effects of the present invention.
• a leveling agent (F) include fluorine additives such as BM-1000 and BM-1100 [manufactured by BM CHEMIE], Megafac F-142D, F-172, F-173, F-183, F-178, F-471, F-477, F-444, F-552, and F-554 [manufactured by DIC Corporation], Surflon S-242, S-420, S-431, S-386, S-611, S-651, S-656, S-658, and S-693 [manufactured by AGC Seimi Chemical Co., Ltd.], etc.
• acrylic leveling agents examples include Disparlon UVX-36 [manufactured by Kusumoto Chemical Co., Ltd.], etc.
• silicone leveling agents examples include BYK-333 (manufactured by BYK Japan KK), KP-423 (manufactured by Shin-Etsu Chemical Co., Ltd.), and Polyflow KL-401 (manufactured by Kyoeisha Co., Ltd.).
• the leveling agent (F) may be used alone or in combination of two or more kinds.
• the curable composition of the present invention may be diluted with an organic solvent (G) as necessary, although this is not essential, within the range that does not impair the effects of the present invention.
• organic solvent (G) include alcohols (methanol, ethanol, isopropanol, butanol, octanol, 1-methoxy-2-propanol, 2-methoxyethanol, and the like); ketones (acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, and the like); esters (ethyl acetate, butyl acetate, ethyl lactate, ⁇ -butyrolactone, propylene glycol monomethyl ether acetate (PGMEA; 2-methoxy-1-methylethyl acetate), propylene glycol monoethyl ether acetate, and the like); ethers (ethylene glycol monomethyl ether, diethylene glycol monobutyl ether, and the like
• methanol isopropanol, butanol, methyl ethyl ketone, methyl isobutyl ketone, ethyl acetate, ethylene glycol monomethyl ether, propylene glycol monomethyl ether, toluene, and xylene.
• the organic solvent (G) may be used alone or in combination of two or more kinds.
• the content of the organic solvent (G) is preferably 0.01% by weight to 800% by weight, more preferably 0.1% by weight to 700% by weight, and particularly preferably 1% by weight to 500% by weight, based on the total weight of the coated particles (A), the photopolymerizable compound (C), and the photopolymerization initiator (D), from the viewpoints of coatability and reduction of volatile organic compounds (VOCs).
• the curable composition of the present invention may further contain additives such as, in addition to the above-mentioned components, an antioxidant, an antistatic agent, a flame retardant, an adhesion imparting agent, a dispersant, an antioxidant, an antifoaming agent, a matting agent, a light stabilizer, a dye, and a pigment, provided that the object of the present invention is not impaired.
• additives such as, in addition to the above-mentioned components, an antioxidant, an antistatic agent, a flame retardant, an adhesion imparting agent, a dispersant, an antioxidant, an antifoaming agent, a matting agent, a light stabilizer, a dye, and a pigment, provided that the object of the present invention is not impaired.
• the content of each of the above additives is preferably 20% by weight or less, more preferably 10% by weight or less, and particularly preferably 5% by weight or less, based on the total weight of the coated particles (A), the photopolymerizable compound (C
• the cured product of the present invention is obtained by curing the active energy ray-curable composition of the present invention, and can be obtained, for example, by irradiating a coating film obtained by molding the active energy ray-curable composition of the present invention with active energy rays to cure it.
• active energy rays include visible light, ultraviolet rays, infrared rays, X-rays, ⁇ rays, ⁇ rays, ⁇ rays, electron beams, etc.
• Ultraviolet rays refer to light rays having a wavelength of 200 nm to 410 nm.
• the wavelength of the active energy ray is not particularly limited as long as it can cure the composition, but is preferably 350 nm to 410 nm, and more preferably 385 nm to 405 nm.
• a representative example of the active energy ray is light with a wavelength of 395 nm.
• the irradiation intensity of the active energy rays is not particularly limited as long as it can cure the composition, but it is preferably 20 mW/cm 2 to 20,000 mW/cm 2 .
• the cumulative exposure dose of the active energy rays is preferably 100 mJ/cm 2 to 4000 mJ/cm 2.
• the irradiation time may be determined according to the irradiation intensity.
• LED light source ultraviolet irradiation device for example, LED light source ultraviolet irradiation device "FJ100" 150 x 20 365, manufactured by Phoseon Technology] can be used.
• the shape of the portion irradiated with active energy rays may be an area type having a certain area, or a line type.
• a line type the entire coating film can be irradiated with light by moving the coating film relative to the light source, or by moving the light source relative to the coating film.
• the irradiation of active energy rays may be carried out in the atmosphere. Since the composition of the present invention has good reactivity, the reaction of the composition can be allowed to proceed and harden even in the atmosphere. It is particularly preferable to irradiate the composition with active energy rays in a dry atmosphere to harden it. In this case, it is possible to prevent the hardened composition from absorbing moisture.
• the cured product may be further heated.
• the curing can be further advanced and the linear expansion coefficient of the cured product can be reduced.
• the heating temperature is preferably 90°C or higher.
• the total light transmittance of the cured product of the present invention is preferably 80% or more when the thickness is 1 ⁇ m.
• the extraction efficiency of light that passes through the optical components and is emitted to the outside can be particularly improved.
• the active energy ray-curable composition comprises: coated particles (A) in which at least a portion of the surface of inorganic particles (A0) containing a titanic acid compound represented by MTiO 3 (M is Ba and/or Sr) is coated with a surface treatment agent (B); a photopolymerizable compound (C); and a photopolymerization initiator (D), wherein the average particle size of the coated particles (A) is 10 nm to 40 nm, and the content of the surface treatment agent (B) in the coated particles (A) is 5 wt % to 20 wt % based on the weight of the inorganic particles (A0).
• coated particles (A) in which at least a portion of the surface of inorganic particles (A0) containing a titanic acid compound represented by MTiO 3 (M is Ba and/or Sr) is coated with a surface treatment agent (B); a photopolymerizable compound (C); and a photopolymerization initiator (D),
• the active energy ray-curable composition according to [1], wherein the surface treatment agent (B) is a coupling agent (B1) and/or a surfactant (B2), the coupling agent (B1) is at least one selected from the group consisting of a silane coupling agent, a titanate coupling agent, and an aluminate coupling agent, and the surfactant (B2) is a surfactant having a hydroxy group, an ester group, a phosphoric acid group, a carboxy group, or an amino group.
• the surface treatment agent (B) is a coupling agent (B1) and/or a surfactant (B2)
• the coupling agent (B1) is at least one selected from the group consisting of a silane coupling agent, a titanate coupling agent, and an aluminate coupling agent
• the surfactant (B2) is a surfactant having a hydroxy group, an ester group, a phosphoric acid group, a carboxy group, or an amino group
• the average particle size of the coated particles is a value measured by dynamic light scattering using an ELSZ-1000 manufactured by Otsuka Electronics Co., Ltd.
• a dispersion of coated particles (A-2) was produced using the composition shown in Table 2 in the same manner as in Production Example 1.
• the average particle size of the coated particles (A-2) in the dispersion was 18 nm.
• dispersion treatment was carried out at room temperature for 6 hours. After completion of the dispersion treatment, the liquid was collected to obtain a dispersion liquid of coated particles (A-4).
• the average particle size of the coated particles (A-4) in the dispersion liquid was 20 nm.
• the average particle size of the coated particles (A-5) in the dispersion liquid was 20 nm.
• a dispersion of comparative coated particles (A'-1) was produced using the composition shown in Table 2 in the same manner as in Production Example 1.
• the average particle size of the coated particles (A'-1) in the dispersion was 18 nm.
• the mixture was filtered through a 2300 mesh to recover the filtrate, and a dispersion liquid of comparative coated particles (A'-2) was obtained.
• the average particle size of the coated particles (A'-2) in the dispersion liquid was 82 nm.
• the refractive index, total light transmittance, haze, light resistance, and transferability of the cured product of the active energy ray curable compositions prepared in each Example and Comparative Example were evaluated by the following methods.
• the active energy ray-curable composition was dropped onto a glass substrate [Eagle XG, manufactured by Corning Corporation] and coated by spin coating at a rotation speed of 3000 rpm for 30 seconds, and then dried at 80°C for 1 minute. After that, the composition was cured by irradiating with ultraviolet light at 1000 mJ/ cm2 using an ultraviolet irradiation device [VPS/I600, manufactured by Fusion UV Systems Co., Ltd.] under a nitrogen atmosphere, to obtain a cured product with a film thickness of 100 nm for refractive index evaluation.
• the refractive index of the cured product prepared as described above was measured at 589 nm using a reflection spectroscopic film thickness meter [FE-3000, manufactured by Otsuka Electronics Co., Ltd.]. In this case, a refractive index of 1.70 or more is considered to be good.
• the active energy ray-curable composition was dropped onto a microslide glass [S1214, manufactured by Matsunami Glass Industry Co., Ltd.], coated with a bar coater, and then dried at 80°C for 3 minutes. After that, the composition was cured by irradiating with ultraviolet light at 1000 mJ/ cm2 using an ultraviolet irradiation device [VPS/I600, manufactured by Fusion UV Systems Co., Ltd.] in a nitrogen atmosphere, to obtain a cured product with a film thickness of approximately 1 ⁇ m for evaluating the total light transmittance and haze.
• the total light transmittance and haze of the cured product prepared on the microslide glass as described above were measured using a haze meter [haze-gard dual, manufactured by BYK Corporation].
• the haze of the cured product is good if it is 1.5% or less, and more preferably 1.0% or less.
• the active energy ray curable composition was dropped onto a microslide glass [S1214, manufactured by Matsunami Glass Industry Co., Ltd.] and coated with a bar coater. After drying at 80°C for 3 minutes, the composition was cured by irradiating with 2000 mJ/ cm2 of ultraviolet light using an ultraviolet irradiator [VPS/I600, manufactured by Fusion UV Systems Co., Ltd.] under a nitrogen atmosphere, and a cured product with a film thickness of about 5 ⁇ m was produced on a microslide glass substrate.
• the cured product was placed together with the glass substrate in a light resistance tester [Eye Super UV Tester SUV-131, manufactured by Iwasaki Electric Co., Ltd.] and irradiated with ultraviolet light intensity of 25 mW/ cm2 for 15 hours.
• the obtained substrate was evaluated by a spectrophotometer/colorimeter [SE7700, manufactured by Nippon Denshoku Kogyo Co., Ltd.] using the yellow index ( ⁇ Y.I.) before and after the test according to the following criteria.
• Example 1 514.7 parts by weight of the dispersion of the coated particles (A-1) obtained in Production Example 1 (83.7 parts by weight of the coated particles (A-1), 431 parts by weight of 2-methoxyethanol (G-1)), 11.8 parts by weight of N-vinyl-2-pyrrolidone (C-8), 1.5 parts by weight of dipropylene glycol diacrylate (C-12), 1.5 parts by weight of ethoxylated bisphenol A diacrylate (C-13), 1.5 parts by weight of Omnirad TPO H (D-1) as a photopolymerization initiator, and 0.6 parts by weight of a fluorine additive (F-1) as a leveling agent were blended and mixed uniformly to obtain an active energy ray-curable composition.
• Example 2 419.9 parts by weight of the dispersion of the coated particles (A-2) obtained in Production Example 2 (70.9 parts by weight of the coated particles (A-2), 349 parts by weight of 2-methoxyethanol (G-1)), 18.9 parts by weight of o-phenoxyphenylethyl acrylate (C-3), 4.7 parts by weight of 1,4-butanediol diacrylate (C-10), 2.4 parts by weight of Omnirad TPO H (D-1) as a photopolymerization initiator, 3.1 parts by weight of surfactant 2 (B2-2), and 1.0 part by weight of a fluorine additive (F-1) as a leveling agent were blended and mixed uniformly to obtain an active energy ray curable composition.
• Example 3 An active energy ray curable composition was obtained by blending 478.8 parts by weight of the dispersion of the coated particles (A-2) obtained in Production Example 2 (80.8 parts by weight of the coated particles (A-2) and 398 parts by weight of 2-methoxyethanol (G-1)), 11.4 parts by weight of o-phenoxyphenylethyl acrylate (C-3), 2.9 parts by weight of 1,4-butanediol diacrylate (C-10), 1.4 parts by weight of Omnirad TPO H (D-1) as a photopolymerization initiator, 3.5 parts by weight of surfactant 2 (B2-2), and 0.6 parts by weight of a fluorine additive (F-1) as a leveling agent, and mixing them uniformly.
• Example 4 507.4 parts by weight of the dispersion of the coated particles (A-3) obtained in Production Example 3 (84.4 parts by weight of the coated particles (A-3), 423 parts by weight of PGME (G-2)), 11.4 parts by weight of o-phenoxyphenylethyl acrylate (C-3), 2.8 parts by weight of 1,4-butanediol diacrylate (C-10), 1.4 parts by weight of Omnirad TPO H (D-1) as a photopolymerization initiator, and 0.6 parts by weight of a fluorine additive (F-1) as a leveling agent were blended and mixed uniformly to obtain an active energy ray-curable composition.
• Examples 5 to 10 The components in the composition shown in Table 3-1 were mixed uniformly in the same manner as in Example 2 to obtain active energy ray-curable compositions.
• Example 11 The components in the composition shown in Table 3-2 were mixed uniformly in the same manner as in Example 2, except that toluene (G-3) was added so as to reach the weight shown in Table 3-2, to obtain an active energy ray-curable composition.
• Example 12 The components were mixed uniformly in the same manner as in Example 2, except that PGMEA (G-4) was added to the composition shown in Table 3-2 so as to reach the weight shown, to obtain an active energy ray-curable composition.
• Example 13 to 21 The components in the compositions shown in Table 3-2 or Table 3-3 were mixed uniformly in the same manner as in Example 2 to obtain active energy ray-curable compositions.
• Example 22 to 25 The components in the composition shown in Table 3-3 were mixed uniformly in the same manner as in Example 2, except that the fluorine additive (F-1) was not added, to obtain an active energy ray-curable composition.
• Example 26 266.4 parts by weight of the dispersion of the coated particles (A-4) obtained in Production Example 4 (85.4 parts by weight of the coated particles (A-4), 181 parts by weight of MEK (G-5)), 11.4 parts by weight of o-phenoxyphenylethyl acrylate (C-3), 2.8 parts by weight of 1,4-butanediol diacrylate (C-10), 0.4 parts by weight of Omnirad TPO H (D-1) as a photopolymerization initiator, 0.6 parts by weight of the silicone leveling agent (F-2) as a leveling agent, and 220 parts by weight of MEK (G-5) were blended and mixed uniformly to obtain an active energy ray-curable composition.
• Omnirad TPO H D-1
• F-2 silicone leveling agent
• MEK 220 parts by weight of MEK
• Examples 27 to 28 The components in the composition shown in Table 3-3 were mixed uniformly in the same manner as in Example 26 to obtain active energy ray-curable compositions.
• Example 29 251.4 parts by weight of the dispersion of the coated particles (A-5) obtained in Production Example 5 (85.4 parts by weight of the coated particles (A-5), 166 parts by weight of PGMEA (G-4)), 11.4 parts by weight of o-phenoxyphenylethyl acrylate (C-3), 2.8 parts by weight of 1,4-butanediol diacrylate (C-10), 0.4 parts by weight of Omnirad TPO H (D-1) as a photopolymerization initiator, 0.6 parts by weight of silicone leveling agent (F-2) as a leveling agent, and 235 parts by weight of PGMEA (G-4) were blended and mixed uniformly to obtain an active energy ray-curable composition.
• Omnirad TPO H D-1 as a photopolymerization initiator
• F-2 silicone leveling agent
• 235 parts by weight of PGMEA (G-4) were blended and mixed uniformly to obtain an active energy ray-curable composition.
• Example 30 to 34 The compositions shown in Table 3-3 or Table 3-4 were mixed uniformly in the same manner as in Example 29 to obtain active energy ray-curable compositions.
• Example 35 266.4 parts by weight of the dispersion of the coated particles (A-6) obtained in Production Example 6 (85.4 parts by weight of the coated particles (A-6), 181 parts by weight of PGMEA (G-4)), 11.4 parts by weight of o-phenoxyphenylethyl acrylate (C-3), 2.8 parts by weight of 1,4-butanediol diacrylate (C-10), 0.4 parts by weight of Omnirad TPO H (D-1) as a photopolymerization initiator, 0.6 parts by weight of silicone leveling agent (F-2) as a leveling agent, and 220 parts by weight of PGMEA (G-4) were blended and mixed uniformly to obtain an active energy ray-curable composition.
• Comparative Example 4 in which surface-treated titanium oxide particles were used, the light resistance of the cured product was poor.
• Comparative Example 3 in which coated particles containing a large amount of surface treatment agent and having a large particle size were used, the refractive index of the cured product was low, and the transparency and transferability were also poor.
• Comparative Examples 1 and 2 in which coated particles containing a large amount of surface treatment agent were used, the refractive index of the cured product was low.
• a cured product having excellent transparency, light resistance, and transferability and a high refractive index was obtained.
• the cured product of the active energy ray-curable composition of the present invention has a high refractive index and is excellent in transparency, light resistance and transferability, and is therefore useful as an optical member, specifically, as an optical component such as a plastic lens (prism lens, lenticular lens, microlens, Fresnel lens, viewing angle improving lens, etc.), an optical compensation film, a retardation film, a prism, an optical fiber, a solder resist for flexible printed wiring, a plating resist, an interlayer insulating film for multilayer printed wiring boards, and a photosensitive optical waveguide.
• a plastic lens prism
• an optical compensation film such as a plastic lens (prism lens, lenticular lens, microlens, Fresnel lens, viewing angle improving lens, etc.)
• an optical compensation film such as a retardation film, a prism, an optical fiber, a solder resist for flexible printed wiring, a plating resist, an interlayer insulating film for multilayer printed wiring boards, and

Landscapes

• Chemical & Material Sciences (AREA)
• Health & Medical Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Organic Chemistry (AREA)
• Paints Or Removers (AREA)
• Pigments, Carbon Blacks, Or Wood Stains (AREA)
• Polymerisation Methods In General (AREA)

Priority Applications (3)

Applications Claiming Priority (2)

Publications (1)

Family

ID=93059254

Family Applications (1)

Country Status (5)

Citations (3)

Family Cites Families (2)

• 2024
  • 2024-04-03 WO PCT/JP2024/013702 patent/WO2024214603A1/ja not_active Ceased
  • 2024-04-03 TW TW113112741A patent/TW202506744A/zh unknown
  • 2024-04-03 JP JP2025513913A patent/JPWO2024214603A1/ja active Pending
  • 2024-04-03 CN CN202480024467.1A patent/CN121039169A/zh active Pending
  • 2024-04-03 KR KR1020257034463A patent/KR20250162850A/ko active Pending

Patent Citations (3)

Also Published As

Similar Documents

Legal Events