TW201630656A - Dispersion composition and cured product thereof, and laminate - Google Patents

Abstract

Provided is a dispersion composition that makes it possible to satisfactorily disperse metal oxide microparticles as well as to achieve both good optical performance and good surface smoothness in a cured product after curing. The dispersion composition pertaining to the invention contains dispersoid particles (A) that are metal oxide microparticles having an average particle size of less than 50 nm, a dispersant (B) comprising a compound shown by formula (1), and a polymerizable compound (C). The dispersant (B) is combined within a range of 3-20% by mass relative to the total solids content. (in formula (1), R is a C3-24 linear alkyl group or linear alkenyl group, AO is a C1-4 oxyalkylene group, n is an average added alkylene oxide mole count of 5-30, X is a linking group comprising a carbon atom, hydrogen atom and/or oxygen atom).

Description

Dispersion composition and hardened material thereof, and laminated body

The present invention relates to a dispersion composition containing a polymerizable compound and dispersed in metal oxide fine particles, a cured product thereof, and a laminate including a layer obtained by curing the dispersion composition.

The liquid crystal panel is widely used as a display unit of a television, a computer display, or a smart phone. The basic configuration of the liquid crystal panel includes a liquid crystal layer sandwiched inside the pair of light-transmitting substrates, and a polarizing film laminated on the outer surface of each of the light-transmitting substrates. A surface protective film is usually provided on the display surface of the liquid crystal panel, and an anti-reflection (AR) film or an anti-glare (AG) film is always used for such a surface protective film.

Further, in a display device such as a touch panel, a laminate in which a pattern-shaped transparent conductor layer is provided on a transparent resin substrate such as a glass substrate or a polyethylene terephthalate (PET) film has been used. As the material of the transparent conductor layer, indium tin oxide (ITO) is typically used. In the laminated body, the difference in optical characteristics (refractive index) between the substrate and the transparent conductor layer is large. Therefore, when the laminated body is disposed on the front surface of a display device such as a touch panel, the display surface of the liquid crystal panel may be viewed. The pattern to the ITO electrode film (for example, referred to as "pattern visible"). Therefore, it is known to realize the invisibility of the pattern of the ITO electrode film by using an optical adjustment (Index Matching (IM)) film.

For example, the resin composition for an optical material disclosed in Patent Document 1 or the resin disclosed in Patent Document 2 can be used as the resin composition for use in an optical film such as an AR film, an AG film, or an IM film. Composition. In addition, as an example of the AG film, for example, an anti-glare film disclosed in Patent Document 3 can be cited. [Prior Art Document] [Patent Literature]

[Patent Document 1] Japanese Patent Laid-Open Publication No. JP-A No. Hei. No. Hei. No. Hei. No. Hei.

[Problems to be solved by the invention]

The resin composition for an optical material disclosed in Patent Document 1 uses a difunctional (meth) acrylate compound having a specific fluorene skeleton structure, thereby realizing a high refractive index. However, for example, when used as an IM layer, the refractive index is insufficient, so that the pattern of the ITO electrode film cannot be sufficiently invisible.

Further, in the resin composition disclosed in Patent Document 2, metal oxide fine particles such as zirconia and/or titanium oxide are added as a component for increasing the refractive index. However, in the case of adding zirconia, in order to sufficiently disperse the zirconia, the amount of the dispersant added is also increased, so that the refractive index cannot be sufficiently increased. Further, since titanium oxide has photocatalytic activity, it has various effects when used as an additive component of an optical film. Further, as is well known as "Titanium white", titanium oxide has excellent performance as a white pigment. Therefore, if it is used as an additive component of an optical film, it may cause whitening of this optical film.

Further, the anti-glare film disclosed in Patent Document 3 has a structure in which an anti-glare layer, a high refractive index layer, and a low refractive index layer are laminated on a transparent base film, and a metal having a predetermined range is contained in the high refractive index layer. Oxide microparticles. Here, the average particle diameter of the metal oxide fine particles may be not more than the thickness of the high refractive index layer, and is, for example, 0.1 μm or less. Therefore, the surface roughness of the high refractive index layer may increase due to the addition of the metal oxide fine particles, the surface smoothness may be lowered, and coating unevenness may occur in the low refractive index layer which becomes the upper layer, or interference may occur as an optical film. All.

The present invention has been made to solve such a problem, and an object of the invention is to provide a fine dispersion of a metal oxide fine particle in a dispersion composition containing metal oxide fine particles, and to obtain a cured product after curing. Both optical properties and good surface smoothness. [Means for solving the problem]

In order to solve the above problems, the dispersion composition of the present invention has a configuration comprising (A) a dispersed particle, (B) a dispersing agent, and (C) a polymerizable compound, wherein the (A) dispersed particle has an average particle diameter. The metal oxide fine particles of less than 50 nm, wherein the (B) dispersant contains a compound represented by the following formula (1), and when the total solid content contained in the dispersion composition is 100% by mass, The amount of the dispersing agent (B) is in the range of 3% by mass to 20% by mass based on the total solid content.

[Chemical 1]

(wherein R in the formula (1) is a linear alkyl group having 3 to 24 carbon atoms or a linear alkenyl group having 3 to 24 carbon atoms; AO is an alkyloxy group having 1 to 4 carbon atoms; and n is a ring representing n. The value of the average addition molar number of oxane in the range of 5 to 30, and X is a linking group containing a carbon atom, a hydrogen atom and/or an oxygen atom. According to the above configuration, the average particle size of (A) is dispersed. When the metal oxide fine particles having a particle diameter of less than 50 nm are used, if the (B) dispersing agent containing the compound of the formula (1) is used, the metal can be a metal, in particular, the linear group of the hydrophobic group R of the formula (1) The oxide fine particles are well dispersed. Further, the cured product obtained by curing the dispersion composition can achieve good optical properties, and can also achieve good surface smoothness, and can further improve physical properties such as alkali resistance and scratch resistance.

The dispersion composition of the above configuration may be one in which the (C) polymerizable compound is at least one compound having one or more carboxyl groups and two or more ethylenically unsaturated groups in one molecule.

Further, the cured product of the present invention is obtained by curing the dispersion composition of the above composition. Further, the laminate of the present invention contains a layer obtained by curing the dispersion composition of the above composition, and the surface roughness (Sa) of the laminate is in the range of 0.1 nm to 1.0 nm. [Effects of the Invention]

In the present invention, the above-described configuration exhibits an effect that the metal oxide fine particles can be well dispersed in the dispersion composition containing the metal oxide fine particles, and the cured product after curing can achieve good optical properties and Good surface smoothness for both.

The dispersion composition of the present invention contains (A) a dispersed particle, (B) a dispersing agent, and (C) a polymerizable compound, and (A) a dispersed particle is a metal oxide fine particle having an average particle diameter of 50 nm or less, and As shown in the formula (1), the (B) dispersant has the following chemical structure: a hydrophobic group R having a linear alkyl group having 3 to 24 carbon atoms or a linear alkenyl group having 3 to 24 carbon atoms, and a carbon number (AO) _{n of} an oxygen-extended alkyl group of 1 to 4 (n is an average addition molar number of alkylene oxide, a value in the range of 5 to 30) bonded via an oxygen atom, and (AO) _{n is} via The group X is bonded to the carboxyl group (COOH).

Hereinafter, a representative example of the dispersion composition of the present invention, a cured product obtained by curing the dispersion composition of the present invention, and a layered body containing a layer obtained by curing the dispersion composition of the present invention A representative example is specifically described.

[(A) Dispersed Particles] The (A) dispersed particles contained in the dispersion composition of the present invention may be metal oxide fine particles having an average particle diameter of less than 50 nm. The metal oxide constituting the metal oxide fine particles is not particularly limited, and examples thereof include monooxidation such as titania, alumina, zirconia, magnesia, and silica. Potassium titanate, barium titanate, barium titanate, calcium titanate, magnesium titanate, lead titanate, aluminum titanate, lithium titanate, lead zirconate titanate (PZT), indium tin oxide (ITO), etc. Composite oxides, etc. These metal oxides may be used alone or in combination of two or more as (A) dispersed particles.

The specific configuration of the metal oxide fine particles used as the (A) dispersed particles is not particularly limited as long as the average particle diameter thereof is less than 50 nm. When the average particle diameter is 50 nm or more, the transparency of the obtained cured product may be lowered, the haze may be increased, and the surface smoothness may be lowered. The lower limit of the average particle diameter of the metal oxide fine particles is not particularly limited, and may be, for example, 1 nm or more. Therefore, the range of the representative average particle diameter of the metal oxide fine particles is 1 nm or more and less than 50 nm, and more preferably in the range of 1 nm to 40 nm.

Further, the metal oxide fine particles may be crystalline or amorphous, and the isotropic particles may be anisotropic particles or may be fibrous. Further, the metal oxide fine particles may be in the form of a usual powder or may be a fine particle sol. When the metal oxide fine particles are fine particle sols, depending on the type or amount of other components, good optical performance and good surface smoothness can be achieved. For example, in the examples described later, a fine particle sol (zirconia sol) of zirconium oxide is used as the (A) dispersed particle.

The method for producing the fine particle sol of the (A) dispersed particles is not particularly limited, and can be produced by a known method such as a metal or a semimetal produced by a known wet synthesis method (or dry synthesis method). The fine particles are prepared by using a known solvent or the like, and are sol-geled. Further, in the present invention, a commercially available fine particle sol may be used as the (A) dispersed particle as described later.

The production method (preparation method) of the metal oxide fine particles used as the (A) dispersed particles is not particularly limited, and a known method can be preferably used. For example, a typical production method includes a top-down method in which coarse particles are mechanically pulverized and refined, and a plurality of unit particles are formed, and the unit particles are condensed. The resulting cluster state forms a bottom up manner of the particles; it can be prepared by any method. Further, the manufacturing method of these modes may be either a wet method or a dry method. Further, the medium used in the production method of the above embodiments may be a water system or a non-aqueous system, or may be a gas layer.

In addition, there are physical methods and chemical methods in the bottom-up manner, and any method can be utilized. A typical example of the physical method is a gas evaporation method in which a bulk metal is evaporated in an inert gas and cooled and condensed by collision with a gas to form nano particles. Further, representative examples of the chemical method include a liquid phase reduction method (reduction of a metal ion in the presence of a protective agent in a liquid phase to stabilize a generated zero-valent metal in a nanometer size), and a metal complex. Thermal decomposition method, etc. More specific examples of the liquid phase reduction method include a chemical reduction method, an electrochemical reduction method, a photoreduction method, a method of combining a chemical reduction method and a light irradiation method, and the like.

Furthermore, as described later, the dispersion composition of the present invention can be prepared (manufactured) by mixing and stirring the metal oxide fine particles (B) as a (A) dispersed particle, (B) a dispersing agent, and (C) a polymerizable compound. (B) The dispersing agent can be used in the production step of using metal oxide fine particles in a top-down manner or a bottom-up manner. Further, when metal oxide fine particles are produced by various methods or methods described above, a protective agent may be used in order to take out metal oxide fine particles from the medium used in the production step. The protective agent may, for example, be a surface modifying agent that modifies the surface of the metal oxide fine particles or a surface protecting agent that protects the surface of the metal oxide fine particles. The protective agent is used to coat the surface, or the protective agent is used for impregnation, whereby the metal oxide fine particles can be stably taken out from the medium. Here, (B) a dispersant can also be used as the protective agent.

[(B) Dispersant] The (B) dispersant contained in the dispersion composition of the present invention is a compound having the chemical structure represented by the above formula (1).

[Chemical 2]

The hydrophobic group R in the compound of the formula (1) is a linear alkyl group or an alkenyl group having 3 to 24 carbon atoms, and may be, for example, a hydrocarbon group derived from an alcohol. When the hydrophobic group R is derived from an alcohol, the raw material alcohol may be a single type of alcohol (that is, an alcohol having the same carbon number), or a mixture of alcohols having different carbon numbers. In addition, the raw material alcohol may be derived from synthesis or may be derived from nature, and the chemical structure may be a single composition or a mixture containing a plurality of isomers.

As the raw material alcohol which can be used, a known alcohol can be selected. Specifically, for example, the following alcohol can be preferably used as a representative raw material alcohol: propanol, butanol, pentanol, hexanol, heptanol, octanol, Sterols, sterols; trade names manufactured by Shell Chemicals: Neodol 23, Neodol 25, Neodol 45, etc. derived from synthetic higher alcohols; laurel Alcohol (1-dodecanol), tridecyl alcohol, myristyl alcohol (1-tetradecanol), cetyl alcohol (1-hexadecanol), stearyl alcohol (1-octadecyl alcohol), oleyl alcohol (cis The formula-9-octadecen-1-ol) is derived from a natural higher alcohol or the like. As described above, these raw material alcohols may be used alone or in combination of two or more.

The oxygen alkyl group (AO) _n in the compound of the formula (1) has a carbon number of 1 to 4, and n is a value in the range of 5 to 30 which represents the average addition mole number of the alkylene oxide. The specific monomer structure of the oxygen alkyl group is not particularly limited, and examples thereof include an oxymethylene group (carbon number 1), an oxygen extension ethyl group (ethylene glycol, carbon number 2), and an oxygen extension propyl group (carbon number 3). ), an oxygen-extended butyl group (carbon number 4), tetrahydrofuran (carbon number 4), and the like. Examples of the oxygen-extension butyl group include 1,2-oxybutylene or 2,3-oxobutylene.

The oxygen alkyl group may be a homopolymer chain composed of only one of the monomer structures, or may be a copolymer chain of two or more monomer structures. Further, the copolymer chain may be a random polymer chain or a block polymer chain, or a combination of the polymer chains. By using a homopolymer chain or various copolymer chains as a polymer chain of an oxygen-extended alkyl group, the affinity of the compound of the formula (1), that is, the dispersant to the dispersion medium (the (D) dispersing aid described later) can be adjusted.

The linking group X in the compound of the formula (1) is a linking group containing a carbon atom, a hydrogen atom and/or an oxygen atom. More specifically, the linking group X may be a hydrocarbon group composed of a carbon atom and a hydrogen atom, or may be only an oxygen atom, or may be an organic group containing an oxygen atom (consisting of a carbon atom, a hydrogen atom, and an oxygen atom). Group).

The specific configuration of the linking group X is not particularly limited, and a known structure can be employed. For example, one selected from the group consisting of a saturated hydrocarbon group, an unsaturated hydrocarbon group, an ether group, a carbonyl group, and an ester group can be mentioned. Further, the linking group X may also have a ring structure (alicyclic structure, aromatic ring structure, etc.), and may also contain a repeating unit. In addition, when the linking group X contains a nitrogen atom, a sulfur atom, and/or a phosphorus atom, the effect of the affinity of the carboxyl group on the (A) dispersed particle is weakened. Therefore, the linking group X is preferably composed of a carbon atom, a hydrogen atom and/or an oxygen atom.

The compound of the formula (1) can be produced by a known method. Specifically, for example, a method of using a conventional nonionic surfactant compound obtained by adding an alkylene oxide to an alcohol, an amine or a mercaptan by a known method as a raw material, and using a monohalogenated lower carboxylic acid or A method of reacting a salt with a hydroxyl group at the terminal of an alkylene oxide in the presence of a base; or a method of using a ring opening reaction with a hydroxyl group at the terminal of an alkylene oxide using an acid anhydride. Of course, the method for producing the compound of the formula (1) is of course not limited to these methods.

The dispersion composition of the present invention contains the compound of the formula (1) as the (B) dispersant, whereby the cured film-like or layer-like cured product can achieve good surface smoothness. In particular, in the compound of the formula (1), the hydrophobic group R has a linear structure, so the linear structure contributes to good surface smoothness. On the other hand, when the hydrophobic group R is a branched chain, the surface smoothness of the obtained film-like or layered cured product is lowered.

[(C) Polymerizable Compound] The (C) polymerizable compound contained in the dispersion composition of the present invention is not particularly limited as long as it is a known compound which is polymerizable and hardened by polymerization under predetermined conditions. Specially limited.

A typical compound which can be used as the (C) polymerizable compound is a compound having an ethylenically unsaturated group in the molecule (vinyl compound), a compound having an epoxy group at the terminal (epoxy compound), and An amine group compound, a compound having a carboxyl group or a derivative thereof, a compound having a hydroxyl group, and the like. These compounds are classified based on functional groups which contribute to polymerizability contained in the molecule, and may contain a plurality of functional groups in the structure of one compound. For example, the vinyl compound may contain an amine group or a carboxyl group in addition to the ethylenically unsaturated group. Further, as the compound which can be used as the (C) polymerizable compound, the same type of functional group in one compound may be only one (monofunctional) or two or more (polyfunctional). Further, these compounds may be used alone or in combination of two or more. A typical example is a compound having one or more carboxyl groups and two or more ethylenically unsaturated groups in one molecule.

The type of the polymer (resin) obtained by the polymerization of the (C) polymerizable compound is not particularly limited, and can be appropriately selected according to the use, the use conditions, the production conditions, and the like of the dispersion composition or the cured product of the present invention. In addition, the polymerization conditions of the (C) polymerizable compound are not particularly limited, and depending on the type of the compound to be used as the (C) polymerizable compound, polymerization by heating, irradiation by radiation or the like, and use of a curing agent can be used. Polymerization (hardening), etc. Similarly, the molecular weight of the polymer is not particularly limited, and can be appropriately set according to various conditions similar to those described above.

Representative examples of the compound which can be used as the (C) polymerizable compound include an alkyl ester selected from a carboxylic acid group-containing unsaturated polymerizable monomer, a carboxylic acid group-containing unsaturated polymerizable monomer, and a vinyl compound. At least one compound of the group consisting of urethane acrylates and epoxy compounds.

First, examples of the unsaturated polymerizable monomer having a carboxylic acid group in the group include (meth)acrylic acid, crotonic acid, maleic acid, itaconic acid and the like.

Further, examples of the alkyl ester of the carboxylic acid group-containing unsaturated polymerizable monomer in the group include methyl (meth)acrylate, ethyl (meth)acrylate, and propyl (meth)acrylate. Isopropyl (meth)acrylate, butyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, hexyl (meth)acrylate, (meth)acrylic acid-2 -ethylhexyl ester, octyl (meth) acrylate, decyl (meth) acrylate, decyl (meth) acrylate, stearyl (meth) acrylate, isostearyl (meth) acrylate, ( Lauryl (meth)acrylate, cyclohexyl (meth)acrylate, t-butylcyclohexyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, (methyl) Bicyclo[3,3,1]nonyl acrylate, 2-methoxyethyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, benzyl (meth)acrylate, (meth)acrylic acid Allyl ester, diethylaminoethyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxyl (meth)acrylate Propyl ester, 4-hydroxybutyl (meth)acrylate, methoxy Ethylene glycol (meth) acrylate, methoxy polyethylene glycol (meth) acrylate, ethoxyethylene glycol (meth) acrylate, ethoxy polyethylene glycol (meth) acrylate , propoxyethylene glycol (meth) acrylate, propoxy polyethylene glycol (meth) acrylate, methoxy propylene glycol (meth) acrylate, methoxy polypropylene glycol (meth) acrylate , ethoxypropanediol (meth) acrylate, ethoxypolypropylene glycol (meth) acrylate, propoxy propylene glycol (meth) acrylate, propoxy polypropylene glycol (meth) acrylate, etc. Acrylate; ethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, triethylene glycol Di(meth) acrylate compound such as alcohol di(meth) acrylate or 9,9-bis[4-(2-hydroxyethoxy)phenyl] quinone di(meth) acrylate; pentaerythritol tris (a) a tris(meth)acrylate compound such as acrylate, trimethylolpropane tri(meth)acrylate or tris(meth)acrylate; pentaerythritol tetra(meth)acrylate, etc. (Meth) acrylate compound; dipentaerythritol hexa (meth) acrylate, sorbitol hexa (meth) acrylate, hexa (meth) acrylate compound.

Further, examples of the vinyl compound in the group include vinyl acetate, vinyl propionate, styrene, α-methylstyrene, vinyl toluene, acrylonitrile, methacrylonitrile, butadiene, and isoprene. Diene, etc.

Further, the urethane acrylate in the group is a compound obtained by reacting a polyisocyanate with a hydroxyl group-containing (meth) acrylate. First, examples of the polyisocyanate which can be used for the urethane acrylate include toluene diisocyanate, diphenylmethane diisocyanate, polyphenylmethane polyisocyanate, phenyl diisocyanate, naphthalene diisocyanate, xylene diisocyanate, and tetradecyl. Xylylene diisocyanate, hexamethylene diisocyanate, trimethyl hexamethylene diisocyanate, diazonic acid diisocyanate, isocyanuric acid triisocyanate, dicyclohexylmethane diisocyanate, hydrogenated xylene diisocyanate, different buddha Mercapone diisocyanate, 1,3-bis(isocyanatemethyl)cyclohexane, norbornene diisocyanate, modified products of these diisocyanates, and urethane prepolymers having an isocyanate group at the end.

Here, the urethane prepolymer having an isocyanate group at the end is a compound obtained by reacting a polyisocyanate with a polyhydric alcohol, and examples thereof include a polyhydric alcohol such as an alkyl diol, a trimethylol alkane, glycerin or pentaerythritol. a compound; a polymer compound such as a polyether polyol, a polyester polyol, a polycaprolactone polyol, a polyolefin polyol, a polybutadiene polyol, or a polycarbonate polyol.

Then, the hydroxyl group-containing (meth) acrylate which can be used for the urethane acrylate may be a (meth) acrylate type compound having one or more hydroxyl groups in the molecule. Examples of such a (meth) acrylate-based compound include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, and 2-hydroxybutyl (meth)acrylate. 4-hydroxybutyl (meth)acrylate, 2-hydroxyethylpropenyl phosphate, 2-(methyl)propenyloxyethyl-2-hydroxypropyl phthalate, glycerol Methyl) acrylate, 2-hydroxy-3-propenyl propyl (meth) acrylate, pentaerythritol tri(meth) acrylate, dipentaerythritol penta (meth) acrylate, caprolactone modification ( 2-hydroxyethyl methacrylate, cyclohexanedimethanol mono(meth) acrylate, and the like.

Further, the epoxy compound in the group is typically a compound having two or more epoxy groups in the molecule. Examples of such an epoxy compound include polyglycidyl ether, glycidyl ether ester, polyglycidyl ester, glycidyl aminoglycidyl ether, glycidyl aminoglycidyl ester, and glycidylamine.

Among these epoxy compounds, examples of the polyglycidyl ether include an aromatic polyglycidyl ether obtained by reacting a polyhydric phenol compound with epichlorohydrin, and an aliphatic polyglycidol obtained by reacting an aliphatic polyol with epichlorohydrin. Ether, alicyclic polyglycidyl ether, and the like.

Among these compounds, examples of the polyhydric phenol compound which can be used for the aromatic polyglycidyl ether include bisphenol A, bisphenol F, bisphenol S, tetramethyl bisphenol A, diaryl bisphenol A, and terephthalic acid. Phenol, catechol, resorcinol, cresol, tetrabromobisphenol A, trihydroxybiphenyl, benzophenone, bis resorcinol, bisphenol hexafluoroacetone, tetramethyl bisphenol A, Tetramethylbisphenol F, tris(hydroxyphenyl)methane, dimethicone, phenol novolac, cresol novolac, and the like.

Further, examples of the aliphatic polyhydric alcohol which can be used for the aliphatic polyglycidyl ether include glycerin, neopentyl glycol, ethylene glycol, propylene glycol, butanediol, hexanediol, polyethylene glycol, and polypropylene glycol.

Further, examples of the alicyclic polyglycidyl ether include glycidyl hexahydrobisphenol A, 3,4-epoxycyclohexenylmethyl-3', 4'-epoxycyclohexene carboxylate, and 1 , 3,5-tris(2,3-epoxypropyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione and the like.

Further, examples of the glycidyl ether ester in the epoxy compound include compounds obtained by reacting a hydroxycarboxylic acid with epichlorohydrin. Examples of the hydroxycarboxylic acid include p-oxybenzoic acid and β-oxynaphthoic acid.

Further, examples of the polyglycidyl ester in the epoxy compound include compounds obtained by reacting a polycarboxylic acid with epichlorohydrin. Examples of the polycarboxylic acid include phthalic acid, methyl phthalic acid, isophthalic acid, terephthalic acid, tetrahydrophthalic acid, endomethylene tetrahydrophthalic acid, and inner ylene. Hexahydrophthalic acid, trimellitic acid, polymeric fatty acids, and the like.

Further, examples of the glycidylaminoglycidyl ether in the epoxy compound include compounds obtained by reacting an aminophenol and an aminoalkylphenol with epichlorohydrin.

Further, examples of the glycidylaminoglycidyl ester in the epoxy compound include compounds obtained by reacting an aminobenzoic acid with epichlorohydrin.

Further, examples of the glycidylamine in the epoxy compound include compounds obtained by reacting an amine compound with epichlorohydrin. Examples of the amine compound include aniline, toluidine, tribromoaniline, xylene diamine, diaminocyclohexane, bisaminomethylcyclohexane, 4,4'-diaminodiphenylmethane, and 4, 4'-Diaminodiphenylphosphonium and the like.

In the dispersion composition of the present invention, the (C) polymerizable compound may be used singly or in combination of two or more kinds as appropriate. Further, when the (C) polymerizable compound is an epoxy compound of the group, a polyhydric phenol compound, an aliphatic polyhydric alcohol, a hydroxycarboxylic acid, a polycarboxylic acid, used for the synthesis reaction of the epoxy compounds, The aminophenol compound, the amine compound, and the like may be used singly or in a mixture of two or more kinds as appropriate.

The polymerization reaction of the (C) polymerizable compound is not particularly limited, and a known photopolymerization reaction, thermal polymerization reaction or the like may be employed. Any of the polymerization conditions may be used in the polymerization. Further, as long as a known polymerization initiator is used in the polymerization reaction.

Specific examples of the photopolymerization initiator include a benzophenone polymerization initiator, an acetophenone polymerization initiator, and a calender polymerization initiator. In addition, examples of the thermal polymerization initiator include an azo polymerization initiator, a substituted ethane polymerization initiator, and a redox polymerization initiator. The redox polymerization initiator may be a combination of a peroxide-based initiator such as a persulfate or a peroxide, and a reducing agent such as a sulfite, a bisulfite or a metal salt. The amount of the polymerization initiator to be used is not particularly limited, and may be within a known range. With respect to 100 parts by mass of the (C) polymerizable compound, a polymerization initiator is typically included in the range of 0.005 to 10 parts by mass.

Further, when an epoxy compound is used as the (C) polymerizable compound, a known curing agent can be used. Specific examples of the curing agent include aliphatic acid anhydrides such as hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, trialkyltetrahydrophthalic anhydride, and hydrogenated methylic acid anhydride.

[Other components] The dispersion composition of the present invention may contain components other than the metal oxide fine particles (A) dispersed as described above, (B) a dispersing agent, and (C) a polymerizable compound. Specific examples of the other components include various additives known in the field of dispersion compositions such as surfactants, antioxidants, ultraviolet absorbers, light stabilizers, antistatic agents, leveling agents, and antifoaming agents. . In the present embodiment, for example, in order to further improve the dispersibility of the (A) dispersed particles, (D) a dispersing aid can be used as a representative other component. The (D) dispersing aid can be appropriately selected from known solvents by the type, physical properties, use conditions, and the like of the components (A) to (C).

Specific examples of the solvent usable as the (D) dispersing aid include methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, second butanol, third butanol, and glycol. Alcohol, n-pentanol, second pentanol, n-hexanol, tetrahydrofurfuryl alcohol, decyl alcohol, allyl alcohol, ethyl chlorohydrin, octyldodecanol, 1-ethyl-1-propanol, 2-methyl 1-butanol, isoamyl alcohol, third pentanol, second isoamyl alcohol, neopentyl alcohol, hexanol, 2-methyl-1-pentanol, 4-methyl-2-pentanol, heptanol , n-octanol, 2-ethylhexanol, decyl alcohol, decyl alcohol, undecyl alcohol, lauryl alcohol, cyclopentanol, cyclohexanol, benzyl alcohol, α-terpineol, terpineol C, L-α - terpineol, dihydroterpineol, terpineoloxyethanol, dihydroterpineol oxyethanol, cyclohexanol, 3-methoxybutanol, diacetone alcohol, 1,4-butanediol, octane An alcohol solvent such as a diol; an aromatic hydrocarbon solvent such as toluene or xylene; a hydrocarbon solvent such as n-hexane, cyclohexane or n-heptane; a halogenated hydrocarbon solvent such as dichloromethane, chloroform or dichloroethane; , isopropyl ether, dioxane, tetrahydrofuran, dibutyl ether, butyl ether, methyl-tert-butyl ether, An ether solvent such as oleyl methyl ether, dihydroterpine oil methyl ether, diethylene glycol dimethyl ether or 1,3-dioxolane; acetone, acetophenone, methyl ethyl ketone, methyl Propyl ketone, diethyl ketone, methyl n-butyl ketone, methyl isobutyl ketone, diacetone, diisobutyl ketone, methyl amyl ketone, acetone acetone, isophorone, cyclohexanone, a ketone solvent such as methylcyclohexanone or 2-(1-cyclohexenyl)cyclohexanone; ethyl formate, propyl formate, butyl formate, isobutyl formate, amyl formate, methyl acetate, acetic acid Ethyl ester, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, second butyl acetate, isoamyl acetate, cyclohexyl acetate, ethyl lactate, 3-methoxy acetate Butyl ester, second hexyl acetate, 2-ethyl butyl acetate, 2-ethylhexyl acetate, benzyl acetate, methyl propionate, ethyl propionate, methyl monochloroacetate, monochloroacetic acid Ester, butyl chloroacetate, methyl acetoacetate, ethyl acetate, butyl propionate, isoamyl propionate, γ-butyrolactone and other ester solvents; ethylene glycol monoethyl ether, ethylene glycol Monoisopropyl ether, ethylene glycol monobutyl ether, Ethylene glycol monoethyl ether, diethylene glycol mono-n-butyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-propyl ether, propylene glycol mono-n-butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol single N-propyl ether, dipropylene glycol mono-n-butyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, triethylene glycol mono-n-propyl ether, triethylene glycol mono-n-butyl ether, tripropylene glycol monoethyl ether, three a glycol ether solvent such as propylene glycol mono-n-propyl ether or tripropylene glycol mono-n-butyl ether; and an acetate-based solvent of the monoethers (for example, propylene glycol monoethyl ether acetate used in Example 14 to be described later); a dialkyl ether solvent such as glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl isobutyl ether, dipropylene glycol dimethyl ether or dipropylene glycol diethyl ether; ethylene glycol, diethylene glycol, a glycol solvent such as triethylene glycol, propylene glycol, dipropylene glycol, 1,3-butylene glycol, hexanediol, polyethylene glycol, or polypropylene glycol; dimethylacetamide, dimethylformamide, etc. An amine solvent or the like. These solvents may be used alone as the (D) dispersing aid, or may be used in combination of two or more kinds as the (D) dispersing aid.

Further, depending on the type of the (C) polymerizable compound, it is of course possible to use water as the (D) dispersing aid. Further, when water is used as the (D) dispersing aid, a polar organic solvent which can be mixed with water may be used in combination.

[Dispersion Composition, Cured Product, and Laminate] The dispersion composition of the present invention may be any of the components (A) to (C) described above and optionally (D) a dispersion aid. The components are formulated in a predetermined composition, stirred or homogenized until the metal oxide fine particles as the (A) dispersed particles are sufficiently dispersed. Specific examples of the dispersing device for dispersing the metal oxide fine particles include a roll mill such as two rolls and three rolls; a ball mill such as a ball mill or a vibrating ball mill; a paint shaker; a continuous disk type bead mill and a continuous ring; A bead mill such as a bead mill; a sand mill; a jet mill or the like is not particularly limited. Alternatively, the dispersion treatment may be carried out in an ultrasonic generation bath.

In the dispersion composition of the present invention, the amount (content or addition amount) of each component (A) to (C) described above is not particularly limited, and may be determined according to the type, physical properties, and dispersion composition of each component. A preferred range is appropriately set for each condition such as the use of the substance. In addition, the (B) dispersing agent can be blended in a predetermined range in order to disperse the metal oxide fine particles as the (A) dispersed particles.

Specifically, when the total solid content of the dispersion composition is 100% by mass, the amount of the (B) dispersant may be in the range of 3% by mass to 30% by mass of the total solid content, and more preferably It is in the range of 4% by mass to 20% by mass. When the amount of the (B) dispersant is too small relative to the total solid content, the surface smoothness of the obtained cured product may be lowered depending on the respective conditions. In addition, when the amount of the (B) dispersant is too large relative to the total solid content, the transparency of the obtained cured product may be lowered depending on the respective conditions, and the physical properties of the cured product (for example, described later) Scratch resistance, alkali resistance, etc.) are insufficient.

In addition, the total solid content of the dispersion composition corresponds to the total amount of the (A) dispersed particles, (B) dispersant, and (C) polymerizable compound.

In addition, the amount of the metal oxide fine particles to be dispersed as the (A) dispersion particle is not particularly limited. For example, when the total amount of the dispersion composition is 100% by mass, the range is preferably 0.5% by mass to 80% by mass. Just inside. Depending on the above conditions, if the metal oxide fine particles are in this range, the optical properties and physical properties of the obtained cured product can be improved, and can also be assisted by the combination with the (B) dispersant. Improve surface smoothness.

In the same manner, the amount of the polymerizable compound (C) is not particularly limited. For example, when the total amount of the dispersion composition is 100% by mass, it may be in the range of 10% by weight to 90% by weight. Depending on the above conditions, if the (C) polymerizable compound is blended in this range, when the obtained film-like or layered cured product (hardened film or hardened layer) is formed, it can be A) In the state in which the dispersed particles are well dispersed, good physical properties as a cured product are achieved. Further, it is also possible to improve the surface smoothness of the cured product by the combination with the (B) dispersant.

Further, the other component such as the (D) dispersing aid may be added as long as it can exhibit a desired function by adding the component.

As shown in the examples to be described later, the dispersion composition of the present invention not only has good dispersion stability as a dispersion composition, but also exhibits good optical properties (high refractive index, high transparency) when formed into a cured product. , low haze, etc.), surface smoothness, and physical properties (scratch resistance, alkali resistance). In particular, regarding the surface smoothness, the arithmetic mean surface roughness (Sa) of the cured product can be set in the range of 0.1 nm to 1.0 nm.

Therefore, the cured product formed using the dispersion composition of the present invention can be preferably used as a high refractive index layer such as an AR film or an AG film, or an optical adjustment layer of an IM film. Therefore, the cured product of the present invention can be preferably used as a cured film or coating layer coated on a substrate, and can also be preferably used as an optical layer of a laminate of an AR film, an AG film, an IM film, or the like. Since the optical layer can set the surface roughness (Sa) in the range of 0.1 nm to 1.0 nm, it is possible to effectively suppress uneven coating of the upper layer or uneven interference as an optical film.

Needless to say, the use of the dispersion composition of the present invention is not limited to a film or a coating, or a film such as an optical layer of a laminate, and may be based on the type of metal oxide fine particles (A) dispersed as a particle. It is used in various molded products or industrial chemicals. [Examples]

The present invention will be more specifically described based on examples and comparative examples, but the present invention is not limited thereto. Various changes, modifications, and changes can be made by those skilled in the art without departing from the scope of the invention. In addition, the evaluation of the dispersion composition and the cured product in the following examples and comparative examples was carried out as follows.

(Evaluation Method of Dispersion Composition) [Average Particle Size] The average particle size of the dispersed fine particles in the obtained dispersion composition was measured using Nanotrac (registered trademark) manufactured by Microtrac Incorporated. The path is evaluated. At this time, a particle diameter of 50% accumulated from the small diameter side was taken as an average particle diameter.

[Dispersion Stability] The obtained dispersion composition was allowed to stand at 50 ° C for 1 week. Thereafter, it was visually confirmed whether or not some sedimentation was observed in the dispersion composition, and it was evaluated as "○" when no sedimentation was observed, and as "X" when the sedimentation was observed.

(Evaluation method of cured product) [Total light transmittance and haze] The total light transmittance of the obtained cured film was measured using a Haze Meter NDH4000 (product name) manufactured by Nippon Denshoku Industries Co., Ltd. Haze and evaluation.

[Refractive Index] The obtained film-shaped cured product (cured film) was measured and measured using a ruthenium coupler (product name) manufactured by Metricon Corporation, and measured at a wavelength of 589 nm.

[Transparency] The transparency of the obtained cured film was visually observed, and it was evaluated as "○" when no turbidity, blurring, or unevenness was observed, and it was evaluated as "X" when turbidity, blurring, unevenness, and the like were observed.

[Surface smoothness] The arithmetic mean surface roughness Sa of the obtained cured film was measured using a three-dimensional white light interference type microscope Contour GT-K (product name) manufactured by Bruker, Inc., thereby evaluating the surface smoothing Sex.

[Alkalization Resistance] The obtained cured film was visually confirmed to have an appearance after immersion in a 2% NaOH aqueous solution at 60 ° C for 3 minutes. When no change in turbidity or unevenness was observed in the cured film, it was evaluated as "○", and when it was found to be turbid or uneven, it was evaluated as "x".

[Scratch resistance] The obtained cured film was rubbed with a rubbing tester (product name) manufactured by Daping Chemical Industry Co., Ltd., and steel wool was used in a state where a weight of 200 gf was applied to the surface of the cured film. Wool) (manufactured by Nippon Steel Wool Co., Ltd., product name: Bonstar #0000) The surface of the cured film was rubbed back and forth 10 times. The change in appearance due to friction marks, scratches, and the like on the surface of the cured film was visually evaluated, and it was evaluated as "○" when no scratches were observed, and "x" was observed when a plurality of scratches or the like were observed.

((B) Production Example of Dispersant) [Production Example 1: Synthesis of Dispersant A] 626 g (1 mol) of lauryl alcohol oxide 10 mol addition product and 151 g in a toluene solvent (1.3 mol) sodium monochloroacetate was taken into the reactor and stirred to make it uniform. Thereafter, 52 g (1.3 mol) of sodium hydroxide was added under the conditions of a reaction system temperature of 60 °C. Then, the temperature of the reaction system was raised to 80 ° C and aged for 3 hours. After the aging, 117 g (1.2 mol) of 98% sulfuric acid was added dropwise to the reaction system at 50 ° C, whereby a white suspension solution was obtained. Then, the white suspension solution was washed with distilled water, and the solvent was distilled off under reduced pressure. Thus, a dispersant A (R: linear lauryl group, AO: oxygen extended ethyl group, n: 10, X: CH ₂ ) as the (B) dispersing agent of the present invention was obtained.

[Production Example 2: Synthesis of Dispersant B] 446 g (1 mol) of lauryl alcohol ethylene oxide 5 mol addition product and 151 g (1.3 mol) of sodium monochloroacetate in a toluene solvent It was taken to the reactor and stirred to make it uniform. Thereafter, 52 g (1.3 mol) of sodium hydroxide was added under the conditions of a reaction system temperature of 60 °C. Then, the temperature of the reaction system was raised to 80 ° C and aged for 3 hours. After the aging, 117 g (1.2 mol) of 98% sulfuric acid was added dropwise to the reaction system at 50 ° C, whereby a white suspension solution was obtained. Then, the white suspension solution was washed with distilled water, and the solvent was distilled off under reduced pressure. Thus, a dispersing agent B (R: linear lauryl group, AO: oxygen extended ethyl group, n: 10, X: CH ₂ ) as the (B) dispersing agent of the present invention was obtained.

[Production Example 3: Synthesis of Dispersant C] 986 g (1 mol) of lauryl alcohol ethylene oxide 20 mol addition product and 151 g (1.3 mol) of sodium monochloroacetate in a toluene solvent It was taken to the reactor and stirred to make it uniform. Thereafter, 52 g (1.3 mol) of sodium hydroxide was added under the conditions of a reaction system temperature of 60 °C. Then, the temperature of the reaction system was raised to 80 ° C and aged for 3 hours. After the aging, 117 g (1.2 mol) of 98% sulfuric acid was added dropwise to the reaction system at 50 ° C, whereby a white suspension solution was obtained. Then, the white suspension solution was washed with distilled water, and the solvent was distilled off under reduced pressure. Thus, a dispersing agent C (R: linear lauryl group, AO: oxygen extended ethyl group, n: 10, X: CH ₂ ) as the (B) dispersing agent of the present invention was obtained.

[Production Example 4: Synthesis of Dispersant D] 500 g (1 mol) of propanol ethylene oxide 10 mol addition product and 151 g (1.3 mol) of sodium monochloroacetate in a toluene solvent It was taken to the reactor and stirred to make it uniform. Thereafter, 52 g (1.3 mol) of sodium hydroxide was added under the conditions of a reaction system temperature of 60 °C. Then, the temperature of the reaction system was raised to 80 ° C and aged for 3 hours. After the aging, 117 g (1.2 mol) of 98% sulfuric acid was added dropwise to the reaction system at 50 ° C, whereby a white suspension solution was obtained. Then, the white suspension solution was washed with distilled water, and the solvent was distilled off under reduced pressure. Thus, a dispersant D (R: propyl, AO: oxygen-extended ethyl group, n: 10, X: CH ₂ ) as the (B) dispersant of the present invention was obtained.

[Production Example 5: Synthesis of Dispersant E] 710 g (1 mol) of C18 alkyl alcohol oxide 10 mol addition product and 151 g (1.3 mol) of monochloro group in a toluene solvent Sodium acetate was taken into the reactor and stirred to make it uniform. Thereafter, 52 g (1.3 mol) of sodium hydroxide was added under the conditions of a reaction system temperature of 60 °C. Then, the temperature of the reaction system was raised to 80 ° C and aged for 3 hours. After the aging, 117 g (1.2 mol) of 98% sulfuric acid was added dropwise to the reaction system at 50 ° C, whereby a white suspension solution was obtained. Then, the white suspension solution was washed with distilled water, and the solvent was distilled off under reduced pressure. Thus, a dispersing agent E (R: linear C18 alkyl group, AO: oxygen extended ethyl group, n: 10, X: CH ₂ ) as the (B) dispersing agent of the present invention was obtained.

[Production Example 6: Synthesis of Dispersant F] 584 g (1 mol) of 9-nonen-1-ol ethylene oxide 10 mol addition product and 151 g (1.3 m) in a toluene solvent The sodium monochloroacetate is taken into the reactor and stirred to make it uniform. Thereafter, 52 g (1.3 mol) of sodium hydroxide was added under the conditions of a reaction system temperature of 60 °C. Then, the temperature of the reaction system was raised to 80 ° C and aged for 3 hours. After the aging, 117 g (1.2 mol) of 98% sulfuric acid was added dropwise to the reaction system at 50 ° C, whereby a white suspension solution was obtained. Then, the white suspension solution was washed with distilled water, and the solvent was distilled off under reduced pressure. Thus, a dispersant F (R: linear C10 alkenyl group, AO: oxygen extended ethyl group, n: 10, X: CH ₂ ) as the (B) dispersant of the present invention is obtained.

[Production Example 7: Synthesis of Dispersant G] In a toluene solvent, 640 g (1 mol) of a branched C11-14 alkyl alcohol (product name: Exxel (EXXAL) 13, Exxon Mobil ( Exxon Mobil) manufactured an ethylene oxide 10 molar addition and 151 g (1.3 moles) of sodium monochloroacetate were taken to the reactor and stirred to make it uniform. Thereafter, 52 g (1.3 mol) of sodium hydroxide was added under the conditions that the temperature of the reaction system was 60 °C. Then, the temperature of the reaction system was raised to 80 ° C and aged for 3 hours. After the aging, 117 g (1.2 mol) of 98% sulfuric acid was added dropwise to the reaction system at 50 ° C, whereby a white suspension solution was obtained. Then, the white suspension solution was washed with distilled water, and the solvent was distilled off under reduced pressure. Thereby, a dispersing agent G (R: branched C11-14 alkyl group, AO: oxygen extended ethyl group, n: 10, X: CH ₂ ) as a comparative dispersing agent was obtained.

[Production Example 8: Synthesis of Dispersant H] 415 g (1 mol) of styrenated phenol and 1 g (0.018 mol) of potassium hydroxide were added to an autoclave, and uniformly mixed. Thereafter, 352 g (8 moles) of ethylene oxide was dropwise added to the reaction system under the conditions of a reaction system temperature of 130 °C. After completion of the dropwise addition of ethylene oxide, the mixture was aged at a temperature of 0.1 MPa at this temperature for 1 hour to obtain an styrene phenol 8 ethylene oxide (Ethylene Oxide, EO) adduct. In a toluene solvent, 767 g (1 mol) of a styrenated phenol 8EO adduct and 152 g (1.3 mol) of sodium monochloroacetate were taken into the reactor and stirred to make it uniform. Thereafter, 52 g (1.3 mol) of sodium hydroxide was added under the conditions of a reaction system temperature of 60 ° C, and then the temperature of the reaction system was raised to 80 ° C and aged for 3 hours. After the aging, 117 g (1.2 mol) of 98% sulfuric acid was added dropwise to the reaction system at 50 ° C, whereby a white suspension solution was obtained. Then, the white suspension solution was washed with distilled water, and the solvent was distilled off under reduced pressure. Thereby, a dispersing agent H (R: styrenated phenyl group, AO: oxygen extended ethyl group, n: 8, X: CH ₂ ) as a comparative dispersing agent was obtained.

(Example 1) As a commercially available zirconia sol I (manufactured by Suga Chemical Industry Co., Ltd., product name: SZR-M, average particle diameter: 3 nm, a methanol dispersion containing 30% by weight of zirconia) was used. (A) Metal oxide fine particles in which the particles are dispersed, and dipentaerythritol hexaacrylate (manufactured by Nippon Kayaku Co., Ltd., product name: KAYARAD DPHA) is used as the (C) polymerizable compound, and a production example is used. Dispersant A produced in 1 as (B) dispersant, and using Methyl Isobutyl Ketone (MIBK) and Propylene Glycol Methyl Ether (PGME), Kuraray shares Made by the company, product name: glycol ether PM) as (D) dispersing aid.

60 parts by mass of zirconia sol I, 34 parts by mass of dipentaerythritol hexaacrylate, 6 parts by mass of dispersant A, 75 parts by mass of MIBK, and 75 parts by mass of PGME, respectively, in terms of solid content, are used, and are mixed and used. The dispersion composition of the present invention was prepared by subjecting the sol to a reduced pressure with a solvent (methanol) under a rotary evaporator. Further, in this formulation, the amount of the dispersing agent A (6 parts by mass) is a part by mass relative to the total solid content of the dispersion composition. The dispersion composition was measured for the average particle diameter of (A) dispersed particles (zirconia particles) as described above, and the dispersion stability was evaluated. The results are shown in Table 1. (Further, in Table 1, the zirconia sol is simply referred to as "ZrO ₂ sol").

When the obtained dispersion composition was diluted with a solid content concentration of 20% by weight in a mixed solvent of MIBK/PGME (mass ratio: 1/1), the total solid content of the dispersion composition was 100% by mass. A photopolymerization initiator (manufactured by BASF Japan Co., Ltd., product name (registered trademark): Irgacure 184) was added in an amount of 3% by mass. Thereafter, a polyethylene terephthalate (PET) film (manufactured by Toyobo Co., Ltd., product name: A4300) was used as a substrate, and a dispersion was coated on the surface of the substrate using a 6 μm bar coater. Composition.

Thereafter, 90 ℃, 90 seconds to evaporate the solvent conditions, using a high pressure mercury lamp having accumulated 500 mJ / cm ² (an oxygen concentration of 0.3% or less) of light, whereby the dispersion composition is cured. Thereby, a film (cured film) having a film thickness of 1 μm as a cured product of the present invention was formed. The cured product was evaluated for optical characteristics (total light transmittance, haze, transparency, refractive index) as described above, and surface smoothness (surface roughness Sa) and physical properties (alkali resistance and scratch resistance) were evaluated. . The results are shown in Table 2.

(Example 2) Operations were carried out in the same manner as in Example 1 except that the amount of the dispersant A as the dispersant (B) was 3 parts by mass based on the total solid content of the dispersion composition. The dispersion composition of the present invention and a cured product thereof are obtained. The results of the average particle diameter and dispersion stability of the dispersion composition are shown in Table 1, and the results of optical properties, surface smoothness, and physical properties of the cured product are shown in Table 2.

(Example 3) Operations were carried out in the same manner as in Example 1 except that the amount of the dispersant A as the dispersant (B) was 12 parts by mass based on the total solid content of the dispersion composition. The dispersion composition of the present invention and a cured product thereof are obtained. The results of the average particle diameter and dispersion stability of the dispersion composition are shown in Table 1, and the results of optical properties, surface smoothness, and physical properties of the cured product are shown in Table 2.

(Example 4) The dispersion of the present invention was obtained in the same manner as in Example 1 except that the dispersant B produced in Production Example 2 was used in the same manner as the dispersant (B). Body composition and its hardened material. The results of the average particle diameter and dispersion stability of the dispersion composition are shown in Table 1, and the results of optical properties, surface smoothness, and physical properties of the cured product are shown in Table 2.

(Example 5) The dispersion of the present invention was obtained in the same manner as in Example 1 except that the dispersant C produced in Production Example 3 was used in the same manner as the dispersant (B). Body composition and its hardened material. The results of the average particle diameter and dispersion stability of the dispersion composition are shown in Table 1, and the results of optical properties, surface smoothness, and physical properties of the cured product are shown in Table 2.

(Example 6) The dispersion of the present invention was obtained in the same manner as in Example 1 except that the dispersant D produced in Production Example 4 was used in the same manner as the dispersant (B). Body composition and its hardened material. The results of the average particle diameter and dispersion stability of the dispersion composition are shown in Table 1, and the results of optical properties, surface smoothness, and physical properties of the cured product are shown in Table 2.

(Example 7) The dispersion of the present invention was obtained in the same manner as in Example 1 except that the dispersant E produced in Production Example 5 was used in the same manner as the dispersant (B). Body composition and its hardened material. The results of the average particle diameter and dispersion stability of the dispersion composition are shown in Table 1, and the results of optical properties, surface smoothness, and physical properties of the cured product are shown in Table 2.

(Example 8) The dispersion of the present invention was obtained in the same manner as in Example 1 except that the dispersant F produced in Production Example 6 was used in the same manner as the dispersant (B). Body composition and its hardened material. The results of the average particle diameter and dispersion stability of the dispersion composition are shown in Table 1, and the results of optical properties, surface smoothness, and physical properties of the cured product are shown in Table 2.

(Example 9) An oxidized zirconium sol II manufactured by Solar Co., Ltd. was used instead of the zirconia sol I (product name: NANON 5 ZR-010, average particle diameter: 15 nm) A dispersion composition of the present invention and a cured product thereof were obtained in the same manner as in Example 1 except that (A) a dispersion of the particles was carried out. The results of the average particle diameter and dispersion stability of the dispersion composition are shown in Table 1, and the results of optical properties, surface smoothness, and physical properties of the cured product are shown in Table 2.

(Example 10) In place of the zirconia sol I, an equivalent amount of zirconia sol III (product name: OZ-S30M, average particle diameter: 30 nm) manufactured by Nissan Chemical Industries Co., Ltd. was used as (A) dispersed particles. Except for the above, the dispersion composition of the present invention and a cured product thereof were obtained in the same manner as in Example 1. The results of the average particle diameter and dispersion stability of the dispersion composition are shown in Table 1, and the results of optical properties, surface smoothness, and physical properties of the cured product are shown in Table 2.

(Example 11) In place of the zirconia sol I, zirconia powder I (product name: PCS60, primary particle diameter: 15 nm) manufactured by Shin-Japan Electric Co., Ltd. was used as (A) dispersed particles, and other settings were made. The same composition and the same amount of formulation as in Example 1. Then, the components are mixed and subjected to dispersion treatment using a paint shaker, whereby the dispersion composition of the present invention and a cured product thereof are obtained. The results of the average particle diameter and dispersion stability of the dispersion composition are shown in Table 1, and the results of optical properties, surface smoothness, and physical properties of the cured product are shown in Table 2.

(Example 12) Dipentaerythritol hexaacrylate (manufactured by Nippon Kayaku Co., Ltd., product name: KAYARAD DPHA) and 9,9-bis[4-(2-hydroxyethoxy)benzene茀 茀 di acrylate (manufactured by Shin-Nakamura Chemical Co., Ltd., product name: A-BPEF) was used in combination at a mass ratio of 3/7 as (C) polymerizable compound, and the examples were 1 The same operation was carried out to obtain a dispersion composition of the present invention and a cured product thereof. The results of the average particle diameter and dispersion stability of the dispersion composition are shown in Table 1, and the results of optical properties, surface smoothness, and physical properties of the cured product are shown in Table 2.

(Example 13) Instead of dipentaerythritol hexaacrylate (manufactured by Nippon Kayaku Co., Ltd., using pentaerythritol triacrylate (manufactured by Daiichi Kogyo Co., Ltd., product name: PET-3), product name: Kayala ( A dispersion composition of the present invention and a cured product thereof were obtained in the same manner as in Example 1 except that (C) a polymerizable compound was used. The results of the average particle diameter and dispersion stability of the dispersion composition are shown in Table 1, and the results of optical properties, surface smoothness, and physical properties of the cured product are shown in Table 2.

(Example 14) Using propylene glycol monomethyl ether acetate (manufactured by Kuraray Co., Ltd., product name: PGM-AC) instead of MIBK and PGME as (D) dispersing aid, in addition to In the same manner as in Example 1, the dispersion composition of the present invention and a cured product thereof were obtained. The results of the average particle diameter and dispersion stability of the dispersion composition are shown in Table 1, and the results of optical properties, surface smoothness, and physical properties of the cured product are shown in Table 2.

(Comparative Example 1) A comparative dispersion was obtained in the same manner as in Example 1 except that the dispersant G produced in Production Example 7 was used in the same manner as the dispersant (B). Composition and hardened material thereof. The results of the average particle diameter and dispersion stability of the dispersion composition are shown in Table 1, and the results of optical properties, surface smoothness, and physical properties of the cured product are shown in Table 2.

(Comparative Example 2) A comparative dispersion was obtained in the same manner as in Example 1 except that the dispersant H produced in Production Example 8 was used in the same manner as the dispersant (B). Composition and hardened material thereof. The results of the average particle diameter and dispersion stability of the dispersion composition are shown in Table 1, and the results of optical properties, surface smoothness, and physical properties of the cured product are shown in Table 2.

(Comparative Example 3) Operation was carried out in the same manner as in Example 1 except that the amount of the dispersing agent A as the dispersing agent (B) was 2 parts by mass based on the total solid content of the dispersion composition. The dispersion composition of the present invention and a cured product thereof are obtained. The results of the average particle diameter and dispersion stability of the dispersion composition are shown in Table 1, and the results of optical properties, surface smoothness, and physical properties of the cured product are shown in Table 2.

(Comparative Example 4) Operation was carried out in the same manner as in Example 1 except that the amount of the dispersing agent A as the dispersing agent (B) was 35 parts by mass based on the total solid content of the dispersion composition. The dispersion composition of the present invention and a cured product thereof are obtained. The results of the average particle diameter and dispersion stability of the dispersion composition are shown in Table 1, and the results of optical properties, surface smoothness, and physical properties of the cured product are shown in Table 2.

(Comparative Example 5) Operation was carried out in the same manner as in Example 9 except that the amount of the dispersing agent A as the dispersing agent (B) was 2 parts by mass based on the total solid content of the dispersion composition. The dispersion composition of the present invention and a cured product thereof are obtained. The results of the average particle diameter and dispersion stability of the dispersion composition are shown in Table 1, and the results of optical properties, surface smoothness, and physical properties of the cured product are shown in Table 2.

(Comparative Example 6) Operation was carried out in the same manner as in Example 9 except that the amount of the dispersing agent A as the dispersing agent (B) was 35 parts by mass based on the total solid content of the dispersion composition. The dispersion composition of the present invention and a cured product thereof are obtained. The results of the average particle diameter and dispersion stability of the dispersion composition are shown in Table 1, and the results of optical properties, surface smoothness, and physical properties of the cured product are shown in Table 2.

(Comparative Example 7) Operation was carried out in the same manner as in Example 10 except that the amount of the dispersing agent A as the dispersing agent (B) was 2 parts by mass based on the total solid content of the dispersion composition. The dispersion composition of the present invention and a cured product thereof are obtained. The results of the average particle diameter and dispersion stability of the dispersion composition are shown in Table 1, and the results of optical properties, surface smoothness, and physical properties of the cured product are shown in Table 2.

(Comparative Example 8) Operation was carried out in the same manner as in Example 10 except that the amount of the dispersing agent A as the dispersing agent (B) was 35 parts by mass based on the total solid content of the dispersion composition. The dispersion composition of the present invention and a cured product thereof are obtained. The results of the average particle diameter and dispersion stability of the dispersion composition are shown in Table 1, and the results of optical properties, surface smoothness, and physical properties of the cured product are shown in Table 2.

(Comparative Example 9) Operations were carried out in the same manner as in Example 1 except that the zirconia sol IV having an average particle diameter of 50 nm was used as the (A) dispersed particles instead of the zirconia sol I. The dispersion composition of the present invention and a cured product thereof. The results of the average particle diameter and dispersion stability of the dispersion composition are shown in Table 1, and the results of optical properties, surface smoothness, and physical properties of the cured product are shown in Table 2.

[Table 1]

[Table 2]

(Comparative Example and Comparative Example) As shown by the results of Tables 1 and 2, the dispersion compositions of Examples 1 to 14 are excellent in dispersion stability, and the cured product obtained from the dispersion compositions The optical characteristics are good, and in particular, a refractive index of 1.65 or more is achieved. Further, in the cured products of Examples 1 to 14, since the surface roughness Sa is 0.8 nm or less, the surface smoothness is good, and the alkali resistance and the scratch resistance are also improved.

On the other hand, in the dispersion composition of Comparative Example 1 and Comparative Example 2, the hydrophobic group R of the compound of the formula (1) as the (B) dispersant is a branched chain, so that the dispersion stability is excellent, but the cured product is The optical characteristics are poor, and the surface roughness Sa is also 1.0 nm or more. Further, in the dispersion compositions of Comparative Example 3, Comparative Example 5, and Comparative Example 7, the amount of the dispersant (B) was insufficient, so that the cured product had low transparency and the surface roughness Sa was 1.0 nm or more.

Further, in the dispersion compositions of Comparative Example 4, Comparative Example 6, and Comparative Example 8, (B) the amount of the dispersing agent was excessive, so that the cured product had a haze of 1.1 or more, and whitening was observed, so that the transparency was low and the refractive index was low. It is also reduced to 1.60, which has an adverse effect on alkali resistance and scratch resistance. Further, in the dispersion composition of Comparative Example 9, since the average particle diameter of the (A) dispersed particles is large, the optical properties other than the refractive index are lowered, and the surface roughness Sa is also 1.3 nm or more.

The physical properties of the dispersion composition of the comparative example are such that when the cured product is used as an AR film, an AG film, an IM film or the like, the properties of the optical films are greatly impaired.

In addition, the present invention is not limited to the description of the above-described embodiments, and various modifications can be made within the scope of the claims, and the respective embodiments disclosed in the different embodiments or the modifications may be combined as appropriate. The form is also included in the technical scope of the present invention. [Industrial availability]

The present invention can be preferably used in the field of a cured film or a coating, etc., and can also be preferably widely used in the field of laminated bodies such as an AR film, an AG film, and an IM film.

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Claims (4)

A dispersion composition comprising: (A) a dispersed particle, (B) a dispersing agent, and (C) a polymerizable compound, wherein the (A) dispersed particle is a metal oxide having an average particle diameter of less than 50 nm The (B) dispersant includes a compound represented by the following formula (1), and when the total solid content contained in the dispersion composition is 100% by mass, the (B) dispersant The amount of the compound is in the range of 3% by mass to 20% by mass based on the total solid content. (wherein R in the formula (1) is a linear alkyl group having 3 to 24 carbon atoms or a linear alkenyl group having 3 to 24 carbon atoms; AO is an alkyloxy group having 1 to 4 carbon atoms; and n is a ring representing n. The average addition molar number of the oxane is in the range of 5 to 30, and X is a linking group containing a carbon atom, a hydrogen atom and/or an oxygen atom. The dispersion composition according to claim 1, wherein the (C) polymerizable compound uses at least one compound having one or more carboxyl groups and two or more ethylenically unsaturated groups in one molecule. A cured product obtained by hardening a dispersion composition as described in claim 1 or 2 of the patent application. A laminate comprising a layer obtained by hardening a dispersion composition as described in claim 1 or 2, and characterized in that the surface roughness (Sa) is 0.1 nm to 1.0. Within the range of nm.