JP5643155B2 - Hard coat dispersion composition, hard coat coating composition and hard coat coating - Google Patents

Description

  The present invention relates to a hard coat dispersion composition, a hard coat coating composition, and a hard coat coating, and more particularly to obtain a coating film having high transparency and refractive index when cured and having a low haze. The present invention relates to a dispersion composition for hard coat and a coating composition for hard coat, and a hard coat coating obtained thereby.

  Inorganic materials are used as the main material of hard coat coating agents in the fields of sunglasses, optical materials, electronic materials such as LED sealing resins and liquid crystal displays. In this case, the material derived from the inorganic substance is used as a substance that contributes to the improvement of the coating film hardness by preparing and using a dispersion as fine particles in an aqueous dispersion medium or a non-aqueous dispersion medium.

  On the other hand, there is a problem that stable dispersion of the dispersoid becomes difficult by changing the material of the dispersoid, reducing the particle size, and controlling the shape, and the dispersoid is aggregated in the dispersion medium in a short time. Agglomeration of dispersoids not only causes a decrease in productivity, processing characteristics, handling characteristics, and yield in the production of the dispersion, but also causes deterioration in product characteristics, material properties and quality of the final product. In addition, it is known that undesired phenomena such as transparency, gloss, reduction in coloring power, color separation, and generation of cracks also occur in appearance. A dispersant is used to suppress such aggregation of the dispersoid and achieve dispersion stabilization.

  As an organic compound having a carboxyl group as the proposed low molecular weight dispersant, for example, formic acid, acetic acid, propionic acid, butanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, lauric acid In addition to saturated and unsaturated carboxylic acids having 1 to 20 carbon atoms such as myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, and linolenic acid, hydroxycarboxylic acids, alicyclic groups having 6 to 34 carbon atoms, There are aromatic carboxylic acids. Examples of alkenyl succinic anhydrides include octenyl succinic anhydride, dodecenyl succinic anhydride, hexadecenyl succinic anhydride, and the like. Examples of the organic compound having a thiol group include mercaptoethanol, mercapto-2-propanol, 1-mercapto-2, 3-propanediol, 3-mercaptopropyltrimethoxysilane, mercaptosuccinic acid, hexanethiol, pentanedithiol, and dodecanethiol. And alkanethiols such as undecanethiol and decanethiol. Examples of the organic compound having a phenol ring include triphenylphosphine, tributylphosphine, trioctylphosphine, and tributylphosphine. Examples of the organic compound having an amino group include propylamine, butylamine, hexylamine, heptylamine, octylamine, 2-ethylhexylamine, nonylamine, decylamine, dodecylamine, hexadecylamine, and oleylamine. In addition, as a high molecular weight dispersant, a polymer type dispersion having a skeleton such as a carboxyl group, an amino group, a hydroxyl group, an ester bond, an amide bond, an aromatic ring, and a heterocyclic ring, which was mainly developed as a dispersant for pigments and the like. The agent has also been diverted to this application, the DISPERBYK series manufactured by BYK Chemie, the Ciba EFKA series manufactured by EFKA Additives, the Solsperse series manufactured by Lubrizol, The Dispalon series manufactured by Enomoto Kasei is available on the market.

  In addition, the use of existing surfactants as dispersants has also been proposed. Examples of anionic surfactants include higher fatty acid salts, alkyl sulfonates, alpha olefin sulfonates, alkane sulfonates, and alkylbenzenes. Sulfonates, sulfosuccinates, alkyl sulfates, alkyl ether sulfates, alkyl phosphates, alkyl ether phosphates, alkyl ether carboxylates, alpha sulfo fatty acid methyl esters, methyl taurates and so on. Examples of the nonionic surfactant include glycerin fatty acid ester, polyglycerin fatty acid ester, sucrose fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene alkyl ether, polyoxyethylene alkylphenyl ether, polyoxyethylene. Examples include fatty acid esters, fatty acid alkanolamides, and alkyl glucosides. Examples of amphoteric surfactants include alkyl betaines, fatty acid amidopropyl betaines, and alkylamine oxides. Examples of the cationic surfactant include alkyl trimethyl ammonium salt, dialkyl dimethyl ammonium salt, alkyl dimethyl benzyl ammonium salt, and alkyl pyridinium salt. In addition, there are polymer surfactants such as fluorine-based surfactants, cellulose derivatives, polycarboxylates, and polystyrene sulfonates.

  Studies have been made to obtain a stable dispersion composition by suppressing the aggregation of the dispersion using the above existing dispersant, but the dispersion medium, diversification of the dispersoid, and the particle size of the dispersoid are very small. In spite of the development of various types of materials and diversification of shapes, the proposed dispersants have not fully satisfied the required properties in terms of transparency when cured, refractive index, haze, etc. .

  For example, when the dispersion medium is water, the interfacial adsorption action based on the hydrophobic interaction of the dispersant, the electroadsorption action due to the ionic group, the π-electron interaction derived from the aromatic ring, and between the particles, Use of electrostatic repulsion between particles by formation of multi-layers, dispersion stabilization by formation of steric barriers, and addition of protective colloids and thickeners as stabilizers are also effective, stabilizing dispersion and suppressing aggregation. A variety of measures that can achieve this can be adopted.

  On the other hand, in non-aqueous dispersion media, the effects of hydrophobic interaction, electrical interface adsorption by ionic groups, and electrostatic repulsion are extremely limited. It depends greatly on the acid-base interaction between the specific sites of the particles and the dispersant. In other words, in practice, the selection of the dispersant is individually optimized depending on the surface characteristics of the dispersoid, and the use of the dispersant is extremely limited, and the affinity of the dispersant to the dispersion medium is also combined. In reality, it is necessary to select an optimum dispersant individually according to the dispersion medium to be used.

  The various ionic surfactants described above are extremely effective as aqueous dispersants, but many of them cannot be dissolved in a non-aqueous dispersion medium, and their application range is extremely limited.

  In addition, when the size of the dispersoid particles is a micrometer size, it is possible to design a dispersion system by adopting multi-point adsorption by a plurality of adsorption points and forming a high density and thick protective layer of a three-dimensional barrier, so that a high molecular weight dispersant However, when the size of the dispersoid particles is nanometer size or sub-nanometer size, the dispersion system design with a high molecular weight dispersant is considered due to the difference between the size of the dispersoid particles and the size of the dispersant molecules. Can be difficult or limited. That is, when a high molecular weight dispersant having a remarkably large molecular size relative to the size of the dispersoid particles is used, there are many points between the dispersoid particles and the dispersant and between the dispersant molecule and the dispersant molecule. Adsorption, entanglement, and bridging occur, and aggregation of dispersoid particles is promoted, which has an essential problem in terms of dispersion stabilization.

  Furthermore, in order to direct dispersion stabilization, it is a regular method to design a dispersion system using stronger interaction between the dispersoid particles and the dispersant. In addition to ensuring the mechanical and chemical stability of the dispersion composition, taking out the dispersoid particles, and forming a film (high gloss, low temperature and short film-forming properties), in removing the dispersant, Easy separation from the interface is also required as a required performance, which is an important factor in improving the productivity of the final product, processing characteristics, and stabilizing the quality. Also in this respect, the hard coat dispersion composition using the existing dispersant does not sufficiently satisfy the required performance.

  A composite material in which nanometer-sized inorganic fine particles (particle diameter of 1 to 100 nm) are finely dispersed in a resin is called a polymer nanocomposite. However, nanometer-sized particles tend to aggregate and have a low affinity for the resin. It is extremely difficult to disperse uniformly in the resin. In order to uniformly disperse nanometer-sized particles in a resin, it is difficult or limited to use an aqueous dispersion medium. Usually, a nanoparticle is uniformly dispersed in a non-aqueous dispersion medium using a dispersant. It is effective to prepare a dispersion, and dissolve and mix the resin in the dispersion, or mix and dissolve and disperse the dispersion in a solution in which the resin is dissolved in a solvent. .

  In addition, as a pretreatment for easily redispersing metal particles, metal oxides, pigments and various fillers in a dispersion medium or resin, the dispersoid particles are coated with a surface modifier or a surface protective agent or dispersed. Technology (Patent Documents 1 and 2) of impregnating a surface particle with a surface modifier and the like and technology of surface modification with an organic acid (Patent Document 3) are known. There are many cases where the kind and the amount of dispersoid added are limited, and the range of use is extremely limited, and no dispersant, surface modifier or surface protective agent that can solve this problem has been found.

JP 2007-217242 A, Claim 1 JP 2007-119617 A, Claim 1 JP 2009-191167 A, Claim 1

  The present invention has been made in view of such problems of the prior art, and the purpose thereof is not limited by the type of dispersion medium and the amount of dispersoid added, and when cured, the transparency and It is an object to provide a hard coat dispersion composition and a hard coat coating composition capable of obtaining a coating film having a high refractive index and a small haze, and a hard coat coating obtained thereby.

  The dispersion composition for hard coat of the present invention contains dispersoid particles composed of inorganic particles, a dispersant composed of a compound represented by the following formula (1), a polymerizable compound, and a film-forming aid. It is characterized by.

ここで、式（１）のＲは、炭素数が１ないし２４であるアルキル基および／又はアルケニル基であって、炭素数が３ないし２４の分岐鎖を有するアルキル基および／又はアルケニル基を含有するものであり、式（１）のＡＯは炭素数が１ないし４のオキシアルキレン基を示し、ｎはアルキレンオキシドの平均付加モル数を示す１ないし３０の範囲の数値であり、式（１）のＸは炭素原子、水素原子及び／又は酸素原子からなる連結基である。

Here, R in formula (1) is an alkyl group and / or alkenyl group having 1 to 24 carbon atoms, and includes an alkyl group and / or alkenyl group having a branched chain having 3 to 24 carbon atoms. In the formula (1), AO represents an oxyalkylene group having 1 to 4 carbon atoms, n is a numerical value in the range of 1 to 30 indicating the average number of added moles of alkylene oxide, and the formula (1) X in the formula is a linking group composed of a carbon atom, a hydrogen atom and / or an oxygen atom.

  Here, X in the formula (1) in the dispersant is preferably an alkylene group having 1 to 15 carbon atoms.

  2. The hard coat dispersion composition according to claim 1, wherein X in the formula (1) in the dispersant is a linking group represented by the following formula (2).

ただし、式（２）のＹは、炭素数が１ないし１５のアルキレン基、ビニレン基、フェニレン基およびカルボキシル基含有フェニレン基の中から選択されるいずれかである。

However, Y in the formula (2) is any selected from an alkylene group having 1 to 15 carbon atoms, a vinylene group, a phenylene group, and a carboxyl group-containing phenylene group.

  The dispersoid particles are preferably inorganic particles. In addition, when a high refractive index is required, the inorganic particles are preferably zirconium oxide particles.

  The hard coat coating composition of the present invention is characterized by containing any of the hard coat dispersion compositions described above and a solvent.

  The hard coat coating of the present invention is obtained by applying the above-mentioned hard coat coating composition on a substrate, evaporating the solvent, and then curing it.

  By using the hard coat dispersion composition and the hard coat coating composition of the present invention, it is possible to obtain a coating film having high transparency and a high refractive index and a small haze. Therefore, the hard coat coating obtained by this is hardly scratched and has an excellent appearance.

1. Dispersoid particles The inorganic-derived particles that are dispersoid particles in the hard coat dispersion composition of the present invention include iron, aluminum, chromium, nickel, cobalt, zinc, tungsten, indium, tin, palladium, zirconium, titanium, and copper. , Silver, gold, platinum, and the like, and alloys thereof or mixtures thereof can be used. At that time, in order to stably take out the aforementioned metal particles from the medium, alkanoic acids and fatty acids, hydroxycarboxylic acids, alicyclic, aromatic carboxylic acids, alkenyl succinic anhydrides, thiols, phenol derivatives, You may coat | cover with protective agents, such as amines, an amphiphilic polymer, a high molecular surfactant, and a low molecular surfactant. Others, kaolin, clay, talc, mica, bentonite, dolomite, calcium silicate, magnesium silicate, asbestos, calcium carbonate, magnesium carbonate, barium carbonate, calcium sulfate, barium sulfate, aluminum sulfate, aluminum hydroxide, iron hydroxide, Aluminum silicate, zirconium oxide, magnesium oxide, aluminum oxide, titanium oxide, iron oxide, zinc oxide, antimony trioxide, indium oxide, indium tin oxide, silicon carbide, silicon nitride, boron nitride, barium titanate, diatomaceous earth, carbon black , Graphite, rock wool, glass wool, glass fiber, carbon fiber, carbon nanofiber, carbon nanotube (single wall nanotube, double wall nanotube, multiwall nanochu B) etc.
In the present invention, the dispersoid particles dispersed by the dispersant may be crystalline or amorphous. Further, the dispersoid particles dispersed by the dispersant in the present invention may be isotropic particles, anisotropic particles, or fibrous.

  As the dispersoid particles to be dispersed in the present invention, those obtained by a known method can be used. As a method for preparing fine particles, a top-down method in which coarse particles are mechanically pulverized and refined, and a bottom in which particles are formed through a cluster state in which several unit particles are generated and aggregated. Although there are two types of up systems, any one prepared by any method can be suitably used. Further, they may be either a wet method or a dry method. The bottom-up method includes a physical method and a chemical method, and any method may be used. The dispersant in the present invention may be used in a top-down process in which coarse particles are mechanically pulverized and refined to form several unit particles, which pass through a cluster state in which they are aggregated. May be used in a bottom-up process in which particles are formed, or after preparing fine particles in advance by the above-described method, a surface modifier or surface may be used to stably remove the dispersoid particles from the medium. It is also possible to use particles taken out by being coated or impregnated with a known protective agent called a protective agent. As the protective agent, the above-mentioned known dispersants can be substituted.

  In order to more specifically explain the bottom-up method, a method for preparing metal nanoparticles among the dispersoid particles will be exemplified. Among the bottom-up methods, a representative example of a physical method is an in-gas evaporation method in which bulk metal is evaporated in an inert gas and cooled and condensed by collision with the gas to generate nanoparticles. Chemical methods include a liquid phase reduction method in which metal ions are reduced in the liquid phase in the presence of a protective agent, and the generated zero-valent metal is stabilized at the nanosize, and a metal complex thermal decomposition method. is there. As the liquid phase reduction method, a chemical reduction method, an electrochemical reduction method, a photoreduction method, a method combining a chemical reduction method and a light irradiation method, or the like can be used.

  Further, as described above, the dispersoid particles that can be suitably used in the present invention may be those obtained by any of the top-down method and the bottom-up method, and they are aqueous, non-aqueous, and in the gas phase. It may be prepared in any environment. In addition, when using these dispersoid particle | grains, you may use what disperse | distributed dispersoid particle | grains beforehand in various solvents.

  In the present invention, when zirconium oxide is used as the dispersoid particles, the refractive index of the coating film increases, and when a resin film or the like obtained by coating the coating film is used for a flat panel display with a backlight, for example, Brightness can be improved.

A preferable blending amount of the dispersoid particles is 0.5 to 80% by weight, more preferably 30 to 70% by weight, and further preferably 35 to 60% by weight with respect to the entire dispersion composition for hard coat of the present invention. It is.
The average particle size of the dispersoid particles is preferably in the range of 1 to 500 nm, and more preferably in the range of 10 to 100 nm.

2. About the hydrophobic group (R) of the dispersant
The hydrophobic group (R) of the dispersant in the present invention is an alkyl group and / or alkenyl group having 1 to 24 carbon atoms, and an alkyl group and / or alkenyl having a branched chain having 3 to 24 carbon atoms. It contains a group. The content of the alkyl group having a branched chain having 3 to 24 carbon atoms and / or alkenyl is preferably 70% by weight or more based on the entire R.

  The raw material alcohol that can be used to generate R may have a single carbon number or a mixture of alcohols having different carbon numbers. The raw material alcohol may be synthetically or naturally derived, and the chemical structure may be a single composition or a mixture of a plurality of isomers. As the raw material alcohol that can be used, known alcohols can be selected. Specific examples include butanol, isobutanol, pentanol and / or its isomer, hexanol and / or its isomer, heptanol and / or its isomer derived from synthesis. , Octanol and / or its isomer, 3,5,5-trimethyl-1-hexanol, isononanol, isodecanol, isounol produced by the oxo process via higher olefins derived from propylene or butene, or mixtures thereof Decanol, isododecanol, isotridecanol, Neodol 23, 25, 45 manufactured by Shell Chemicals, SAFOL23 manufactured by Sasol, EXXAL7, EXXAL8N, EXXAL9, EXXAL10, EXXXAL11 and EXXXA manufactured by Exxon Mobil 13 illustrates another example of a higher alcohol which can be suitably used. Furthermore, natural octyl alcohol, decyl alcohol, lauryl alcohol (1-dodecanol), myristyl alcohol (1-tetradecanol), cetyl alcohol (1-hexadecanol), stearyl alcohol (1-octadecanol), oleyl alcohol (Cis-9-octadecen-1-ol) and the like are also examples of higher alcohols that can be used. In addition, a single composition of Guerbet Alcohol having a 2-alkyl-1-alkanol type chemical structure, or a mixture thereof is an example of a higher alcohol that can be suitably used. 2-ethyl-1-hexanol 2-propyl-1-hexanol, 2-butyl-1-hexanol, 2-ethyl-1-heptanol, 2-propyl-1-heptanol, 2-ethyl-1-octanol, 2-hexyl-1-decanol, 2 In addition to heptyl-1-undecanol, 2-octyl-1-dodecanol, 2-decyl-1-tetradecanol, there are isostearyl alcohols derived from branched alcohols. Moreover, it is also possible to mix | blend and use 2 or more types of said various alcohol. However, in the dispersant of the present invention, as described above, the hydrophobic group (R) contains a branched alkyl group and / or alkenyl group having 3 to 24 carbon atoms.

  In addition, when the hydrophobic group (R) is hydrogen or a hydrocarbon group having 1 to 2 carbon atoms, when the carbon number exceeds 25, and when the hydrophobic group (R) has a carbon number in the range of 3 to 24 However, when the content of the linear alkyl group and / or alkenyl group exceeds 30% by weight, the dispersoid cannot be stably dispersed in the dispersion medium, or the selection range of the dispersion medium that can be used is It may be limited, or substitution or mixing with a different type of dispersion medium may occur in the dispersion preparation process. As a result, the stability of the dispersion is significantly reduced, resulting in immediate sedimentation, and the stability over time is significantly reduced, resulting in problems such as a decrease in added value, productivity, processing characteristics, and quality deterioration of the final product. . In order to avoid these problems and make the action of the dispersant particularly effective in the present invention, the hydrophobic group (R) is more preferably a branched alkyl group having 8 to 18 carbon atoms. .

3. Dispersant oxyalkylene group (AO) n
In the present invention, the alkylene oxide species suitably selected as the dispersant in the formula (1) is that in which AO represents an oxyalkylene group having 1 to 4 carbon atoms, specifically, an alkylene oxide having 2 carbon atoms is ethylene oxide. It is. The alkylene oxide having 3 carbon atoms is propylene oxide. The alkylene oxide having 4 carbon atoms is tetrahydrofuran or butylene oxide, preferably 1,2-butylene oxide or 2,3-butylene oxide. In the dispersant, the oxyalkylene chain (-(AO) n-) is blocked by either a homopolymer chain or a random polymer chain of two or more alkylene oxides for the purpose of adjusting the dispersion medium affinity of the dispersant. It may be a polymer chain or a combination thereof. N which shows the average added mole number of the alkylene oxide of Formula (1) is in the range of 1 to 30, but is preferably in the range of 3 to 20.

4). Dispersing agent linking group (X)
The linking group (X) can be selected from a known structure consisting of a carbon atom, a hydrogen atom, and an oxygen atom, preferably a saturated hydrocarbon group, an unsaturated hydrocarbon group, an ether group, a carbonyl group, or an ester group. It may have an alicyclic structure or an aromatic ring structure, and may have a repeating unit. When the linking group X contains a nitrogen atom and / or a sulfur atom and / or a phosphorus atom, it has an action of weakening the affinity effect of the carboxyl group on the dispersoid, and thus is not suitable as a structural factor of the dispersant in the present invention. .

  X in the formula (1) is preferably an alkylene group having 1 to 15 carbon atoms, and more preferably an alkylene group having 1 to 8 carbon atoms.

  Further, X in the formula (1) is preferably a substance represented by the above formula (2). However, Y in Formula (2) is any selected from an alkylene group having 1 to 15 carbon atoms, a vinylene group, a phenylene group, and a carboxyl group-containing phenylene group.

5. More preferable dispersant In the present invention, it is more preferable to use a dispersant described in the following formula (3).

但し、式（３）においてＲは炭素数が８ないし１８の分岐型のアルキル基が好適で、ｎはエチレンオキシドの平均付加モル数を示し、３ないし２０の範囲が好適である。分散剤の組成をこの範囲に限定することで、分散体の調製に使用できる分散媒の選択範囲の拡大、異種の分散媒の混合、置換に対する適用性が向上する。このように、分散剤の組成範囲を限定することで、分散体の経時安定性に対して更に好適に作用し、その結果、最終製品の付加価値向上、生産性向上、加工特性向上および品質安定化などを達成できる。

However, in formula (3), R is preferably a branched alkyl group having 8 to 18 carbon atoms, and n represents the average number of moles of ethylene oxide added, preferably in the range of 3 to 20. By limiting the composition of the dispersant to this range, the applicability to expansion of the selection range of the dispersion medium that can be used for preparation of the dispersion, mixing of different types of dispersion medium, and substitution is improved. In this way, by limiting the composition range of the dispersant, it works more favorably with respect to the stability of the dispersion over time. Can be achieved.

6). The blending amount of the dispersant in the present invention is not particularly limited, but is 0.1 to 300% by weight, preferably 0.5 to 20% by weight, based on the dispersoid particles. -15 wt% is more preferable, and 2-10 wt% is more preferable.

7). Dispersant Production Method The dispersant in the present invention can be produced by a known method. For example, using a general nonionic surfactant compound obtained by adding an alkylene oxide to an alcohol, amine, or thiol by a known method as a raw material, a monohalogenated lower carboxylic acid or a salt thereof is used. Although it can manufacture by the method of making it react with a hydroxyl group, or the method of ring-opening reaction with the hydroxyl group of the alkylene oxide terminal using an acid anhydride, it is not limited to these methods.

  In addition, the types of hydrophobic groups, alkylene oxide types and addition forms thereof, addition molar amounts, linking groups, etc. are particularly limited within the above-mentioned range, so that a wider range of types than known dispersants can be selected. The industrial utility value is great in that it can disperse various dispersoids and can disperse and stabilize the dispersoids in a wider variety of dispersion media.

  In addition, the dispersant used in the present invention should be used by reducing the content of ionic species, particularly alkali metal ions, alkaline earth metal ions, heavy metal ions, and halogen ions, contained by a known purification method. Can do. The ionic species in the dispersant is greatly affected by the dispersion stability, touch resistance, oxidation resistance, electrical properties (conductive properties, insulation properties), aging stability, heat resistance, low humidity, and weather resistance of the dispersion. However, it is desirable that the content of the ions is less than 10 ppm in the dispersant.

  The dispersion composition for hard coat of the present invention can be prepared using a known stirring means, homogenizing means, and dispersing means. Examples of dispersers that can be adopted include roll mills such as two rolls and three rolls, ball mills such as ball mills and vibration ball mills, paint shakers, continuous disk type bead mills, bead mills such as continuous annular type bead mills, sand mills, and jets. Mill etc. are mentioned. Further, the dispersion treatment can be performed in an ultrasonic wave generation bath.

8). Polymerizable compound The polymerizable compound that can be used in the present invention is not particularly limited as long as it has a polymerizable functional group capable of undergoing a curing reaction after the formation of the coating film, but contains a carboxylic acid group. An unsaturated polymerizable monomer, an alkyl ester of a carboxylic acid group-containing unsaturated polymerizable monomer, a vinyl compound, a urethane acrylate, and an epoxy compound can be suitably used.

  Examples of the carboxylic acid group-containing unsaturated polymerizable monomer include (meth) acrylic acid, crotonic acid, maleic acid and itaconic acid.

  Examples of alkyl esters of carboxylic acid group-containing unsaturated polymerizable monomers include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth) acrylate, butyl (meth) acrylate, (Meth) acrylic acid-n-butyl, (meth) acrylic acid isobutyl, (meth) acrylic acid hexyl, (meth) acrylic acid-2-ethylhexyl, (meth) acrylic acid octyl, (meth) acrylic acid nonyl, (meta ) Decyl acrylate, stearyl (meth) acrylate, isostearyl (meth) acrylate, lauryl (meth) acrylate, cyclohexyl (meth) acrylate, (meth) acrylic acid-t-butylcyclohexyl, (meth) acrylic acid Isobornyl, adamantyl (meth) acrylate, (meth) acrylic acid Cyclo [3,3,1] nonyl, 2-methoxyethyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, benzyl (meth) acrylate, allyl (meth) acrylate, diethylamino (meth) acrylate Ethyl, (meth) acrylic acid-2-hydroxyethyl, (meth) acrylic acid-2-hydroxypropyl, (meth) acrylic acid-3-hydroxypropyl, (meth) acrylic acid-4-hydroxybutyl, methoxyethylene glycol ( (Meth) acrylate, methoxypolyethylene glycol (meth) acrylate, ethoxyethylene glycol (meth) acrylate, ethoxypolyethylene glycol (meth) acrylate, propoxyethylene glycol (meth) acrylate, propoxypolyethylene glycol (meta) Acrylate, methoxypropylene glycol (meth) acrylate, methoxypolypropylene glycol (meth) acrylate, ethoxypropylene glycol (meth) acrylate, ethoxypolypropylene glycol (meth) acrylate, propoxypropylene glycol (meth) acrylate and propoxypolypropylene glycol (meth) acrylate, etc. Mono (meth) acrylic acid ester, ethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate and triethylene glycol di (meth) acrylate, etc. Di (meth) acrylate compound, trimethylolpropane tri ( Tri) acrylate and glycerol tri (meth) acrylate and other tri (meth) acrylate compounds, tetra (meth) acrylate compounds such as pentaerythritol tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate and sorbitol hexa (meth) acrylate And hexa (meth) acrylate compounds. In addition, (meth) acrylate means an acrylate or a methacrylate.

  Examples of the vinyl compound include vinyl acetate, vinyl propionate, styrene, α-methylstyrene, vinyl toluene, acrylonitrile, methacrylonitrile, butadiene and isoprene.

  Urethane acrylate is obtained by reacting polyisocyanate with a hydroxyl group-containing (meth) acrylate.

  Although it does not specifically limit as polyisocyanate which can be used for urethane acrylate, Tolylene diisocyanate, diphenylmethane diisocyanate, polyphenylmethane polyisocyanate, phenylene diisocyanate, naphthalene diisocyanate, xylylene diisocyanate, tetramethylxylylene diisocyanate, hexamethylene diisocyanate, trimethyl Examples include hexamethylene diisocyanate, lysine diisocyanate, lysine triisocyanate, dicyclohexylmethane diisocyanate, hydrogenated xylylene diisocyanate, isophorone diisocyanate, 1,3-bis (isocyanatomethyl) cyclohexane, norbornene diisocyanate, and modified products thereof.

  Further, an isocyanate group-terminated urethane prepolymer obtained by reacting a polyisocyanate and a polyol can also be used as the polyisocyanate. Examples of such polyols include, but are not limited to, polyol compounds such as alkylene glycol, trimethylolalkane, glycerin and pentaerythritol, as well as polyether polyols, polyester polyols, polycaprolactone polyols, polyolefin polyols, polybutadiene polyols, polycarbonates. A polyol etc. are also mentioned.

  The hydroxyl group-containing (meth) acrylate that can be used for urethane acrylate is a (meth) acrylate compound having one or more hydroxyl groups in the molecule. Examples of such compounds include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, and 2-hydroxyethylacryloyl. Phosphate, 2- (meth) acryloyloxyethyl-2-hydroxypropyl phthalate, glycerin di (meth) acrylate, 2-hydroxy-3-acryloyloxypropyl (meth) acrylate, pentaerythritol tri (meth) acrylate, dipenta Examples include erythritol penta (meth) acrylate, caprolactone-modified 2-hydroxyethyl (meth) acrylate, and cyclohexanedimethanol mono (meth) acrylate.

  The epoxy compound preferably has two or more epoxy groups in the molecule, and examples thereof include polyglycidyl ether, glycidyl ether ester, polyglycidyl ester, glycidylaminoglycidyl ether, glycidylaminoglycidyl ester, and glycidylamine.

  Examples of polyglycidyl ether include bisphenol A, bisphenol F, bisphenol S, tetramethylbisphenol A, diaryl bisphenol A, hydroquinone, catechol, resorcin, cresol, tetrabromobisphenol A, trihydroxybiphenyl, benzophenone, bisresorcinol, bisphenol hexa Aromatic polyglycidyl ethers obtained by reacting polychlorophenols such as fluoroacetone, tetramethylbisphenol A, tetramethylbisphenol F, tris (hydroxyphenyl) methane, bixylenol, phenol novolac and cresol novolac with epichlorohydrin, glycerin , Neopentyl glycol, ethylene glycol, propylene glycol Aliphatic polyglycidyl ether, glycidyl hexahydrobisphenol A, 3,4-epoxycyclohexenylmethyl-3 obtained by reacting an aliphatic polyhydric alcohol such as butylene glycol, hexylene glycol, polyethylene glycol and polypropylene glycol with epichlorohydrin Such as', 4'-epoxycyclohexenecarboxylate and 1,3,5-tris (2,3-epoxypropyl) -1,3,5-triazine-2,4,6 (1H, 3H, 5H) -trione An alicyclic polyglycidyl ether etc. are mentioned.

  Examples of the glycidyl ether ester include those obtained by reacting a hydroxycarboxylic acid such as p-oxybenzoic acid and β-oxynaphthoic acid with epichlorohydrin.

  Examples of the polyglycidyl ester include polycarboxylic acids such as phthalic acid, methylphthalic acid, isophthalic acid, terephthalic acid, tetrahydrophthalic acid, endomethylenetetrahydrophthalic acid, endomethylenehexahydrophthalic acid, trimellitic acid and polymerized fatty acid. And those obtained by reacting with epichlorohydrin.

  Examples of the glycidylaminoglycidyl ether include those obtained by reacting aminophenol, aminoalkylphenol and epichlorohydrin.

  Examples of the glycidylaminoglycidyl ester include those obtained by reacting aminobenzoic acid and epichlorohydrin.

  As glycidylamine, for example, aniline, toluidine, tribromoaniline, xylylenediamine, diaminocyclohexane, bisaminomethylcyclohexane, 4,4′-diaminodiphenylmethane and 4,4′-diaminodiphenylsulfone are reacted with epichlorohydrin. Can be obtained.

  The dispersion composition for hard coat of the present invention can be polymerized by a known polymerization reaction such as a photopolymerization reaction or a thermal polymerization reaction. At that time, a known polymerization initiator such as a photopolymerization initiator or a thermal polymerization initiator can be used.

  Examples of the photopolymerization initiator include a benzophenone polymerization initiator, an acetophenone polymerization initiator, and an anthraquinone photopolymerization initiator.

As thermal polymerization initiators, in addition to azo polymerization initiators and substituted ethane polymerization initiators, peroxide initiators such as persulfates and peroxides, sulfites, hydrogen sulfites and metal salts, etc. And redox polymerization initiators in combination with other reducing agents.
The amount of the polymerization initiator used is usually suitably 0.005 to 10 parts by weight with respect to 100 parts by weight of the polymerizable compound.

  Moreover, when using an epoxy compound as a polymeric compound, you may use a conventionally well-known hardening | curing agent. Examples of such a curing agent include aliphatic acid anhydrides such as hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, trialkyltetrahydrophthalic anhydride, and hydrogenated methylnadic acid anhydride.

  As the polymerization method, a known method such as emulsion polymerization is used.

  Although superposition | polymerization temperature is adjusted with the kind of said polymerization initiator, 20 to 100 degreeC is preferable, for example.

  In the present invention, among the polymerizable compounds, those having three or more polymerizable functional groups in one molecule are preferable from the viewpoint of increasing hardness and preventing damage.

  Furthermore, a dispersion composition for hard coat, which uses a polymerizable compound having three or more polymerizable functional groups in one molecule and zirconium oxide as the above-mentioned dispersoid particles, has a higher refractive index. A film can be provided, and can be used in various fields.

  The preferable compounding quantity of a polymeric compound is 1 to 80 weight% with respect to the whole dispersion composition for hard-coats of this invention, More preferably, it is 5 to 30 weight%.

9. Film-forming aid The film-forming aid used in the present invention is a compound having a boiling point of 100 to 300 ° C at 1 atmosphere.
Such compounds include alcohol compounds such as n-butanol (117 ° C) and 3-methoxy-3-methyl-1-butanol (174 ° C), ethyl butyrate (121 ° C), octyl acetate (211 ° C), diethylene glycol Ester compounds such as monobutyl ether acetate (247 ° C.) and propylene glycol monomethyl ether acetate (145 ° C.), ether compounds such as diethylene glycol monobutyl ether (230 ° C.) and propylene glycol monomethyl ether (120 ° C.), methyl isobutyl ketone (116 ° C.) And ketone compounds such as dibutyl ketone (186 ° C.). In addition, the inside of a parenthesis shows the boiling point in 1 atmosphere of each compound.

  Among these, since high wettability is exhibited with respect to substrates such as PET and glass, and the blending amount of the dispersoid particles with respect to the entire dispersion composition for hard coat can be increased, the boiling point at 1 atm is 100 to 100. An alcohol compound at 300 ° C. is preferred, and 3-methoxy-3-methylbutanol is more preferred.

  A preferable blending amount of the film-forming auxiliary is 5 to 80% by weight with respect to the whole hard coat dispersion composition of the present invention. More preferably, it is 20-70%, More preferably, it is 30-55%.

10. Optional components In addition to the above components, the hard coat dispersion composition or hard coat coating composition of the present invention includes various resins and oligomers that are used for ordinary paints, adhesives, and moldings. And monomers can be used without particular limitation. Specifically, acrylic resin, polyester resin, alkyd resin, urethane resin, silicone resin, fluorine resin, epoxy resin, polycarbonate resin, polyvinyl chloride resin, polyvinyl alcohol, or the like may be added. Moreover, you may add the organic solvent whose boiling point in 1 atmosphere is less than 100 degreeC.

11. Method of Use The hard coat coating composition of the present invention is obtained by applying the hard coating coating composition of the present invention on a substrate, evaporating the solvent, and then curing the coating composition. Examples of the base material to be coated include glass, resin films such as polyethylene terephthalate (PET), glass composites, ceramics, metals, and steel plates. Examples of the coating method include spin coating, bar coating, spraying, screen, gravure, offset, letterpress, intaglio, and ink jet, but are not limited to these, and generally used apparatuses and instruments. Can be used. For curing the coated film, known materials such as heat, ultraviolet rays and radiation can be used.

  Examples of the present invention and comparative examples will be described below. In the following, “part” indicating the blending amount indicates “part by weight” and “%” indicates “% by weight”. Needless to say, the present invention is not limited to the following examples, and appropriate changes and modifications can be made without departing from the technical scope of the present invention.

<Synthesis of dispersant>
[Production Example 1 (Synthesis of Dispersant A)]
In a toluene solvent, 640 g (1 mol) of ethylene oxide 10 mol adduct and 152 g (1.3 mol) of sodium monochloroacetate were added to a reactor and homogeneously branched C11-14 alkyl alcohol (product name: EXXAL13, manufactured by ExxonMobil). It stirred until it became. Thereafter, 52 g of sodium hydroxide was added at a reaction system temperature of 60 ° C. Subsequently, the temperature of the reaction system was raised to 80 ° C. and aged for 3 hours. After aging, 117 g (1.2 mol) of 98% sulfuric acid was added dropwise with the reaction system at 50 ° C. to obtain a white suspension. Subsequently, this white suspension solution is washed with distilled water, and the solvent is distilled off under reduced pressure to obtain a dispersant A (R: branched C11-14 alkyl, AO: ethylene oxide, n: 10, X: CH ₂ ). It was.

[Production Example 2 (Synthesis of Dispersant B)]
Dispersant B was produced in the same manner as in Production Example 1 except that 598 g (1 mol) of isodecyl alcohol ethylene oxide 10 mol adduct was used instead of the branched C11-14 alkyl alcohol ethylene oxide 10 mol adduct in Production Example 1. (R: isodecyl, AO: ethylene oxide, n: 10, X: CH ₂ ) was obtained.

[Production Example 3 (Synthesis of Dispersant C)]
In Production Example 1, in place of C11-14 alkyl alcohol ethylene oxide 10 mol adduct, 420 g (1 mol) of C11-14 alkyl alcohol ethylene oxide 5 mol adduct was used. C (R: branched C11~14 alkyl, AO: ethylene oxide, n: 5, X: CH 2) was obtained.

[Production Example 4 (Synthesis of Dispersant D)]
By reacting 640 g (1 mol) of branched C11-14 alkyl alcohol ethylene oxide 10 mol adduct and 100 g (1 mol) of succinic anhydride at 120 ° C. for 2 hours, dispersant D (R: branched C11-14 alkyl, AO : Ethylene oxide, n: 10, X: COCH ₂ CH ₂ ).

[Production Example 5 (Synthesis of Dispersant E)]
In Production Example 1, the same procedure as in Production Example 1 was carried out except that 570 g (1 mol) of 2-ethylhexyl alcohol ethylene oxide 10 mol adduct was used instead of the branched C11-14 alkyl alcohol ethylene oxide 10 mol adduct. E (R: 2-ethylhexyl, AO: ethylene oxide, n: 10, X: CH ₂ ) was obtained.

[Production Example 6 (Synthesis of Dispersant a)]
In Production Example 1, in place of the branched C11-14 alkyl alcohol ethylene oxide 10 mol adduct, 472 g (1 mol) of methanol ethylene oxide 10 mol adduct was used, and the same procedure as in Production Example 1 was carried out. : Methyl, AO: ethylene oxide, n: 10, X: CH ₂ ).

[Production Example 7 (Synthesis of urethane acrylate A)]
504 g (1 mol) of a trimer of hexamethylene diisocyanate (HMDI), 894 g (3 mol) of pentaerythritol triacrylate (trade name: PET-3, manufactured by Daiichi Kogyo Seiyaku Co., Ltd.), and 0.8 g of hydroquinone monomethyl ether It was added and reacted at 70 ° C. to 80 ° C. until the residual isocyanate concentration became 0.1% by weight or less to obtain urethane acrylate A.

[Example 1]
Dispersant A described in Production Example 1 was added to 100 parts of a commercially available zirconium oxide dispersion (trade name SZR-M manufactured by Sakai Chemical Co., Ltd., a methanol dispersion containing zirconium oxide having a primary particle diameter of 3 nm and 30% by weight). 1.5 parts, 11 parts of dipentaerythritol hexaacrylate (trade name: KAYARAD DPHA, Nippon Kayaku Co., Ltd.) and 21 parts of 3-methoxy-3-methylbutanol were added and mixed, and then the rotary evaporator was added. The methanol was removed under reduced pressure to obtain a dispersion for hard coat containing zirconium oxide.

[Example 2]
A hard coat dispersion containing zirconium oxide was obtained in the same manner as in Example 1 except that the dispersant A was changed to 0.6 parts and the 3-methoxy-3-methylbutanol was changed to 42 parts.

Example 3
A hard coat dispersion containing zirconium oxide was obtained in the same manner as in Example 1 except that dipentaerythritol hexaacrylate was changed to 28.5 parts and 3-methoxy-3-methylbutanol was changed to 30 parts. .

Example 4
A hard coat dispersion containing zirconium oxide was obtained in the same manner as in Example 1 except that dipentaerythritol hexaacrylate was changed to 18.5 parts and 3-methoxy-3-methylbutanol was changed to 25 parts. .

Example 5
The same procedure as in Example 1 was carried out except that 11 parts of pentaerythritol triacrylate (trade name: PET-3, manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) was used instead of 11 parts of dipentaerythritol hexaacrylate, and zirconium oxide was contained. A dispersion for hard coat was obtained.

Example 6
Hard coat containing zirconium oxide except that 11 parts of tripentaerythritol hexaacrylate was used instead of 11 parts of trimethylolpropane trimethacrylate (trade name: EM311, manufactured by Changxing Chemical Industry Co., Ltd.) A dispersion was obtained.

Example 7
A hard coat containing zirconium oxide except that 11 parts of trimethylolpropane triacrylate (trade name: EM231, manufactured by Changxing Chemical Industry Co., Ltd.) was used instead of 11 parts of dipentaerythritol hexaacrylate. A dispersion was obtained.

Example 8
A hard coat dispersion containing zirconium oxide was obtained in the same manner as in Example 1 except that 11 parts of urethane acrylate A synthesized in Production Example 7 was used instead of 11 parts of dipentaerythritol hexaacrylate.

Example 9
A hard coat dispersion containing zirconium oxide was carried out in the same manner as in Example 1 except that 1.5 parts of the dispersant B described in Production Example 2 was used instead of 1.5 parts of the dispersant A. Obtained.

Example 10
A hard coat dispersion containing zirconium oxide was carried out in the same manner as in Example 1 except that 1.5 parts of Dispersant C described in Production Example 2 was used instead of 1.5 parts of Dispersant A. Obtained.

Example 11
A hard coat dispersion containing zirconium oxide was carried out in the same manner as in Example 1 except that 1.5 parts of the dispersant D described in Production Example 2 was used instead of 1.5 parts of the dispersant A. Obtained.

Example 12
A hard coat dispersion containing zirconium oxide was carried out in the same manner as in Example 1 except that 1.5 parts of Dispersant E described in Production Example 2 was used instead of 1.5 parts of Dispersant A. Obtained.

Example 13
A hard coat dispersion containing zirconium oxide was obtained in the same manner as in Example 1 except that 21 parts of terpineol was used instead of 21 parts of 3-methoxy-3-methylbutanol.

Example 14
The same procedure as in Example 1 was carried out except that 10 parts of 3-methoxy-3-methylbutanol and 11 parts of diethylene glycol monobutyl ether acetate were used instead of 21 parts of 3-methoxy-3-methylbutanol, and contained zirconium oxide. A dispersion for hard coat was obtained.

Example 15
A hard coat dispersion containing zirconium oxide was obtained in the same manner as in Example 1 except that 21 parts of 1-butanol was used instead of 21 parts of 3-methoxy-3-methylbutanol.

[Comparative Example 1]
A hard coat dispersion containing zirconium oxide was obtained in the same manner as in Example 1 except that 1.5 parts of terephthalic acid (manufactured by Nacalai Tesque) was used instead of 1.5 parts of dispersant A. .

[Comparative Example 2]
The same procedure as in Example 1 was carried out except that 1.5 parts of 3-methacryloxypropyltrimethoxysilane (manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of 1.5 parts of dispersant A, and a hard material containing zirconium oxide A coating dispersion was obtained.

[Comparative Example 3]
A hard coat dispersion containing zirconium oxide was obtained in the same manner as in Example 1 except that 1.5 parts of hexanoic acid (manufactured by Nacalai Tesque) was used instead of 1.5 parts of dispersant A. .

[Comparative Example 4]
The same as in Example 1 except that 1.5 parts of polyoxyethylene styrenated phenyl ether phosphate (Pricesurf AL, manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) was used instead of 1.5 parts of dispersant A. To obtain a dispersion for hard coat containing zirconium oxide.

[Comparative Example 5]
A hard coat dispersion containing zirconium oxide was carried out in the same manner as in Example 1 except that 1.5 parts of the dispersant a described in Production Example 6 was used instead of 1.5 parts of the dispersant A. Obtained.

<Characteristic evaluation of dispersion (dispersion)>
The dispersions for hard coats of the above Examples and Comparative Examples were evaluated for dispersibility and viscosity, and the results are shown in Table 1. The evaluation method is as follows.

(Dispersibility)
The presence or absence of precipitates was confirmed by visual observation.

(viscosity)
According to JIS K5600-2-3, the viscosity of the dispersion at 25 ° C. was measured using an E-type viscometer (RE80R manufactured by Toki Sangyo Co., Ltd.).

<Characteristic evaluation of cured coating film>
After adding 0.15 g of Irgacure 184 (trade name, manufactured by BASF Japan), which is a benzophenone polymerization initiator, to 5 g of the hard coat dispersion prepared in Examples 1 to 15 and Comparative Examples 1 to 5, After coating with a select roller on a PET substrate and drying at 80 ° C. for 5 minutes, a coating film was prepared by irradiating and curing with UV of 400 mJ. The coating film was evaluated for appearance, refractive index, Abbe number, haze and pencil hardness. The results are shown in Table 1. The evaluation method is as follows.

(Appearance of coating film)
The appearance of the coating film was visually observed, and a case where no precipitate was observed was indicated as ◯, and a case where a precipitate was observed was indicated as ×.

(Refractive index)
Using a prism coupler (METRICON prism coupler model 2010 manufactured by METRICON), the refractive index at a wavelength of 589 nm was measured.

(Abbe number)
In accordance with JIS K0062, a prism coupler (trade name: METRICON prism coupler model 2010, manufactured by METRICON) was used to measure the refractive index of the dispersion-cured coating film at wavelengths of 405 nm, 532 nm, and 633 nm. From this, the Abbe number was calculated.

(Haze)
According to JIS K 7136, the haze of the coating film was measured using a haze meter (HGM type manufactured by Suga Seisakusho).

(Pencil hardness)
The pencil hardness was measured according to the method described in JIS K 5600-5-4.

＜結果＞
表１から明らかなように、実施例１の分散体は、分散性および粘度の何れの評価においても優れた結果を示している。これに対して、比較例の分散体は、何れかの評価項目において問題があることが分かる。

<Result>
As is clear from Table 1, the dispersion of Example 1 shows excellent results in any evaluation of dispersibility and viscosity. On the other hand, it can be seen that the dispersion of the comparative example has a problem in any of the evaluation items.

  Moreover, the coating film obtained from the dispersion of Examples 1-15 has shown the result excellent in any evaluation of an external appearance, a refractive index, an Abbe number, haze, and pencil hardness. On the other hand, when the dispersions of Comparative Examples 1, 2, 3, and 5 were used, film formation could not be performed. Moreover, it turns out that the coating film obtained from the dispersion of Comparative Example 4 has high haze and inferior transparency as well as deposits are confirmed in the appearance of the coating film. The refractive index and Abbe number could not be measured due to poor transparency.

  The coating composition and hard coat coating composition obtained from the present invention comprises a hybrid material, a surface protective agent, a conductive paste, a conductive ink, a sensor, a precision analysis element, an optical memory, a liquid crystal display element, a nanomagnet, and a heat transfer medium. , High-performance catalysts for fuel cells, organic solar cells, nanoglass devices, abrasives, drug carriers, environmental catalysts, paints, printing inks, ink-jet inks, resists for color filters, inks for writing instruments, optical thin films, adhesives, antireflection It can be used in the field of films, hard coat films and the like. The dispersing agent of the present invention stabilizes the isotropic material and / or anisotropic material derived from the nano-sized inorganic substance, which is a main component in the product and its manufacturing process, in the dispersion medium, and in the dispersion medium It is effective for obtaining desired product characteristics, processing characteristics, quality stabilization, and productivity improvement by suppressing dispersoid aggregation and achieving long-term dispersion stabilization.

Claims (5)

A hard coat dispersion composition comprising dispersoid particles composed of inorganic particles , a dispersant, a polymerizable compound, and a film-forming aid ,
The inorganic particles have an average particle diameter in the range of 1 to 500 nm,
The dispersant is composed of a compound represented by the following formula (1):
The film-forming aid is at least one of an alcohol compound and an ester compound having a boiling point of 100 to 300 ° C. at 1 atmosphere,
Content of the said film forming adjuvant is 5 to 80 weight% with respect to the whole dispersion composition for hard-coats, The dispersion composition for hard-coats characterized by the above-mentioned.

( However, R in Formula (1) is a branched alkyl group having 8 to 18 carbon atoms ,
AO in formula (1) represents an oxyalkylene group having 1 to 4 carbon atoms, n is a numerical value in the range of 1 to 30 indicating the average number of added moles of alkylene oxide,
X in the formula (1) is a linking group composed of a carbon atom, a hydrogen atom and / or an oxygen atom. )   2. The hard coat dispersion composition according to claim 1, wherein X in the formula (1) in the dispersant is an alkylene group having 1 to 15 carbon atoms. 2. The hard coat dispersion composition according to claim 1, wherein X in the formula (1) in the dispersant is a linking group represented by the following formula (2).

( Y in formula (2) is any one selected from an alkylene group having 1 to 15 carbon atoms, a vinylene group, a phenylene group, and a carboxyl group-containing phenylene group. ) A hard coat coating composition comprising the hard coat dispersion composition according to any one of claims 1 to 3. A hard coat coating material obtained by applying the coating composition for hard coat according to claim 4 on a substrate, evaporating the film-forming aid , and then curing the coating aid .