WO2011148661A1

WO2011148661A1 - Dispersion composition

Info

Publication number: WO2011148661A1
Application number: PCT/JP2011/050896
Authority: WO
Inventors: 和幸加藤; 祥太大成; 橋本　賀之
Original assignee: 第一工業製薬株式会社
Priority date: 2010-05-26
Filing date: 2011-01-19
Publication date: 2011-12-01

Abstract

Provided is a dispersion composition wherein nano-sized zirconium oxide particles are excellently dispersed by the addition of a small amount of a dispersant. The dispersion composition can be obtained by dispersing zirconium oxide particles in a dispersion medium using a dispersant consisting of a compound represented by formula (1). In formula (1), R is C_1-24 alkyl and/or alkenyl; AO is C_2-4 oxyalkylene; n represents the average number of alkylene oxide molecules added, and is 5 to 30; and X is a connecting group composed of carbon, hydrogen and/or oxygen.

Description

Dispersion composition

The present invention relates to a dispersion composition, and more particularly to a dispersion composition that can be suitably used for a film having high reflection performance.

In recent years, in flat panel displays with backlights centering on liquid crystal displays, the brightness of the liquid crystal display can be increased without sacrificing the viewing angle or color reproducibility by selectively reflecting and recycling the backlight light. In order to improve, a brightness enhancement film is used. Improving the brightness requires less power to illuminate the display, thus reducing power consumption and reducing the heat load on the electronic components, thus extending the life of the electronic components. Is also possible. Therefore, various proposals for the structure of the brightness enhancement film have been made. For example, trying to improve the brightness of a liquid crystal display by enclosing a large number of fine bubbles in the resin film constituting the brightness enhancement film, and by multiple reflection (high refractive index) at the interface between the gas phase and the solid phase in the resin film. The structure to be known is known.

That is, in order to improve the brightness, it is necessary to increase the refractive index of the resin constituting the brightness enhancement film. As a means for that, there is a method of dispersing fine particles in a resin. For example, fine particles that can be used industrially include titanium oxide particles, barium titanate particles, and zirconium oxide particles. However, when titanium oxide is blended with an organic compound such as a resin, the deterioration of the resin may be promoted, so that its use is limited. In addition, barium titanate may adversely affect the environment. Therefore, it is preferable to use zirconium oxide. For example, in this type of prior art, Patent Document 1 discloses that a first hydrothermal treatment is performed in an aqueous solvent to obtain a zirconia-containing intermediate and a by-product containing zirconia particles having a particle size of 50 nm or less, and Then, a part of this by-product is removed, and further, a second hot water is applied to obtain a zirconia sol, and then the surface of the zirconia particles is modified with a surface modifier to obtain a surface-modified zirconia. A method is described in which particles are obtained, the surface modified zirconia particles and an organic matrix are mixed to obtain a coating composition, and the coating composition is polymerized to form an optical layer.

Special table 2008-533525 gazette

Of course, the brightness enhancement film is required to be transparent. However, in the example of Patent Document 1, 2- [2- (2-methoxyethoxy) ethoxy] acetic acid (MEEAA) is used as the surface modifier, and the weight is about 1/4 of the weight of the zirconia particles. MEEAA is used. That is, MEEAA, which is a dispersant described in Patent Document 1, does not have sufficient dispersion performance. Therefore, it is necessary to add a large amount in order to disperse zirconia particles as a dispersoid well. As a result, there arises a disadvantage that the physical properties and transparency of the resin constituting the brightness enhancement film are lowered. In addition, the method described in Patent Document 1 cannot be said that the size of applicable zirconia particles is sufficiently small, so there is a disadvantage that the range of usable zirconia particles is limited.

In addition, liquid crystal displays are required to have higher luminance and higher durability. The present invention has been made in view of such problems of the prior art, and the purpose thereof is a dispersion having excellent dispersibility by adding a small amount of a dispersant to nano-sized zirconium oxide particles. It is to provide a body composition.

Also, an object of the present invention is to provide a film using the above dispersion composition, which has good appearance transparency, a high refractive index, and excellent durability.

In order to achieve the above object, the dispersion composition of the present invention is a dispersion composition in which zirconium oxide particles are dispersed in a dispersion medium using a dispersant comprising a compound represented by the following formula (1). Consists of.

However, the meaning of the code | symbol of Formula (1) is as follows.
R represents an alkyl group and / or alkenyl group having 1 to 24 carbon atoms.
AO represents an oxyalkylene group having 2 to 4 carbon atoms, n represents the average number of added moles of alkylene oxide, and is in the range of 5 to 30.
X is a linking group consisting of a carbon atom, a hydrogen atom and / or an oxygen atom.
X in the formula (1) is preferably an alkylene group having 1 to 15 carbon atoms.
Further, X in the formula (1) is preferably a substance represented by the following formula (2).

However, the meanings of the symbols in the formula (2) are as follows.
Y 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.
It is preferable to use a double bond curable resin as the dispersion medium.
It is preferable to use a solvent in which the resin is dissolved as the dispersion medium.

A member obtained by applying a coating composition containing the dispersion composition on a substrate and then reacting physically or chemically is preferable.

According to the present invention, it is possible to provide a dispersion composition having excellent dispersibility by adding a small amount of a dispersant to nano-sized zirconium oxide particles. Moreover, the film formed using the dispersion composition of the present invention has good appearance transparency, a high refractive index, and excellent durability.

The dispersion composition of the present invention comprises a dispersion composition in which zirconium oxide particles are dispersed in a dispersion medium using a dispersant comprising a compound represented by the following formula (1).

As described in the formula (1), the dispersant of the present invention comprises a dispersion medium affinity part containing an alkylene oxide chain and a dispersoid affinity part composed of a carboxyl group. The dispersion medium affinity part and the dispersoid affinity part are They are connected by a linking group X.

However, the meaning of the code | symbol of Formula (1) is as follows.
R represents an alkyl group and / or alkenyl group having 1 to 24 carbon atoms.
AO represents an oxyalkylene group having 2 to 4 carbon atoms, n represents the average number of added moles of alkylene oxide, and is in the range of 5 to 30.
X is a linking group consisting of a carbon atom, a hydrogen atom and / or an oxygen atom.

Hereinafter, preferred embodiments of the present invention will be described in detail.

1. About Hydrophobic Group (R) With respect to the hydrophobic group (R) that can be used in the dispersant of the present invention, R is a hydrocarbon group derived from alcohol, and is an alkyl group and / or alkenyl group having 1 to 24 carbon atoms. . When R is an alkyl group and / or an alkenyl group, the raw material alcohol that can be used 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, isoform produced by the oxo process via higher olefins derived from propylene or butene, or mixtures thereof Undecanol, isododecanol, isotridecanol, Neodol 23, 25, 45 manufactured by Shell Chemicals, SAFOL23 manufactured by Sasol, EXXAL7, EXXAL8N, EXXAL9, EXXAL10, EXXAL11 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-octadecene-1-ol) and the like are also examples of higher alcohols that can be used. A single composition of Guerbet Alcohol having a 2-alkyl-1-alkanol type chemical structure, or a mixture thereof is also 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 suitably selected is (R) is a hydrocarbon group derived from an alcohol, and is an alkyl group and / or alkenyl group having 1 to 24 carbon atoms. In this case, it can be suitably used to achieve the object of the present invention.

It should be noted that the stability of the dispersion is significantly reduced and precipitates are formed immediately, or the stability over time is significantly reduced to avoid problems such as a decrease in added value, productivity, processing characteristics, and quality deterioration of the final product. For this purpose, the hydrophobic group (R) is more preferably an alkyl group or alkenyl group having 8 to 18 carbon atoms.

2. Oxyalkylene group (AO) n
With respect to the alkylene oxide species suitably selected for the dispersant of the present invention, in the formula (1), AO represents an oxyalkylene group having 2 to 4 carbon atoms, specifically, the alkylene oxide having 2 carbon atoms is ethylene oxide. The alkylene oxide having 3 carbon atoms is propylene oxide. The alkylene oxide having 4 carbon atoms is tetrahydrofuran or butylene oxide, and is preferably 1,2-butylene oxide or 2,3-butylene oxide. In the dispersant of the present invention, the oxyalkylene chain (-(AO) n-) is a random polymerization of two or more alkylene oxides even if the alkylene oxide is a homopolymer chain for the purpose of adjusting the dispersion medium affinity of the dispersant. It may be a chain, a block polymer chain, or a combination thereof. N representing the average number of added moles of the alkylene oxide of the formula (1) is preferably in the range of 5 to 30.

3. 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, the linking group X is not suitable as a structural factor of the dispersant of the present invention because it has an action of weakening the affinity effect of the carboxyl group on the dispersoid. .

Further, 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 following formula (2).

However, the meanings of the symbols in the formula (2) are as follows.
Y 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.

5. Dispersant Production Method The dispersant of 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.

6). Dispersoid particles Dispersoid particles dispersed by the dispersant of the present invention are zirconium oxide particles. As the zirconium oxide 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 of the present invention may be used in a top-down process in which coarse particles are mechanically pulverized and refined to form a number of unit particles that pass through the agglomerated cluster state. The particles may be used in a bottom-up process in which particles are formed, or after preparing zirconium oxide particles by the above-described method in advance, a surface modifier or the like may be used to stably remove the zirconium oxide 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 surface protective agent.

Example of preparation of nano-sized zirconium particles by bottom-up method. Among the bottom-up methods, a representative example of a physical method is a gas evaporation method in which bulk zirconium is evaporated in an inert gas and cooled and condensed by collision with the gas to generate nanoparticles. In addition, chemical methods include a liquid phase reduction method in which zirconium ions are reduced in the liquid phase in the presence of a protective agent, and the generated zero-valent zirconium is stabilized at a nano size, and a thermal decomposition method of a metal complex. 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 zirconium 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 may be any of aqueous, non-aqueous, and gas phase. It may be prepared in the environment of

7). Dispersion medium The dispersion medium which can be used in the present invention includes toluene, xylene, aromatic hydrocarbon solvents, hydrocarbon solvents such as n-hexane, cyclohexane and n-heptane, and halogenated carbonization such as methylene chloride, chloroform and dichloroethane. Ether solvents such as hydrogen solvents, ethyl ether, isopropyl ether, dioxane, tetrahydrofuran, dibutyl ether, butyl ethyl ether, methyl-t-butyl ether, terpinyl methyl ether, dihydroterpinyl methyl ether, diglyme 1,3-dioxolane Solvent, acetone, acetophenone, methyl ethyl ketone, methyl propyl ketone, diethyl ketone, methyl n-butyl ketone, methyl isobutyl ketone, dipropyl ketone, diisobutyl ketone, methyl amyl ketone, aceto Ketone solvents such as nilacetone, isophorone, cyclohexanone, methylcyclohexanone, 2- (1-cyclohexenyl) cyclohexanone methyl isobutyl ketone, cyclohexanone, isophorone, ethyl formate, propyl formate, butyl formate, isobutyl formate, pentyl formate, methyl acetate, acetic acid Ethyl, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, sec-butyl acetate, (iso) amyl acetate, cyclohexyl acetate, ethyl lactate, 3-methoxybutyl acetate, sec-hexyl acetate, 2-ethylbutyl acetate 2-ethylhexyl acetate, benzyl acetate, methyl propionate, ethyl propionate, methyl monochloroacetate, ethyl monochloroacetate, butyl monochloroacetate, methyl acetoacetate, ethyl acetoacetate, Ester solvents such as butyl lopionate, isoamyl propionate, γ-butyrolactone, ethylene glycol monoethyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monobutyl ether, diethylene 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 mono 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, tripropylene glycol mono n-propyl ether, tripropylene glycol mono n-butyl ether, etc. And glycol ether solvents of these monoethers, and dialkyl ether solvents such as acetate solvents of diethers, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl isobutyl ether, dipropylene glycol dimethyl ether, and dipropylene glycol diethyl ether. Methanol, ethanol, n-propyl alcohol, isopropyl alcohol, n-butyl alcohol, isobutyl alcohol, sec-butyl alcohol, t-butyl alcohol, heptanol, n-amyl alcohol, sec-amyl alcohol, n-hexyl alcohol, tetrahydrofurfuryl Alcohol, furfuryl alcohol, allyl alcohol, ethylene chlorohydrin, octyldodecanol, 1-ethyl-1-propanol, 2-methyl-1-butanol, isoamyl alcohol, t-amyl alcohol, sec-isoamyl alcohol, neoamyl alcohol Hexyl alcohol, 2-methyl-1-pentanol, 4-methyl-2-pentanol, heptyl alcohol, n-octyl alcohol, 2-ethylhexyl Lucol, nonyl alcohol, decyl alcohol, undecyl alcohol, lauryl alcohol, cyclopentanol, cyclohexanol, benzyl alcohol, α-terpineol, terpineol C, L-α-terpineol, dihydroterpineol, terpinyloxyethanol, dihydroterpi Nyloxyethanol, Tersolve MTPH, Tersolve DTO-210, Tersolve THA-90, Tersolve THA-70 manufactured by Nippon Terpene Chemical Co., Ltd., cyclohexanol, 3-methoxybutanol, diacetone alcohol, 1,4-butanediol, octane Diol, etc., Fine Oxocol 140N, Fine Oxocol 1600, Fine Oxocol 180, Fine Oxocol manufactured by Nissan Chemical Industries, Ltd. Alcohol solvents such as 80N, fine oxocol 2000, glycol solvents such as ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, 1,3-butylene glycol, hexylene glycol, polyethylene glycol, and polypropylene glycol Can be mentioned. Other examples include amide solvents such as dimethylacetamide and dimethylformamide. In addition, (meth) acrylic acid having a reactive group as a dispersion medium, (meth) acrylic acid esters, vinyl monomers such as vinyl acetate, vinyl ether derivatives, and ethylenically unsaturated monomers such as polyallyl derivatives Can also be used. In addition, various resins, oligomers, and monomers used for ordinary paints, adhesives, and moldings can be used without any particular limitation. Specific examples include acrylic resins, polyester resins, alkyd resins, urethane resins, silicone resins, fluororesins, epoxy resins, polycarbonate resins, polyvinyl chloride resins, and polypinyl alcohols. In addition, the said dispersion medium can be used suitably individually or in mixture of 2 or more types.

8). Others The dispersant of the present invention can be produced by a known method, and the composition is optimally selected by specifically limiting the type of the hydrophobic group, the alkylene oxide type and its addition form, the added molar amount, the linking group, etc. within the above range. By doing so, the industrial utility value is great in that the zirconium oxide particles can be dispersed and stabilized in a wider variety of dispersion media than known dispersants.

In addition, the dispersant of the present invention can 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. 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 content of the zirconium oxide particles suitably employed in the present invention in the dispersion medium is not particularly limited as long as it can be uniformly dispersed in the non-aqueous dispersion medium, and varies depending on the application. The content is preferably in the range of 0.5 to 70% by mass. Further, the average particle diameter of the zirconium oxide particles is preferably in the range of 1 to 500 nm, and more preferably in the range of 10 to 100 nm. In addition, the preferred use condition of the dispersant of the present invention is preferably in the range of 1 to 300% by weight with respect to the zirconium oxide particles.

Also, the dispersion composition of the present invention can be prepared using known stirring means, homogenizing means, and dispersing means. Examples of dispersers that can be used 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.

Further, the dispersant of the present invention not only exhibits an excellent dispersion stabilization effect compared to known techniques for the dispersion stabilization of zirconium oxide particles in a non-aqueous dispersion medium, but also uses zirconium oxide particles as a medium. It can be used as a protective agent for taking out from inside stably. Functions of the protective agent to stably extract zirconium oxide particles from the medium include aggregation suppression of the generated particles, suppression of adsorption to the container wall surface and prevention of contamination, easy redispersibility, surface modification of the particle surface, functionality Examples include surface deterioration prevention, solvent relaxation and shock mitigation during polarity change, powder flowability improvement, and powder solidification prevention. The dispersant of the present invention is superior to the known protective agents in terms of the above functions, and is more suitable than the known protective agents by optimally selecting the addition form of alkylene oxide and the addition molar amount thereof, the type of hydrophobic group, the linking group, and the like. Zirconium oxide particles can be dispersed and stabilized in a wide range of dispersion media.

As the substrate on which the coating composition containing the dispersion composition of the present invention is applied, for example, glass, resin film, glass composite, ceramics, metal / steel plate and the like can be used.

Hereinafter, examples and comparative examples of the present invention will be described. 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 1)]
In a toluene solvent, 406 g (1 mol) of lauryl alcohol ethylene oxide 5 mol adduct and 151 g (1.3 mol) of sodium monochloroacetate were placed in a reactor and stirred uniformly. Thereafter, 52 g (1.3 mol) of sodium hydroxide was added under the condition that the temperature of the reaction system was 60 ° C., and then the temperature of the reaction system was raised to 80 ° C. and reacted for 3 hours. After the reaction, 120 g (1.2 mol) of 98% sulfuric acid was added dropwise to obtain a white suspension. Subsequently, this white suspension solution was washed with distilled water, and the solvent was distilled off under reduced pressure to obtain a dispersant (R: isodecyl group, AO: ethylene oxide, n: 5, X: CH ₂ ).

[Production Example 2 (Synthesis of Dispersant 2)]
Instead of 406 g (1 mol) of lauryl alcohol ethylene oxide 5 mol adduct, 626 g (1 mol) of lauryl alcohol ethylene oxide 10 mol adduct was used, and the same operation as in Production Example 1 was carried out, and a dispersant (R: lauryl) Group, AO: ethylene oxide, n: 10, X: CH ₂ ).

[Production Example 3 (Synthesis of Dispersant 3)]
Except for replacing with 696 g (1 mol) of lauryl alcohol ethylene oxide 5 mol / propylene oxide 5 mol random adduct, the same procedure as in Production Example 1 was carried out, and the dispersant (R: lauryl group, AO: ethylene oxide and propylene oxide, n: 10, X: CH ₂ ).

<< Preparation of Zirconium Oxide Acrylate Monomer Dispersion (1) >>
Hydrophobic groups (R) having the composition shown in Table 1 below and oxyalkylene mixed with 100 parts of zirconium oxide powder (trade name PCS manufactured by NIPPON Denko Co., Ltd., having a primary particle diameter of 30 nm) and 400 parts of methyl ethyl ketone 10 parts of the dispersants 1 to 3 (Examples 1 to 3) of the present invention comprising the group (-(AO) n-) and the compound represented by the formula (1) containing the linking group (X), or A dispersant for a comparative example comprising a compound represented by the formula (1) containing a hydrophobic group (R), an oxyalkylene group (-(AO) n-) and a linking group (X) having the composition shown in Table 1 (Comparative Examples 1 and 2) To which 10 parts were added, refinement treatment was carried out for 4 hours with the trade name Ultra Apex Mill UAM-005 (peripheral speed 10 m / second using 50 μm diameter zirconia beads) manufactured by Kotobuki Industries To make a zirconium oxide dispersion. Made. To 100 parts of the resulting zirconium oxide dispersion, 10 parts of phenoxyethyl acrylate (trade name New Frontier PHE manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) and pentaerythritol triacrylate (trade name New Frontier PET-made by Daiichi Kogyo Seiyaku Co., Ltd.) 3) After adding and mixing 10 parts, the solvent methyl ethyl ketone was removed under reduced pressure using a rotary evaporator to obtain an acrylate monomer dispersion (1) of zirconium oxide.

<< Preparation of Zirconium Oxide Acrylate Monomer Dispersion (2) >>
100 parts of a commercially available zirconium oxide dispersion (trade name SZR-M manufactured by Sakai Chemical Co., Ltd., a dispersion containing methanol having a primary particle diameter of 3 nm and 30% by weight) has the formula (1 Dispersant 1 to 3 (Examples 4 to 6) of the present invention comprising a compound represented by formula (1) or a comparative dispersant comprising a compound represented by formula (1) having the composition shown in Table 1 below ( Comparative Examples 3 and 4) 3 parts, 15 parts of phenoxyethyl acrylate (trade name New Frontier PHE manufactured by Daiichi Kogyo Seiyaku Co., Ltd.), and pentaerythritol triacrylate (trade name New Frontier PET-3 manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) ) 15 parts was added and mixed, and then the solvent methanol was removed under reduced pressure using a rotary evaporator to obtain a zirconium oxide acrylate monomer dispersion (2). Obtained.

<Characteristic evaluation of dispersion>
a. Transparency of appearance Place the acrylate monomer dispersion of zirconium oxide in a transparent glass container, place a paper with alphabet printed at 12 points under the glass container, and check the transparency of the dispersion over the dispersion. The following criteria were used to evaluate whether the alphabet could be distinguished. The results are shown in Table 1.
A: When the dispersion is put into a glass container having a depth of 5 cm, 12-point alphabet characters can be seen. The dispersion is transparent.
○: When the dispersion is placed in a glass container having a depth of 1 cm, 12-point alphabet characters are clearly visible. There is a slight turbidity in the dispersion.
X: When the dispersion is put into a glass container having a depth of 1 cm, 12-point alphabet characters cannot be clearly seen. The dispersion is turbid.

B. Viscosity Measurement The viscosity of the acrylate monomer dispersion of zirconium oxide was measured at 25 ° C. using an E-type viscometer (trade name RE-80R manufactured by Toki Sangyo Co., Ltd.). The results are shown in Table 1.

C. Refractive index The refractive index of the zirconium oxide acrylate monomer dispersion was measured at 25 ° C. using an Abbe refractometer (trade name NAR-1T manufactured by Atago Co., Ltd.). The results are shown in Table 1.

<< Preparation of photopolymerized cured film of zirconium oxide >>
One part of a photopolymerization initiator (IGACURE184) was added to and mixed with 100 parts of the acrylate monomer dispersion (1) or (2) of zirconium oxide to obtain a zirconium oxide paste. The zirconium oxide paste was applied on a polyethylene terephthalate film with an applicator (YA type manufactured by Kodaira Seisakusho Co., Ltd.) with a film thickness of about 50 μm, and then with a high pressure mercury lamp at a strength of 80 W / cm, about 200 mJ / cm ^2. A photopolymerized cured film of an acrylate monomer dispersion of zirconium oxide was obtained by irradiating with ultraviolet rays having the energy of 1.

<Characteristic evaluation of photopolymerized cured film>
a. Transparency of appearance Place the paper with the alphabet printed at 12 points under the polyethylene terephthalate film, and the transparency of the photopolymerized cured film obtained on the polyethylene terephthalate film can be distinguished through the cured film In terms of whether or not it was evaluated according to the following criteria. The results are shown in Table 1.
A: 12-point alphabet characters can be clearly distinguished.
○: A slight turbidity occurs in the cured film, but 12-point alphabet characters can be identified.
X: The cured film has turbidity, and 12-point alphabet characters cannot be identified.

B. Refractive index The refractive index of the photopolymerized cured film was measured at 25 ° C. using a prism coupler (MODEL 2010 / M) manufactured by Seki Technotron. The results are shown in Table 1.

C. Pencil hardness About the pencil hardness of the photopolymerization cured film, the photopolymerization cured film was scratched with a pencil having a predetermined hardness in accordance with JISK5400. The results are shown in Table 1.

As shown in Table 1, the dispersion of the present invention has excellent dispersibility (transparency of appearance) and a high refractive index, and the photopolymerized cured film of the dispersion of the present invention has excellent transparency and a high refractive index. It can be seen that it has good pencil hardness.

However, since the dispersions of Comparative Examples 1 to 4 were agglomerated, the viscosity and refractive index could not be measured, and there was turbidity. Further, the photopolymerized cured films of Comparative Examples 1 to 4 were turbid, and the refractive index and pencil hardness could not be measured.

In Table 1, EO represents ethylene oxide and PO represents propylene oxide.

The dispersion composition of the present invention includes a coating composition, a hybrid material, a sealant, 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.

Claims

A dispersion composition obtained by dispersing zirconium oxide particles in a dispersion medium using a dispersant composed of a compound represented by the following formula (1).

In the formula (1), R represents an alkyl group and / or alkenyl group having 1 to 24 carbon atoms,
AO in formula (1) represents an oxyalkylene group having 2 to 4 carbon atoms, n represents the average number of moles of alkylene oxide added, and ranges from 5 to 30;
X in the formula (1) is a linking group composed of a carbon atom, a hydrogen atom and / or an oxygen atom.
The dispersion composition according to claim 1, wherein X in the formula (1) is an alkylene group having 1 to 15 carbon atoms.
The dispersion composition according to claim 1, wherein X in the formula (1) is a substance represented by the following 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.
The dispersion composition according to claim 1, 2 or 3, wherein the dispersion medium is a double bond curable resin.
4. The dispersion composition according to claim 1, wherein the dispersion medium is a solvent in which a resin is dissolved.
A coating composition containing the dispersion composition according to claim 1, 2, 3, 4 or 5.
A member obtained by physically or chemically reacting after applying the coating composition according to claim 6 on a substrate.