TWI533925B - Dispersants and dispersant compositions - Google Patents

Description

Dispersant and dispersion composition

The present invention relates to a dispersant and a dispersion composition using the dispersant.

An isotropic material derived from an inorganic substance or an organic substance and/or an anisotropic material is used as a host material in the following fields of use: a hybrid material, a surface protective agent, a conductive paste, a conductive ink, and a sensor. , precision analysis components, optical memory, liquid crystal display components, nano magnets, heat transfer media, high performance catalysts for fuel cells, organic solar cells, nano glass components, abrasives, drug carriers, environmental catalysts, coatings, printing Ink, ink for inkjet, resist for color filters, ink for writing instruments, etc. In this case, the above-mentioned inorganic material or organic-derived isotropic material and/or anisotropic material is used as an inorganic dispersion (aqueous dispersion medium) or a non-aqueous dispersion medium (non-aqueous dispersion medium) as fine particles. By modulating the dispersion and utilizing it, it is industrially utilized as a substance which can improve the processing characteristics, the product characteristics, and the physical properties of the material, contributes to the stability of the quality, and improves the yield at the time of production.

On the other hand, in order to change the material of the dispersoid, to miniaturize the particle size, and to control the shape, it is difficult to stabilize the dispersoid and to disperse the dispersoid in the dispersion medium in a short time. The dispersoid agglomeration causes not only a decrease in productivity, a decrease in processing characteristics, a decrease in handleability, and a decrease in yield in the production of a dispersion, but also a decrease in product characteristics, material properties, and quality of the final product. Others, it is known that appearance, such as transparency, gloss, reduction in coloring power, color separation, and cracking, etc., are also caused. In order to suppress such dispersive agglomeration to achieve dispersion stabilization, a dispersant is used.

As a proposed low molecular weight dispersant, an organic compound having a carboxyl group, for example: in addition to formic acid, acetic acid, propionic acid, butyric acid, caproic acid, heptanoic acid, caprylic acid, capric acid, capric acid, undecanoic acid, laurel Acidic, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linoleic acid, and other saturated and unsaturated carboxylic acids having 1 to 20 carbon atoms, and hydroxycarboxylic acid, carbon number 6 to 34 alicyclic, aromatic carboxylic acids, and the like. The alkenyl succinic anhydrides include octenyl succinic anhydride, dodecenyl succinic anhydride, hexadecenyl succinic anhydride, and the like. An organic compound having a thiol group, for example, mercaptoethanol, mercapto-2-propanol, 1-mercapto-2,3-propanediol, 3-mercaptopropyltrimethoxydecane, mercaptosuccinic acid, hexyl mercaptan, pentane Alkyl mercaptans such as dithiol, dodecanethiol, undecyl mercaptan, and decyl mercaptan. Organic compounds having a phenol ring include, for example, triphenylphosphine, tributylphosphine, trioctylphosphine, tributylphosphine, and the like. Organic compounds having an amine group, such as: propylamine, butylamine, hexylamine, heptylamine, octylamine, 2-ethylhexylamine, decylamine, decylamine, dodecylamine, hexadecylamine, oleylamine ( Oleylamine) and so on.

In addition, a high molecular weight dispersant is mainly a polymer type dispersant having a skeleton such as a carboxyl group, an amine group, a hydroxyl group, an ester bond, a guanamine bond, an aromatic ring or a heterocyclic ring as a dispersant such as a pigment, and the like. For the purpose of this application, the DISPERBYK series manufactured by Byk Chemie, the Ciba EFKA series manufactured by EFKA Additives, the Solsperse series manufactured by Lubrizol, and the DISPARLON series of Nanben Chemical Company are commercially available.

Others, it is also proposed to use the existing surfactant as a dispersing agent, anionic surfactant, for example: higher fatty acid salt, alkyl sulfonate, α-olefin sulfonate, alkane sulfonate, alkyl benzene sulfonic acid Salt, sulfosuccinate salt, alkyl sulfate salt, alkyl ether sulfate salt, alkyl phosphate salt, alkyl ether phosphate salt, alkyl ether carboxylate, α-sulfo fatty acid methyl ester salt , methyl taurate and the like. Nonionic surfactants include, for example, glycerin fatty acid esters, polyglycerin fatty acid esters, sucrose fatty acid esters, sorbitan fatty acid esters, polyoxyethyl sorbitan fatty acid esters, polyoxygenated ethylene Alkyl ether, polyoxyethylene ethyl phenyl ether, polyoxyethyl alcohol ester, fatty acid alkanolamine, alkyl glucoside, and the like. The amphoteric surfactants include, for example, an alkylbetaine, a fatty acid guanamine propyl betaine, an alkylamine oxide, and the like. Examples of the cationic surfactant include an alkyltrimethylammonium salt, a dialkyldimethylammonium salt, an alkyldimethylbenzylammonium salt, an alkylpyridinium salt, and the like. Others include a fluorine-based surfactant and a polymer surfactant such as a cellulose derivative, a polycarboxylate or a polystyrene sulfonate.

In order to suppress the aggregation of the dispersion by using the above-mentioned conventional dispersant to obtain a stable dispersion composition, research is being conducted, but the dispersion medium and the dispersoid are diversified, the particle size of the dispersoid is miniaturized, and the shape is diverse. From the viewpoints of high quality, high product quality, high productivity, and high processing characteristics, the proposed dispersant cannot fully satisfy the required characteristics.

For example, when the dispersing medium (dispersion medium) is water, use: interface adsorption according to hydrophobic interaction of the dispersant, electro-adsorption by the ionic group, and π-electron interaction derived from the aromatic ring, Moreover, between the particles, the electrostatic repulsion between the particles caused by the formation of the electric double layer, the dispersion stabilization caused by the formation of the three-dimensional barrier, and the addition of the protective colloid and the thickener are effective methods, and the energy can be used. A variety of methods for achieving dispersion stabilization and agglutination inhibition are achieved.

On the other hand, in the non-aqueous dispersion medium, the effect of hydrophobic interaction, electrical interface adsorption caused by ionic groups, and electrostatic repulsion is extremely limited, so the adsorption of the dispersant on the interface of the dispersed particles is greatly determined. The acid-base interaction between the dispersed particles and a specific portion of the dispersing agent. In other words, in fact, the choice of dispersant will be individually optimized according to the surface characteristics of the dispersoid, and the use of the dispersant is in a very limited condition, and the actual situation is also related to the affinity of the dispersant to the dispersing medium. The optimum dispersant must be selected individually in conjunction with the dispersing medium used.

The above various ionic surfactants are extremely effective as a dispersing agent in water systems, but they are often difficult to dissolve in nonaqueous dispersion media, and their application range is extremely limited.

Further, when the size of the dispersed particles is a micron size, since the dispersion can be designed by a plurality of adsorption points and a high density and a thick protective layer of a three-dimensional barrier, it is preferable to select a high Molecular weight dispersant, but when the size of the dispersed particles is nanometer size and sub-nano size, the size of the dispersed particles is different from the size of the dispersant molecules, so it is designed by a high molecular weight dispersant. Dispersed systems are difficult or limited. In other words, since a high molecular weight dispersant having a size which is significantly larger than the size of the dispersed particles is used, a plurality of points may occur between the dispersed particles and the dispersing agent and between the molecules of the dispersing agent and the molecules of the dispersing agent. Adsorption, intertwining, and bridging promote the aggregation of dispersed particles, so there is a fundamental problem in terms of dispersion stabilization.

Furthermore, in order to achieve dispersion stabilization, the usual method is to design a dispersion system by using a stronger interaction between the dispersed particles and the dispersant, but in addition to the displacement and polarity change of the dispersion medium, the dispersion composition is ensured. In addition to the mechanical and chemical stability of the material, the removal of the dispersed particles, and the formation of a film (high gloss, film formation at a low temperature and in a short period of time), when the dispersant is removed, it is required to have both performance and ease. The property of detachment from the interface of the dispersant is an important factor in the improvement of productivity, processing characteristics, and quality stabilization of the final product. In this regard, existing dispersants also do not adequately meet the required properties.

In addition, a composite material in which nanometer-sized inorganic fine particles (particle diameter: 1 to 100 nm) or organic fillers and pigments are finely dispersed in a resin is called a polymer nanocomposite, but a nanometer-sized particle system is used. Since it is easy to aggregate and has low affinity for the resin, it is extremely difficult to uniformly disperse in the resin. When the nanoparticles having a nanometer size are uniformly dispersed in the resin, it may be difficult or limited to use the aqueous dispersion medium. In an effective method, a dispersion agent is usually used to uniformly disperse the nanoparticles in a non-aqueous dispersion medium to prepare a dispersion, and The resin is dissolved in the dispersion and mixed, or the solution in which the resin is dissolved in a solvent is mixed with the above dispersion, and dissolved and dispersed.

Further, as the metal particles, metal oxides, pigments, and various fillers can be easily redispersed in the dispersion medium and the resin, it is known to coat the particles with a surface modifier and a surface protective agent. Or a technique in which a surface modifying agent or the like is impregnated into a dispersed particle to be utilized, but the prior art is often limited by the kind of the dispersing medium and the amount of the dispersing substance added, and the utilization range is extremely limited, and no dispersion has been found which can solve the problem. Agent or surface modifier and surface protectant. A dispersant which solves the above problems, that is, a dispersant which is versatile for a wide range of materials without being limited by the kind of the dispersing medium and the amount of the dispersing agent, and a non-aqueous dispersion using the dispersing agent, And in the form of a powdery, granular or syrup which is obtained by dispersing or impregnating the dispersing agent with a dispersing agent as a surface modifying agent or a surface protecting agent of a dispersing agent, such a solvent replacement and From the viewpoint of changing the polarity and mixing with a resin or a resin solution, industrial use is extremely valuable.

For example, as such a prior art, Patent Document 1 discloses a metal colloidal particle composed of a metal nanoparticle (A) and a protective colloid (B) coated with the metal nanoparticle (A), and The protective colloid (B) is composed of an organic compound (B1) having a carboxyl group and a polymer dispersant (B2).

[Previous Technical Literature]

(Patent Literature)

Patent Document 1: Japanese Patent Laid-Open Publication No. 2009-74171

Patent Document 1 discloses a dispersing agent having a carboxyl group. This dispersing agent is useful when the dispersing medium is water, but has poor dispersibility in the non-aqueous dispersing medium.

The present invention has been developed in view of the problems of the prior art, and an object thereof is to provide a dispersant for a non-aqueous dispersion medium which is applicable to a wide range of dispersoids and which exhibits excellent performance by adding a small amount. Decentralized stability.

Further, it is an object of the present invention to provide a dispersion composition which is obtained by using the dispersant.

Further, an object of the present invention is to provide an organic particle or an inorganic particle which is coated with the dispersing agent or impregnated with the dispersing agent.

In order to achieve the above object, the dispersant for a non-aqueous dispersion medium of the present invention is composed of a compound represented by the following formula (1).

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

However, the meaning of the symbol of the formula (2) is as follows. Y is any one selected from the group consisting of an alkyl group having 1 to 15 carbon atoms, a vinyl group, a phenyl group, and a phenyl group having a carboxyl group. Preferably, it is an organic particle and/or inorganic particle which is coated with the above dispersing agent or impregnated with the dispersing agent. It is preferably a dispersion composition obtained by dispersing organic particles or inorganic particles in a non-aqueous dispersion medium using the above dispersant. Preferably, it is a member obtained by physically or chemically reacting a coating composition onto a substrate, the coating composition comprising: the above dispersion composition, the dispersion composition The system uses a resin as a non-aqueous dispersion medium. Preferably, it is a member obtained by physically or chemically reacting a coating composition onto a substrate, the coating composition comprising: mixing the dispersion composition with a resin As a result, the dispersion composition uses a solvent as a non-aqueous dispersion medium.

[Preferred form of implementing the invention]

The dispersant for a non-aqueous dispersion medium of the present invention is composed of a compound represented by the following formula (1).

The dispersant for a non-aqueous dispersion medium of the present invention comprises, as shown in the formula (1), a dispersing medium affinity portion comprising an alkylene oxide chain and a dispersing affinity portion. It is composed of a carboxyl group; wherein the dispersing medium affinity portion and the dispersing substance affinity portion are linked by a linking group X. However, the meaning of the symbol of the formula (1) is as follows. R represents an alkyl group and/or an alkenyl group having a branched alkyl group and/or an alkenyl group and having a carbon number of 1 to 24. AO represents an oxygen alkyl group having a carbon number of 1 to 4, and n represents an average addition mole number of the alkylene oxide and is in the range of 1 to 30. X represents a linking group composed 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. Hydrophobic group (R)

The hydrophobic group (R) which can be used in the dispersant of the present invention, R is a hydrocarbon group derived from an alcohol, and R is an alkyl group and/or an alkenyl group having a carbon number of 1 to 24 and a branched form. When R is an alkyl group and/or an alkenyl group, the carbon number of the starting material alcohol which can be used may be a single one or a mixture of alcohols having different carbon numbers. Further, the starting material alcohol may be derived from synthesis or derived from nature, and further, the chemical structure may be a single composition or a mixture of a plurality of isomers.

The raw material alcohols which can be used may be selected from conventional ones, and specific examples include butanol, isobutanol, pentanol and/or its isomers, hexanol and/or its isomers, heptanol and/or Or an isomer thereof, octanol and/or its isomer, 3,5,5-trimethyl-1-hexanol, a higher olefin derived from propylene or butene or a mixture thereof and a ketone Isodecyl alcohol, isodecyl alcohol, isoundecyl alcohol, isododecyl alcohol, isotridecyl alcohol manufactured by the oxo method, NEODOL 23, 25, 45 manufactured by Shell Chemicals Co., Ltd., manufactured by Sasol Co., Ltd. SAFOL 23, EXXAL 7, EXXAL 8N, EXXAL 9, EXXAL 10, EXXAL 11, and EXXAL 13, manufactured by Exxon Mobil Co., Ltd. are also examples of higher alcohols which can be preferably used. Also, it is derived from natural octanol, decyl alcohol, lauryl alcohol (1-dodecanol), myristyl alcohol (1-tetradecanol), cetyl alcohol (1-hexadecanol), stearyl alcohol ( 1-octadecyl alcohol), oleyl alcohol (cis-9-octadecen-1-ol), etc., are also examples of higher alcohols that can be used. Further, a single composition of a Guerbet Alcohol having a chemical structure of a 2-alkyl-1-alkanol type, or a mixture thereof, is also an example of a higher alcohol which can be preferably used, except for 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-nonanol, 2-heptyl-1-undecyl alcohol, 2-octyl-1-dodecanol, 2-mercapto-1-beta In addition to the alkanol, there are also isostearyl alcohol derived from a branched alcohol. Further, the above various alcohols may be used in combination of two or more kinds. However, the dispersant of the present invention, as described above, when the preferred hydrophobic group (R) is a hydrocarbon group derived from an alcohol, and is a C 3-24 group and a branched alkyl group and/or an alkenyl group. When it is 70% by weight or more, it can be preferably used for the purpose of the present invention.

Further, when the hydrophobic group (R) is hydrogen or a hydrocarbon group having 1 to 2 carbon atoms, or a carbon number exceeding 25, and even if the carbon number of the hydrophobic group (R) is in the range of 3 to 24, when linear When the content of the alkyl group and/or alkenyl group exceeds 30% by weight, the dispersion may not be stably dispersed in the non-aqueous dispersion medium, or the range of the dispersion medium that can be used may be limited, or in the dispersion. In the modulating step, different types of dispersing media are replaced or mixed. As a result, the stability of the dispersion is remarkably lowered, and deposits are immediately generated, or the stability over time is remarkably lowered to cause problems such as a decrease in the added value of the final product, a decrease in productivity, a decrease in processing characteristics, and deterioration in quality. In order to avoid such problems and to make the action of the dispersing agent of the present invention particularly effective, the hydrophobic group (R) is preferably a branched alkyl group having 8 to 18 carbon atoms.

2. Oxyalkylene (AO) _n

In the dispersant of the present invention, a preferred alkylene oxide type, in the formula (1), AO represents an oxygen alkyl group having a carbon number of 1 to 4, specifically, a carbon number 2 alkylene oxide is a ring. Oxyethane. The alkylene oxide having a carbon number of 3 is propylene oxide. The alkylene oxide having a carbon number of 4 is tetrahydrofuran or butylene oxide, preferably 1,2-butylene oxide or 2,3-butylene oxide. In the dispersant of the present invention, the alkyl chain (-(AO) _n -) is an alkylene chain, and the alkylene oxide may be a single polymer chain or two or more rings for the purpose of adjusting the dispersion medium affinity of the dispersant. A random polymeric chain or a block polymeric chain of oxane, and may also be a combination thereof. The formula (1) represents an average addition molar number of alkylene oxides in the range of 1 to 30, preferably in the range of 3 to 20.

3. Linkage base (X)

The linking group (X) may be selected from a conventional structure composed of a carbon atom, a hydrogen atom or an oxygen atom, and is preferably composed of a saturated hydrocarbon group, an unsaturated hydrocarbon group, an ether group, a carbonyl group or an ester group, and may have an alicyclic ring. Construction, aromatic ring construction, and may also have repeating units. When the linking group X contains a nitrogen atom and/or a sulfur atom and/or a phosphorus atom or the like, it has an effect of lowering the affinity of the carboxyl group for the dispersing substance, and thus is not suitable as a structural factor of the dispersing agent of the present invention.

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

Further, X of the formula (1) is preferably a substance represented by the following formula (2).

However, the meaning of the symbol of the formula (2) is as follows.

Y is any one selected from the group consisting of an alkyl group having 1 to 15 carbon atoms, a vinyl group, a phenyl group, and a phenyl group having a carboxyl group.

4. Better dispersant

In the present invention, the dispersing agent described in the following formula (3) can be more preferably used.

However, in the formula (3), R is preferably a branched alkyl group having 8 to 18 carbon atoms, and n is an average addition molar number of ethylene oxide, preferably in the range of 3 to 20. When the composition of the dispersing agent is limited to this range, the applicability to the following cases can be improved: the range of selection of the non-aqueous dispersing medium which can be used when preparing the dispersion is expanded; and the different kinds of dispersing media are mixed and replaced. Thus, by limiting the composition range of the dispersant, the stability of the dispersion can be more preferably achieved, and as a result, the added value of the final product can be improved, the productivity can be improved, the processing characteristics can be improved, and the quality can be stabilized. .

5. Method for producing dispersant

The dispersant of the present invention can be produced by a known method. It can be produced by, for example, using a conventional nonionic surfactant compound in which an alkylene oxide is added to an alcohol, an amine or a mercaptan by a conventional method. a method of reacting a monohalogenated lower carboxylic acid or a salt thereof with a hydroxyl group at the terminal of an alkylene oxide in the presence of a base, or a ring opening reaction with a hydroxyl group at the terminal of an alkylene oxide by using an acid anhydride, but is not limited thereto These methods.

6. Dispersing the particles

The dispersed particles dispersed by the dispersing agent of the present invention can be selected from particles derived from inorganic substances and/or particles derived from organic substances.

For example, particles derived from inorganic materials may be used: iron, aluminum, chromium, nickel, cobalt, zinc, tungsten, indium, tin, palladium, zirconium, titanium, copper, silver, gold, platinum, etc.; and such alloys; a mixture of these. In this case, in order to stably remove the metal particles from the medium, they may be coated with the following protective agents: alkanic acids and fatty acids, hydroxycarboxylic acids, alicyclic, aromatic carboxylic acids, alkenyl succinic anhydrides, sulfur Alcohols, phenol derivatives, amines, amphiphilic polymers, polymeric surfactants, low molecular surfactants, and the like. Others include: 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 citrate, zirconium oxide, magnesium oxide, aluminum oxide, titanium oxide, iron oxide, zinc oxide, antimony trioxide, indium oxide, indium tin oxide, antimony carbide, antimony nitride, boron nitride, titanic acid钡, diatomaceous earth, carbon black, graphite, rock wool, glass wool, glass fiber, carbon fiber, carbon nanofiber, carbon nanotube (single-walled nanotube, double-walled nanotube, multi-walled nanotube) Wait.

Further, the particles derived from organic substances include azo-based, diazo-based, condensed azo-based, thioindole-based, indanthrone-based, quinacridone-based, lanthanide, and benzimidazole. Ketone system, perylene system, phthalocyanine system, anthrapyridine system, two (dioxazine) and other organic pigments; polyethylene resin, polypropylene resin, polyester resin, nylon resin, polyamide resin, aromatic polyamide resin, acrylic resin, vinylon resin, amine ester ( Urethane) resin, melamine resin, polystyrene resin, polylactic acid, acetate fiber, cellulose, hemicellulose, lignin, chitin, chitosan, starch, polyacetal, aromatic Polyamide, polycarbonate, polyphenylene ether, polyetheretherketone, polyetherketone, polybutylene terephthalate, polyethylene naphthalate, polybutylene naphthalate, polysulfone ), polyphenylene sulfide, polyimine, and the like.

The dispersion particles dispersed in the dispersant of the present invention may be crystalline or amorphous. Further, the dispersion particles dispersed in the dispersant of the present invention may be anisotropic particles or anisotropic particles, or may be fibrous.

In the present invention, the above-mentioned dispersed particles which are dispersed may be obtained by a known method. There are two methods for preparing fine particles: a top-down method in which coarse particles are mechanically ground and refined, and a cluster in which a plurality of unit particles are generated and agglomerated by the particles. The state is to form a bottom-up manner of the particles, and it is preferred to use a method modulated by either method. In addition, these may be by any of the wet method and the dry method. In addition, the bottom-up approach has physical methods and chemical methods, but can be by any method. The dispersing agent of the present invention can be used in a step of mechanically grinding and refining coarse particles in a top-down manner, or can be formed in a cluster state in which a plurality of unit particles are formed and agglomerated by the particles. It is used in the step of the bottom-up method, or the following particles may be used: after the particles are prepared in advance by the aforementioned method, the surface-modified agent or surface protection is called in order to stably take out the dispersed particles from the medium. A conventional protective agent for coating or removing particles after impregnation. The protective agent can be used in place of the aforementioned conventional dispersing agent.

In order to more specifically explain the bottom-up method, a method of modulating the metal nanoparticles in the dispersion particles is exemplified. In the bottom-up mode, a representative example of the physical method is an evaporation method in which a bulk metal is evaporated in an inert gas and condensed by collision with a gas to form a nanoparticle. In addition, the chemical method includes: a liquid phase reduction method in which a metal ion is reduced in a liquid phase in the presence of a protective agent, and the generated zero-valent metal is stabilized in a nanometer size; and a thermal decomposition method of the metal complex Wait. The liquid phase reduction method can be carried out by a chemical reduction method, an electrochemical reduction method, a photoreduction method, or a method in which a chemical reduction method and a light irradiation method are combined.

Further, the dispersed particles which can be preferably used in the present invention can be obtained by any one of the top-down manner and the bottom-up manner as described above, and these can be used in the water system, the non-aqueous system, and the gas phase. Modulation in an environment.

7. Dispersing media

Examples of the dispersing medium which can be used in the present invention include toluene, xylene, an aromatic hydrocarbon solvent, a hydrocarbon solvent such as n-hexane, cyclohexane or n-heptane; dichloromethane, chloroform, dichloroethane, etc. Halogenated hydrocarbon solvent; ether, isopropyl ether, two Dioxane, tetrahydrofuran, dibutyl ether, butyl ethyl ether, methyl tertiary butyl ether, terpinyl methyl ether, dihydroterpine methyl ether, diethylene glycol An ether solvent such as diglyme or 1,3-dioxolane; acetone, acetophenone, methyl ethyl ketone, methyl propyl ketone, diethyl ketone, methyl butyl ketone Ketone, methyl isobutyl ketone, dipropyl ketone, diisobutyl ketone, methyl amyl ketone, acetonyl acetone, isophorone, cyclohexanone, methylcyclohexanone, 2-(1- a ketone solvent such as cyclohexenyl)cyclohexanone, methyl isobutyl ketone, cyclohexanone or isophorone; ethyl formate, propyl formate, butyl formate, isobutyl formate, amyl formate, acetic acid Methyl ester, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, butyl acetate, isoamyl acetate, cyclohexyl acetate, ethyl lactate, acetic acid 3-methoxybutyl ester, diethylhexyl acetate, 2-ethylbutyl acetate, 2-ethylhexyl acetate, benzyl acetate, methyl propionate, ethyl propionate, methyl chloroacetate, Ethyl chloroacetate, butyl chloroacetate, B An ester solvent such as methyl acetate, ethyl acetate, butyl propionate, isoamyl propionate or γ-butyrolactone; ethylene glycol monoethyl ether, ethylene glycol monoisopropyl ether, 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, a glycol ether solvent such as triethylene glycol mono-n-propyl ether, triethylene glycol mono-n-butyl ether, tripropylene glycol monoethyl ether, tripropylene glycol mono-n-propyl ether or tripropylene glycol mono-n-butyl ether; The monoether type acetate solvent; diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl isobutyl ether, dipropylene glycol dimethyl ether, dipropylene glycol A dialkyl ether solvent such as diethyl ether. Methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, secondary butanol, tertiary butanol, heptanol, n-pentanol, secondary pentanol, n-hexanol, tetrahydrofurfuryl alcohol, decyl alcohol , allyl alcohol, chlorohydrin, octyldodecanol, 1-ethyl-1-propanol, 2-methyl-1-butanol, isoamyl alcohol, tertiary pentanol, secondary isoamyl alcohol, Neopentyl alcohol, hexanol, 2-methyl-1-pentanol, 4-methyl-2-pentanol, heptanol, n-octanol, 2-ethylhexanol, decyl alcohol, decyl alcohol, undecane Alcohol, lauryl alcohol, cyclopentanol, cyclohexanol, benzyl alcohol, alpha-terpineol, terpineol C, L-alpha-terpineol, dihydroterpineol, terpineoloxyethanol, Dihydroterpineol oxyethanol, Tersorb MTPH, Tersorb DTO-210, Tersorb THA-90, Tersorb THA-70, and cyclohexanol, 3-methoxybutanol, diacetone alcohol, manufactured by Japan Terpene Chemical Co., Ltd. , 1,4-butanediol, octanediol, etc., and alcoholic solvents such as FINEOXOCOL 140N, FINEOXOCOL 1600, FINEOXOCOL 180, FINEOXOCOL 180N, FINEOXOCOL 2000, manufactured by Nissan Chemical Industries, Ltd.; ethylene glycol, diethylene glycol , triethylene glycol, propylene glycol, dipropylene A glycol-based solvent such as a diol, 1,3-butanediol, hexanediol, polyethylene glycol or polypropylene glycol. Other examples include a guanamine-based solvent such as dimethylacetamide or dimethylformamide. Further, as the dispersion medium, ethylene such as a (meth)acrylic acid, a (meth) acrylate or a vinyl monomer such as a vinyl acetate, a vinyl ether derivative or a polyallyl derivative may be used. Is an unsaturated monomer.

Others may be used without any particular limitation: various types of resins, oligomers, and monomers which are used for coating, adhesion, and molding. Specific examples thereof include an acrylic resin, a polyester resin, an alkyd resin, an amine ester resin, a silicone resin, a fluororesin, an epoxy resin, a polycarbonate resin, a polyvinyl chloride resin, and a polyethylene. Alcohol, etc. Further, the above-mentioned dispersion medium may be used singly or in combination of two or more kinds as appropriate.

Furthermore, the purpose of the dispersing agent of the present invention is to provide a fine particle dispersion in a non-aqueous environment, but for the above-mentioned dispersion medium, either intentionally or accidentally, in the manufacturing step of the fine particle dispersion, or for the intended use, or When designing the final product, there is no denying that water will mix in and mix.

8. Other

The dispersing agent of the present invention can be produced by a known method, and the type of the hydrophobic group, the type of the alkylene oxide, the addition form thereof, the amount of the added molar amount, the linking group, and the like are particularly limited in the above range. Optimum composition, and in comparison with the conventional dispersant, a wider variety of dispersoids can be dispersed, and the dispersibility can be dispersed and stabilized in a wider variety of dispersing media, and the industrial use value is equivalent. Big.

Further, the dispersant of the present invention can be used by a conventional purification method to reduce the content of the ion species contained therein, particularly the content of each ion of an alkali metal ion, an alkaline earth metal ion, a heavy metal ion, and a halogen ion. The ionic species in the dispersant, due to dispersion stability to the dispersion, corrosion resistance, oxidation resistance, electrical properties of the dispersed coating film (conductive properties, insulating properties), stability over time, heat resistance, low humidity, weather resistance Sexual influence is greatly affected, so the content of the above ions can be appropriately determined, but it is preferably less than 10 ppm in the dispersant.

In the present invention, the content of the dispersion medium in which the particles are dispersed is not particularly limited as long as it can be uniformly dispersed in the non-aqueous dispersion medium, and varies from 0.5 to 70% by mass, depending on the use and the like. The range is better. Further, the average particle diameter of the dispersed particles is preferably in the range of 1 to 500 nm, and more preferably in the range of 10 to 100 nm. Further, the preferred use conditions of the dispersant of the present invention are preferably in the range of from 1 to 300% by weight based on the dispersed particles.

Further, the dispersion composition of the present invention can be prepared by a conventional stirring means, a homogenizing means, or a dispersing means. Examples of the dispersing machine that can be used include, for example, a roll mill such as a 2-roll or a 3-roll mill, a ball mill such as a ball mill or a vibrating ball mill, a paint shaker, a continuous disc type bead mill, and a continuous loop type bead mill. Such as bead mill, sand mixer, jet mill, etc. In addition, dispersion treatment can also be carried out in an ultrasonic generation bath.

Further, the dispersant of the present invention not only stabilizes the dispersion of the dispersed particles in the non-aqueous dispersion medium, but also exhibits a superior dispersion stabilization effect by a known technique, and can also serve as a dispersion carrier. Use a protective agent that is safely removed from the media. The function of the protective agent for removing the dispersed particles from the medium in a stable manner is, for example, inhibition of aggregation of generated particles, inhibition of adsorption on the wall surface of the container, prevention of contamination, impartability of redispersibility, prevention of oxidation of metal particles, The surface modification of the particle surface, the deterioration of the functional surface, the relaxation of the solvent and the change of the polarity, the improvement of the fluidity of the powder, and the prevention of the curing of the powder. The dispersant of the present invention is more excellent than the conventional protective agent, and the desired form can be obtained by selecting the optimum addition form of the alkylene oxide, the addition amount of the molybdenum, the type of the hydrophobic group, and the linking group. The dispersoids are dispersed and stabilized in a dispersion medium which is broader than conventional protective agents.

a substrate to which a coating composition comprising the dispersion composition of the present invention is applied, and the dispersion composition uses a resin as a non-aqueous dispersion medium or a mixture comprising the dispersion composition of the present invention and a resin. The composition is applied and the dispersion composition is a non-aqueous dispersion medium using, for example, glass, a resin film, a glass composite material, a ceramic, a metal/steel plate, or the like.

According to the present invention, it is possible to provide a dispersant for a non-aqueous dispersion medium which is applicable to a wide range of dispersoids and which exhibits excellent dispersion stability by adding a small amount. Further, a dispersion composition which is formed using the dispersant and which provides a film composed of the dispersion composition can be provided. Further, an organic particle or an inorganic particle may be provided which is coated with the dispersing agent or impregnated with the dispersing agent.

[Examples]

Hereinafter, examples and comparative examples of the present invention will be described. In addition, hereinafter, "parts" indicating the amount of blending means "parts by weight", and "%" means "weight%". The present invention is not limited to the following embodiments, and may be appropriately modified and modified without departing from the technical scope of the invention.

<Synthesis of Dispersant> [Production Example 1 (Synthesis of Dispersant 1)]

To the reactor, 598 g (1 mol) of 10 mol of an isodecyl alcohol ethylene oxide and 151 g (1.3 mol) of sodium chloroacetate were added to the reactor, and the mixture was stirred to be uniform. Then, 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 to carry out a reaction for 3 hours. After the reaction, a white suspension solution was obtained by dropwise addition of 120 g (1.2 mol) of 98% sulfuric acid. Next, the white suspension solution was washed with distilled water, and the solvent was distilled off under reduced pressure to obtain a dispersant 1 (R: isodecyl group, AO: ethylene oxide, n: 10, X: CH ₂ ) .

[Production Example 2 (Synthesis of Dispersant 2)]

The same procedure as in Production Example 1 was carried out, except that 598 g (1 mol) of a 2-methyl-1-heptanol ethylene oxide 10 mol adduct was used, and 598 g (1 mol) of an isodecyl alcohol ethylene oxide 10 mol adduct was substituted. Operation was carried out to obtain Dispersant 2 (R: 2-propyl-1-heptyl, AO: ethylene oxide, n: 10, X: CH ₂ ).

[Production Example 3 (Synthesis of Dispersant 3)]

The same operation as in Production Example 1 was carried out, except that 640 g (1 mol) of an isotridecyl alcohol ethylene oxide 10 mol adduct was used, and 598 g (1 mol) of an isodecyl alcohol ethylene oxide 10 mol adduct was substituted. Dispersant 3 (R: isotridecyl, AO: ethylene oxide, n: 10, X: CH ₂ ).

[Production Example 4 (Synthesis of Dispersant 4)]

The same operation as in Production Example 1 was carried out, except that 1080 g (1 mol) of an isotridecyl alcohol ethylene oxide 20 mol adduct was used, and 598 g (1 mol) of an isodecyl alcohol ethylene oxide 10 mol adduct was substituted. Dispersant 4 (R: isotridecyl, AO: ethylene oxide, n: 20, X: CH ₂ ).

[Production Example 5 (Synthesis of Dispersant 5)]

In addition to using branched C11-14 alcohol (product name: EXXAL 13, manufactured by Exxon Mobil Co., Ltd.), ethylene oxide 5 mol / propylene oxide 5 mol random adduct 710 g (1 mol), substituted isodecyl alcohol ethylene oxide 10 mol The same operation as in Production Example 1 was carried out except for the addition of 598 g (1 mol) to obtain a dispersing agent 5 (R: branched C11-14 alkyl group, AO: ethylene oxide and propylene oxide, n: 10, X: CH ₂ ).

[Manufacturing Example 6 (Synthesis of Dispersing Agent 6)]

In addition to the use of branched C11-14 alcohol (product name: EXXAL 13, manufactured by Exxon Mobil), propylene oxide 2 mol / ethylene oxide 8 mol block adduct 668 g (1 mol), substituted isodecyl alcohol ethylene oxide 10 mol The same operation as in Production Example 1 was carried out except for the addition of 598 g (1 mol) to obtain a dispersing agent 6 (R: branched C11-14 alkyl group, AO: propylene oxide and ethylene oxide, n: 10, X: CH ₂ ).

[Production Example 7 (Synthesis of Dispersant 7)]

A dispersant was obtained in the same manner as in Production Example 1, except that 954 g (1 mol) of an isobutanol ethylene oxide 20 mol adduct was used, and 598 g (1 mol) of an isodecyl alcohol ethylene oxide 10 mol adduct was substituted. 7 (R: isobutyl, AO: ethylene oxide, n: 20, X: CH ₂ ).

[Production Example 8 (synthesis of dispersant 8)]

The same operation as in Production Example 1 was carried out except that 306 g (1 mol) of an isobutanol propylene oxide 4 mol adduct was used instead of 598 g (1 mol) of an isodecyl alcohol ethylene oxide 10 mol adduct, and a dispersing agent 8 was obtained. (R: isobutyl group, AO: propylene oxide, n: 4, X: CH ₂ ).

[Production Example 9 (Dispersant Synthesis of Dispersant 9)]

A mixture of 954 g (1 mol) of isobutanol ethylene oxide 20 mol of adipate and 156 g (1 mol) of suberic anhydride was reacted at 120 ° C for 2 hours to obtain a dispersant 9 (R: isobutyl group, AO: ethylene oxide, n: 20, X: CO(CH ₂ ) ₆ ).

[Production Example 10 (Dispersant Synthesis of Dispersant 10)]

510 g (1 mol) of a 2-methyl-1-heptanol ethylene oxide 8 mol adduct and 100 g (1 mol) of succinic anhydride were reacted at 120 ° C for 2 hours to obtain a dispersing agent 10 (R: 2-propyl-1). -heptyl, AO: ethylene oxide, n: 8, X:COCH ₂ CH ₂ ).

[Production Example 11 (Dispersant Synthesis of Dispersant 11)]

A mixture of 598 g (1 mol) of isodecyl alcohol ethylene oxide and 98 g (1 mol) of maleic anhydride was reacted at 120 ° C for 2 hours to obtain a dispersant 11 (R: isodecyl group, AO: ethylene oxide, n: 10, X: COCH = CH).

[Production Example 12 (Dispersant Synthesis of Dispersant 12)]

A reaction product of 640 g (1 mol) of isotridecyl alcohol ethylene oxide and 98 g (1 mol) of maleic anhydride was reacted at 120 ° C for 2 hours to obtain a dispersant 12 (R: isotridecyl group, AO: ring) Oxyethane, n: 10, X: COCH = CH).

[Production Example 13 (Synthesis of Dispersant 13)]

In addition to the use of an isotridecyl alcohol (80% by weight) / lauryl alcohol (20% by weight) mixture of ethylene oxide 10 mol adduct 637 g (1 mol), substituted isodecyl alcohol ethylene oxide 10 mol adduct 598 g (1 mol The same operation as in Production Example 1 was carried out, except that Dispersant 13 (R: isotridecyl and lauryl, AO: ethylene oxide, n: 10, X: CH ₂ ) was obtained.

[Production Example 14 (Dispersant Synthesis of Dispersant 14)]

A solution of 954 g (1 mol) of isobutanol ethylene oxide 20 mol and 192 g (1 mol) of trimellitic anhydride were reacted at 120 ° C for 2 hours to obtain a dispersant 14 (R: isobutyl group, AO: ethylene oxide) , n: 20, X: COC ₆ H ₃ ).

[Example 1]

1.5 parts (in terms of solid content) of the dispersing agent of the present invention or 1.5 parts of a dispersing agent of a comparative example (in terms of solid content), dissolved in a solvent (isopropanol or diethylene glycol monobutyl) In 68.5 parts of the ether ether acetate, 30 parts of magnesium oxide (MgO) as a dispersoid and 100 mL of zirconia balls having a diameter of 10 mm were further added, and the obtained solution was subjected to a refining treatment for 24 hours using a ball mill. The dispersant is composed of a compound represented by the formula (1) comprising a hydrophobic group (R), an oxygen extended alkyl group (-(AO) _n -) and a linking group (X) having the composition shown in Table 1 below. The dispersant of this comparative example is a compound represented by the formula (1) comprising a hydrophobic group (R), an oxygen extended alkyl group (-(AO) _n -) and a linking group (X) having the composition shown in Table 2 below. Composition. As a result, after the obtained treatment liquid was transferred to a transparent container, the treatment liquid was observed with the naked eye, and the dispersibility of the treatment liquid in the container was evaluated on the basis of the following criteria. The results are shown in Tables 1 and 2.

◎: All the dispersoids were dispersed in the solution, and no deposit was observed at the bottom of the container.

○: Most of the dispersoid was dispersed in the solution, but a very small deposit was observed at the bottom of the container.

×: A small piece of the dispersoid was observed in the solution, or the solution was cloudy.

As is clear from Table 1, the dispersing agent of the present invention is excellent in dispersibility.

[Embodiment 2]

The dispersant of the present invention (numbered as 1, 2, 3, 4, 7, 10, 12, 13 shown at the left end of Table 3) is a predetermined amount or a dispersant of the comparative example (Comparative Example 1 shown in Table 3) , 2, 3, 5, 11) a predetermined amount, dissolved in a predetermined amount of methyl ethyl ketone as a dispersing medium, and then added 5 parts of zirconium oxide (ZrO ₂ ) as a dispersoid, and then used by Shou Industrial Co., Ltd. The obtained solution was subjected to miniaturization treatment for 2 hours under the trade name ULTRA APEX MILL UAM-005 (using a zirconia bead having a diameter of 50 μm at a peripheral speed of 10 m/sec), and the dispersant of the present invention was contained in the following Table 3. The composition of the hydrophobic group (R), the oxygen extended alkyl group (-(AO) _n -) and the linking group (X) is represented by the formula (1), and the dispersing agent of the comparative example is composed of the following Table 3. A compound represented by the formula (1) of the hydrophobic group (R), the oxygen-extended alkyl group (-(AO) _n -) and the linking group (X) of the composition shown. As a result, after the obtained treatment liquid was transferred to a transparent container, the treatment liquid was observed with the naked eye, and the dispersibility of the treatment liquid in the container immediately after the miniaturization treatment was evaluated on the same basis as above, and 24 The dispersion stability of the treatment liquid (0.25 parts of dispersant and 5 parts of dispersion liquid) in the container after an hour. Further, a part of the treatment liquid (the dispersion liquid was 0.25 parts and the dispersion liquid was 5 parts), and the particle size of the zirconia immediately after the miniaturization treatment was measured using Microtrac UPA MODEL 9230. Further, the blending amount of methyl ethyl ketone relative to the dispersing agent is 0.5 parts, 0.25 parts, 0.15 parts, 0.05 parts with respect to the dispersing agent, and methyl ethyl ketone is 94.5 parts, 94.75 parts, 94.85 parts, and 94.95, respectively. Share. The visual evaluation of the above dispersibility and dispersion stability and the particle size measurement results of zirconia are shown in Table 3.

Further, the dispersant of the present invention or the dispersant of the comparative example, methyl ethyl ketone as a dispersing medium, and zirconium oxide as a dispersing substance were prepared into a dispersion in a ratio of 0.25 parts: 94.75 parts: 5 parts. And 70 parts of this dispersion was mixed with 70 parts of a methyl ethyl ketone solution containing 25 parts of an acrylic resin (trade name ACRYPET VH by Mitsubishi Rayon Co., Ltd.), and after obtaining a dispersion liquid, the product of Shou Industrial Co., Ltd. was used. The dispersion was subjected to a refinement treatment for 2 hours by ULTRA APEX MILL UAM-005 (using a zirconia bead having a diameter of 50 μm at a peripheral speed of 10 m/sec), and the dispersant of the present invention was composed of the composition shown in Table 3 below. A compound represented by the formula (1) is used, and the dispersant of the comparative example is composed of a compound represented by the formula (1) having the composition shown in the following Table 3. As a result, after the obtained treatment liquid was transferred to a transparent container, the treatment liquid was observed with the naked eye, and the dispersibility of the treatment liquid in the container was evaluated on the same basis as above. The results are shown in Table 3.

Further, the dispersion (the latter was subjected to a refining treatment for 2 hours) was applied onto a clean glass plate having a thickness of 10 mm, and then dried at 120 ° C for 1 hour using a dryer to obtain a coating film. Next, after the paper having the letter printed in the 12th mark is placed under the glass plate, the transparency of the coating film obtained on the glass plate is evaluated from the viewpoint of whether or not the letter can be recognized through the coating film. . The results are shown in Table 3.

◎: The letter text of the 12th word can be clearly recognized.

○: The coating film produced a slight turbidity, but the letter text of the 12th word was still recognized.

×: The coating film is turbid, and the letter of the 12th word cannot be recognized.

[table 3]

As is clear from Table 3, the dispersing agent and the dispersion stability of the present invention were excellent. Further, as shown in Table 3, the particle diameter of the dispersoid in the dispersion obtained by using the dispersant of the present invention is much smaller than the particle diameter of the dispersoid in the dispersion of the comparative example, and this fact is the dispersion of the present invention. Evidence of excellent dispersion. Further, as shown in Table 3, the coating film composed of the dispersion of the present invention was excellent in transparency, and it was confirmed that the dispersion of the present invention has excellent dispersibility.

Further, the dispersion stability of the dispersant of the comparative example was not measured. Further, the particle diameters of the zirconia of Comparative Example 3, Comparative Example 5, and Comparative Example 11 were not measured.

[Example 3]

Dispersion of 1 part of the dispersant of the present invention (numbered 1, 2, 3, 4, 12 shown at the left end of Table 4) or comparative example (comparative examples 1, 2, 3, and 14 shown in Table 4) 1 part of the solution, dissolved in 70 parts of diethylene glycol monobutyl ether acetate as a dispersing medium, and then added as a dispersing multi-walled carbon nanotube (trade name VGCF-X by Showa Denko Co., Ltd.) After one part, the resulting solution was subjected to a refining treatment for 12 hours using a paint shaker (ROCKING MILL developed by SEIWA, trade name RM-5, using a zirconia bead having a diameter of 0.5 mm), the dispersant of the present invention It is composed of a compound represented by the formula (1) containing a hydrophobic group (R), an oxygen extended alkyl group (-(AO) _n -), and a linking group (X) having the composition shown in the following Table 4, and this comparative example The dispersant is composed of a compound represented by the formula (1) comprising a hydrophobic group (R), an oxygen alkyl group (-(AO) _n -) and a linking group (X) having the composition shown in Table 4 below. As a result, after the obtained treatment liquid was transferred to a transparent container, the treatment liquid was observed with the naked eye, and the dispersibility of the treatment liquid in the container immediately after the miniaturization treatment was evaluated on the same basis as above. Dispersion stability of the treatment liquid in the container after 24 hours. The results are shown in Table 4.

Further, the dispersant of the present invention or a dispersant of a comparative example, diethylene glycol monobutyl ether acetate as a dispersing medium, and a multi-walled carbon nanotube as a dispersing substance (made by Showa Denko Co., Ltd.) The ratio of the trade name VGCF-X) is 1 part: 70 parts: 1 part to prepare a dispersion, and after adding 30 parts of diethylene glycol monobutyl ether acetate to 10 parts of the dispersion, the above-mentioned The coating shaker was subjected to a refining treatment for one hour, and the dispersing agent of the present invention was composed of a compound represented by the formula (1) having the composition shown in Table 4 below, and the dispersing agent of the comparative example was obtained from the following Table 4. The composition shown in the formula (1) is composed of the composition shown. The dispersion stability of the treatment liquid diluted with diethylene glycol monobutyl ether acetate was defined as dilution stability, and the dilution stability was evaluated on the same basis as the dispersibility. The results are shown in Table 4.

Further, the dispersant of the present invention or the dispersant of the comparative example, diethylene glycol monobutyl ether acetate as a dispersing medium, and the same multi-walled carbon nanotube as the above-mentioned dispersoid The ratio was changed to 1 part: 70 parts: 1 part, and the refining treatment was carried out for 12 hours using the above-mentioned paint shaker, and after obtaining a dispersion, 25 parts of an acrylic resin (trade name ACRYPET VH manufactured by Mitsubishi Rayon Co., Ltd.) was dissolved. After 70 parts of the dispersion was mixed in 70 parts of the ethyl ethyl ketone solution to obtain a dispersion, the dispersion was applied onto a clean glass plate having a thickness of 10 mm, and then dried at 120 ° C for 1 hour using a dryer. The coating film, the dispersing agent of the present invention is composed of a compound represented by the formula (1) having the composition shown in the following Table 4, and the dispersing agent of the comparative example is a formula having the composition shown in Table 4 below ( 1) The compound shown is composed of. Next, after the paper on which the letter printed in the 12th letter is recorded is placed under the glass plate, the coating film obtained on the glass plate is evaluated on the same basis as described above from the viewpoint of whether or not the letter can be recognized through the coating film. Transparency. The results are shown in Table 4.

As is clear from Table 4, the dispersing agent, the dispersion stability, and the dilution stability of the present invention were excellent. Further, as shown in Table 4, the coating film composed of the dispersion of the present invention was excellent in transparency, and it was confirmed that the dispersion of the present invention has excellent dispersibility. Further, the transparency of the dispersant of the comparative example was not measured.

[Example 4] "Production of zirconia acrylate monomer dispersion (1)"

When 100 parts of zirconia powder (trade name: PCS, manufactured by Nippon Denshi Co., Ltd., primary particle diameter: 30 nm) and 400 parts of methyl ethyl ketone were mixed, the dispersant of the present invention was added (the left end of Table 5 is shown). The number of (1)-1 to (1)-6) 10 parts or the dispersant of the comparative example ((1) - Comparative Example 1, (1) - Comparative Example 1" shown in Table 5) after 10 parts The obtained solution was subjected to a refining treatment using a trade name ULTRA APEX MILL UAM-005 (using a zirconia bead of 50 μm in diameter and a peripheral speed of 10 m/sec) manufactured by Shou Industrial Co., Ltd. for 4 hours to prepare a zirconia dispersion. The dispersant of the invention is composed of a compound represented by the formula (1) comprising a hydrophobic group (R), an oxygen alkyl group (-(AO) _n -) and a linking group (X) having the composition shown in Table 5 below. The dispersant of the comparative example is represented by the formula (1) comprising a hydrophobic group (R), an oxygen alkyl group (-(AO) _n -) and a linking group (X) having the composition shown in Table 5 below. Composition of compounds. To 100 parts of the obtained zirconia dispersion, 10 parts of phenoxyethyl acrylate (trade name: NEW FRONTIER PHE, manufactured by Dai-ichi Kogyo Co., Ltd.) and pentaerythritol triacrylate (trade name NEW FRONTIER, manufactured by Dai-ichi Kogyo Co., Ltd.) were added. After PET-3) was mixed and mixed, the solvent methyl ethyl ketone was removed under reduced pressure using a rotary evaporator to obtain a zirconia acrylate monomer dispersion (1).

"Production of zirconia acrylate monomer dispersion (2)"

The dispersant of the present invention was added to 100 parts of a commercially available zirconia dispersion (trade name SZR-M, manufactured by Seiko Chemical Co., Ltd., a dispersion having a primary particle diameter of 3 nm and containing 30% by weight of methanol) (left end of Table 5) 3 parts of the number shown as (2)-1 to (2)-13) or a dispersing agent of a comparative example ((2) - Comparative Example 2, (2) - Comparative Example 2') shown in Table 5) 15 parts of phenoxyethyl acrylate (trade name NEW FRONTIER PHE, manufactured by Dai-ichi Kogyo Co., Ltd.) and 15 parts of pentaerythritol triacrylate (trade name NEW FRONTIER PET-3, manufactured by Dai-ichi Kogyo Co., Ltd.) The methyl ethyl ketone of the solvent was removed under reduced pressure using a rotary evaporator to obtain a zirconia acrylate monomer dispersion (2). The dispersant of the present invention was composed of the composition shown in Table 5 below. (1) The compound shown in the comparative example is composed of a compound represented by the formula (1) having the composition shown in the following Table 5.

<Evaluation of the characteristics of the dispersion>

a. The transparency of the appearance

The zirconia acrylate monomer dispersion is added to a transparent glass container, and after the paper having the letter printed in the 12th mark is placed under the container, from the viewpoint of whether the dispersion can recognize the letter, The transparency of the dispersion was evaluated on the basis of the following criteria. The results are shown in Table 5.

◎: After the dispersion was added to a glass container having a depth of 5 cm, the letter of the 12th letter was observed. The dispersion is transparent.

○: After the dispersion was added to a glass container having a depth of 1 cm, the letter of the 12th letter was clearly observed. The dispersion was slightly turbid.

×: After the dispersion was added to a glass container having a depth of 1 cm, the letter of the 12th word could not be clearly observed. The dispersion was cloudy.

b. Viscosity measurement

The viscosity of the zirconia acrylate monomer dispersion 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 5.

c. refractive index

The refractive index of the zirconia 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 5.

"Production of Photopolymerization and Curing Film of Zirconia"

To 100 parts of the zirconia acrylate monomer dispersion (1) or (2), 1 part of a photopolymerization initiator (IGACURE 184) was added and mixed to obtain a zirconia paste. The zirconia paste was applied to a film of polyethylene terephthalate film to a film thickness of about 50 μm by using an applicator (type YA manufactured by Kobayashi Seisakusho Co., Ltd.), and then irradiated with a high-pressure mercury lamp to have an intensity of 80 W/ An ultraviolet ray having an energy of about 200 mJ/cm ² and a photopolymerization cured film of a zirconia acrylate monomer dispersion.

<Evaluation of characteristics of photopolymerization cured film>

a. The transparency of the appearance

After placing a paper having a letter printed on the 12th mark under the polyethylene terephthalate film, the polyethylene terephthalate was evaluated based on the following criteria from the viewpoint of whether or not the cured film was recognizable. The transparency of the photopolymerization cured film obtained on the film. The results are shown in Table 5. ◎: The letter text of the 12th word can be clearly recognized. ○: The cured film produced a slight turbidity, but the letter of the 12th word could still be recognized. ×: The cured film is turbid, and the letter of the 12th word cannot be recognized.

b. refractive index

The refractive index of the photopolymerization cured film was measured at 25 ° C using a PRISM COUPLER (MODEL 2010/M) manufactured by Seki Technotron Co., Ltd. The results are shown in Table 5.

c. Pencil hardness

For the pencil hardness of the photopolymerization cured film, a scratch test of the photopolymerization cured film was carried out using a pencil of a predetermined hardness in accordance with JIS K5400. The results are shown in Table 5.

[table 5]

As is clear from Table 5, the dispersion system of the present invention has excellent dispersibility (transparency in appearance) and high refractive index, and the photopolymerization cured film of the dispersion of the present invention has excellent transparency, high refractive index, and good Pencil hardness.

However, the dispersion of the comparative example ((1) - Comparative Example 1, (1) - Comparative Example 1 ', (2) - Comparative Example 2, (2) - Comparative Example 2') was not able to measure viscosity due to aggregation. And refractive index, and turbid. Further, the photopolymerization cured film of the dispersion of the comparative example was turbid, and the refractive index and pencil hardness could not be measured.

In Tables 1 to 5, EO represents ethylene oxide, and PO represents propylene oxide.

Further, the refractive index of the dispersion composed of the dispersant of the comparative example could not be measured. Further, the refractive index and pencil hardness of the photopolymerization cured film of the dispersion composed of the dispersant of the comparative example could not be measured.

The dispersion composition of the present invention can be used in the following fields: a mixed 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 nano magnet, and a heat conduction. High-performance catalyst for medium and fuel cell, organic solar cell, nano glass element, abrasive, drug carrier, environmental catalyst, paint, printing ink, ink for inkjet, resist for color filter, printing with writing instrument Ink, optical film, adhesive, anti-reflective film, hard coating film, etc. The dispersant of the present invention can effectively disperse an inorganic material derived from an inorganic substance or an organic substance-derived isotropic material and/or an anisotropic material in a nanometer size as a main component in the above-mentioned use article and its production step. The dispersion in the medium is stabilized, and the dispersing agglomeration in the dispersion medium is suppressed, and the dispersion stability is achieved for a long period of time, thereby obtaining desired product characteristics, processing characteristics, quality stability, and productivity.

The present invention has been described in detail and with reference to the specific embodiments of the present invention. Easy to know.

The present application is based on a Japanese patent application filed on May 26, 2010 (Japanese Patent Application No. 2010-120122) and Japanese Patent Application No. 2010-286489 filed on Dec. 22, 2010, The contents of these are hereby incorporated by reference.

Claims (4)

A dispersion composition using a dispersant for a non-aqueous dispersion medium composed of a compound represented by the following formula (1) to disperse organic particles or inorganic particles having an average particle diameter of 1 to 500 nm in a non-aqueous form. Made in the dispersion medium: However, R of the formula (1) represents a branched alkyl group having a carbon number of 8 to 18, AO of the formula (1) represents an oxygen alkyl group having a carbon number of 1 to 4, and n represents an average addition of an alkylene oxide. The Mo number is in the range of 1 to 30, and the X of the formula (1) is a substance represented by the following formula (2): However, Y of the formula (2) is any one selected from the group consisting of an alkyl group having 1 to 15 carbon atoms, a vinyl group, a phenyl group, and a phenyl group having a carboxyl group. A coating composition comprising: the dispersion composition according to claim 1, wherein the dispersion composition uses a resin as a non-aqueous dispersion medium. A coating composition comprising: a mixture of a dispersion composition according to claim 1 and a resin, wherein the dispersion composition uses a solvent as a non-aqueous dispersion medium. A member which is subjected to physical reaction or chemical reaction by applying the coating composition described in claim 2 or 3 to a substrate. Deserved.