TW201412388A - Dispersion agent for non-aqueous dispersion medium and dispersion body - Google Patents

Abstract

The present invention provides a dispersion agent, which serves as a dispersion agent for non-aqueous dispersion medium that is applicable to a wide range of dispersion substance and dispersion media and has sustained excellent stability of dispersion, and also provides a dispersion body formed by using the dispersion agent. The dispersion agent is constituted by a compound expressed by the following general formula (I). However, in formula (I), R1 represents a hydrocarbon group of a straight chain of carbon number 8-22 or having a side chain; R2 represents a hydrocarbon group of a straight chain of carbon number 8-22 or having a side chain; m and n respectively denotes the average degree of substitution, m being a number of 1-2, n being a number of 0-2, and the sum of m and n being 1-4.

Description

Dispersant and dispersion for non-aqueous dispersion medium

The present invention relates to a dispersant and a dispersion for a non-aqueous dispersion medium obtained by dispersing organic particles or inorganic particles in a non-aqueous dispersion medium using the dispersant for a non-aqueous dispersion medium.

Dispersion, dispersion composition, and resin composition obtained by dispersing an inorganic material or an organic-derived isotropic material and/or an anisotropic material or a non-crystalline material using a dispersant for a non-aqueous dispersion medium Materials, film-like compositions, and the like have been used in various industrial fields. It has been used, for example, as a coating or ink obtained by dispersing a pigment or a filler in a resin solution; a flooring material obtained by dispersing a filler such as calcium carbonate or titanium oxide and a plasticizer in a polyvinyl chloride resin or the like (flooring) Material, wallpaper; resin composition for sealing material; resin composition in which inorganic and/or organic filler is dispersed; film-like composition; spray detergent containing inorganic abrasive. In addition, in recent years, substances derived from inorganic substances or organic substances are dispersed in a non-aqueous dispersion medium such as an organic solvent, an oil, a plasticizer, or a resin, and are used as a host material or as a functional property. Additives for the purpose of use in the following fields of application: inorganic/organic hybrid materials, surface protectants, conductive pastes, conductive inks, sensor compositions, precision analysis components, Optical memory, liquid crystal display element, nano magnet, heat transfer medium, high performance catalyst for fuel cell, organic solar cell, nano glass element, abrasive, drug carrier, environmental catalyst, printing ink, inkjet ink, Resist for color filter, ink for writing instrument, optical film, adhesive, anti-reflection film, hard coating film, hydraulic oil, lubricating oil, processing oil, etc.

As such a dispersing agent for a nonaqueous dispersion medium, various dispersing agents are known. For example, as an anionic surfactant, for example, a higher fatty acid salt, an alkyl sulfonate, an α-olefin sulfonate, an alkane sulfonate, an alkylbenzene sulfonate, a sulfosuccinate, an alkyl sulfate A salt, an alkyl ether sulfate salt, an alkyl phosphate salt, an alkyl ether phosphate salt, an alkyl ether carboxylate, an α-sulfo fatty acid methyl ester salt, a methyl taurate salt, or the like. Examples of the nonionic surfactant include glycerin fatty acid ester, polyglycerin fatty acid ester, sucrose fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, and polyoxyethylene alkyl group. Ether, polyoxyethylene alkylphenyl ether, polyoxyethylene fatty acid ester, fatty acid alkanolamine, alkyl glucoside, etc. (for example, Patent Document 1).

Further, a polymer surfactant such as a fluorine-based surfactant or a cellulose derivative, a polyvalent carboxylic acid, a maleic anhydride copolymer derivative or a polystyrene sulfonate may be used. Further, a lower fatty acid having a carboxyl group, a higher fatty acid, a hydroxycarboxylic acid, an alicyclic group having 6 to 34 carbon atoms, an aromatic carboxylic acid, an alkenyl succinic anhydride, a thiol derivative, or a phosphine derivative can be used. , alkylamine derivatives. In addition, a polymer type dispersant which is mainly used as a dispersant for pigments and the like, which has a carboxyl group, an amine group, a hydroxyl group, an ester bond, a guanamine bond, and a fragrance, has been used. A ring, a hetero ring or the like (for example, Patent Document 2). As a dispersing agent for such pigments and the like, commercially available: The DISPERBYK series manufactured by Byk Chemie, the EFKA series manufactured by BASF, and the SolsPerse series manufactured by Lubrizol.

When a dispersion is prepared using such a dispersant, a dispersant suitable for the dispersoid or dispersion medium is selected and used. In this case, as a performance required for the dispersant, it is possible to easily disperse the dispersoid in the non-aqueous dispersion medium in a short time, and to prevent the dispersoid from settling for a long period of time, thereby stabilizing the dispersoid. The ground is dispersed, or even if the dispersoid is settled, it can be easily redispersed or the like. Further, when the viscosity of the dispersion rises due to the dispersion of the dispersoid and it is difficult to use it for the intended use, the following effects can be expected: the dispersion property is exhibited, and the viscosity of the dispersion is lowered until the viscosity is appropriate. Further, by well-dispersing specific particles in an appropriate particle size range, the processing characteristics, product characteristics, or raw material properties of the raw material can be greatly improved. Further, in terms of appearance, it is also expected to improve transparency, gloss, colorability, or suppression of color separation, cracking, and the like of the dispersion.

However, the conventional dispersant cannot fully correspond to the diversification of the dispersion medium or the dispersoid, the miniaturization of the particle size of the dispersoid, and the diversification of the shape, and the high quality, productivity, processing characteristics, and raw materials of the final product. From the viewpoint of the high requirements of characteristics, the required characteristics are not sufficiently satisfied.

When the dispersion medium is water, for example, interface adsorption based on hydrophobic interaction of a dispersant, or electrosorption by an ionic group, π-electron interaction derived from an aromatic ring, and between particles It is also possible to utilize the electrostatic repulsion between the particles caused by the formation of the electric double layer, the dispersion stabilization effect caused by the formation of the three-dimensional barrier, and the addition of the protective colloid and the thickener as the stabilizer. For an effective method, this can be used A variety of methods for achieving dispersion stabilization and inhibiting agglutination.

On the other hand, since the effect of hydrophobic interaction, electrical interface adsorption by ionic groups, and electrostatic repulsion is extremely limited in the non-aqueous dispersion medium, the adsorption of the dispersant on the interface of the dispersed particles largely depends on The acid-base interaction between the dispersed particles and a specific portion of the dispersing agent. In other words, in practice, the dispersant is selected to be individually optimized depending on the surface characteristics of the dispersoid, and the use of the dispersant is in a very limited state. Further, in actuality, from the viewpoint of the affinity of the dispersing agent to the dispersing medium, it is also necessary to individually select the optimum dispersing agent in combination with the dispersing medium to be used, and the scope of application thereof is extremely limited.

In addition, in the dispersion, the resin composition, and the film-form composition obtained by dispersing the dispersion agent for a non-aqueous dispersion medium, even if the dispersion operation itself is satisfactorily completed, depending on the use conditions or storage conditions, the dispersion may be generated. The following problems are caused by long-term stability of the dispersant, poor dilution stability, deterioration of appearance, hue, low-temperature fluidity, viscosity stability, heat resistance, deterioration of hydrolysis resistance, moisture resistance, and resin. Deterioration of physical properties, etc.

Therefore, the dispersing agent which solves the above various problems, and the non-aqueous dispersion which solves the above-mentioned problem by using this dispersing agent can be said to be enormous in industrial use value.

[Previous Technical Literature] (Patent Literature)

Patent Document 1: Japanese Laid-Open Patent Publication No. 2000-262883

Patent Document 2: Japanese Laid-Open Patent Publication No. 2005-325213

The present invention has been made in view of the above problems, and an object of the invention is to provide a dispersant for a non-aqueous dispersion medium which is a particle derived from an inorganic material (hereinafter also referred to as an inorganic particle) or an organic-derived particle ( Hereinafter, it is also applicable to a wide range of dispersoids and dispersion media, and exhibits excellent dispersion stability, and further suppresses dispersion or dispersion caused by deterioration of structural characteristics or composition of the dispersant. The properties of the bulk composition deteriorate.

In order to solve the above problems, the dispersant for a nonaqueous dispersion medium of the present invention is composed of a compound represented by the following general formula (I).

However, in the general formula (I), R ¹ represents a linear or branched hydrocarbon group having 8 to 22 carbon atoms, and R ² represents a linear or branched hydrocarbon group having 8 to 22 carbon atoms; m and n represent The average degree of substitution, m is a number from 1 to 2, n is a number from 0 to 2, and the total number of m and n is 1 to 4.

The dispersion of the present invention is obtained by dispersing organic particles and/or inorganic particles in a non-aqueous dispersion medium using the dispersant for a non-aqueous dispersion medium of the present invention.

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

Dispersing agent

In order to solve the above problems, the dispersant for a nonaqueous dispersion medium of the present invention is composed of a compound represented by the following general formula (I).

However, in the general formula (I), R ¹ represents a linear or branched hydrocarbon group having 8 to 22 carbon atoms, and R ² represents a linear or branched hydrocarbon group having 8 to 22 carbon atoms. When these R ¹ and R ² are each less than 8 and more than 22, the stability of the dispersion tends to decrease.

Further, m and n respectively represent the average degree of substitution, m is a number from 1 to 2, n is a number from 0 to 2, and the total number of m and n is 1 to 4.

By appropriately selecting the kind and degree of substitution of the alkyl group from the above range, a dispersant can be obtained which can disperse a wider variety of dispersoids than conventional dispersants, and can be used in a wider variety of dispersoids. The dispersion is stabilized in the dispersion medium.

The compound represented by the above formula (I) is not particularly limited, and it can be produced by a known method, and a commercially available product can also be used.

2. Dispersing the particles

The dispersed particles dispersed by the dispersant of the present invention are not particularly limited, and isotropic properties derived from inorganic substances and/or organic substances derived from organic substances can be used. The material and/or the anisotropic material may be one or more of inorganic particles or organic particles obtained from various materials of amorphous. Moreover, these materials and particles may be colored or colorless.

As the inorganic particles, for example, iron, aluminum, chromium, nickel, cobalt, zinc, tungsten, indium, tin, palladium, zirconium, titanium, copper, silver, gold, platinum, or the like; and these alloys; or the like can be used. a mixture. Further, these metal particles can be easily removed from the medium and can be coated with the following protective agents: alkanic acids and fatty acids, hydroxycarboxylic acids, aliphatic, aromatic carboxylic acids, alkenyl succinic anhydrides, thiols. Classes, phenol derivatives, amines, amphiphilic polymers, polymeric surfactants, low molecular surfactants, and the like.

Also, kaolin, clay, talc, mica, bentonite, dolomite, calcium silicate, magnesium silicate, asbestos, potassium carbonate, calcium carbonate, magnesium carbonate, barium carbonate, barium sulfate, aluminum sulfate, aluminum hydroxide, hydroxide Iron, aluminum silicate, zirconium oxide, magnesium oxide, aluminum oxide, titanium oxide, iron oxide, zinc oxide, antimony trioxide, indium oxide, indium tin oxide, antimony carbide, tantalum nitride, boron nitride, barium titanate, 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), etc. It can also be dispersed by the dispersing agent of the present invention. Further, the dispersant of the present invention is also applicable to a rust inhibitor component such as sodium sulfite, ammonium chromate or ammonium thiocyanate; a flame retardant component such as magnesium hydroxide.

As the organic particles, an azo-based, diazo-based, condensed azo-based, thioindole-based, indanthrone-based, quinacridone-based, guanidine-based, benzimidazolone-based system can be used. , perylene, phthalocyanine, anthrapyridine, two (dioxazine) is an organic pigment. Further, the dispersant of the present invention is also applicable to a solid flame retardant such as hexabromocyclododecane or ginseng (2,3-dibromopropyl)isocyanurate, which is derived from benzotriazole. An immobilization agent such as an antioxidant or a UV absorber composed of a substance or a phenol derivative; and a fixed substance such as a metal sealant, a chelating agent, or an antistatic agent. Further, the dispersant of the present invention can be suitably used for: polyethylene resin, polypropylene resin, polyester resin, nylon resin, polyamide resin, aromatic polyamide resin, acrylic resin, vinylon resin, Urethane resin, melamine resin, polystyrene resin, polylactic acid, acetate fiber, cellulose, hemicellulose, lignin, chitin, chitosan, starch, polyacetal , aromatic polyamide resin, polycarbonate, polyphenylene ether, polyether ketone, polybutylene terephthalate, polyethylene naphthalate, polybutylene naphthalate, polysulfone , polyphenylene sulfide, polyimine, polyphenols, and the like.

Further, the dispersed particles dispersed by using the dispersing agent of the present invention may be an inorganic-derived material having an antioxidant, an ultraviolet absorber, a light stabilizer, a flame retardant, etc., and/or an organic-derived material. Particles of materials.

The above dispersed particles may be crystalline or amorphous. Further, it may be an isotropic particle or an anisotropic particle, or may be fibrous.

As the above-mentioned dispersed particles, those obtained by a known method can be used. There are two methods for preparing fine particles: a top-down method in which coarse particles are mechanically ground and gradually refined; and a plurality of unit particles are generated and agglomerated by the particles. The clustering state forms a bottom-up manner of the particles, and it can be preferably used by any one of the methods. Moreover, the methods may be modulated by any of the wet method and the dry method. By. Further, these may be prepared in an environment of any of a water system, a non-aqueous system, and a gas phase. In addition, from the bottom up, there are physical methods and chemical methods, which can be modulated by either method.

As described above, the dispersing agent of the present invention can be used in a step from the top-down manner in which coarse particles are mechanically ground and gradually refined, or a plurality of unit particles can be formed and agglomerated by the particles. The clustering state is used in the step of forming the bottom-up mode of the particles.

Further, it is also possible to use particles in which the fine particles are prepared in advance by the above method, and the dispersed particles are stably taken out from the medium to be coated with the above-mentioned conventional protective agent called a surface modifying agent or a surface protecting agent. Particles removed after impregnation.

The average particle diameter of the dispersion particles is not particularly limited. However, from the viewpoint of excellent stability of the dispersion, it is preferably in the range of 0.01 to 5.0 μm, more preferably in the range of 0.1 to 2.0 μm.

3. Dispersing medium

The dispersion medium used in the present invention is not particularly limited as long as it is a non-aqueous dispersion medium, and for example, the following may be mentioned. Further, the dispersion medium may be used singly or in combination of two or more.

For example, an aromatic hydrocarbon solvent such as toluene or xylene, a hydrocarbon solvent such as n-hexane, cyclohexane or n-heptane; a halogenated hydrocarbon solvent such as dichloromethane, chloroform or dichloroethane; diethyl ether or isopropyl ether; 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 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 or cyclohexanone; ethyl formate, propyl formate, butyl formate, isobutyl formate, amyl formate, methyl acetate, acetic acid Ethyl ester, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, butyl acetate, isoamyl acetate, cyclohexyl acetate, ethyl lactate, 3-methoxy acetate Butyl ketone, secondary hexyl acetate, 2-ethyl butyl acetate, 2-ethylhexyl acetate, benzyl acetate, methyl propionate, ethyl propionate, methyl chloroacetate, ethyl chloroacetate , butyl chloroacetate, acetamidine acetate Ester, ethyl acetate, butyl propionate, isoamyl propionate, γ-butyrolactone and other ester solvents; ethylene glycol monoethyl ether, ethylene glycol monoisopropyl ether, ethylene glycol single Butyl 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, two Propylene 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 a glycol ether solvent such as alcohol 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, and the like Ether acetate solvent; diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl isobutyl ether, dipropylene glycol dimethyl ether, dipropylene glycol diethyl A dialkyl ether solvent such as ether.

Further, for example, methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, secondary butanol, tertiary butanol, heptanol, n-pentanol, secondary pentanol, and hexanol may be mentioned. Alcohol, tetrahydrofurfuryl alcohol, decyl alcohol, allyl alcohol, chlorohydrin, octyl Dodecanol, 1-ethyl-1-propanol, 2-methyl-1-butanol, isoamyl alcohol, tertiary pentanol, secondary isoamyl alcohol, neopentyl alcohol, hexanol, 2-methyl Base-1-pentanol, 4-methyl-2-pentanol, heptanol, n-octanol, 2-ethylhexanol, decyl alcohol, decyl alcohol, undecyl alcohol, lauryl alcohol, cyclopentanol, ring Hexanol, benzyl alcohol, α-terpineol, Terpineol C, L-α-terpineol, dihydroterpineol, terpineoloxyethanol, dihydroterpineoloxyethanol, manufactured by Japan Terpene Chemical Co., Ltd. Tersorb MTPH, Tersorb DTO-210, Tersorb THA-90, Tersorb THA-70, and cyclohexanol, 3-methoxybutanol, diacetone alcohol, 1,4-butane, manufactured by Terpene Chemical Co., Ltd., Japan Alcohol, 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 A glycol solvent such as dipropylene glycol, 1,3-butylene glycol, hexanediol, polyethylene glycol or polypropylene glycol.

Further, for example, a guanamine-based solvent such as dimethylacetamide or dimethylformamide can be mentioned.

Further, a vinyl-based monomer such as a (meth)acrylic acid, a (meth) acrylate or a vinyl acetate having a reactive group, a vinyl ether derivative, or a polyallyl derivative may be used. Monomers.

Further, synthetic oils such as poly-α-olefins, polybutenes, and hindered esters; mineral oils such as kerosene, light oil, heavy oil, and liquid paraffin; natural oils such as soybean oil and linseed oil; Wait.

Also, it can be used: dioctyl phthalate, di(2-ethylhexyl) phthalate, diisononyl phthalate, diisononyl phthalate, phthalic acid Phthalates such as dibutyl ester; dibutyl sebacate, bismuth Sebacate such as dioctyl acid ester, di(2-ethylhexyl) sebacate or dinonyl sebacate; adipate such as dioctyl adipate or diisononyl adipate And other plasticizers.

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 of the resin include acrylic resin, polyester resin, alkyd resin, amine ester resin, oxime resin, fluororesin, epoxy resin, polycarbonate resin, and polyvinyl chloride resin. , polyvinyl alcohol and the like.

Furthermore, it is an object of the present invention to provide a dispersion of microparticles in a non-aqueous environment, but whether intentionally or accidentally, in the manufacturing step of the microparticle dispersion or in other steps, depending on the convenience of the intended use or designing the final product The necessity does not exclude the case where water is mixed or mixed into the above non-aqueous dispersion medium.

4. Manufacturing dispersions, etc.

The dispersion of the present invention is obtained by dispersing the dispersed particles in the above-mentioned nonaqueous dispersion medium by using the dispersant of the present invention. Further, the term "dispersion" as used in the present invention encompasses the concept of a dispersion composition, and the term "dispersion composition" has nothing to do with its content or form. In other words, for example, a resin composition containing a dispersion medium as a resin may be used, and the form may be any of a liquid form, a paste form, and a film form.

The content of the dispersion particles in the dispersion is not particularly limited as long as the dispersion can be uniformly dispersed in the non-aqueous dispersion medium, and it is preferably in the range of 0.01 to 70% by mass, depending on the use and the like. Further, the amount of the dispersant used in the present invention varies depending on the use, and is usually preferably from 0.1 to 10,000% by mass, and from 1.0 to 5,000, based on the dispersed particles. The range of mass % is better.

Further, the dispersion composition of the present invention can be prepared by a conventional stirring means, a homogenizing means, or a dispersing means. The dispersing machine to be used is not particularly limited, and examples thereof include a roll mill such as a 2-roll or a 3-roll mill, a ball mill such as a ball mill and a vibratory ball mill, a paint shaker, a continuous disc type bead mill, and a continuous machine. Bead mills such as ring bead mills, sand mixers, jet mills, etc. In addition, dispersion treatment can also be carried out in an ultrasonic generation bath.

The dispersant of the present invention can be applied to a wide range of dispersoids and dispersion media, and a dispersant can be used to provide a dispersion having excellent dispersion stability. Therefore, the inorganic material or the organic-derived isotropic material and/or the anisotropic material used in the products for various uses can be dispersed and stabilized in the non-aqueous dispersion medium, and the dispersion medium can be suppressed in the dispersion medium for a long period of time. In the agglutination, it is possible to impart desired product characteristics, processing characteristics, etc., to achieve quality stabilization, and to improve productivity.

[Examples]

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

The details of the dispersing agent of the present invention and the comparative product used in the following examples and comparative examples are shown in Table 1 below.

[Table 1]

[Examples 1 to 7 and Comparative Examples 1 to 5]

As shown in the following Table 2, a specific amount of the dispersant of the present invention or a dispersant of a comparative product is dissolved in di(2-ethylhexyl) phthalate (DOP) as a dispersion medium (Kao) , VINYCIZER 80), and a specific amount of magnesium hydroxide as a dispersing substance and 100 ml of zirconium beads having a diameter of 0.1 mm were added to a bead mill (manufactured by AIMEX Co., Ltd., trade name: RMB, container capacity: 400 ml) to rotate The micronization treatment was carried out for 3 hours at 1000 rpm.

The obtained treatment liquid was evaluated for dispersion stability, low-temperature stability, and hydrolysis stability by the following method. The results are shown in Table 2.

(1) Decentralized stability

100 g of the obtained treatment liquid was transferred to a transparent container, and the micro-fineness was just The dispersion stability of the treatment liquid in the container after the treatment and the dispersion stability of the treatment liquid in the container after 24 hours were visually observed and evaluated according to the following criteria.

◎: All the dispersoids were dispersed in the liquid, and no precipitate was observed at the bottom of the container, and the dispersion was transparent.

△: All the dispersoids were dispersed in the liquid, and no precipitate was observed at the bottom of the container, but the dispersion was cloudy.

×: A precipitate was observed at the bottom of the container.

(2) Low temperature stability

100 g of the treatment liquid immediately after the miniaturization treatment was transferred to a transparent container, and the state after storage at -10 ° C for 24 hours was visually observed and evaluated based on the following criteria.

◎: No thickening.

△: Thickened.

×: No fluidity, solidified.

(3) Hydrolytic stability

100 g of the treatment liquid immediately after the miniaturization treatment was taken in a sample bottle, and stored at 93 ° C for 20 days, and was heated and deteriorated. The acid value of the treatment liquid after storage was measured. The lower the acid value is, the better the hydrolysis stability is judged.

[Table 2]

From the results shown in Table 2, it is understood that the dispersion of the present invention has more excellent dispersion stability, low-temperature stability, and hydrolysis stability than conventional products.

[Examples 8 to 14 and Comparative Examples 6 to 11]

As shown in the following Table 3, a specific amount of the dispersant of the present invention or a comparative product is dissolved in a specific amount of polypropylene glycol (PPG-1000) (manufactured by Daiichi Kogyo Co., Ltd., HIFLEX D-1000) as a dispersion medium. Thereafter, with a specific amount of 2-(2'-hydroxy-3'-tert-butyl-5'-methylphenyl)-5-chlorobenzotriazole as a dispersoid and a zirconium bead having a diameter of 0.1 mm 100 ml was added together to a bead mill (manufactured by AIMEX Co., Ltd., trade name: RMB, container capacity: 400 ml), and the refining treatment was carried out for 3 hours at a number of revolutions of 1000 rpm.

With respect to the obtained treatment liquid, evaluations of dispersion stability, low-temperature stability, and hydrolysis stability were carried out in the same manner as in the above Examples 1 to 7. Further, the evaluation of the dilution stability was carried out by the following method. These results are shown in Table 3.

(4) Dilution stability

10 g of the obtained treatment liquid was added to 90 g of the dispersion medium to be used for dilution, and then transferred to a transparent container to disperse the stability of the treatment liquid in the container immediately after dilution and after 24 hours. The dispersion stability of the treatment liquid in the container was visually observed for the treatment liquid and evaluated based on the following criteria.

◎: All the dispersoids were dispersed in the liquid, and no precipitate was observed at the bottom of the container, and the dispersion was transparent.

△: All the dispersoids were dispersed in the liquid, and no precipitate was observed at the bottom of the container, but the dispersion was cloudy.

×: A precipitate was observed at the bottom of the container.

[table 3]

From the results shown in Table 3, it is understood that the dispersion of the present invention has more excellent dispersion stability, low-temperature stability, and hydrolysis stability than conventional products.

[Examples 15 to 21 and Comparative Examples 12 to 17]

As shown in Table 4 below, a specific amount of the dispersant of the present invention or a comparative product is dissolved in a specific amount of the liquid paraffin as a dispersion medium, and a specific amount of sodium sulfite as a dispersoid and a zirconium bead having a diameter of 0.1 mm. 100 ml was added together to a bead mill (manufactured by AIMEX Co., Ltd., trade name: RMB, container capacity: 400 ml), and the refining treatment was carried out for 3 hours at a number of revolutions of 1000 rpm.

With respect to the obtained treatment liquid, evaluations of dispersion stability, low-temperature stability, and hydrolysis stability were carried out in the same manner as in the above Examples 1 to 14. The results are shown in Table 4.

[Table 4]

From the results shown in Table 4, it is understood that the dispersion of the present invention has more excellent dispersion stability, low-temperature stability, and hydrolysis stability than conventional products.

The dispersant of the present invention can be used in the following fields: flooring materials, wallpapers, resin compositions for sealing materials, film-like compositions, spray detergents, inorganic/organic hybrid materials, surface protective agents, conductive pastes, conductive inks , sensor composition, precision analysis element, optical memory, liquid crystal display element, nano magnet, heat transfer medium, high performance catalyst for fuel cell, organic solar cell, nano glass element, abrasive, drug carrier, environment Catalyst, printing ink, ink for inkjet, resist for color filter, ink for writing instrument, optical film, adhesive, antireflection film, hard coat film, hydraulic oil, lubricating oil, processing oil, and the like.

The present invention has been described in detail and with reference to the specific embodiments of the present invention, and various modifications and changes can be made without departing from the spirit and scope of the invention. Easy to know.

The present application is based on Japanese Patent Application No. 2012-185709, filed on Jan.

Claims (2)

A dispersant for a nonaqueous dispersion medium comprising a compound represented by the following general formula (I): However, in the general formula (I), R ¹ represents a linear or branched hydrocarbon group having 8 to 22 carbon atoms, and R ² represents a linear or branched hydrocarbon group having 8 to 22 carbon atoms; m and n represent The average degree of substitution, m is a number from 1 to 2, n is a number from 0 to 2, and the total number of m and n is 1 to 4. A dispersion obtained by dispersing organic particles and/or inorganic particles in a non-aqueous dispersion medium using the dispersant for a non-aqueous dispersion medium according to Claim 1.