JP5882603B2 - Pigment dispersion, yellow toner - Google Patents

Description

  The present invention relates to a pigment dispersion used in the production process of paints, inks, toners, resin molded products and the like. Further, the present invention relates to a yellow toner used in a recording method such as an electrophotographic method, an electrostatic recording method, a magnetic recording method, a toner jet method, and a liquid developing method using the pigment dispersion as a colorant.

  Azo pigments have a wide range of uses as colorants, and are widely used in fields such as paints, inkjet inks, electrophotographic toners, and color filters. The colorant used in such a field must be finely dispersed in various media in order to improve spectral characteristics such as coloring power and transparency. However, in general, when the azo pigment is miniaturized, it aggregates in a dispersion process or a subsequent manufacturing process, thereby causing problems such as a reduction in coloring power and transparency. In order to improve such problems, various pigment dispersants have been proposed.

  Patent Documents 1 to 3 include C.I. I. A yellow toner using Pigment Yellow 180 is disclosed, but a toner prepared using this pigment has poor coloring power and cannot be said to have good transparency, and further improvement is required as a full color toner. Met.

  Patent Document 4 discloses an electrophotographic toner in which pigments are finely divided, the specific surface area of the pigment is improved, and transparency and coloring power are increased. However, C.I. I. When the pigment classified as Pigment Yellow 180 is made finer, its own self-condensation is strong. Therefore, even if this method is used, dispersion in the colored resin constituting the toner is insufficient.

Japanese Patent Laid-Open No. 06-230607 Japanese Patent Laid-Open No. 06-266163 JP 08-262799 A Japanese Patent Laid-Open No. 08-209017

  An object of the present invention is to provide a pigment dispersion having a high coloring power by suppressing an increase in the dispersion viscosity of the colorant in the dispersion medium and improving the dispersibility of the colorant in the dispersion medium. To do. Another object of the present invention is to provide a yellow toner having good dispersibility of the colorant in the binder resin.

  The present invention relates to a pigment dispersion containing a compound represented by the general formula (1) and a yellow pigment represented by the general formula (2) in a dispersion medium. The present invention also relates to a yellow toner using the pigment dispersion.

  The present invention can provide a pigment dispersion having a high coloring power by suppressing an increase in the dispersion viscosity of the colorant in the dispersion medium and improving the dispersibility of the colorant in the dispersion medium. In addition, it is possible to provide a yellow toner having good dispersibility of the colorant in the binder resin.

In _{DMSO-d 6} of the compound represented by the general formula (1) (7) is a diagram showing the IH NMR spectrum at room temperature, at 400 MHz. It is a figure showing the SEM photograph of the pigment dispersion (15) using the compound (1) represented by General formula (1).

  As a result of intensive studies to solve the problems of the prior art described above, the present inventors have found that the compound represented by the general formula (1) and the yellow pigment represented by the general formula (2) are contained in the dispersion medium. It has been found that a pigment dispersion containing a colorant has excellent dispersibility of the colorant. Further, it has been found that by producing a yellow toner using the obtained pigment dispersion, a yellow toner having excellent coloring power can be obtained in the toner production process.

In the general formula (1), R _{1 to} R ₃ and R ′ _{1 to} R ′ ₃ each independently represent a hydrogen atom, an alkyl group, an aryl group, or an aralkyl group.

The alkyl group in _R 1 to R _3, and R _'1 to R' ₃ in the general formula (1), is not particularly limited, for example, methyl group, butyl group, octyl group, dodecyl group, Examples thereof include a linear, branched, or cyclic alkyl group having 1 to 20 carbon atoms such as a nonadecyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a methylcyclohexyl group, or an ethylhexyl group.

The aryl group in the general formula (1) of _R 1 to R _3, and R _'1 to R' _3, is not particularly limited, for example, a phenyl group, or a 6 to 14 such as phenyl or naphthyl Examples include membered monocyclic or polycyclic aryl groups.

The aralkyl group in the general formula (1) of _R 1 to R _3, and R _'1 to R' _3, is not particularly limited, for example, benzyl group, or a phenethyl group.

In the general formula (1), R _{1 to} R ₃ and R ′ _{1 to} R ′ ₃ represent the above-described substituents. If the compounds do not significantly inhibit the stability of the compound, these substituents are Furthermore, you may have a substituent. In this case, for example, an alkyl group such as a methyl group, an ethyl group, a propyl group, or a butyl group; an aryl group such as a phenyl group; an alkoxyl group such as a methoxy group, an ethoxy group, or a butoxy group; a methylamino group, a propylamino group, or the like Monosubstituted amino groups; disubstituted amino groups such as dimethylamino group, dipropylamino group, N-ethyl-N-phenyl group and the like.

In the general formula (1), R ₁ , R ₂ and R ₃ are preferably the same, and R ′ ₁ , R ′ ₂ and R ′ ₃ are preferably the same. This is because when they are the same, the production of the compound represented by the general formula (1) is facilitated, and cost reduction is expected.

The case where R _{1 to} R ₃ in the general formula (1) are alkyl groups is preferable. This is because the solubility of the compound represented by the general formula (1) in a solvent can be improved and the dispersibility of the pigment can be improved. In particular, when R _{1 to} R ₃ in the general formula (1) have a branched substituent such as a cyclohexyl group, a methylcyclohexyl group, and an ethylhexyl group, or include a coordinating heteroatom such as a butoxypropyl group. It is preferable to have a structure. In the general formula (1), it is preferred that R _'1 to R' ₃ is a hydrogen atom.

  Specific examples of the compound represented by the general formula (1) used in the present invention are shown below. In addition, the compound represented by General formula (1) is not limited to the following example.

When R _{1 to} R ₃ in the general formula (1) have an alkyl group having a ring structure as in the compound (1) or the compound (2), an alkyl group having a branched structure as in the compound (5) is used. When it has, when it has an alkyl group which has a coordinating hetero atom (oxygen atom etc.) like a compound (7), especially high effect is acquired.

  Next, one aspect of the method for producing the compound represented by the general formula (1) is shown below. That is, compound B can be obtained by condensing compound A with an amine or an amine derivative. Compound C can be obtained by further condensing compound B with the same or different amine or amine derivative as described above. Moreover, reaction, such as well-known protection and deprotection reaction and hydrolysis, can be added to the functional group of each compound as necessary. In addition, the manufacturing method of the compound represented by General formula (1) is not limited to this.

In the general formula (2), R _{4 to} R ₈ are each independently a hydrogen atom, an alkoxy group, a phenyl group, a carboxylic acid group, a carboxylic acid ester group, a carbamoyl group, a nitro group, a trifluoromethyl group, or a halogen atom. R _{9 to} R ₁₃ each independently represents a hydrogen atom, an alkyl group, an alkoxy group, an acylamino group, or a halogen atom, and R ₁₀ and R ₁₁ may be bonded to each other to form a ring.

Although it does not specifically limit as an alkoxyl group in R < ₄ > -R < ₈ > and R < ₉ > -R < ₁₃ > in the said General formula (2), For example, a methoxy group, an ethoxy group, a propoxy group, a butoxy group etc. are mentioned. It is done.

Although it does not specifically limit as carboxylic acid ester group in R < ₄ > -R < ₈ > in the said General formula (2), For example, carboxylic acid methyl ester group, carboxylic acid ethyl ester group, carboxylic acid propyl ester group, Or a carboxylic acid butyl ester group etc. are mentioned.

Examples of the halogen atom in R _{4 to} R ₈ and R _{9 to} R ₁₃ in the general formula (2) include a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

Although it does not specifically limit as an alkyl group in R < ₉ > -R < ₁₃ > in the said General formula (2), For example, a methyl group, a butyl group, an octyl group, a dodecyl group, a nonadecyl group, a cyclobutyl group, a cyclopentyl group , A cyclohexyl group, a methylcyclohexyl group, or an ethylhexyl group, and a linear, branched, or cyclic alkyl group having 1 to 20 carbon atoms.

The acylamino group in R _{9 to} R ₁₃ in the general formula (2) is not particularly limited, and examples thereof include an acetylamino group and a propionic acid amino group.

The ring formed by combining R ₁₀ and R ₁₁ in the general formula (2) is not particularly limited, and examples thereof include a benzimidazolone ring.

R _{4 to} R ₁₃ in the general formula (2) represent a substituent as described above, and these may further have a substituent unless the stability of the compound is significantly inhibited. In this case, the substituent which may be substituted is not particularly limited. For example, an alkyl group such as a methyl group, an ethyl group, a propyl group or a butyl group, an alkylene such as a methylene group, an ethylene group or a propylene group. Group, aryl group such as phenyl group, alkoxyl group such as methoxy group, ethoxy group, butoxy group, mono-substituted amino group such as methylamino group, propylamino group, dimethylamino group, dipropylamino group, or N-ethyl And di-substituted amino groups such as -N-phenyl group.

  Examples of the yellow pigment represented by the general formula (2) include C.I. I. Pigment Yellow 3, C.I. I. Pigment Yellow 12, C.I. I. Pigment Yellow 13, C.I. I. Pigment Yellow 14, C.I. I. Pigment Yellow 17, C.I. I. Pigment Yellow 74, C.I. I. Pigment Yellow 83, C.I. I. Pigment Yellow 120, C.I. I. Pigment Yellow 151, C.I. I. Pigment Yellow 154, C.I. I. Pigment Yellow 180 and yellow pigments classified as derivatives thereof. Among these, C.I. has high coloring power and low cost. I. Pigment Yellow 74, C.I. I. It is preferable to use one or more yellow pigments selected from the group consisting of Pigment Yellow 180. In particular, C.I. I. Pigment Yellow 180 is preferably used. These yellow pigments can be used alone or in combination of two or more kinds of yellow pigments represented by the general formula (2) and known yellow pigments.

<About pigment dispersion>
The pigment dispersion of the present invention will be described.
The dispersion medium referred to in the present invention refers to water, an organic solvent, or a mixture thereof.

  The pigment dispersion of the present invention can be obtained by dispersing a compound represented by the general formula (1) and a yellow pigment represented by the general formula (2) in a dispersion medium. Specifically, the following method is mentioned, for example. The compound represented by the general formula (1) in the dispersion medium and the resin as necessary are dissolved, and the pigment powder represented by the general formula (2) is gradually added to the dispersion medium while stirring. Adapt to the dispersion medium. Furthermore, a pigment can be stably finely dispersed into uniform fine particles by applying mechanical shearing force with a dispersing machine such as a ball mill, paint shaker, dissolver, attritor, sand mill, high speed mill or the like.

  In the present invention, the amount of yellow pigment in the pigment dispersion is preferably 1.0 to 30.0 parts with respect to 100 parts of the dispersion medium. More preferably, it is 2.0-20.0 parts, Most preferably, it is 3.0-15.0 parts. If the content of the yellow pigment is within the above range, an increase in viscosity and a deterioration in pigment dispersibility can be prevented, and good coloring power can be exhibited.

  The content of the compound represented by the general formula (1) is preferably 0.05 to 10 parts by mass with respect to 100 parts by mass of the yellow pigment represented by the general formula (2). More preferably, it is 5 parts by mass.

  In the present invention, the pigment dispersion can be dispersed in water using an emulsifier. Examples of the emulsifier include a cationic surfactant, an anionic surfactant, and a nonionic surfactant. Examples of the cationic surfactant include dodecyl ammonium chloride, dodecyl ammonium bromide, dodecyl trimethyl ammonium bromide, dodecyl pyridinium chloride, dodecyl pyridinium bromide, hexadecyl trimethyl ammonium bromide and the like. Examples of the anionic surfactant include fatty acid soaps such as sodium stearate and sodium dodecanoate, sodium dodecyl sulfate, sodium dodecylbenzene sulfate, and sodium lauryl sulfate. Nonionic surfactants include dodecyl polyoxyethylene ether, hexadecyl polyoxyethylene ether, nonylphenyl polyoxyethylene ether, lauryl polyoxyethylene ether, sorbitan monooleate polyoxyethylene ether, monodecanoyl sucrose, etc. It is done.

  Examples of the organic solvent that can be used as the dispersion medium include the following. Methyl alcohol, ethyl alcohol, modified ethyl alcohol, isopropyl alcohol, n-butyl alcohol, isobutyl alcohol, tert-butyl alcohol, sec-butyl alcohol, tert-amyl alcohol, 3-pentanol, octyl alcohol, benzyl alcohol, cyclohexanol, etc. Alcohols; methyl cellosolve, ethyl cellosolve, glycols such as diethylene glycol, diethylene glycol monobutyl ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone; esters such as ethyl acetate, butyl acetate, ethyl propionate, cellosolve acetate; hexane , Octane, petroleum ether, cyclohexane, benzene, toluene, xylene and other hydrocarbon solvents; tetrachloride Halogenated hydrocarbon solvents such as silicon, trichloroethylene and tetrabromoethane; ethers such as diethyl ether, dimethyl glycol, trioxane and tetrahydrofuran; acetals such as methylal and diethyl acetal; organic acids such as formic acid, acetic acid and propionic acid; Sulfur / nitrogen-containing organic compounds such as nitrobenzene, dimethylamine, monoethanolamine, pyridine, dimethylsulfoxide, dimethylformamide.

  Moreover, a polymerizable monomer can also be used as the organic solvent. The polymerizable monomer is an addition polymerizable or condensation polymerizable monomer, and is preferably an addition polymerizable monomer. Specific examples include the following. Styrene monomers such as styrene, o- (m-, p-) methylstyrene, o- (m-, p-) ethylstyrene; methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate, acrylic Acrylate monomers such as octyl acid, dodecyl acrylate, stearyl acrylate, behenyl acrylate, 2-ethylhexyl acrylate, dimethylaminoethyl acrylate, diethylaminoethyl acrylate, acrylonitrile, acrylate amide; methyl methacrylate, methacrylic acid Ethyl acetate, propyl methacrylate, butyl methacrylate, octyl methacrylate, dodecyl methacrylate, stearyl methacrylate, behenyl methacrylate, 2-ethylhexyl methacrylate, dimethylaminoethyl methacrylate, diethyl methacrylate Methacrylate monomers such as minoethyl, methacrylonitrile, methacrylamide; olefin monomers such as ethylene, propylene, butylene, butadiene, isoprene, isobutylene, cyclohexene; vinyl chloride, vinylidene chloride, vinyl bromide, iodide Vinyl halides such as vinyl; vinyl esters such as vinyl acetate, vinyl propionate and vinyl benzoate; vinyl ethers such as vinyl methyl ether, vinyl ethyl ether and vinyl isobutyl ether; vinyl methyl ketone, vinyl hexyl ketone and methyl iso Examples thereof include vinyl ketone compounds such as propenyl ketone. These can be used alone or in combination of two or more according to the intended use. When producing a polymerized toner using the pigment dispersion of the present invention, among the polymerizable monomers, styrene or a styrene-based monomer may be used alone or mixed with another polymerizable monomer. It is preferable to use it. Styrene is preferred because of its ease of handling.

  A resin may be further added to the pigment dispersion. Specific examples include the following. Polystyrene resin, styrene copolymer, polyacrylic acid resin, polymethacrylic acid resin, polyacrylic acid ester resin, polymethacrylic acid ester resin, acrylic acid copolymer, methacrylic acid copolymer, polyester resin, polyvinyl ether resin , Polyvinyl methyl ether resin, polyvinyl alcohol resin, polyvinyl butyral resin, polyurethane resin, polypeptide resin. These resins can be used alone or in admixture of two or more.

  The viscosity of the pigment dispersion of the present invention is preferably in the range of 100 to 2000 mPa · s, more preferably in the range of 200 to 1500 mPa · s at a measurement temperature of 25 ° C., and 300 to 1300 mPa · s. It is particularly preferable that the value falls within the range. If the viscosity of the pigment dispersion is within the above range, the yellow pigment is sufficiently finely dispersed. In addition, when used for the production of a polymerized toner, the dispersion efficiency is good and the transfer after the dispersion treatment is performed smoothly.

<About toner>
Next, the toner of the present invention will be described.
The pigment dispersion of the present invention can be used as a colorant when producing toner particles containing a binder resin, a yellow pigment, a wax component and the like. By using the pigment dispersion of the present invention as a colorant, an increase in the dispersion viscosity in the dispersion medium can be suppressed, so that handling in the toner production process is facilitated and the dispersibility of the colorant is kept good. . As a result, a yellow toner having a high coloring power can be obtained.

  Examples of the binder resin used in the toner include styrene-methacrylic acid copolymer, styrene-acrylic acid copolymer, polyester resin, epoxy resin, and styrene-butadiene copolymer. In a method of directly obtaining toner particles by a polymerization method, a polymerizable monomer for forming them is used. The following are mentioned as a polymerizable monomer. Styrene monomers such as styrene, α-methylstyrene, α-ethylstyrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, o-ethylstyrene, m-ethylstyrene, p-ethylstyrene; methacryl Methyl methacrylate, ethyl methacrylate, propyl methacrylate, butyl methacrylate, octyl methacrylate, dodecyl methacrylate, stearyl methacrylate, behenyl methacrylate, 2-ethylhexyl methacrylate, dimethylaminoethyl methacrylate, diethylaminoethyl methacrylate, methacrylate Methacrylic acid ester monomers such as rhonitrile and methacrylamide, methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate, octyl acrylate, dodecyl acrylate, stearyl acrylate Acrylate monomers such as benzene, acrylate, behenyl acrylate, 2-ethylhexyl acrylate, dimethylaminoethyl acrylate, diethylaminoethyl acrylate, acrylonitrile, acrylate amide, etc .; olefin monomers such as butadiene, isoprene, cyclohexene, etc. body. These can be used alone, or the theoretical glass transition temperature (Tg) described in Polymer Handbook 2nd edition, pages III-139 to 192 (manufactured by John Wiley & Sons) is 40 to 75 ° C. It can also be used as a mixture.

  The toner may contain a polar resin such as a polyester resin or a polycarbonate resin. For example, when a toner is manufactured by a suspension polymerization method or the like, when a polar resin is added from the dispersion step to the polymerization step, it is added according to the balance of polarity exhibited by the polymerizable monomer composition and the aqueous dispersion medium. The polar resin forms a thin layer on the surface of the toner base particles, or exists with a gradient from the surface of the toner base particles toward the center. At this time, by using the pigment dispersion of the present invention and the polar resin, the presence state of the colorant in the toner can be changed to a desired form.

  In order to increase the mechanical strength of the toner particles and to control the molecular weight of the toner molecules, a crosslinking agent can also be used during the synthesis of the binder resin. Examples of the bifunctional crosslinking agent include the following. Divinylbenzene, bis (4-acryloxypolyethoxyphenyl) propane, ethylene glycol diacrylate, 1,3-butylene glycol diacrylate, 1,4-butanediol diacrylate, 1,5-pentanediol diacrylate, 1,6 -Hexanediol diacrylate, neopentyl glycol diacrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, tetraethylene glycol diacrylate, polyethylene glycol # 200, # 400, # 600, dipropylene glycol diacrylate, polypropylene glycol diacrylate, Polyester type diacrylate, and those obtained by replacing the above diacrylate with dimethacrylate. The following are mentioned as a polyfunctional crosslinking agent. Pentaerythritol triacrylate, trimethylolethane triacrylate, trimethylolpropane triacrylate, tetramethylolmethane tetraacrylate, oligoester acrylate and methacrylate, 2,2-bis (4-methacryloxyphenyl) propane, diallyl phthalate, triallylcia Nurate, triallyl isocyanurate and triallyl trimellitate. These crosslinking agents are preferably used in an amount of 0.05 to 10 parts by mass, more preferably 0.1 to 5.0 parts by mass, with respect to 100 parts by mass of the polymerizable monomer.

  In the toner of the present invention, the pigment dispersion of the present invention is used. However, as long as the dispersibility of the pigment dispersion of the present invention is not inhibited, the pigment dispersion and another colorant can be used in combination. Examples of the colorant that can be used in combination include condensed azo compounds, anthraquinone compounds, azo metal complexes, methine compounds, and allylamide compounds.

  Examples of the wax component used in the toner include the following. Petroleum waxes and derivatives thereof such as paraffin wax, microcrystalline wax, petrolatum, montan wax and derivatives thereof, hydrocarbon waxes and derivatives thereof obtained by the Fischer-Tropsch method, polyolefin waxes and derivatives thereof typified by polyethylene, carnauba wax Natural waxes such as candelilla wax and derivatives thereof. The derivatives include oxides, block copolymers with vinyl monomers, and graft modified products. Further, alcohols such as higher aliphatic alcohols, aliphatics such as stearic acid and palmitic acid or derivatives thereof, hardened castor oil and derivatives thereof, plant waxes, and animal waxes can be mentioned. These can be used alone or in combination.

  As the addition amount of the wax component, the total content with respect to 100 parts by mass of the binder resin is preferably in the range of 2.5 to 15.0 parts by mass, and more preferably in the range of 3.0 to 10.0 parts by mass. It is more preferable that

  In the toner of the present invention, a charge control agent can be mixed with toner particles and used as necessary. This makes it possible to control the triboelectric charge amount according to the development system.

  As the charge control agent, a known one can be used, and a charge control agent that has a high charging speed and can stably maintain a constant charge amount is particularly preferable. Further, when the toner is produced by a direct polymerization method, a charge control agent having a low polymerization inhibitory property and substantially free from a solubilized product in an aqueous dispersion medium is particularly preferable.

  The charge control agent is, for example, a polymer or copolymer having a sulfonic acid group, a sulfonic acid group or a sulfonic acid ester group, a salicylic acid derivative and a metal complex thereof, a monoazo metal compound, for controlling the toner to be negatively charged. Acetylacetone metal compounds, aromatic oxycarboxylic acids, aromatic mono- and polycarboxylic acids, their metal salts, anhydrides, esters, phenol derivatives such as bisphenol, urea derivatives, metal-containing naphthoic acid compounds, boron compounds, 4 Examples include quaternary ammonium salts, calixarene, and resin charge control agents. The toner is controlled to be positively charged, for example, nigrosine-modified products with nigrosine and fatty acid metal salts, guanidine compounds, imidazole compounds, tributylbenzylammonium-1-hydroxy-4-naphthosulfonate, tetrabutylammonium tetra Quaternary ammonium salts such as fluoroborate, and onium salts such as phosphonium salts and analogs thereof, and lake pigments thereof, triphenylmethane dyes and lake lake pigments (as rake agents include phosphotungstic acid, phosphomolybdenum Acid, phosphotungstic molybdic acid, tannic acid, lauric acid, gallic acid, ferricyanide, ferrocyanide, etc.), metal salts of higher fatty acids, dibutyltin oxide, dioctyltin oxide, dicyclohexyltin oxide Diorganotin oxide such as de, dibutyltin tin borate, dioctyl tin borate, diorgano tin borate such as dicyclohexyl tin borate, resin charge control agent and the like. These can be used alone or in combination of two or more.

  The toner may be externally added with inorganic fine powder as a fluidizing agent. As the inorganic fine powder, silica, titanium oxide, alumina, or a double oxide thereof, or a surface-treated product thereof can be used.

Examples of the production method for obtaining toner particles constituting the toner include conventionally used pulverization method, suspension polymerization method, suspension granulation method, emulsion polymerization method and the like. From the viewpoint of environmental load during production and controllability of the particle diameter, among these production methods, particularly obtained by a production method for granulating toner particles in an aqueous medium such as suspension polymerization or suspension granulation. In the following, a method for producing toner particles by suspension polymerization will be described. First, a colorant containing a pigment dispersion according to the present invention, a polymerizable monomer, a wax component, a polymerization initiator and the like are mixed to prepare a polymerizable monomer composition. Next, the polymerizable monomer composition is dispersed in an aqueous medium to granulate particles of the polymerizable monomer composition. Then, the polymerizable monomer in the particles of the polymerizable monomer composition is polymerized in an aqueous medium to obtain toner particles.

  The polymerizable monomer composition is preferably prepared by mixing a dispersion obtained by dispersing the colorant in the first polymerizable monomer with the second polymerizable monomer. . That is, after sufficiently dispersing the colorant containing the pigment composition of the present invention with the first polymerizable monomer, the colorant is mixed with the second polymerizable monomer together with the other toner material, thereby obtaining the pigment. Can be present in the toner particles in a better dispersed state.

  Examples of the polymerization initiator used in the suspension polymerization method include the following. 2,2′-azobis (isobutyronitrile), 2,2′-azobis (2-methylbutyronitrile), 2,2′-azobis (4-methoxy-2,4-dimethylvaleronitrile), 2, Azo polymerization initiators such as 2'-azobis (2,4-dimethylvaleronitrile) and dimethyl 2,2'-azobis (isobutyrate); benzoyl peroxide, di-tert-butyl peroxide, tert-butylperoxyisopropyl mono Organic peroxide polymerization initiators such as carbonate, tert-hexylperoxybenzoate, and tert-butylperoxybenzoate; inorganic peroxide polymerization initiators such as potassium persulfate and ammonium persulfate; hydrogen peroxide-first Iron-based, BPO-dimethylaniline-based, cerium (IV) salt-alcohol-based redox, etc. Initiator. Examples of the photopolymerization initiator include acetophenone series, benzoin ether series, and ketal series. These polymerization initiators can be used alone or in combination of two or more.

  The concentration of the polymerization initiator is preferably in the range of 0.1 to 20 parts by mass, more preferably in the range of 0.1 to 10 parts by mass with respect to 100 parts by mass of the polymerizable monomer. The kind of the polymerizable initiator is slightly different depending on the polymerization method, but is used alone or in combination with reference to the 10 hour half-life temperature.

  The aqueous medium used in the suspension polymerization method preferably contains a dispersion stabilizer. As the dispersion stabilizer, known inorganic and organic dispersion stabilizers can be used. Examples of the inorganic dispersion stabilizer include the following. Calcium phosphate, magnesium phosphate, aluminum phosphate, zinc phosphate, magnesium carbonate, calcium carbonate, calcium hydroxide, magnesium hydroxide, aluminum hydroxide, calcium metasilicate, calcium sulfate, barium sulfate, bentonite, silica, alumina. Examples of organic dispersion stabilizers include the following. Polyvinyl alcohol, gelatin, methyl cellulose, methyl hydroxypropyl cellulose, ethyl cellulose, carboxymethyl cellulose sodium salt, starch. Nonionic, anionic and cationic surfactants can also be used. Sodium dodecyl sulfate, sodium tetradecyl sulfate, sodium pentadecyl sulfate, sodium octyl sulfate, sodium oleate, sodium laurate, potassium stearate, olein An acid calcium etc. are mentioned.

  Of the dispersion stabilizers, it is preferable to use a poorly water-soluble inorganic dispersion stabilizer that is soluble in acid. Further, when preparing an aqueous dispersion medium using a hardly water-soluble inorganic dispersion stabilizer, the dispersion stabilizer is 0.2 to 2.0 parts by mass with respect to 100 parts by mass of the polymerizable monomer. It is preferable to use it in such a ratio that it falls within the range from the viewpoint of droplet stability of the polymerizable monomer composition in an aqueous medium. Moreover, it is preferable to prepare an aqueous medium using water within a range of 300 to 3000 parts by mass with respect to 100 parts by mass of the polymerizable monomer composition.

  When preparing an aqueous medium in which a slightly water-soluble inorganic dispersion stabilizer is dispersed, a commercially available dispersion stabilizer may be used as it is, but dispersion stabilizer particles having a fine uniform particle size may be used. In order to obtain, it is preferable to prepare by preparing a poorly water-soluble inorganic dispersion stabilizer under high-speed stirring in water. For example, when calcium phosphate is used as a dispersion stabilizer, a preferable dispersion stabilizer can be obtained by mixing a sodium phosphate aqueous solution and a calcium chloride aqueous solution under high speed stirring to form calcium phosphate fine particles.

  The pigment dispersion of the present invention can be suitably used even when toner particles are produced by a suspension granulation method. Since the suspension granulation method does not have a heating step, it suppresses the compatibilization of the resin and the wax component that occurs when using a low-melting wax, and reduces the glass transition temperature of the toner due to the compatibilization. Can be prevented. In addition, the suspension granulation method has a wide range of options for the toner material used as the binder resin, and it is easy to use a polyester resin, which is generally advantageous for fixability, as a main component. Therefore, this is an advantageous production method for producing a toner having a resin composition to which the suspension polymerization method cannot be applied.

  Toner particles produced by the suspension granulation method are produced, for example, as follows. First, a colorant, a binder resin, a wax component and the like containing the pigment dispersion according to the present invention are mixed in a solvent to prepare a solvent composition. Next, the solvent composition is dispersed in an aqueous medium and particles of the solvent composition are granulated to obtain a toner particle suspension. Then, the toner particles can be obtained by heating the obtained suspension or removing the solvent by reducing the pressure.

  The solvent composition in the step is preferably prepared by mixing a dispersion in which a colorant is dispersed in a first solvent with a second solvent. That is, the colorant containing the pigment composition is sufficiently dispersed in the first solvent, and then mixed with the second solvent together with the other toner materials, so that the pigment is more well dispersed in the toner particles. Can exist.

  Examples of the solvent that can be used in the suspension granulation method include the following. Hydrocarbons such as toluene, xylene, hexane; halogen-containing hydrocarbons such as methylene chloride, chloroform, dichloroethane, trichloroethane, carbon tetrachloride; alcohols such as methanol, ethanol, butanol, isopropyl alcohol; ethylene glycol, propylene glycol, Polyhydric alcohols such as diethylene glycol and triethylene glycol; cellosolves such as methyl cellosolve and ethyl cellosolve; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; ethers such as benzyl alcohol ethyl ether, benzyl alcohol isopropyl ether and tetrahydrofuran; Esters such as methyl acetate, ethyl acetate and butyl acetate. These solvents can be used alone or in admixture of two or more. Of the above solvents, in order to easily remove the solvent in the toner particle suspension, it is preferable to use a solvent having a low boiling point and capable of sufficiently dissolving the binder resin.

  As a usage-amount of a solvent, the case where it is the range of 50-5000 mass parts with respect to 100 mass parts of binder resin is preferable, and the case where it is the range of 120-1000 mass parts is more preferable.

  The aqueous medium used in the suspension granulation method preferably contains a dispersion stabilizer. As the dispersion stabilizer, the same dispersion stabilizers as mentioned in the suspension polymerization method can be used.

  The toner has a weight average particle diameter D4 of 4.0 to 8.0 μm and a ratio of the weight average particle diameter D4 to the number average particle diameter D1 (hereinafter also referred to as D4 / D1) of 1.35 or less. preferable. Furthermore, it is more preferable that the weight average particle diameter D4 is 4.9 to 7.5 μm and D4 / D1 is 1.30 or less. The adjustment method of the weight average particle diameter D4 and the number average particle diameter D1 of the toner differs depending on the toner particle manufacturing method. For example, in the case of the suspension polymerization method, it can be adjusted by controlling the concentration of the dispersing agent used at the time of preparing the aqueous dispersion medium, the reaction stirring speed, or the reaction stirring time.

  The average circularity of the toner measured by the flow type particle image analyzer is preferably 0.950 to 0.995, and 0.960 to 0.990 greatly improves the transferability of the toner. This is more preferable.

  The yellow toner of the present invention can also be used as a magnetic toner containing a magnetic material. Examples of such magnetic materials include iron oxides such as magnetite, maghemite, and ferrite, iron oxides including other metal oxides, metals such as Fe, Co, and Ni, or these metals and Al, Co, Examples thereof include alloys with metals such as Cu, Pb, Mg, Ni, Sn, Zn, Sb, Be, Bi, Cd, Ca, Mn, Se, Ti, W, and V, and mixtures thereof.

<Liquid developer>
The pigment dispersion of the present invention can be used as a developer (hereinafter referred to as a liquid developer) used in a liquid development method. Hereinafter, a method for producing a liquid developer will be described.

  In order to obtain a liquid developer, a compound represented by the general formula (1), a yellow pigment represented by the general formula (2), a dispersant resin used as a dispersant, and if necessary, a charge control agent, An auxiliary agent such as wax is produced by dispersing or dissolving in an electrically insulating carrier liquid. Alternatively, it may be prepared by a two-stage method in which a concentrated toner is first prepared and further diluted with an electrically insulating carrier solution to prepare a developer.

The disperser is not particularly limited, and for example, a media-type disperser such as a rotary shearing homogenizer, a ball mill, a sand mill, or an attritor, a high-pressure opposed collision disperser, or the like is preferably used.
A coloring agent can also be used individually or in combination of 2 or more types.
The same resin and wax as described above are used.

  The charge control agent is not particularly limited as long as it is used in a liquid developer for electrostatic charge development. For example, cobalt naphthenate, copper naphthenate, copper oleate, cobalt oleate, Zirconium octylate, cobalt octylate, sodium dodecylbenzenesulfonate, calcium dodecylbenzene sulfonate, soybean lecithin, aluminum octoate and the like.

The electrically insulating carrier liquid is not particularly limited, but it is preferable to use an organic solvent having a high electric resistance of, for example, 10 ⁹ Ω · cm or more and a low dielectric constant of 3 or less. Specific examples include aliphatic hydrocarbon solvents such as hexane, pentane, octane, nonane, decane, undecane, and dodecane, Isopar H, G, K, L, and M (manufactured by Exxon Chemical Co., Ltd.), linearlen dimer The thing of the temperature range whose boiling point is 68-250 degreeC, such as A-20 and A-20H (made by Idemitsu Kosan Co., Ltd.), is preferable. These may be used alone as long as the viscosity of the system does not increase, or two or more of them may be used in combination.

In the examples, “parts” and “%” are based on mass unless otherwise specified. The obtained reaction product was identified by a plurality of analysis methods using the following apparatuses. That is, ¹ H nuclear magnetic resonance spectroscopy (ECA-400, manufactured by JEOL Ltd.), LC / TOF MS (LC / MSD TOF, manufactured by Agilent Technologies) was used as the analyzer used.

[Production of Compound Represented by General Formula (1)]
As the compound represented by the general formula (1), compounds (1), (4), (5) and (7) were obtained as follows. In addition, the compounds (1), (4), (5), and (7) in this example are compounds (1), (4), (7) in the specific examples of the compound represented by the general formula (1). This corresponds to 5) and (7).
As the compound (1), a trade name “Rika Clear PC1” (manufactured by Shin Nippon Rika Co., Ltd.) was obtained and used.

<Production Example of Compound (4)>
To a solution of 13.0 g (120 mmol) of cresol, 7.0 g (40 mmol) of 1,2,3-propanetricarboxylic acid, 1.0 g (14.4 mmol) of diboron trioxide in 150 mL of xylene, 44.5 g (240 mmol) of n-dodecylamine. ) And heated to reflux for 6 hours for dehydration. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, and then suspended and washed by stirring with 50 mL of acetonitrile at 50 ° C. for 1 hour. The solid was filtered to obtain 10.0 g (yield 37%) of compound (4).

<Analysis results for compound (4)>
[1] ¹ H NMR (400 MHz, DMSO-d ₆ , room temperature): δ [ppm] = 0.85 (t, 9H, J = 6.64 Hz), 1.17 (m, 60H), 2.50 ( t, 11H, J = 1.83 Hz), 7.64 (s, 1H), 8.03 (s, 1H), 10.8 (s, 1H)
[2] Mass spectrometry (ESI-TOF): m / z = 676.414 (M−H) ⁻

<Production Example of Compound (5)>
Manufactured in the same manner as in Production Example 1 except that n-dodecylamine of Compound (1) in Production Example 1 was changed to 2-ethylhexylamine, to obtain 7.3 g (yield 36%) of Compound (5). It was.

<Analysis results for compound (5)>
[1] ¹ H NMR (400 MHz, DMSO-d ₆ , room temperature): δ [ppm] = 0.80 (td, 9H, J = 7.44, 3.51 Hz), 0.86 (t, 9H, J = 6.87 Hz), 1.2 (t, 24 H, 8.47 Hz), 1.32 (dd, 3 H, J = 11.7, 5.72 Hz), 2.10 (dd, 2 H, J = 14. 7, 6.87 Hz), 2.32 (dd, 2 H, J = 14.9, 8.01 Hz), 2.50 (t, 1 H, J = 1.83 Hz), 2.96 (dtd, 6 H, J = 39.1, 13.1, 6.41 Hz), 7.60 (t, 1H, 6.00 Hz), 7.68 (t, 2H, 6.00 Hz)
[2] Mass spectrometry (ESI-TOF): m / z = 508.524 (M−H) ⁻

<Production Example of Compound (7)>
Manufactured in the same manner as in Production Example 1 except that n-dodecylamine of Compound (1) in Production Example 1 was changed to 3-butoxypropylamine, and 4.8 g of Compound (7) (23% yield) was obtained. Obtained.

<Analysis result about compound (7)>
[1] ¹ H NMR (400 MHz, DMSO-d ₆ , room temperature): δ [ppm] = 0.92 to 0.82 (m, 9H), 1.3 (td, 6H, J = 14.9, 7 .48 Hz), 1.46 (dt, 6H, J = 15.7, 5.95 Hz), 1.57 (td, 6H, J = 13.3, 6.4 Hz), 2.07 (dd, 2H, J = 14.7, 6.41 Hz), 2.28 (dd, 2H, J = 14.7, 7.79 Hz), 2.5 (t, 1H, J = 1.60 Hz), 2.99 (tt 7H, J = 22.4, 7.56 Hz), 3.36-3.30 (m, 12H), 7.72 (dt, 3H, J = 29.5, 5.61 Hz)
[2] Mass spectrometry (ESI-TOF): m / z = 5144.3906 (M−H) ⁻
[Production of pigment dispersion]
<Example 1>
C. I. Pigment Yellow 180 (manufactured by Clariant, trade name “TONER YELLOW HG”) 12 parts and compound (1) 0.12 part in a mixture of polyester resin (monomer composition (molar ratio) / polyoxypropylene (2.2) -2) , 2-bis (4-hydroxyphenyl) propane: polyoxyethylene (2.0) -2,2-bis (4-hydroxyphenyl) propane: terephthalic acid: fumaric acid: trimellitic acid = 30: 20: 26: 20: 4, acid value is 11 mg KOH / g, weight average molecular weight (Mw) is 11,000, molecular weight of 500 to less than 2,000 is 8.5%, Tg is 56 ° C.) 48 parts and ethyl acetate 120 parts The mixture was mixed and dispersed for 3 hours by an attritor (manufactured by Mitsui Mining) to obtain a pigment dispersion (1).

<Examples 2 and 3>
Pigment dispersions (2) and (3) were obtained in the same manner as in Example 1 except that ethyl acetate was changed to toluene and ethyl methyl ketone in Example 1.

<Examples 4 and 5>
In Example 1, the same procedure as in Example 1 was carried out except that the polyester resin was not added and that ethyl acetate was changed to styrene or an ethyl acetate / toluene mixture (60 parts / 60 parts). Dispersions (4) and (5) were obtained.

<Example 6>
Example 1 Example 1 except that the polyester resin was not added and the compound (7) was used instead of the compound (1) and the ethyl acetate was changed to a styrene / xylene mixture (70 parts / 50 parts). A pigment dispersion (6) was obtained in the same manner as in.

<Example 7>
C. I. Pigment Yellow 180 6 parts, Compound (1) 0.06 part, sodium dodecyl sulfate 1.2 parts is mixed with water 60 parts, and dispersed for 3 hours with an attritor (Mitsui Mining Co., Ltd.) to obtain a pigment dispersion. (7) was obtained.

<Comparative Examples 1-7>
In Examples 1 to 7, pigment dispersions (8) to (14) were obtained in the same manner as in Examples 1 to 7, except that compound (1) or compound (7) was not added.

[Dispersibility]
The dispersibility of the pigment dispersion was evaluated as follows. The particle size was determined by measuring the size of the texture particles of the pigment using a particle size measuring device (grind meter) (Tester Sangyo Co., Ltd.).
A: The size of the tissue grain of the pigment is less than 2.5 μm. (Very good dispersibility)
B: The size of the pigment tissue grain is 2.5 μm or more and less than 4.5 μm. (Dispersibility is good)
C: The size of the tissue grain of the pigment is 4.5 μm or more. (Dispersibility is bad)
The pigment dispersion was developed on an aluminum substrate, and a sample from which the solvent was removed by natural drying was magnified 100,000 times with a scanning electron microscope S-4800 (manufactured by Hitachi, Ltd.) to confirm dispersibility. .

The evaluation results of Examples 1 to 7 and Comparative Examples 1 to 7 are summarized in Table 1.
(In Table 1, PY180 represents CI Pigment Yellow 180.)

  As is clear from Table 1, the pigment dispersions of Examples 1 to 7 were compared with the pigment dispersion for comparison in which the compound represented by the general formula (1) was not used. Excellent dispersibility.

<Example 8>
C. I. A mixture of 12 parts of Pigment Yellow 180 and 0.12 part of Compound (1) was mixed with 120 parts of styrene and dispersed with an attritor (manufactured by Mitsui Mining Co., Ltd.) for 3 hours to obtain a pigment dispersion (15).

  An SEM photograph of the pigment dispersion (15) when observed by the above method is shown in FIG.

<Examples 9 and 10>
In Example 8, pigment dispersions (16), (17) were obtained in the same manner as in Example 8, except that the parts by mass of compound (1) used were changed to 0.06 parts and 0.36 parts, respectively. )

<Example 11>
In Example 8, C.I. I. Instead of using Pigment Yellow 180, C.I. I. A pigment dispersion (18) was obtained in the same manner as in Example 8, except that it was changed to Pigment Yellow 74.

<Examples 12 to 14>
In Example 8, pigment dispersions (19) to (21) were obtained in the same manner as in Example 8, except that compound (1) was changed to compound (4), compound (5), and compound (7). )

<Example 15>
In Example 8, C.I. I. Pigment Yellow 180, C.I. I. Pigment Yellow 74 was changed, compound (1) was changed to compound (5), and pigment dispersion (22) was obtained in the same manner as in Example 8 except that.

<Comparative Example 9>
In Example 8, a pigment dispersion (23) for comparison was obtained in the same manner as in Example 8, except that compound (1) was not added.

<Comparative Example 10>
In Example 11, a pigment dispersion (24) for comparison was obtained in the same manner as in Example 11, except that compound (1) was not added.

[Viscosity of pigment dispersion]
The viscosity of the pigment dispersion was measured with a rheometer PHYSICA MCR 300 (Pear Physica). The pigment dispersions (15) to (17) and (19) to (21) are different from the pigment dispersion (23), while the pigment dispersions (18) and (22) are the pigment dispersion (24). Viscosity reduction rate was determined for each.
Cone plate type measuring jig: 75 mm diameter, 1 °
Shear rate: 10 s ^-1
A: The rate of viscosity reduction with respect to the comparative pigment dispersion is 15% or more.
B: Viscosity decreasing rate relative to the comparative pigment dispersion is 5% or more and less than 15%.
C: The rate of viscosity reduction with respect to the comparative pigment dispersion is less than 5%.

[Glossiness]
The glossiness of the pigment dispersion was evaluated as follows. Scoop the pigment dispersion with a dropper and place it straight on top of art paper (made by Oji Paper Co., Ltd., trade name “SA Kanofuji +, weighing 209.3 g / m ² ”), and use a wire bar (# 10) And evenly coated on art paper. After drying, the glossiness (reflection angle: 60 °) of the line on the art paper was measured with a gloss meter VG7000 (Nippon Denshoku Industries Co., Ltd.). The pigment dispersions (15) to (17) and (19) to (21) are different from the pigment dispersion (23), while the pigment dispersions (18) and (22) are the pigment dispersion (24). The glossiness magnification for each was determined.
A: The magnification of the glossiness with respect to the comparative pigment dispersion is 2 times or more.
B: The gloss ratio with respect to the comparative pigment dispersion is 1.5 times or more and less than 2 times.
C: The gloss ratio with respect to the comparative pigment dispersion is less than 1.5 times.
(In Table 2, PY180 represents CI Pigment Yellow 180. PY74 represents CI Pigment Yellow 74.)

  As is clear from Table 2, the pigment dispersions of Examples 8 to 15 have a lower viscosity of the colorant in the dispersion medium than the corresponding pigment dispersion for comparison. Further, since the dispersibility of the colorant in the dispersion medium is good, the glossiness is improved.

[Manufacture of yellow toner]
<Example 16>
High-speed stirrer K. 710 parts of ion-exchanged water and 450 parts of 0.1 mol / l-trisodium phosphate aqueous solution were added to a 2 L four-necked flask equipped with a homomixer (manufactured by PRIMIX Co., Ltd.), and the rotational speed was adjusted to 12000 rpm. Warmed to 60 ° C. To this, 68 parts of a 1.0 mol / l-calcium chloride aqueous solution was gradually added to prepare an aqueous dispersion medium containing a minute poorly water-soluble dispersion stabilizer calcium phosphate.
-Pigment dispersion (15): 133.2 parts-Styrene monomer: 46.0 parts-n-butyl acrylate monomer: 34.0 parts-Aluminum salicylate compound: 2.0 parts (Orient Chemical Co., Ltd.) Manufactured by Bontron E-88)
Polar resin: 10.0 parts (polycondensation product of propylene oxide modified bisphenol A and isophthalic acid, Tg: 65 ° C., Mw: 10,000, Mn: 6000)
Ester wax: 25.0 parts (peak temperature of maximum endothermic peak in DSC measurement: 70 ° C., Mn: 704)
・ Divinylbenzene monomer: 0.10 parts

  The above material is heated to 60 ° C. K. It was uniformly dissolved and dispersed at 5000 rpm using a homomixer. In this, 10 parts of 2,2'-azobis (2,4-dimethylvaleronitrile) as a polymerization initiator was dissolved to prepare a polymerizable monomer composition. The polymerizable monomer composition was charged into the aqueous medium and granulated for 15 minutes while maintaining the rotation speed of 12000 rpm. Thereafter, the stirrer was changed from a high-speed stirrer to a propeller stirring blade, and the polymerization was continued for 5 hours at a liquid temperature of 60 ° C. Then, the liquid temperature was raised to 80 ° C. and the polymerization was continued for 8 hours. After completion of the polymerization reaction, the residual monomer was distilled off at 80 ° C./reduced pressure, and then the liquid temperature was cooled to 30 ° C. to obtain a polymer fine particle dispersion.

  Next, the polymer fine particle dispersion was transferred to a washing container, and while stirring, dilute hydrochloric acid was added to adjust the pH to 1.5, followed by stirring for 2 hours. Solid-liquid separation was performed with a filter to obtain polymer fine particles. Redispersion of polymer fine particles in water and solid-liquid separation were repeated until the phosphoric acid-calcium compound containing calcium phosphate was sufficiently removed. Thereafter, the polymer fine particles finally solid-liquid separated were sufficiently dried with a dryer to obtain yellow toner particles (1).

  1.00 part of hydrophobic silica fine powder (number average primary particle diameter 7 nm) surface-treated with hexamethyldisilazane, rutile type titanium oxide fine powder (number average primary particle diameter) with respect to 100 parts of the obtained yellow toner particles 45 nm) 0.15 part and rutile-type titanium oxide fine powder (number average primary particle diameter 200 nm) 0.50 part were dry-mixed for 5 minutes with a Henschel mixer (manufactured by Nippon Coke Kogyo Co., Ltd.) to give yellow toner (1). Obtained.

<Example 17>
In Example 16, a yellow toner (2) was obtained in the same manner as in Example 16 except that the aluminum salicylate compound was not added.

<Example 18>
In Example 16, a yellow toner (3) was obtained in the same manner as in Example 16 except that the pigment dispersion (15) was changed to the pigment dispersion (21).

<Comparative Example 10>
In Example 16, a yellow toner (4) was obtained in the same manner as in Example 16 except that the pigment dispersion (15) was changed to the pigment dispersion (23).

<Comparative Example 11>
In Example 17, a yellow toner (5) was obtained in the same manner as in Example 17, except that the pigment dispersion (15) was changed to the pigment dispersion (23).
The yellow toners (1) to (5) were evaluated as follows.

(1) Number average particle diameter (D1), weight average particle diameter (D4 measurement, amount of coarse powder of toner) The number average particle diameter (D1) and weight average particle diameter (D4) of the toner are determined by particle size distribution by Coulter method. The measurement was performed using a Coulter Multisizer II (manufactured by Beckman Coulter Co., Ltd.) as the measuring device, and the measurement was performed according to the operation manual of the device.The electrolyte was ISOTON-II (Coulter Scientific Japan). As a specific measuring method, about 0.1 ml of a surfactant (alkylbenzene sulfonate) as a dispersant was added to 100 ml of the electrolytic aqueous solution, and a measurement sample (toner particles) was further added. About 2 mg was added to the electrolyte solution in which the sample was suspended by an ultrasonic disperser for about 1 to 3 minutes. The volume and the number distribution of the toner were calculated by measuring the volume and the number of toners of 2.00 μm or more with the above-described measuring apparatus equipped with a 100 μm aperture as the aperture, and obtained from the toner particle number distribution. The number average particle diameter (D1), the weight average particle diameter (D4) of the toner particles determined from the volume distribution of the toner particles (the median value of each channel is the representative value for each channel), and D4 / D1 were determined.

  The channels include 2.00 to 2.52 μm, 2.52 to 3.17 μm, 3.17 to 4.00 μm, 4.00 to 5.04 μm, 5.04 to 6.35 μm, 6.35 to 8 0.000, 8.00-10.08, 10.08-12.70, 12.70-16.00, 16.00-20.20, 20.20-25.40, 25.40-32.00 13 channels from 32.00 to 40.30 μm were used.

  Particles larger than twice the number average particle diameter (D1) were used as coarse powder. The amount of dust in the toner particle size distribution was evaluated according to the following criteria. “None” when the amount of coarse powder is 0%, “Yes” when the amount of coarse powder is greater than 0% and less than 1%, and “Large” when the amount of coarse powder is greater than 1% "

(2) Measurement of average circularity of toner Measured using a flow type particle image measuring device “FPIA-2100 type” (manufactured by Sysmex Corporation), calculated circularity using the following formula, and calculated average circularity. did.

  Here, the “particle projected area” is the area of the binarized toner particle image, and the “peripheral length of the particle projected image” is the length of the contour line obtained by connecting the edge points of the toner particle image. Define. The degree of circularity is an index indicating the degree of unevenness of particles, and is 1.000 when the particles are completely spherical, and the degree of circularity becomes smaller as the surface shape becomes more complicated.

(3) Toner Colorability Evaluation Under normal environment (temperature 25 ° C./humidity 60% RH), a 16-tone image sample with the maximum toner loading adjusted to 0.45 mg / cm ² was converted into a color copier CLC-1100 An image sample was output using a machine (manufactured by Canon Inc., omitting the fixing oil application mechanism). CLC color copy paper (manufactured by Canon Inc.) was used as the base paper for the image samples. The density OD (Y) of the yellow color of the obtained image sample was measured using SpectroLino (manufactured by Gretag Machbeth).
A: OD (Y) is 1.6 or more. (Colorability is very good)
B: OD (Y) is 1.5 or more and less than 1.6. (Good coloring)
C: OD (Y) is less than 1.5. (Colorability is bad)

  As can be seen from Table 3, the toner produced using the pigment dispersion that satisfies the conditions of the present invention was suppressed in the formation of coarse powder and exhibited good coloring power.

According to the present invention, a pigment dispersion having excellent dispersibility of a colorant in a dispersion medium can be obtained. This pigment dispersion can be used as a toner, an inkjet ink, a thermal transfer recording sheet, a colorant for a color filter, and a dye for an optical recording medium.

Claims (6)

A pigment dispersion containing, in a dispersion medium, a compound represented by the general formula (1) and a yellow pigment,
The yellow pigment is C.I. I. Pigment yellow 74, or C.I. I. Pigment Yellow 180, a pigment dispersion.

[In General Formula (1), R _{1 to} R ₃ and R ′ _{1 to} R ′ ₃ are each independently a hydrogen atom, a linear alkyl group, a branched alkyl group, a cyclic alkyl group, or an alkoxyl group. Chain alkyl group, linear alkyl group substituted with amino group, linear alkyl group substituted with carboxyl group, branched alkyl group substituted with amino group, cyclic alkyl group substituted with methyl group, aryl group, methyl Represents an aryl group or an aralkyl group substituted with a group. ] _2. The pigment dispersion according to claim 1, wherein in the general formula (1), R ₁ , R ₂ and R ₃ are the same, and R ′ ₁ , R ′ ₂ and R ′ ₃ are the same. _3. The pigment dispersion according to claim 1, wherein, in the general formula (1), R _{1 to} R ₃ are alkyl groups, and R ′ _{1 to} R ′ ₃ are hydrogen atoms. The pigment dispersion according to any one of claims 1 to 3, wherein the compound represented by the general formula (1) is a compound selected from the group consisting of the following compounds (1) to (13).
The compound represented by the general formula (1) is a compound selected from the group consisting of the following compounds (1), (4), (5) and (7). The pigment dispersion described in 1.
A method for producing a yellow toner having yellow toner particles containing a binder resin, a yellow pigment and a wax component, comprising:
With pigment dispersion according to any one of claims 1 to 5, yellow method for producing a toner, which comprises preparing said yellow toner particles by the suspension polymerization method or a suspension granulation method.