JP2007155861A - Method for manufacturing yellow toner for electrostatic image development - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a method for manufacturing a yellow toner for electrostatic image development by which when the toner is manufactured by suspension polymerization, there is less risk of environmental pollution in disposal and by-product irregular toner is less. <P>SOLUTION: The method for manufacturing a yellow toner for electrostatic image development includes the steps of: forming liquid droplets by dispersing a polymerizable monomer composition comprising a polymerizable monomer comprising a monovinyl monomer and a yellow colorant in an aqueous dispersion medium; and obtaining yellow colored resin particles comprising a binder which is a polymer of the polymerizable monomer and the yellow colorant by carrying out polymerization, wherein the yellow colorant is a halogen element-free pigment and the polymerizable monomer composition further comprises an aluminum coupling agent in an amount of 0.01-1.0 part by weight based on 100 parts by weight of the monovinyl monomer. <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

  The present invention relates to an electrostatic charge image developing yellow toner (hereinafter referred to as an electrostatic charge image developing yellow toner) used for developing an electrostatic latent image in electrophotography, electrostatic recording method, electrostatic printing method and the like. , Simply referred to as “yellow toner”).

  A method of forming a desired image by developing an electrostatic latent image with toner for developing an electrostatic image is widely used. For example, in electrophotography, an electrostatic latent image formed on a photoreceptor is developed with toner, transferred to a recording material such as paper or an OHP sheet, and then fixed to obtain a printed matter.

The toner mainly contains colored resin particles, and further contains other particles such as external additives and carriers as required.
The production method of the colored resin particles which are the main constituent elements of the toner is roughly classified into a dry method and a wet method.
Examples of the dry method include a pulverization method, which is a method for producing colored resin particles by pulverizing and classifying a solid body of a colored resin obtained by melt-kneading a binder and a colorant.
On the other hand, the wet method includes a polymerization method and a dissolution suspension method, and includes a step of granulating colored resin particles in an aqueous dispersion medium.
As the polymerization method, for example, a polymerizable monomer composition containing a polymerizable monomer and a colorant is formed into droplets in an aqueous dispersion medium, and the droplets are polymerized to produce colored resin particles. Examples thereof include a suspension polymerization method and an emulsion polymerization aggregation method in which an emulsified polymerizable monomer is polymerized to obtain resin fine particles and aggregated with a colorant or the like to produce colored resin particles.
In the dissolution suspension method, a solution in which a toner component such as a binder resin or a colorant is dissolved or dispersed in an organic solvent is formed into droplets in an aqueous dispersion medium, and the organic solvent is removed to produce colored resin particles. It is a method to do.

The colored resin particles obtained by the pulverization method are indefinite, whereas the colored resin particles obtained by a wet method such as the suspension polymerization method, the emulsion polymerization aggregation method, and the dissolution suspension method are nearly spherical in shape. Small particle size and sharp particle size distribution. From the viewpoint of improving image quality such as image reproducibility and fineness, a toner obtained by the above-described wet method and having a highly controlled shape and particle size distribution has been used.
In particular, the solution suspension method requires the removal of the organic solvent, and the emulsion polymerization aggregation method requires the removal of the emulsifier, and the suspension polymerization method is particularly a promising production method. It has become.

However, even in the suspension polymerization method, when the toner obtained by the method is closely observed, there is a case where “deformed toner” which is a colored resin particle having a large particle size or an irregular shape is mixed. .
When such a toner containing a deformed toner is used, poor fine line reproducibility or the like occurs, and high resolution cannot be obtained.

In Patent Document 1, a pigment previously coupled in an organic solvent (methyl ethyl ketone) with a coupling agent selected from an organoaluminum compound, an organotitanium compound, an organozirconium compound, and an organosilicone compound is used as a colorant. By doing so, it is disclosed that the dispersibility of the colorant in the toner particles can be improved. The toner disclosed in this document is an emulsion polymerization aggregate (Emulsion) in which a composition containing a monomer and an initiator is emulsion-polymerized in an appropriate dispersion medium and then aggregated with a colorant and the like in an appropriate dispersion medium. (Aggregation), and the sphericity of the toner particles can be increased in the aggregation stage.
Patent Document 2 discloses a toner obtained by using 2.5 parts by weight of an aluminum coupling agent having a specific structure with 100 parts by weight of a polymerizable monomer together with a yellow colorant containing a halogen element. It is described that the dispersibility of the colorant is improved.
However, these patent documents do not take any measures against the resolution reduction caused by the by-product of the deformed toner.

  On the other hand, many yellow colorants used in color toners have conventionally been used containing halogen elements. The halogen contained in this yellow colorant has a problem that it has a great influence on the environment, for example, dioxins are generated during incineration to cause air pollution. In recent years, legislation prohibiting the use of substances harmful to the environment has been established, and the demand for developing halogen-free products has also increased in this field.

JP 2005-165155 A

Japanese Patent Laid-Open No. 2003-195565

  An object of the present invention is to provide a method for producing a yellow toner for developing an electrostatic charge image with less risk of environmental pollution at the time of disposal and less by-product of deformed toner when producing the toner by suspension polymerization. It is to provide.

In the conventional suspension polymerization method, even if the toner has a spherical shape and is close to the target particle size, a toner having cracks and wrinkles on the surface is easily generated as a by-product particularly in the yellow toner (see, for example, Comparative Example 1).
In order to solve the above-described problems and the like, the present inventors have conducted extensive research, and as a result, a polymerizable monomer composition containing a specific amount of an aluminum coupling agent together with a polymerizable monomer and a yellow colorant. When the suspension polymerization method is used, the aluminum coupling agent is found not only to improve the dispersibility of the colorant but also to suppress the by-product of the deformed toner. Invented.

That is, the method for producing a yellow toner for developing electrostatic images provided by the present invention comprises a polymerizable monomer composition containing a monovinyl monomer and a polymerizable monomer composition containing a yellow colorant, and an aqueous dispersion medium. An electrostatic charge image including a step of obtaining a yellow colored resin particle containing a binder resin and a yellow colorant, which is a polymer of a polymerizable monomer, by performing polymerization after forming droplets by dispersing therein In the manufacturing method of yellow toner for development,
The yellow colorant is a pigment containing no halogen element;
The polymerizable monomer composition further contains an aluminum coupling agent, and the content of the aluminum coupling agent is 0.01 to 1.0 part by weight with respect to 100 parts by weight of the monovinyl monomer. Features.

The method for producing a yellow toner for developing an electrostatic charge image according to the present invention comprises mixing a specific amount of an aluminum coupling agent into a polymerizable monomer composition and subjecting a yellow pigment to a surface treatment with the aluminum coupling agent. By carrying out the polymerization step in this step, it is possible to suppress the formation of the deformed toner in the polymerization step.
Further, since the production method of the present invention uses a pigment not containing a halogen element as a yellow colorant, no harmful gas containing halogen or dioxin is generated during incineration.

  The yellow colorant is C.I. I. Pigment Yellow 74, 120, 151, 155, 180, 185, and 213 are preferably selected.

  This is because among the yellow pigments that do not contain a halogen element, the yellow pigments listed above are particularly excellent in preventing the generation of deformed toner by surface treatment using an aluminum coupling agent.

  The polymerizable monomer composition is preferably obtained by mixing the polymerizable monomer, the yellow colorant, and the aluminum coupling agent and then dispersing by a media type disperser. .

  As a mixing order for preparing the polymerizable monomer composition, the yellow colorant is sufficiently uniformly mixed in the polymerizable monomer composition, and the colorant is sufficiently surface-treated with the aluminum coupling agent. In view of the above, it is preferable to first mix a polymerizable monomer, a yellow colorant, and an aluminum coupling agent, and then disperse the pigment with a media type disperser.

The polymerizable monomer composition preferably further contains a charge control resin.
This is because when the charge control resin is used as the charge control agent, the printing durability of the toner is improved, and there is an effect of reducing the by-product of the deformed toner.

  The average circularity of the yellow colored resin particles is preferably 0.970 to 0.995 from the viewpoint of obtaining a high-quality image.

  According to the production method of the present invention, a yellow toner for developing an electrostatic charge image capable of forming a high-resolution image such as good reproducibility of fine lines and having little risk of environmental pollution even after incineration. Is obtained.

The method for producing a yellow toner for developing an electrostatic image according to the present invention comprises dispersing a polymerizable monomer composition containing a monovinyl monomer and a polymerizable monomer composition containing a yellow colorant in an aqueous dispersion medium. An electrostatic charge image developing yellow toner comprising a step of obtaining yellow colored resin particles containing a binder resin and a yellow colorant, which is a polymer of a polymerizable monomer, by forming a droplet and then performing polymerization. In the manufacturing method,
The yellow colorant is a pigment containing no halogen element;
The polymerizable monomer composition further contains an aluminum coupling agent, and the content of the aluminum coupling agent is 0.01 to 1.0 part by weight with respect to 100 parts by weight of the monovinyl monomer. It is a feature.

  Hereinafter, the constituent material and manufacturing method of the yellow toner for developing an electrostatic charge image of the present invention will be described in detail.

(A) Step of obtaining a polymerizable monomer composition In the present invention, a polymerizable monomer, a yellow colorant, an aluminum coupling agent, and other additives as necessary are mixed to obtain a polymerizable monomer. A meter composition is prepared.
As a mixing order for preparing the polymerizable monomer composition, the colorant is sufficiently uniformly mixed in the polymerizable monomer composition, and the colorant is sufficiently surface-treated with an aluminum coupling agent. From the viewpoint, first, the monovinyl monomer, which is the main component of the polymerizable monomer, the yellow colorant, if necessary, other colorants and an aluminum coupling agent are mixed, and the colorant is sufficiently dispersed. It is preferable to prepare an intermediate mixture and further mix other components such as a crosslinking agent, a macromonomer, a molecular weight adjusting agent, a charge control agent and the like with this intermediate mixture.
All or part of the required amount of the aluminum coupling agent may be used in advance for the surface treatment of the yellow colorant before mixing with the polymerizable monomer. In this case, all or part of the aluminum coupling agent is mixed with the polymerizable monomer in a state of being bonded or attached to the surface of the yellow colorant.

The colorant and other additives are preferably mixed so that they are dissolved or dispersed as uniformly as possible in the polymerizable monomer. Such mixing is preferably performed using a media-type disperser.
The media-type disperser is an apparatus that can mix a mixture and media particles at high speed by a rotor and apply shearing force to mix them. The peripheral speed at the tip of the rotor is preferably 2 m / second or more, more preferably 5 m / second or more, and particularly preferably 8 m / second or more.
FIG. 1 is a schematic diagram showing an example of a distributed system including a media type dispersing machine suitable for the present invention. This dispersion system includes a media-type disperser 1, and the media-type disperser 1 and a holding tank 5 are connected by a lower circuit composed of lines 2 and 4 through which a liquid flows and an upper circuit composed of a line 5. ing.
As shown in the sectional view of FIG. 2, the media type dispersing machine 1 is disposed on the drive shaft 19 in the casing 2 having the liquid supply port 3 and the liquid discharge port 4 and is simultaneously rotated by the rotation of the drive shaft 19. A structure in which a rotatable rotor 16 and a media separation screen 18 are installed and a large number of media particles 17 are stored in an internal space is used. A cylindrical portion 24 in which a plurality of media particle discharge slits 23 are formed is provided at one end of the rotor 16, and a media separation screen 18 is disposed inside the cylindrical portion 24. The liquid introduced into the casing 2 from the liquid supply port 3 passes through the media separation screen 18 and is discharged from the liquid discharge port 4 to the outside.
When the drive shaft 19 is rotated by a motor provided in the media type dispersing machine, the rotor 16 and the media separation screen 18 arranged on the drive shaft 19 are rotated simultaneously.

When a mixed liquid composed of a polymerizable monomer, a yellow colorant, an aluminum coupling agent, etc. is continuously supplied from the liquid supply port 3 into the casing 2, the centrifugal force generated by the rotation of the rotor 16 and the function of the media particles 17. As a result, the yellow colorant is finely dispersed in the polymerizable monomer. The polymerizable monomer dispersion liquid in which the yellow colorant is finely dispersed passes through the media separation screen 18 and is discharged to the outside through the liquid discharge path 25. When this dispersion is returned to the holding tank 5 and circulated again in the same media type disperser 1, a dispersion in which the yellow colorant is more uniformly and finely dispersed can be obtained.
When mixing with a media type disperser, the residence time is preferably 0.03 to 0.5 hours.
After the colorant in the mixture is sufficiently dispersed, another component such as a crosslinking agent is further added to the mixture, and mixing is continued again using a media-type disperser to obtain a polymerizable monomer composition. It is done. However, since the colorant dispersion process has already been completed at this stage, the mixing may be performed under milder stirring conditions without using a media-type disperser.

Hereinafter, each component which comprises a polymerizable monomer composition is demonstrated separately.
(Polymerizable monomer)
In the present invention, the polymerizable monomer refers to a polymerizable compound. By polymerizing the polymerizable monomer, a binder resin of colored resin particles is generated.
As the main component of the polymerizable monomer, a monovinyl monomer is used. Examples of the monovinyl monomer include styrene; styrene derivatives such as vinyl toluene and α-methylstyrene; acrylic acid and methacrylic acid; methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate, acrylic acid 2 Acrylic esters such as ethylhexyl and dimethylaminoethyl acrylate; methacrylic esters such as methyl methacrylate, ethyl methacrylate, propyl methacrylate, butyl methacrylate, 2-ethylhexyl methacrylate and dimethylaminoethyl methacrylate; acrylamide Amide compounds of acrylic acid such as methacrylamide, amides of methacrylic acid; olefins such as ethylene, propylene and butylene; halogens such as vinyl chloride, vinylidene chloride and vinyl fluoride Vinyl esters such as vinyl acetate and vinylidene halides; vinyl esters such as vinyl acetate and vinyl propionate; vinyl ethers such as vinyl methyl ether and vinyl ethyl ether; vinyl ketones such as vinyl methyl ketone and methyl isopropenyl ketone; 2-vinyl pyridine, 4 -Nitrogen-containing vinyl compounds such as vinyl pyridine and N-vinyl pyrrolidone;
The said monovinyl monomer may be used independently and may be used in combination of multiple. In particular, styrene, a styrene derivative, and a derivative of acrylic acid or methacrylic acid are preferably used.

The monovinyl monomer is preferably selected so that the glass transition temperature (hereinafter referred to as Tg) of the polymer obtained by polymerizing the monovinyl monomer is 80 ° C. or lower. By using monovinyl monomers alone or in combination of two or more, the Tg of the polymer can be adjusted to a desired range.
The proportion of the monovinyl monomer is preferably at least 80% by weight or more in the polymerizable monomer used to form the binder resin component.

The polymerizable monomer composition may contain a crosslinking agent. As a crosslinking agent, arbitrary crosslinking | crosslinked polymerizable monomers are mentioned. By using such a crosslinkable polymerizable monomer in combination with a monovinyl monomer, fixability, particularly offset characteristics are improved.
Examples of the crosslinkable polymerizable monomer include aromatic divinyl compounds such as divinylbenzene, divinylnaphthalene, and derivatives thereof; diacrylate compounds such as ethylene glycol dimethacrylate and diethylene glycol dimethacrylate; N, N-divinylaniline. , Divinyl ether; a compound having three or more vinyl groups; and the like.
These crosslinkable monomers can be used alone or in combination of two or more.
In the present invention, it is desirable to use the crosslinkable polymerizable monomer in a proportion of usually 0.1 to 5 parts by weight, preferably 0.3 to 2 parts by weight, with respect to 100 parts by weight of the monovinyl monomer. .

The polymerizable monomer composition may contain a macromonomer as a part of the polymerizable monomer. By using a macromonomer together with a monovinyl monomer, a good balance between storage stability and low-temperature fixability can be maintained. The macromonomer in the present invention has a polymerizable carbon-carbon unsaturated double bond at the end of the molecular chain, and is an oligomer or polymer having a number average molecular weight of usually 1,000 to 30,000.
The macromonomer is preferably one that gives a polymer having a Tg higher than the glass transition temperature Tg of the polymer obtained by polymerizing a monovinyl monomer. The amount of the macromonomer is usually 0.01 to 10 parts by weight, preferably 0.03 to 5 parts by weight, and more preferably 0.05 to 1 part by weight with respect to 100 parts by weight of the monovinyl monomer.

(Yellow colorant)
As the yellow colorant used in the present invention, a yellow pigment containing no halogen element is used. Two or more yellow pigments may be used.
The yellow pigment not containing a halogen element is not particularly limited, but is generally appropriately selected from azo pigments, condensed polycyclic pigments, and the like. I. Pigment Yellow 1, 4, 5, 7, 24, 65, 74, 99, 108, 117, 120, 123, 129, 151, 155, 167, 180, 185, and 213, and derivatives thereof. In particular, C.I. I. Pigment Yellow 74, 120, 155, 180, 184, 185, and 213 are preferable because they are excellent in preventing the generation of deformed toner by surface treatment using an aluminum coupling agent, and more preferable. Is C.I. I. Pigment Yellow 74, 120, 155, 184, and 213, and more preferably C.I. I. Pigment Yellow 120, 155, 184, and 213, particularly preferably C.I. I. Pigment Yellow 184 and 213.

  The amount of the yellow colorant is preferably 1 to 10 parts by weight with respect to 100 parts by weight of the monovinyl monomer.

(Aluminum coupling agent)
In the present invention, prior to the formation of droplets in the aqueous dispersion medium, an aluminum coupling agent is added to the polymerizable monomer composition, and the yellow colorant is surface-treated to thereby produce a by-product of the deformed toner. Can be reduced.
In the present invention, the deformed toner refers to a toner having an irregular or irregular shape apart from a spherical shape essential for high-quality printing. In particular, the present invention is effective in reducing irregularly shaped toner that has a non-smooth surface and has many cracks and wrinkles, even if it is nearly spherical.
Only by grasping the conventional average particle size and particle size distribution, it is not possible to accurately grasp the influence of the deformed toner on the toner quality and hence the image quality of the printed matter. This is because the average particle size and particle size distribution are values obtained by averaging the diameters of a large number of particles.
Therefore, the presence of the deformed toner needs to confirm the number of the deformed toner per unit area with an electron microscope at present. However, by obtaining the circularity of a certain amount of sample by using a particle measuring device or the like, it can be used as a standard for the presence of deformed toner for convenience. The circularity will be described later.

  As the aluminum coupling agent, those commonly used in the field can be used, for example, aluminum alcoholate, aluminum chelate, cyclic aluminum oligomer, etc. can be used. Aluminum alcoholates such as acetoalkoxyaluminum diisopropylate represented by “Plenact AL-M” manufactured by Ajinomoto Fine Techno Co., Ltd. are preferably used.

In the present invention, in order to prevent not only the dispersibility of the yellow colorant but also the by-product of the deformed toner, an aluminum coupling agent is added to the polymerizable monomer composition and the monovinyl in the polymerizable monomer. The content is 0.01 to 1.0 part by weight, preferably 0.05 to 0.8 part by weight, based on 100 parts by weight of the monomer.
When the content of the aluminum coupling agent is smaller than the above range, the effect of reducing the by-product of the deformed toner cannot be obtained sufficiently.
On the other hand, when the content of the aluminum coupling agent is larger than the above range, droplets of the polymerizable monomer composition easily aggregate in the polymerization step, and coarse colored resin particles increase.

(Charge control agent)
The polymerizable monomer composition may contain a charge control agent. As the charge control agent, various positively chargeable or negatively chargeable charge control agents can be used. For example, a metal complex of an organic compound having a carboxyl group or a nitrogen-containing group, and a non-resin charge control agent such as a metal-containing dye; a copolymer containing a quaternary ammonium group or a salt group thereof, a sulfonic acid group or a salt thereof And a charge control resin such as a copolymer containing a carboxylic acid group or a salt thereof. A charge control agent that is not a resin and a charge control resin may be used in combination, or the charge control resin may be used alone.
However, it is preferable to use only the charge control resin because the printing durability of the toner is improved and there is an effect of reducing the by-product of the deformed toner.
The charge control resin includes a negative charge control resin and a positive charge control resin, which are selectively used depending on whether the toner of the present invention is a negatively chargeable toner or a positively chargeable toner.

Hereinafter, the negative charge control resin and the positive charge control resin will be described.
Examples of the negative charge control resin include a resin having a substituent selected from a carboxyl group or a salt thereof, a phenol group or a salt thereof, a thiophenol group or a salt thereof, a sulfonic acid group or a salt thereof in a polymer side chain. Is mentioned.
Among these, a resin having a sulfonic acid group or a salt thereof in the side chain of the polymer is preferably used. Specific examples include a resin obtained by copolymerizing a monovinyl monomer containing a sulfonic acid group or a salt thereof and another monovinyl monomer copolymerizable with the monovinyl monomer.
Monovinyl monomers containing sulfonic acid groups or salts thereof include, for example, styrene sulfonic acid, sodium styrene sulfonate, potassium styrene sulfonate, 2-acrylamido-2-methylpropane sulfonic acid, sodium vinyl sulfonate, and Examples include ammonium methacryl sulfonate.
Other monovinyl monomers that can be copolymerized with the monovinyl monomer containing the sulfonic acid group or a salt thereof include ethylenically unsaturated carboxylic acid ester monomers, aromatic vinyl monomers, and ethylenic monomers. Examples thereof include unsaturated nitrile monomers.

The compounding amount of the monovinyl monomer containing a sulfonic acid group or a salt thereof is preferably 0.5 to 15% by weight, more preferably 1 to 10% by weight in the negative charge control resin. When the blending amount of the monovinyl monomer containing a sulfonic acid group or a salt thereof is less than the above range, the charge amount of the toner may be insufficient. There is a case where a decrease in the charge amount becomes large and fogging occurs.
The negative charge control resin preferably has a weight average molecular weight of 2,000 to 50,000, more preferably 4,000 to 40,000, and most preferably 6,000 to 35,000.
The glass transition temperature of the negative charge control resin is preferably 40 to 80 ° C, more preferably 45 to 75 ° C, and most preferably 45 to 70 ° C. When the glass transition temperature is less than the above range, the storage stability of the toner is deteriorated, and when it exceeds the above range, the fixability may be lowered.

Examples of the positive charge control resin include amino such as —NH ₂ , —NHCH ₃ , —N (CH ₃ ) ₂ , —NHC ₂ H ₅ , —N (C ₂ H ₅ ) ₂ , —NHC ₂ H ₄ OH. Resins containing groups, and resins containing functional groups that are ammonium salified. Such a resin is obtained, for example, by copolymerizing a monovinyl monomer containing an amino group and a monovinyl monomer copolymerizable therewith. Further, the copolymer obtained as described above can be obtained by ammonium chloride. Furthermore, although obtained by copolymerizing a monovinyl monomer containing an ammonium base and a monovinyl monomer copolymerizable therewith, it is not limited to these methods. In order to obtain a negative charge control resin, a monovinyl monomer copolymerizable with a monovinyl monomer containing an amino group or a monovinyl monomer copolymerizable with a monovinyl monomer containing an ammonium base What is used is mentioned.

The charge control agent is usually used in a proportion of 0.01 to 10 parts by weight, preferably 0.5 to 8 parts by weight with respect to 100 parts by weight of the monovinyl monomer.
(Molecular weight regulator)
The polymerizable monomer composition may contain a molecular weight modifier (also referred to as a polymerization degree modifier). Examples of the molecular weight modifier include mercaptans such as t-dodecyl mercaptan, n-dodecyl mercaptan, n-octyl mercaptan, 2,2,4,6,6-pentamethylheptane-4-thiol, and the like. The molecular weight modifier can be added before or during polymerization. The amount of the molecular weight modifier is preferably 0.01 to 10 parts by weight, more preferably 0.1 to 5 parts by weight, with respect to 100 parts by weight of the polymerizable monomer.

(Release agent)
The polymerizable monomer composition may contain a release agent. This release agent can improve the releasability of the toner from the fixing roll, particularly when toner is used for printing.
The release agent is not particularly limited as long as it is generally used as a toner release agent. For example, low molecular weight polyolefin waxes such as low molecular weight polyethylene, low molecular weight polypropylene, and low molecular weight polybutylene; molecular end oxidized low molecular weight polypropylene, low molecular weight end modified polypropylene with molecular ends substituted with epoxy groups, and blocks of these with low molecular weight polyethylene Polymers, molecular terminal oxidized low molecular weight polyethylene, low molecular weight polyethylene having molecular terminals substituted with epoxy groups, and terminal modified polyolefin waxes such as block polymers of these and low molecular weight polypropylene; Candelilla, Carnauba, Rice, Wood wax, Jojoba, etc. Natural waxes; petroleum waxes such as paraffin, microcrystalline, and petrolactam, and modified waxes thereof; mineral waxes such as montan, ceresin, and ozokerite; Synthetic waxes such as Chartropsch wax; pentaerythritol esters such as pentaerythritol tetramyristate, pentaerythritol tetrapalmitate, pentaerythritol tetrastearate, and pentaerythritol tetralaurate, dipentaerythritol hexamyristate, dipentaerythritol hexapalmiate Tate and polyhydric alcohol esterified products such as dipentaerythritol esters such as dipentaerythritol hexalaurate; and the like. These may be used individually by 1 type and may be used in combination of 2 or more type.

Among the above release agents, the endothermic peak temperature is 30 to 150 ° C., preferably 50 to 120 ° C., measured from the DSC curve at the time of temperature increase at a temperature increase rate of 10 ° C./min using a differential scanning calorimeter. More preferably, a polyhydric alcohol esterified product such as pentaerythritol ester in the range of 60 to 100 ° C. or dipentaerythritol ester having the same endothermic peak temperature in the range of 50 to 80 ° C. is used in terms of the fixing-peeling balance. Particularly preferred.
The release agent is preferably used in an amount of 0.1 to 30 parts by weight, more preferably 1 to 20 parts by weight, based on 100 parts by weight of the monovinyl monomer.

(B) Step of forming droplets of polymerizable monomer composition The polymerizable monomer composition obtained as described above is dispersed in an aqueous medium by a wet granulation method, and polymerized. A droplet of the monomer composition is formed, and a polymerization initiator is further added to prepare a suspension in which the droplets of the polymerizable monomer composition are dispersed.
The method of forming the droplet is not particularly limited, but for example, an in-line type emulsifier / disperser (manufactured by Ebara Seisakusho, trade name: Ebara Milder), a high speed emulsifier / disperser (manufactured by Tokushu Kika Kogyo Co., Ltd., trade name: TK homomixer) MARK II type) and the like, which is capable of giving a high shearing force to the polymerizable monomer composition and capable of strong stirring.

  In the present invention, the aqueous dispersion medium may be water alone, but a solvent that is soluble in water may be used in combination. Examples of the solvent that can be dissolved in water include lower alcohols such as methanol, ethanol, and isopropanol, and lower ketones such as dimethylformamide, tetrahydrofuran, acetone, and methyl ethyl ketone.

The aqueous dispersion medium usually contains a dispersion stabilizer. Examples of the dispersion stabilizer include sulfates such as barium sulfate and calcium sulfate; carbonates such as barium carbonate, calcium carbonate and magnesium carbonate; phosphates such as calcium phosphate; metal oxides such as aluminum oxide and titanium oxide; Inorganic compounds that can be dissolved in acids or alkalis such as metal hydroxides such as aluminum hydroxide, magnesium hydroxide, and ferric hydroxide. Furthermore, organic polymer compounds such as water-soluble polymers such as polyvinyl alcohol, methyl cellulose, and gelatin; anionic surfactants; nonionic surfactants; amphoteric surfactants; The said dispersion stabilizer can be used 1 type or in combination of 2 or more types.
Among the above dispersion stabilizers, dispersion stabilizers containing colloids of metal compounds, particularly poorly water-soluble metal hydroxides, can narrow the particle size distribution of the colored resin particles, and the dispersion stabilizer remains after washing. Since the amount is small, the obtained polymerized toner is preferable because the image can be clearly reproduced and the environmental stability is not deteriorated.
The dispersion stabilizer is used in an amount of 0.1 to 20 parts, preferably 0.2 to 10 parts, based on 100 parts of the aqueous medium.

Examples of the polymerization initiator for polymerizing the polymerizable monomer composition include persulfates such as potassium persulfate and ammonium persulfate; 4,4′-azobis (4-cyanovaleric acid), 2,2 '-Azobis (2-methyl-N- (2-hydroxyethyl) propionamide, 2,2'-azobis (2-amidinopropane) dihydrochloride, 2,2'-azobis (2,4-dimethylvaleronitrile), And azo compounds such as 2,2′-azobisisobutyronitrile; di-t-butyl peroxide, benzoyl peroxide, t-butylperoxy-2-ethylhexanoate, t-hexylperoxy-2- Ethyl hexanoate, t-butyl peroxypivalate, diisopropyl peroxydicarbonate, di-t-butyl peroxyisophthalate, and -A peroxide such as butyl peroxyisobutyrate, etc. In addition, a redox initiator in which the above polymerization initiator and a reducing agent are combined may be used. It is preferable to use a peroxide because it can be reduced and printing durability is good.
The polymerization initiator may be added to the polymerizable monomer composition before droplet formation, but after the polymerizable monomer composition is dispersed in an aqueous dispersion medium to form droplets, the suspension is performed. It is preferable to add to the liquid.
The addition amount of the polymerization initiator is preferably 0.1 to 20 parts by weight, more preferably 0.3 to 15 parts by weight, and most preferably 1.0 to 100 parts by weight of the monovinyl monomer. -10 parts by weight.

(C) Polymerization process Polymerization is performed in a state where droplets are dispersed in an aqueous dispersion medium by heating a suspension to which a polymerization initiator is added.
The polymerization temperature of the polymerizable monomer composition is preferably 50 ° C. or higher, more preferably 60 to 95 ° C. The polymerization reaction time is preferably 1 to 20 hours, and more preferably 2 to 15 hours.
In addition, in order to perform the polymerization in a state where the droplets are stably dispersed, the polymerization reaction may be performed while continuing a dispersion process for forming or stabilizing the droplets in the polymerization step.
The colored resin particles obtained by polymerization in the droplets may be used as they are or as a polymerized toner by adding an external additive. The colored resin particles are used as a core layer, and a core layer is formed outside the core layer. Colored resin particles of a so-called core-shell type (or also referred to as “capsule type”) obtained by forming different shell layers can also be used. The core-shell type colored resin particles have a balance between lowering the fixing temperature and preventing aggregation during storage by covering the core layer made of a material having a low softening point with a material having a higher softening point. Can do.

  There is no restriction | limiting in particular as a method of manufacturing the said core-shell type colored resin particle, It can manufacture by a conventionally well-known method. For example, colored resin particles obtained by a suspension polymerization method or other wet methods are used as a core layer, and the shell is formed by a conventionally known method such as an in situ polymerization method, a layer separation method, a spray dry method, or an interfacial reaction method. Cover the layer. It is preferable from the viewpoint of production efficiency that the colored resin particles produced by the polymerization method are coated with a shell layer by an in situ polymerization method or a phase separation method.

A method for producing core-shell type colored resin particles by in situ polymerization will be described below.
Addition of a polymerizable monomer (polymerizable monomer for shell) and a polymerization initiator to form a shell layer into an aqueous medium in which colored resin particles are dispersed, and then polymerize to form a core-shell type color. Resin particles can be obtained.

  As the polymerizable monomer for the shell, the same monomers as the aforementioned polymerizable monomers can be used. Among these, it is preferable to use monomers such as styrene, acrylonitrile, and methyl methacrylate that can yield a polymer having a Tg exceeding 80 ° C. alone or in combination of two or more.

  Polymerization initiators used for the polymerization of the polymerizable monomer for shell include potassium persulfate and persulfates such as ammonium persulfate; 2,2′-azobis (2-methyl-N- (2-hydroxyethyl) propion Amides) and azo compounds such as 2,2′-azobis- (2-methyl-N- (1,1-bis (hydroxymethyl) 2-hydroxyethyl) propionamide); be able to. The amount of the polymerization initiator is preferably 0.1 to 30 parts by weight, more preferably 1 to 20 parts by weight with respect to 100 parts by weight of the polymerizable monomer for shell.

  The polymerization temperature of the shell layer is preferably 50 ° C. or higher, more preferably 60 to 95 ° C. The polymerization reaction time is preferably 1 to 20 hours, more preferably 2 to 15 hours.

(D) Washing, dehydration, and drying The colored resin particle aqueous dispersion obtained by the above steps is usually subjected to an acid or alkali washing step, followed by a water washing step, dehydration, and drying. Particles are obtained. In addition, in FIG. 1, the example wash | cleaned with an acid and water is shown.
(D-1) Acid or alkali washing step When the colored resin particle aqueous dispersion uses an inorganic compound such as an inorganic hydroxide soluble in acid as a dispersion stabilizer, the acid to the aqueous dispersion of colored resin particles is used. Is added to dissolve and remove the dispersion stabilizer in water. When the dispersion stabilizer is an inorganic compound that is soluble in alkali, an alkali is used instead of an acid.
When an acid-soluble one is used as the dispersion stabilizer, it is preferable to add an acid so that the pH of the aqueous dispersion of colored resin particles is 6.5 or lower. More preferably, the pH is 6 or less. As the acid to be added, inorganic acids such as sulfuric acid, hydrochloric acid, and nitric acid, and organic acids such as formic acid and acetic acid can be used. Particularly, since the removal efficiency is large and the burden on the manufacturing equipment is small, Sulfuric acid is preferred.

(D-2) Water Washing Step In the water washing step, the aqueous dispersion obtained in the acid or alkali washing step is first filtered and then washed with water by a washing device. The water washing step can be repeated a plurality of times.
(D-3) Dehydration step In the above water washing step, while the washing water is supplied to the colored resin particles on the filter medium and removed through the filter medium at the same time, the dehydration process usually ends at the end of the water washing process. To do.

(D-4) Drying step The wet cake (wet colored resin particles) obtained by the dehydration step is dried by various known methods such as vacuum drying, airflow drying, spray dryer and the like.

(E) Colored resin particles The colored resin particles obtained through the above steps will be described (the following colored resin particles include both core-shell type and those not).
The colored resin particles constituting the yellow toner of the present invention preferably have a volume average particle diameter Dv of 5 to 10 μm, and more preferably 6 to 8 μm. If Dv is less than these ranges, the fluidity of the polymerized toner may decrease, transferability may deteriorate, blurring may occur, and print density may decrease. If these ranges are exceeded, the resolution of the image may be reduced. May decrease.
The ratio Dv / Dp between the volume average particle diameter Dv and the number average particle diameter Dp is preferably 1.0 to 1.3, and more preferably 1.0 to 1.2. When the ratio Dv / Dp is out of the above range, blurring may occur when printing is performed using the obtained polymerized toner, and transferability, print density, and resolution may be reduced.
The volume average particle size and the number average particle size of the colored resin particles can be measured using, for example, a particle size measuring device (Beckman Coulter, trade name: Multisizer).

The average circularity of the colored resin particles is preferably 0.970 to 0.995 because a high-quality image with excellent fine line reproducibility can be obtained.
The circularity in the present invention is defined as a value obtained by dividing the circumference of a circle having the same projected area as the particle image by the circumference of the projected image of the particle. Further, the average circularity in the present invention is used as a simple method for quantitatively expressing the shape of the particles, and is an index indicating the degree of unevenness of the toner. The average circularity is a value obtained when the toner is perfectly spherical. 1 is shown in this case, and the value becomes smaller as the surface shape of the toner becomes more complicated. For the average circularity, the circularity (Ci) of each particle measured for a particle group having a circle-equivalent diameter of 0.4 μm or more was determined for each of n particles from the following formula, and then the average circularity (Ca ).
Circularity (Ci) = perimeter of circle equal to projected area of particle / perimeter of projected particle image

In the above formula, fi is the frequency of particles having a circularity Ci.
The circularity and the average circularity can be measured using a flow type particle image analyzer “FPIA-1000” or “FPIA-2000” manufactured by Sysmex Corporation.

(F) Yellow toner In the present invention, the obtained colored resin particles can be used as they are for the development of electrophotography as a polymerization toner, but in order to adjust the chargeability, fluidity, storage stability, etc. of the toner, Using a high-speed stirrer such as a Henschel mixer, the colored resin particles, the external additive, and other particles as necessary can be mixed to obtain a one-component polymerized toner. Further, in addition to colored resin particles, external additives and other particles as required, carrier particles such as ferrite and iron powder are further mixed by various known methods to obtain a two-component polymerization toner and You can also
The external additive is used for the purpose of improving the fluidity and chargeability of the toner. In the present invention, inorganic particles, organic resin particles, and the like conventionally used as external additives for toner can be used without limitation.
Although the addition amount of an external additive is not specifically limited, Usually, it is 0.1-6 weight part with respect to 100 weight part of colored resin particles.

In the method for producing a yellow toner for developing an electrostatic charge image according to the present invention described above, a specific amount of an aluminum coupling agent is mixed in a polymerizable monomer composition with respect to the polymerizable monomer, and the yellow pigment is mixed with the yellow pigment. By performing the polymerization step after the surface treatment with the aluminum coupling agent, it is possible to suppress the formation of the deformed toner in the polymerization step.
Further, since the production method of the present invention uses a pigment not containing a halogen element as a yellow colorant, no harmful gas containing halogen or dioxin is generated during incineration.
Furthermore, since the production method of the present invention is based on the suspension polymerization method, in addition to obtaining colored resin particles having a high sphericity and a sharp particle size distribution, By the action, an effect of making the dispersed state of the yellow colorant in the colored resin particles uniform and fine can also be obtained.
Therefore, according to the production method of the present invention, it is possible to perform high-resolution image formation such as fine line reproducibility, etc., and for electrostatic image development with little risk of environmental pollution even after incineration. A yellow toner is obtained.

  EXAMPLES Hereinafter, although an Example and a comparative example are given and this invention is demonstrated more concretely, the following Examples are for making an understanding of this invention easy, and do not limit this invention. In the following description, “parts” and “%” are based on weight unless otherwise specified.

1. Production of colored resin particles (Example 1)
80 parts of styrene and 20 parts of butyl acrylate as a polymerizable monomer, and C.I. I. A polymerizable monomer mixture (mixture constituting the polymerizable monomer composition) mixed and stirred with Pigment Yellow 74 (6 parts) is mixed with an in-line type emulsifying disperser (manufactured by Ebara Manufacturing Co., Ltd., trade name: Ebara Mile). The mixture was predispersed using a varnish) to obtain a predispersible polymerizable monomer mixture. Preliminary dispersion conditions were a circumferential speed of 23 m / s and a circulation number θ of 26 times.

次に、この予備分散重合性単量体混合物を、図２に示す上記メディア式分散機を備えた図１に示す上記分散系において、以下の条件で分散工程に供した。
メディア粒子： 直径０．３ｍｍのジルコニアビーズ
駆動軸の周速： ローター先端周速１０ｍ／ｓｅｃ
循環回数θ：４回

Next, this pre-dispersible polymerizable monomer mixture was subjected to a dispersion step under the following conditions in the dispersion system shown in FIG. 1 equipped with the media-type disperser shown in FIG.
Media particles: Zirconia beads with a diameter of 0.3 mm Drive shaft peripheral speed: Rotor tip peripheral speed 10 m / sec
Circulation number θ: 4 times

  To 106 parts of the resulting mixture, 2 parts of negative charge control resin (manufactured by Fujikura Kasei Co., Ltd., trade name: S748N, containing 2% of sulfonic acid functional group) as a charge control agent, and polymethacrylate macromonomer as a macromonomer 0.2 parts of “AA6” manufactured by Toa Gosei Chemical Co., Ltd. and acetoalkoxyaluminum diisopropylate represented by the following formula as an aluminum coupling agent (“Plenact AL-M” manufactured by Ajinomoto Fine Techno Co., Ltd.) 0.3 parts, 10 parts of dipentaerythritol hexamyristate as a release agent, 1.5 parts of t-dodecyl mercaptan as a molecular weight regulator, and 0.5 parts of divinylbenzene as a cross-linking agent are stirred and dissolved. Thus, a polymerizable monomer composition was prepared.

On the other hand, an aqueous solution in which 7.1 parts of magnesium hydroxide is dissolved in 50 parts of ion-exchanged water is gradually added with stirring to an aqueous solution in which 12.8 parts of magnesium chloride is dissolved in 250 parts of ion-exchanged water. A dispersion of magnesium hydroxide colloid was prepared as an aqueous dispersion medium according to the present invention.
The above polymerizable monomer composition was charged into the obtained aqueous dispersion medium, stirred, and then t-butylperoxy-2-ethylhexanoate (“Perbutyl O” manufactured by NOF Corporation) as a polymerization initiator. 5 parts were further added, and the above-mentioned in-line type emulsion disperser (trade name: Ebara Milder, manufactured by Ebara Manufacturing Co., Ltd.) was used for high-shear stirring at a rotational speed of 15000 rpm for 10 minutes to obtain a polymerizable monomer. A droplet of the composition was formed.

A dispersion liquid in which droplets of the polymerizable monomer composition were dispersed was put into a reactor equipped with a stirring blade, and the temperature was raised to 90 ° C. while rotating the stirring blade, thereby carrying out a polymerization reaction. After the polymerization conversion reached almost 100%, the temperature was kept as it was, and 2,2'-azobis [2- (2) dissolved in 1 part of methyl methacrylate and 10 parts of ion-exchanged water as a shell polymerizable monomer. 0.1 part of methyl-N- [1,1-bis (hydroxymethyl) -2-hydroxyethyl] propionamide] (manufactured by Wako Pure Chemical Industries, Ltd., trade name: VA086) was added, After continuing the time reaction, it was cooled with water to obtain an aqueous dispersion of core-shell type colored resin particles. The pH of the aqueous dispersion was 9.5.
While stirring the aqueous dispersion of colored resin particles obtained as described above, sulfuric acid is added to neutralize to pH 6 or less, water is separated by filtration, and 500 parts of ion-exchanged water is newly added to re-add. Slurried and washed with water. Thereafter, again, dehydration and water washing were repeated several times, and the solid content was separated by filtration, followed by drying for 2 days in a dryer set at 40 ° C., and the volume average particle size (Dv) was 7.2 μm, Yellow colored resin particles having a particle size distribution (Dv / Dp) of 1.20 and an average circularity of 0.980 were obtained.
100 parts by weight of the yellow colored resin particles obtained as described above, 1 part of the number of silica fine particles having a primary average particle diameter of 7 nm hydrophobized with a silane coupling agent as an external additive, and the number of hydrophobized parts One part of silica fine particles having a primary average particle size of 40 nm was added and mixed with a high-speed stirrer (trade name: Henschel mixer, manufactured by Mitsui Mining) to obtain a yellow toner.

[Example 2]
C. as a yellow colorant (pigment) I. Instead of CI Pigment Yellow 74, C.I. I. A yellow toner was obtained in the same manner as in Example 1 except that CI Pigment Yellow 120 was used.

Example 3
C. as a yellow colorant (pigment) I. Instead of CI Pigment Yellow 74, C.I. I. A yellow toner was obtained in the same manner as in Example 1 except that CI Pigment Yellow 180 was used.

Example 4
C. as a yellow colorant (pigment) I. Instead of CI Pigment Yellow 74, C.I. I. A yellow toner was obtained in the same manner as in Example 1 except that CI Pigment Yellow 185 was used.

Example 5
Except for the following points, yellow colored resin particles were obtained in the same manner as in Example 1. That is, instead of the negative charge control resin “S748N” as a charge control agent, a positive charge control resin “161P” (manufactured by Fujikura Kasei) is used, and the addition amount is 1.2 parts. The amount of “Plenact AL-M” added was 0.25 parts. As an aqueous dispersion medium, an aqueous solution in which 6.7 parts of sodium hydroxide is dissolved in 50 parts of ion-exchanged water is gradually added with stirring to an aqueous solution in which 12.1 parts of magnesium chloride is dissolved in 250 parts of ion-exchanged water. Thus, a colloidal magnesium hydroxide dispersion medium was prepared. Further, the hydrophobization treatment of the external additive was performed with an aminosilane coupling agent.

Example 6
As a colorant, C.I. I. Instead of CI Pigment Yellow 74 (6 parts), C.I. I. A yellow toner was obtained in the same manner as in Example 1 except that CI Pigment Yellow 213 (6 parts) was used.

Example 7
As a colorant, C.I. I. Instead of CI Pigment Yellow 74 (6 parts), C.I. I. A yellow toner was obtained in the same manner as in Example 1 except that CI Pigment Yellow 155 (6 parts) was used.

[Comparative Example 1]
Yellow colored resin particles were produced in the same manner as in Example 1 except that the aluminum coupling agent was not used.

[Comparative Example 2]
Yellow colored resin particles were produced in the same manner as in Example 5 except that the aluminum coupling agent was not used.

(Comparative Example 3)
Yellow colored resin particles were produced in the same manner as in Example 5, except that the amount of the above-mentioned “Preneact AL-M” was 1.5 parts as the aluminum coupling agent. Since a large amount of coarse aggregates were generated during the polymerization reaction, the polymerization was stopped halfway. In this example, there was 56% of the total solid weight of coarse lumps that could not pass through a 40 mesh screen.
[Comparative Example 4]
As a colorant, C.I. I. Instead of CI Pigment Yellow 74, C.I. is a yellow pigment containing a halogenated element. I. A yellow toner was obtained in the same manner as in Example 1 except that CI Pigment Yellow 17 was used.

2. Evaluation of colored resin particles The colored resin particles obtained in the above Examples and Comparative Examples were evaluated as follows.
(1) Volume average particle diameter The volume average particle diameter of the colored resin particles was measured using a particle size measuring machine (Beckman Coulter, trade name: Multisizer).

(2) Average circularity Into a container, 10 ml of ion-exchanged water is put in advance, and 0.2 g of an alkylbenzene sulfonic acid aqueous solution (manufactured by Fuji Film Co., Ltd., trade name: Drywell) is added as a dispersant. 0.2 g was added, and a dispersion treatment was performed at 60 W for 3 minutes using an ultrasonic disperser. The concentration of the colored resin particles at the time of measurement is adjusted to 3,000 to 10,000 particles / μL, and 1,000 to 10,000 colored resin particles having an equivalent circle diameter of 0.4 μm or more are flow-type particle images. Measurement was performed using an analyzer (trade name: FPIA-2100, manufactured by Sysmex Corporation). The average circularity was determined from the measured value.
The circularity is expressed by the following formula, and the average circularity is an average of the circularity.
(Circularity) = (Perimeter of circle equal to projected area of particle) / (Perimeter of particle projection image)

(3) Ratio of deformed toner The analysis was performed using the same flow type particle image analyzer as in (2).
200 particles classified into class 6 (corresponding to a particle size of approximately 7 to 11 μm) were judged from the image, and the proportion of deformed toner was calculated.

(4) Fine line reproducibility (print durability)
Using the yellow toner obtained in the example, the following printing test was conducted.
Set copy paper in a commercially available non-magnetic one-component development type printer (22 sheets), leave it for one day in an environment of temperature 23 ° C and humidity 50%, then use 2 x 2 dot lines (width: about 85 µm) Line images were continuously formed, and each 500 sheets were measured by a print evaluation system (trade name “RT2000”, manufactured by YA-MA), and density distribution data of the line images were collected.
At this time, with the full width at the half maximum of the density as the line width and the line width of the first line image as a reference, if the difference in the line width is 10 μm or less, the first line image is reproduced. The number of sheets that can maintain the line width difference of 10 μm or less was examined up to 10,000 sheets.
In the above printing test, fine line reproducibility is good (◯) when the number of maintained sheets is 10,000 sheets or more, while fine line reproducibility is poor when the number of maintained sheets is less than 10,000 sheets. (X) was determined.

3. Results Table 1 shows the test results.

The notes in Table 1 are as follows.
* 1)
<Toner composition of Example 1 (added parts by weight)>
・ Binder resin: Styrene (80 parts) / Butyl acrylate (20 parts) / Divinylbenzene (0.5 parts) copolymer ・ Polymethacrylic acid ester macromonomer: Toagosei Co., Ltd., trade name “ AA6 "(0.2 parts)
・ Yellow colorant: Pigment Yellow 74 (PY74) (6 parts)
Aluminum coupling agent: acetoalkoxy aluminum diisopropylate (Ajinomoto Fine Techno Co., Ltd. “Plenact AL-M”) (0.3 parts)
Release agent: Dipentaerythritol hexamyristate (10 parts)
Charge control resin: Resin containing 2% of negatively charged sulfonic acid group (manufactured by Fujikura Kasei Co., Ltd., trade name “S748N”)
-Molecular weight regulator: t-dodecyl mercaptan (1.5 parts)
・ Shell monomer: Methyl methacrylate (1 part)

* 2)
<Toner compositions of Examples 2 to 7 and Comparative Examples 1 to 4>
In the composition of Example 1, the yellow colorant, the aluminum coupling agent, and the charge control resin were changed as shown in Table 1. Details of the changes are as follows.
・ PY120: Pigment Yellow 120
・ PY180: Pigment Yellow 180
・ PY185: Pigment Yellow 185
・ PY74: Pigment Yellow 74
・ PY213: Pigment Yellow 213
・ PY155: Pigment Yellow 155
・ PY17: Pigment Yellow 17
Charge control resin 161P: Positively chargeable charge control resin (product name: FCA-161P, manufactured by Fujikura Kasei)

In Table 1, the ratio of the modified toner based on the class 6 standard was 0.9% to 2.7% in the colored resin particles according to the example, whereas in Comparative Example 1, The range was 45.1%, Comparative Example 2 was 53.8%, and Comparative Example 4 was 44.4%. In Comparative Example 3, the polymerization was interrupted due to the generation of a large amount of gravel, so measurement was impossible.
From this result, it was confirmed that the generation of deformed toner was remarkably suppressed according to the production method of the present invention. This result is also reflected in the reproducibility of thin lines.
In addition, the circularity of the colored resin particles according to the example was in the range of 0.970 to 0.995.

It is the schematic which shows the structural example of the dispersion system used in order to manufacture the toner for electrostatic charge development of this invention. It is sectional drawing which shows the cross section of the media-type disperser 1 employ | adopted as the system shown in FIG.

Explanation of symbols

1 Media Disperser 2 Casing 3 Liquid Supply Port 4 Liquid Discharge Port 5 Holding Tank 6 Stirring Motor 7 Stirring Blade 8 Jacket 9 Temperature Control Medium Inlet 10 Temperature Control Medium Outlet 11 Valve 12 Line 13 Circulation Pump 14 Line 15 Line 16 Rotor 17 Media particle 18 Media dispersion screen 19 Drive shaft 20 Cooling medium inlet 21 Cooling medium outlet 22 Jacket 23 Media particle discharge slit 24 Rotor cylindrical portion 25 Liquid discharge path

Claims (5)

A polymerizable monomer composition containing a monovinyl monomer and a polymerizable monomer composition containing a yellow colorant are dispersed in an aqueous dispersion medium to form droplets, and then polymerized by performing polymerization. In a method for producing a yellow toner for developing an electrostatic charge image comprising a step of obtaining yellow colored resin particles containing a binder resin and a yellow colorant, which are monomers,
The yellow colorant is a pigment containing no halogen element;
The polymerizable monomer composition further contains an aluminum coupling agent, and the content of the aluminum coupling agent is 0.01 to 1.0 part by weight with respect to 100 parts by weight of the monovinyl monomer;
A method for producing a yellow toner for developing an electrostatic charge image.   The yellow colorant is C.I. I. 2. The yellow toner for developing electrostatic images according to claim 1, wherein the yellow toner is selected from the group consisting of CI Pigment Yellow 74, 120, 151, 155, 180, 185, and 213. Production method.   The polymerizable monomer composition is obtained by mixing the polymerizable monomer, the yellow colorant, and the aluminum coupling agent, and then dispersing by a media type disperser. A method for producing a yellow toner for developing electrostatic images according to claim 1 or 2.   4. The method for producing a yellow toner for developing an electrostatic charge image according to claim 1, wherein the polymerizable monomer composition further contains a charge control agent. The method for producing a yellow toner for developing an electrostatic charge image according to any one of claims 1 to 4, wherein the yellow colored resin particles have an average circularity of 0.970 to 0.995.

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