JPH0572807A - Production of electrostatic charge image developing toner - Google Patents

Abstract

PURPOSE:To provide an electrostatic charge image developing toner showing uniform electrifying property, stable environmental stability and excellent durability and having a small particle size with sharp distribution of particle size. CONSTITUTION:This toner is produced by using a thermoplastic resin as the essential component and effecting the reaction of metal salt (inorg. salt or org. salt of metal which can form chelates (iron, nickel, cobalt, chromium, etc.) with metal ligand (especially preferably, o,o'-oxyazo compd.) to make metal complex salt. With the obtd. toner particles, images of good qualities can be obtd. even when the environment largely changes.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing a novel toner for developing an electrostatic image used in electrophotography, electrostatic recording, electrostatic printing and the like.

[0002]

2. Description of the Related Art In recent years, electrophotographic systems and the like are required to have a small particle size of toner, a sharp particle size distribution, sufficient coloring power, and uniform charge control in order to achieve high image quality and high durability. There is. A toner for developing an electrostatic image is generally produced by melt-kneading a thermoplastic resin, a colorant, and a charge control agent (dyes and pigments, various metal complex salts, quaternary ammonium salts, etc.), crushing, and then classifying. Has been done. When the toner manufactured in this way is to have a small particle size and a narrow particle size distribution, the production capacity and the yield will be significantly reduced, and the cost will be high. Poor toner charging characteristics may occur due to uneven dispersion of the control agent. In addition, the surface shape of the particles obtained by pulverization has a large number of protrusions, and fusion with the carrier or the toner thinning member is likely to occur. Further, the toner contains a large amount of an expensive charge control agent or the like that originally exerts its function on the toner surface, resulting in a high cost.

For this reason, researches and developments have been made everywhere on toners which can provide high image quality and high durability, and manufacturing methods thereof, and many proposals have been made. For example, resin particles containing a color pigment and a charge control agent inside are formed by (1) suspension polymerization method or (2) spray granulation method. The above (1) is disclosed in Japanese Patent Publication Nos. 47-51830 and 51-14895, and the above (2) is disclosed in Japanese Patent Publication 56-56.
It is disclosed in Japanese Patent Publication No. 13945, Japanese Patent Publication No. 57-494, and the like.

However, the toner particles obtained by the above method (1) are difficult to remove the dispersion stabilizer and the like adhering to the surface thereof and are prone to charge deterioration, and the toner particles are internally contained in the production of the toner particles. Since the polymerization method is adopted, there is a drawback that it is difficult to stably obtain a small particle size and a narrow narrow particle size distribution. In addition, the method (2) has a drawback that it is very difficult to control the particle size and that classification treatment is required after granulation, or that a polymer resin effective for preventing hot offset cannot be used. ing.

As a method for obtaining a uniform particle size, a seed polymerization method in which the particle size is formed and then the particles are grown by polymerization,
Dispersion polymerization methods are known in which a monomer is a good solvent, but a polymer is a poor solvent. Polymerization is performed using these methods. Although obtained, there is a disadvantage that it is difficult to internally add the charge control agent. Therefore, for example, a method of embedding a charge control agent on the surface of particles by applying mechanical strain (Japanese Patent Laid-Open No. 62-209541) and a method of providing a coating layer of a resin and a charge control agent on the toner surface (special feature: Japanese Laid-Open Patent Publication No. 63-27853) has been proposed, but these methods have a problem that the fixing property of the toner is deteriorated due to the influence of the charge control agent particles existing on the surface and an offset occurs. It was

As mentioned above, even if the charge control agent is dispersed in the toner particles, the triboelectrification is mainly determined by the particles existing in the vicinity of the surface of the powder.
Therefore, it has been attempted to form a charge control agent layer on the toner surface with the smallest possible amount of charge control agent to efficiently control the charge.

For example, JP-A-62-209541 and JP-A-63-138358 propose a method of attaching charge control particles to the toner surface by mechanical impact force. This method is a simple method because it is a dry process, but the ratio of the toner particle size to the charge control particle size is limited, and the processing method and conditions must be strictly controlled. In addition, since the charge control particles having a high melting point are present on the surface, there is a drawback that the fixing property of the toner is disturbed.

Further, Japanese Patent Laid-Open No. 59-151159 and Japanese Patent Laid-Open No. 63-49767 propose a method for producing a toner chemically bonded by a charge control substance that reacts with the toner surface. Although the toner obtained by this method is strong because the charge control substance and the surface of the toner are chemically bonded, it is necessary to introduce a special functional group into the charge control substance and the surface of the toner during the production of the toner. However, there are drawbacks such as high cost and complicated manufacturing process, which makes it practically difficult.

Furthermore, JP-A-57-54953 discloses a method of adding a solution of a charge control substance to toner particles and adhering it to the surface, and JP-A-63-53559 discloses a layer containing a fluorine-containing compound. Although a method of providing the toner on the surface has been proposed, in any case, there are drawbacks such that the charge control is unstable and the charge amount changes during use because the toner is not uniformly and firmly attached to the toner surface.

[0010]

SUMMARY OF THE INVENTION The present invention solves the drawbacks and problems of these conventional techniques. The first object of the present invention is to obtain an electrostatic charge image having a sharp particle size distribution and a small particle size. A method of manufacturing a developing toner is provided. A second object of the present invention is to provide a method for producing a toner in which a charge control agent is unevenly distributed on the particle surface. A third object of the present invention is to provide a method for producing a toner having uniform charging property, good environmental stability and high durability.

[0011]

The method for producing a toner for developing an electrostatic charge image according to the present invention comprises the steps of reacting a metal salt with powder particles containing a thermoplastic resin as a main component and containing a metal ligand to form a metal complex salt. It is characterized by including a step of performing. The inventors of the present invention have conducted a lot of research on toners for developing electrostatic images, but the use of the toners produced by the above-mentioned means can achieve the above-mentioned objects and obtain high-quality images. Confirmed. The present invention is made by this.

The method of the present invention will be described in more detail below. The thermoplastic resin used in the toner production of the present invention can be pulverized particles or suspension polymerized particles, but in order to obtain a toner having a sharp particle size distribution and a small particle size, it can be obtained by a seed polymerization method or a dispersion polymerization method. It is preferable to use the polymerized particles obtained (particularly, it is preferable to use the one synthesized by the dispersion polymerization method).

In the dispersion polymerization method here, a dispersant is dissolved in a hydrophilic organic solvent, and the resulting polymer (copolymer) is dissolved in this solution but is dissolved in the hydrophilic organic solvent. One or more vinyl monomers which are swollen or hardly dissolved in a hydrophilic organic solvent are polymerized.

As the resin for forming such polymerized particles, conventionally known resins can be widely used. For example, styrene, parachlorostyrene, vinyltoluene,
Vinyl chloride, vinyl bromide, vinyl fluoride, vinyl acetate, vinyl propionate, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate,
N-Butyl (meth) acrylate, isobutyl (meth) acrylate, dodecyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, lauryl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, ( Hydroxypropyl (meth) acrylate, 2-chloroethylene (meth) acrylate, (meth) acrylonitrile,
Polymers of monomers such as (meth) acrylamide, (meth) acrylic acid, vinyl methyl ether, vinyl ethyl ether, vinyl isobutyl ether, vinyl methyl ketone, N-vinyl pyrrolidone, N-vinyl pyridine, ethylene, propylene and butadiene. Or a copolymer composed of two or more kinds of these monomers, or a mixture thereof. Other polyesters, polyurethanes, polyamides, epoxy resins, rosins, modified rosins, terpene resins, phenol resins, aliphatic or alicyclic hydrocarbon resins, aromatic petroleum resins and the like can be used alone or in combination.

The metal ligand may be a compound having a chelate-forming ability, but from the viewpoint of charge control and charge stability, an o, o'-oxyazo compound represented by the following general formula 1 is used. Preferably.

[Chemical 1]

Some specific examples of the o, o'-oxyazo compound are shown in Table 1 below.

[Table 1- (1)]

[Table 1- (2)]

The metal salt is an inorganic or organic salt of a metal capable of forming a chelate, and the metal is iron, nickel, cobalt, chromium or the like.

Kneading the above-mentioned thermoplastic resin and ligand
Although it may be pulverized, especially when polymerized particles obtained by a seed polymerization method or a dispersion polymerization method are used, the resin particles and the ligand are stirred in a solvent in which the ligand is dissolved and the resin particles are insoluble. It is achieved by mixing.

As the solvent used here, a general-purpose organic solvent can be used, but alcohols such as methanol, ethanol, n-propyl alcohol, iso-propyl alcohol, n-butyl alcohol, iso-butyl alcohol and tert-butyl alcohol. System solvent, n-hexane,
Paraffinic or aparaffinic solvents such as iso-octane, ligroin, and kerosene are preferred. The amount of solvent is appropriately about 3 to 10 times the weight of the resin particles.

The ratio of the resin particles to the ligand depends on the monomer composition of the resin particles, the particle size and the structure of the ligand, but the ligand is about 0.1 to 5% by weight based on the resin particles. Is appropriate.

The colorant used in the production of the toner of the present invention includes black pigments: carbon black (oil furnace black, channel black, lamp black, acetylene black, activated carbon, charcoal, etc.); azine pigments such as aniline black; metals. Salt azo dye, metal oxide, complex metal oxide, oil black. Yellow pigments: yellow lead, zinc, cadmium yellow, mineral fast yellow, nickel titanium yellow, navel yellow, naphthol yellow S, Hansa yellow G,
Hansa Yellow 10G, Benzidine Yellow GR, Quinoline Yellow Lake, Permanent Yellow NCG, Tartrazine Lake. Orange pigments: red yellow lead, molybdenum orange, permanent orange GTR, pyrazolone orange, vulcan orange, indanthrene brilliant orange RK, benzidine orange G, indanthrene brilliant orange GK. Red pigments: red iron oxide, cadmium red, permanent red 4R, resole red, pyrazolone red, watching red calcium salt, lake red D, brilliant carmine 6B, eosin lake, rhodamine lake B, alizarin lake, brilliant carmine 3B. Purple pigment: manganese purple, fast violet B, methyl violet lake. Blue pigments: navy blue, cobalt blue, alkali blue, Victoria blue lake, phthalocyanine blue, metal-free phthalocyanine blue, phthalocyanine blue partially chlorinated, fast sky blue, indanthrene blue BC. Examples of green pigments include chrome green, chrome oxide, pigment green B, and malachite green lake. These may be used alone or in combination of two or more.

As a method for dyeing resin particles with a colorant, a disperse dye and resin particles are dispersed and heated in water for dyeing, or a solvent dyeing method in which a dye is dissolved in an organic solvent and the resin particles are dyed in a solvent. For dyeing, solvent dyeing is preferable when dyeing with the colorant of the present invention. As the solvent used here, a general-purpose organic solvent can be used, but alcohol solvents such as methanol, ethanol, n-propyl alcohol, iso-propyl alcohol, n-butyl alcohol, iso-butyl alcohol, and tert-butyl alcohol are preferable. Depending on the solubility of the resin, it is also possible to add another solvent to the above alcohol solvent and perform dyeing with a mixed solvent, or dye with a system to which a surfactant or an alcohol-soluble polymer is added. When coloring the ligand by dyeing,
Disperse dyes and oil-soluble dyes are suitable.

Examples of the dyes include CI Solvent Yellow 6, CI Solvent Yellow 9, CI Solvent Yellow 16, CI Solvent Yellow 105, CI Solvent Yellow 17, CI Solvent Yellow 100, CI Solvent Yellow 98, CI Solvent Yellow 104, CI Solvent Yellow 93, CI Solvent Yellow 160, CI Solvent Yellow 112, CI Solvent Yellow 114, CI Solvent Yellow 31, CI Solvent Yellow 35, CI Solvent Yellow 33, CI Solvent Yellow 93, CI Solvent Yellow 100, CI Solvent Yellow 102, CI Solvent Yellow 103, CI Solvent Yellow 105, CI Solvent Yellow 14, CI Solvent Yellow 141, CI Solvent Orange 2, CI Solvent Orange 7, CI Solvent Orange 13, CI Solvent Orange 66, CI Solvent Orange 68, CI Solvent Orange 60, CI Solvent Orange 72, CI Solvent Red 52, CI Solvent Red 145, CI Solvent Red 146, CI Solvent Red 152, CI Solvent Red 155, CI Solvent Red 177, CI Solvent Red 179, CI Solvent Red 84, CI Solvent Red 5, CI Solvent Red 16, CI Solvent Red 17, CI Solven t Red 18, CI Solvent Red 19, CI Solvent Red 22, CI Solvent Red 23, CI Solvent Red 143, CI Solvent Red 145, CI Solvent Red 146, CI Solvent Red 149, CI Solvent Red 150, CI Solvent Red 151, CI Solvent Red 157, CI Solvent Red 158, CI Solvent Violet 31, CI Solvent Violet 13, CI Solvent Violet 33, CI Solvent Violet 32, CI Solvent Violet 33, CI Solvent Violet 37, CI Solvent Blue 33, CI Solvent Blue 14, CI Solvent Blue 56, CI Solvent Blue 35, CI Solvent Blue 83, CI Solvent Blue 70, CI Solvent Blue 22, CI Solvent Blue 94, CI Solvent Blue 78, CI Solvent Blue 63, CI Solvent Blue 84, CI Solvent Blue 83, CI Solvent Blue 86, CI Solvent Blue 85, CI Solvent Blue 94, CI Solvent Blue 91, CI Solvent Blue 104, CI Solvent Blue 95, CI Solvent Blue 95, CI Solvent Green 3, CI Solvent Brown 3, CI Solvent Brown 5 CI Solvent Green 24, CI Solvent Green 25 CI Solvent Brown 3, CI Solvent Brown 3 CI Solvent Black 3, etc. It is.

A coating layer of a releasing material may be provided on the surface of the particles thus dyed. As the releasing agent, low molecular weight polyolefins such as low molecular weight polyethylene, low molecular weight polypropylene and polyethylene oxide; natural waxes such as beeswax, carnauba wax and montan wax;
Examples include higher fatty acids such as stearic acid, palmitic acid and myristic acid, metal salts of higher fatty acids, and higher fatty acid amides. These may be used alone or in combination of two or more, but it is preferable to use a low molecular weight polyolefin such as polypropylene.

As a method for coating the surface of the dyed particles with these releasing substances, a generally known method can be adopted.
For example, the dyed particles and a release agent may be mixed, and mechanical energy may be applied to the mixture to implant a release agent on the surface of the powder particles to coat the particles. Here, the method of applying mechanical energy includes a method of applying a crushing force, a method of applying an impact force to a mixture by a blade rotating at a high speed, a method of causing particles to collide with each other or a collision plate in a high-speed air stream. Mechanofusion (manufactured by Hosokawa Micron Co., Ltd.), a type I mill (manufactured by Nippon Pneumatic Mfg. Co., Ltd.), which has a lower grinding air pressure than in the case of normal grinding, a turbo mill (manufactured by Turbo Kogyo Co., Ltd.),
A hybridizer (manufactured by Nara Machinery Co., Ltd.), a cosmomizer (manufactured by Nara Machinery Co., Ltd.), an automatic mortar and the like can be mentioned.

Production examples of the resin used in the present invention will be described below. Production Example 1 Polyvinylpyrrolidone (15 parts by weight) was dissolved in methanol (150 parts by weight), the inside of the reaction vessel was replaced with nitrogen using nitrogen gas, and then a solution of styrene (52 parts by weight) and azobisisobutylnitrile (0.82 parts by weight) was added. 8 at 60 ° C
After stirring for an hour, polymerization was performed, and the mixture was allowed to stand at room temperature for 24 hours, then decanted to remove the supernatant liquid, 100 parts by weight of methanol was added, stirred for 30 minutes, filtered, and dried to obtain 48 parts by weight of a white powder. The volume average particle diameter (Dv) of this powder is about 7.28 μm, and the ratio with the number average particle diameter (Dp) is Dv / Dp.
Was 1.10.

Production Examples 2 to 9 The following monomers were used in place of styrene in Production Example 1,
Polymerization was performed in the same manner as in Production Example 1 except for the above, and the results shown in Table 2 below were obtained.

In the toner according to the present invention, the thermoplastic resin (particle size of 3 to 9 μm is suitable) contains 3 to 10 colorants (including dyes for dyeing when the colorant cannot be added internally).
It is preferable to make up about 2% to 8% by weight of the metal ligand and about 2% by weight of the metal ligand. Further, when actually manufacturing the toner of the present invention, it is advantageous that the amount of the solvent is used at a concentration of 5 to 70% of the solute.

The toner of the present invention may be used as a one-component dry developer, or may be used as a two-component dry developer together with a carrier. As the carrier, known carriers such as iron powder, glass beads, those coated with a fluororesin, or those treated with various coupling agents can be used.

[0030]

[Table 2]

[0031]

EXAMPLES All parts herein are by weight.

Example 1 0.1 part of the compound (2), 0.1 part of PS Yellow S3G (manufactured by Mitsui Toatsu Dyestuff Co., Ltd.), Kayaron Brilliant Blue-
0.3 parts of FRS (manufactured by Nippon Kayaku Co., Ltd.) and 0.1 part of Macrolex Red Violet R (manufactured by Bayer) are dissolved by heating in 100 parts of methanol, and 10 parts of the resin particles obtained in Production Example 2 are added and heated under reflux. Dyeing was carried out for 1 hour below. Then, the mixture was cooled to room temperature and suction-filtered to obtain a black-colored powder. When the particles were triboelectrically charged with an iron powder carrier and the charge amount was measured by the blow-off method, it was +63 μc / g. Subsequently, 10 parts of the dyed particles and 50 parts of methanol are stirred and dispersed to maintain the internal temperature at 50 ° C., a solution of 0.58 parts of chromium acetate and 5 parts of water is added, and the mixture is stirred for 5 hours and then cooled to room temperature. Then, it was filtered and dried to obtain black spherical particles. When the charge amount of the black spherical particles was measured by the above method, it was -18.8 μc / g. Three parts of the black spherical particles thus obtained were mixed with 100 parts of iron powder carrier to prepare a two-component developer. This developer was put in a magnetic brush developing device to develop an electrostatic charge image formed on a selenium photoreceptor by a normal electrophotographic method, and this was transferred onto a plain paper while applying corona discharge and heat-fixed. A clear copy image of was obtained.

Example 2 Polyester resin 100 parts Carbon black 10 parts A mixture of 2 parts of the compound of Production Example 6 was heated and kneaded with a hot roll to obtain a powder having a volume average particle diameter of 7.5 μm. Then, 10 parts of this powder and 50 parts of methanol are stirred, the internal temperature is maintained at 50 ° C., and a solution of 0.1 part of cobalt chloride and 5 parts of water is added.
After stirring at 0 ° C. for 5 hours, the mixture was cooled to room temperature, filtered and dried to obtain a black powder. When the charge amount of this powder was measured with the same blow-off device as in Example 1, it was −23.4 μc / g. Three parts of the toner thus obtained was mixed with 100 parts of iron powder carrier to prepare a two-component developer. This developer was put in a magnetic brush developing device to develop an electrostatic charge image formed on a selenium drum photoconductor by a normal electrophotographic method, and this was transferred to plain paper and further heat-fixed. A duplicate image was obtained.

Example 3 Similar to Example 1 except that the compound (9) was used in place of the compound (2) of Example 1 and the resin of Production Example 4 was used instead of the resin obtained in Production Example 2. Dyeing and complexing were performed to obtain black spherical particles. Next, 3 parts of the spherical particles and 100 parts of iron powder carrier were mixed to prepare a two-component developer. When this developer was put in a magnetic brush developing device, an electrostatic charge image formed on a selenium photoconductor by a normal electrophotographic method was developed, and transferred onto a plain paper while applying corona discharge, and heat-fixed. A clear copy image was obtained. Further 50,00
As a result of performing repeated copying test of 0 sheets, a stable and good image was obtained during the test, the density was maintained at 1.4 to 1.5, no fog was observed, and the line image and the photographic image were good. Maintained at. Furthermore, under low temperature and low humidity of 10% RH at 15 ° C,
Similar results were obtained under high temperature and high humidity conditions of 30 ° C. and 85% RH.

Example 4 100 parts of styrene / methyl acrylate copolymer A mixture of 10 parts of carbon black was kneaded by heating with a hot roll, pulverized and classified to obtain a black powder having a volume average particle diameter of 8 μm. When this black powder was triboelectrically charged with an iron carrier and the charge amount was measured by the blow-off method, it was +8 μC. Then, the compound (1) was dispersed in 10 parts of black powder particles and 100 parts of methanol.
6) After adding 0.35 part, the mixture was stirred at 60 ° C. for 5 hours to impregnate the powder particles with the compound (16). Then, 0.08 part of cobalt acetate was added, and the mixture was further stirred at 60 ° C. for 5 hours, cooled to room temperature, filtered and dried to obtain a black powder. When the charge amount of this black powder was measured by the above method, it was −28.4 μ.
It was c / g. 3 parts of this toner is used as an iron powder carrier 100
To prepare a two-component developer. This developer is put into a magnetic brush developing device to develop an electrostatic charge image formed on a selenium photoreceptor by a normal electrophotographic method, and this is transferred to a plain paper while being corona-discharged and fixed to give a clear black color. I got an image. Further, in order to examine the environmental stability of the charging of this toner, a high humidity (30 ° C., 90% RH) and color image were obtained. In addition, in order to investigate the environmental stability of charging of this toner, high humidity (30
The amount of charge was measured under low humidity (10 ° C, 15% RH) and -27μc under high humidity.
/ G and -25 μc / g under low humidity. The ratio of the charge amount under high humidity to the charge amount under low humidity (charge amount under high humidity / charge amount under low humidity) was 1.08, and the toner had good environmental stability.

Example 5 70 parts of styrene, 30 parts of n-butyl methacrylate and 10 parts of carbon were uniformly dispersed in a 2% aqueous solution of polyvinyl alcohol using a homogenizer, and suspension polymerization was carried out using 2 parts of azobisisobutylnitrile. Then, the fine powder portion and the coarse powder portion were cut to obtain black suspension particles having an average particle diameter of 7.5 μm. 100 parts of the particles were mixed with 5 parts of the compound (22) and 500 parts of methanol, and the compound of (22) was impregnated in the same manner as in Example 2 to chelate the surface of the particles with 0.8 part of chromium acetate. Using this powder, a developer was prepared and copied in the same manner as in Example 4 to obtain a clear black copy image. As a result of repeating the 1000-sheet copying test using this developer, a clear black copied image was maintained during the test.

70 parts of styrene and 30 parts of 2-ethylhexylmethacrylate were copolymerized in a methyl alcohol solvent in the presence of polyvinylpyrrolidone as a dispersion stabilizer to obtain a deposited average particle diameter Dv of 6.3 μm and a number average particle diameter (D).
p) was 5.8 and Dv / Dp was 1.0, and spherical powder particles having a narrow particle size distribution were obtained. Next, 100 parts of the powder particles are dispersed in 400 parts of methyl alcohol, and while stirring at room temperature, 4 parts of Oil Black 860 (manufactured by Orient Chemical Co.), 1 part of Macrolex Orange R (manufactured by BAYER), and the compound (24). After adding 2 parts and stirring for 8 hours for dyeing, 0.8 part of chromium acetate was used to chelate the particle surface.
Then, it was dried by a medium fluidized drier to obtain a black powder. Using this powder, copying was performed in the same manner as in Example 4 to obtain a clear copied image. The charge amount of this toner is -19.6.
It was μc / g. Further, after repeatedly copying 50,000 sheets, clear and fog-free copied images of fine lines and photographic images were maintained. The charge amount after repeating 50,000 copies was -18.
It was 9 μc / g.

Comparative Example 1 A black powder was obtained in the same manner as in Example 5, except that the compound (24) was not used. The toner had a positive charge of +42.3 μc / g.

Comparative Example 2 A chromium complex salt dye of the compound (24) was prepared in advance,
2 parts of the chromium complex salt dye was formed on the surface of 100 parts of a black powder obtained in the same manner as in Comparative Example 1 using a hybridizer (manufactured by Nara Machinery). Toner charge is -21.3
Although it was μc / g, the charge amount after repeatedly copying 50,000 sheets in the same manner as in Example 4 was −6.3 μc / g, and fogging occurred on the copied image.

[0040]

【The invention's effect】

(1) According to the invention of claim 1, a toner excellent in environmental stability and charge controllability can be obtained. In claims 5 and 6, such an effect is more remarkable. (2) According to the invention of claim 2, since the thermoplastic resin is synthesized by the dispersion polymerization method, the particle size of the toner is well controlled and a sharp particle size distribution can be achieved. Therefore, high image quality and high image quality can be achieved. Durability can be achieved. (3) Coloring by dyeing is effective for obtaining color toner having excellent transparency. Further, the resin particles synthesized by dispersion polymerization cannot be internally added with a coloring agent, but can be colored by dyeing. (4) According to the invention of claim 4, the occurrence of the filming phenomenon is effectively prevented.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Takayuki Hoshina 1-3-6 Nakamagome, Ota-ku, Tokyo Within Ricoh Co., Ltd. (72) Yoshihiko Jomon, 1-3-6 Nakamagome, Ota-ku, Tokyo Shares Company Ricoh Company (72) Inventor Toru Takagishi 2-21 Nitto-cho, Kawachinagano City, Osaka Prefecture

Claims (6)

[Claims] 1. A method for producing a toner for developing an electrostatic charge image, which comprises a step of causing a metal salt to act on a powder particle containing a thermoplastic resin as a main component and containing a metal ligand to carry out a metal complex salt formation. .. 2. The method for producing a toner for developing an electrostatic charge image according to claim 1, wherein the plastic resin is synthesized by a dispersion polymerization method. 3. The thermoplastic resin has an average particle size of 3
2. The method for producing an electrostatic charge image developing toner according to claim 1, wherein the toner has a substantially spherical shape in the range of .about.9 .mu.m. 4. The method for producing a toner for developing an electrostatic charge image according to claim 1, wherein the metal ligand is impregnated in a thermoplastic resin. 5. The method for producing a toner for developing an electrostatic charge image according to claim 1, wherein the metal ligand is an o, o′-oxyazo compound. 6. The method for producing a toner for developing an electrostatic charge image according to claim 5, wherein the o, o′-oxyazo compound is a compound represented by the following general formula. [Chemical 1]