JPH03188466A - Toner for developing electrostatic charge image - Google Patents

Abstract

PURPOSE:To improve moisture resistance and durability and to enhance image quality by treating the suspension polymerized particles obtd. by dispersing a polymer monomer and a coloring agent in an aq. phase contg. a dispersion stabilizer and subjecting the dispersion to suspension polymn. with an org. acid having a specific carbon fluoride group. CONSTITUTION:The suspension polymerized particles obtd. by dispersing the polymer monomer and the coloring agent in the aq. phase contg. the dispersion stabilizer and subjecting the dispersion to the suspension polymn. is treated with the org. acid having the carbon fluoride group expressed by formula I. In the formula I, m=1 to 3, w=1 to 3; RF is CF3(CY2)n [where n=0 to 9; Y is hydrogen or fluorine atom; respectively Y may be the same or different]; Ar is a bivalent arom. hydrocarbon group or arom. hydrocarbon group; X is a carboxy group, sulfonic acid group or hydroxyl group. The moisture resistance and durability are improved in this way and further, the image quality is enhanced.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a dry toner for developing electrostatic images produced by a suspension polymerization method.

[Prior art and problems to be solved by the invention] Dry toners (-component type, two-component type) used for developing electrostatic images formed in electrophotography, electrostatic recording, electrostatic printing, etc. , etc.) generally has a thermoplastic resin as its main component, and if necessary contains a colorant, a magnetic substance, a polarity control agent, etc., and after melting and mixing these, it is pulverized and classified. Getting toner. Since this toner has many advantages such as good colorant dispersibility, most dry toners are produced by this method.

However, since this type of toner has a fine particle size through pulverization, it has the disadvantage that the fine powder toner produced by pulverization cannot be completely removed and remains in the toner.

In addition, since a resin that is relatively easy to crush is used in the production of dry toner, if it is used as a developer for a long time, it will gradually become crushed, and the toner will be spent on the frictional charging member, causing a change in the amount of toner charge. or cause filming to occur on the photoreceptor.

This may cause background smearing or a decrease in sharpness.

In addition, in recent years, there has been a demand for toners with small particle sizes in order to improve the image quality of copying machines, but a large amount of energy is required during pulverization, making it difficult to efficiently produce toners with small particle sizes.

Therefore, a method for producing toner using a suspension polymerization method as described in Japanese Patent Application Laid-Open No. 53-17735 has been proposed. Toners made by the suspension polymerization method do not require consideration of pulverizability as in the case of cross-line toners, so it is possible to use resins that do not cause the toner to become pulverized even after long periods of use. Further, since the toner is perfectly spherical, it is difficult to be crushed in the developer, and furthermore, toner with a small particle size can be easily produced, and high image quality can be achieved.

However, toners made by suspension polymerization have the following drawbacks. That is, the dispersion stabilizer dispersed in the aqueous phase prevents particles from becoming uniform during polymerization by adsorbing or adhering to the surface of the suspended polymerizable monomer composition. However, since dispersion stabilizers are generally hydrophilic and therefore hygroscopic, they must be removed from the toner surface after polymerization. However, it is very difficult to remove the dispersant adhering to the polymer particles, and as a result, when the temperature is high, the toner charge amount changes, resulting in changes in image density and background smearing.

Various proposals have been made to improve these phenomena, and the following are representative ones.

(i) Particles obtained by suspension polymerization are treated with a reactive silane (Japanese Unexamined Patent Publication No. 17736/1983).

(it) Particles obtained by suspension polymerization are treated with a silane coupling agent or a titanate coupling agent (JP-A-5
9-152446).

(m) Polymerizing a polymerizable monomer in the presence of a sparingly water-soluble inorganic salt and an anionic amide type surfactant (JP-A-57-
53756).

(Cry) After granulation and polymerization, when washing by reacting the dispersing agent with an alkaline solution, washing and filtration are repeated many times (Japanese Patent Laid-Open No. 63-53563).

(v) Bringing the dispersion stabilizer and ionic substance remaining on the toner surface into contact with a solid surface having ion exchange ability (Japanese Unexamined Patent Publication No. 63-247759).

(vi) Polyvinyl alcohol as a dispersion stabilizer is converted into 7-cetal by surface treatment with an aldehyde (Japanese Unexamined Patent Publication No. 1-137268).

However, although all of the above methods reduce the influence of the dispersion stabilizer remaining on the toner surface, the current situation is that they still do not exhibit sufficient effects.

The purpose of the present invention is to improve the above-mentioned drawbacks, provide good moisture resistance,
It is an object of the present invention to provide a toner for developing electrostatic images that has good resolution, does not cause background smearing, and has good durability.

[Means to solve the problem]

In order to achieve the above-mentioned object, the present inventors conducted extensive research and discovered that a suspension polymer obtained by dispersing a polymerizable monomer and a colorant in an aqueous phase containing a dispersion stabilizer and carrying out suspension polymerization. It has been found that the above object can be achieved by an electrostatic image developing toner whose particles are treated with an organic acid having a fluorinated carbon group.

In the present invention, the characteristics of the toner treated with an organic acid having a specific fluorinated carbon group as described above are stable because the hydrophobicity of the toner surface is greatly increased, and moisture absorption does not occur even under high temperature and high humidity conditions. This is probably because the number is decreasing.

The particles to be treated with the above-mentioned organic acid having a carbon fluoride group are those that have been washed after suspension polymerization and are either in the aqueous phase, passed through filtration, or after drying. Although it may be in a dry state, it is more preferable to use it after drying. As a treatment method, a method such as spray coating or dip coating by mixing an organic acid having a fluorinated carbon group with a solvent can be used. As the solvent in this case, methyl alcohol, ethyl alcohol, isopropyl alcohol, etc. can be used.

The amount of these organic acids having carbon fluoride groups used may be sufficient as long as it covers the entire surface of the toner, but it is more preferable to use the amount of the organic acids having carbon fluoride groups that form the toner (toner excluding the organic acids having carbon fluoride groups that form the coating layer). ) is 0.01 to 5.0% by weight.

Among organic acids having a fluorinated carbon group for treating suspension polymerized particles, organic acid compounds represented by Noshiro (1) and (II) below are particularly preferably used.

Rf-X or (RfO)m-Ar-Xw
-(1) (However, Otori = 1 to 3, So = 1 to 3, Rf is CF, (CY, )n (However, n = o-9
and Y is a hydrogen or fluorine atom, and each Y may be the same or different.].

Ar is a divalent aliphatic hydrocarbon group or aromatic hydrocarbon group, and X is a carboxyl group, sulfonic acid group or hydroxyl group. ) ■ Rn-P-Q tumor
...(II) (where n = 1 to 3, (Rf is a fluorinated carbon group.] Q is oxygen, a hydroxyl group, or an alkoxy group of 01 to 04.) Compounds corresponding to the above formula (1) include the following.

fCOOH RfCH, CH yo C00H RfO-◎-C○0H RfO-◎-CH, GOOH RfSO,H Specific examples of the organic acid compound include the following.

(1-2) C,F,,CH,CH,COOH (1-3) (1-4) (I-5) (1-6) (1-7) (1-8) C,F17COOH C, F Yu, CH Specific examples of phosphoric acid compounds include the following.

(ll-4) .

(C4F, O), -P-OH ■ (II-19) (C, Fl, CH, CH, O) □
-P〇(n-20) C,F,,CH,CH,0-P-
(OH)! The toner of the present invention can be obtained by treating (coating) particles after polymerization with an organic acid having a specific fluorinated carbon group, and the polymerizable monomer preferably used when polymerizing these particles is polymerizable. It has an unsaturated group, and specifically includes the following. That is, styrene, 0-methylstyrene, ■-methylstyrene, P-methylstyrene, p-ethylstyrene, 2,4-dimethylstyrene, p-n-butylstyrene, p-tert-butylstyrene, p-n-hexyl. Styrene, p-n
- Styrene derivatives such as octyl styrene, methyl acrylate, ethyl acrylate, n-butyl acrylate, isobutyl acrylate, propyl acrylate, n-octyl acrylate, dodecyl acrylate, 2-ethylhexyl acrylate, stearyl acrylate, Dimethylaminoethyl acrylate, diethylaminoethyl acrylate,
Methyl methacrylate, ethyl methacrylate, propyl methacrylate, n-butyl methacrylate, isobutyl methacrylate, n-octyl methacrylate, dodecyl methacrylate, 2-ethylhexyl methacrylate, stearyl methacrylate, phenyl methacrylate, dimethylamino methacrylate Acrylic acid or methacrylic acid derivatives such as ethyl and diethylaminoethyl methacrylate; vinyl esters such as vinyl acetate and vinyl propionate;
Nitrile compounds such as acrylonitrile and methacrylonitrile; vinyl ethers such as vinyl methyl ether, vinyl ethyl ether, and vinyl isobutyl ether;
Vinyl ketones such as vinyl methyl ketone, vinyl hexyl ketone, and methyl isopropenyl ketone; N-vinyl compounds such as N-vinylpyrrole, N-vinylcarbazole, N-vinylindole, and N-vinylpyrrolidone;
Vinyl chloride or the like can be used.

These polymerizable monomers can be used alone or in combination.

In order to produce a crosslinked polymer, the following crosslinking agent may be added to the monomer composition for suspension polymerization. That is,
Divinylbenzene, divinylnaphthalene, polyethylene glycol dimethacrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, l,3-butylene glycol dimethacrylate,
6-Hexane gelicol dimethacrylate, neopentyl glycol dimethacrylate, dipropylene glycol dimethacrylate, polypropylene glycol dimethacrylate, 2,2'-bis(4-methacryloxyjethoxyphenyl)propane, 2,2'-bis(4 - Common crosslinking agents such as acryloxyjetoxyphenyl)propane, trimethylolpropane trimethacrylate, trimethylolpropane triacrylate, tetramethylolmethanetetraacrylate, dibromneopentyl glycol dimethacrylate, diallyl phthalate, etc. can be used. .

The crosslinking agent is 0.0 parts by weight per 100 parts by weight of the polymerizable monomer.
It is desirable to use 0.01 to 15 parts by weight, more preferably 0.1 to 10 parts by weight.

If the amount of crosslinking agent is small, the melt viscosity necessary for the toner cannot be ensured, and it becomes difficult to prevent the offset phenomenon in which a portion of the toner adheres to the roller surface. Furthermore, if the amount of crosslinking agent is too large, the toner will be difficult to melt due to heat, and it will be difficult to fix the toner unless the roller temperature is extremely high.

Furthermore, the monomer composition can contain a mold release agent to prevent offset. As the mold release agent, polyolefin polymers such as low molecular weight polyethylene and polypropylene are preferred. This low molecular weight olefin polymer is preferably dispersed in the polymerizable monomer together with the colorant used in the present invention.

The mold release agent is usually preferably used in an amount of 1 to 15 parts by weight per 100 parts by weight of the vinyl monomer.
If it is less than 15 parts by weight, a sufficient mold release effect will not be obtained and an offset will occur on the roller, and if it is more than 15 parts by weight, the mold release agent will be spent on the triboelectric charging member, and the toner will flow. sex becomes very bad.

As the coloring agent contained in the monomer composition, conventionally known dyes and pigments, carbon black, and pigments such as grafted carbon black obtained by coating the surface of carbon black with a resin can be used. The colorant is used in an amount of 1 to 30 parts by weight per 100 parts by weight of the polymerizable monomer.

The following can be used as the dispersion stabilizer.

Namely, water-soluble polymers such as polyvinyl alcohol, starch, methyl cellulose, carboxymethyl cellulose, hydroxyethyl cellulose, sodium polyacrylate, and sodium polymethacrylate, barium sulfate, calcium sulfate, barium carbonate, magnesium carbonate, calcium phosphate, talc, viscosity, and diatom. Soil, metal oxide powder, etc. are used. It is preferable to use these in an amount of 0.1 to 10% by weight based on water.

In the present invention, the polymerization initiator may be added to the dispersion containing the monomer composition after granulation, but from the point of uniformly applying the polymerization initiator to each monomer composition particle, It is preferable to include it in the monomer composition before granulation.

As such a polymerization initiator, 2,2'-azobis-
(2,4-dimethylvaleronitrile), 2,2'-azobisisobutyronitrile, ■, 1'-azobis(cyclohexane-1-carbonitrile), 2,2'-azobis-4-methoxy-2, Azo or diazo polymerization initiators such as 4-dimethylvaleronitrile, azobisisobutyronitrile, benzoyl peroxide, methyl ethyl ketone peroxide, isopropyl peroxy carbonate, 2,4-diglolyl benzoyl peroxide, lauroyl peroxide. Examples include peroxide-based polymerization initiators such as.

If an aqueous phase polymerization inhibitor is included during polymerization, the formation of transparent fine particles can be suppressed to a relatively small amount at the end of one polymerization. Examples of such aqueous phase polymerization inhibitors include alkali metal salts, ammonium salts, and magnesium salts of molybdic acid, alkali metal salts of nitrite, and alkaline earth metal salts, and examples of halides include potassium bromide and bromide. Sodium, potassium iodide, sodium iodide, calcium iodide, ammonium iodide, etc., as well as manganese chloride, manganese sulfate, calcium chloride, magnesium chloride, potassium ferricyanide, potassium phosphite, water-soluble nigrosine, etc. can be used. . If a large amount of water phase polymerization inhibitor is used, suspension polymerization itself will be inhibited. Therefore, the amount of water phase polymerization inhibitor added is 0.01 to 5%
Weight % is appropriate.

Alternatively, suspension polymerization may be carried out by making the monomer composition contain a polymer that dissolves in the polymerizable monomer. In this case, there are effects such as improved electrical properties and thermal properties and adjustment of viscosity depending on the properties of the polymer. As the polymer that can be used, general known polymers can be used as long as they are soluble in the monomer.For example, polystyrene, styrene copolymer, acrylic resin, rosin, modified rosin, phenolic resin, terpene resin, etc. can be used alone. It can be used alone or in combination.

The toner of the present invention may be a type of magnetic toner containing a magnetic substance. To obtain a magnetic toner, magnetic particles may be added to the monomer composition. Examples of the magnetic material that can be used in the present invention include powders of ferromagnetic metals such as iron, cobalt, and nickel, and powders of alloys and compounds such as magnetite, hematite, and ferrite. These magnetic materials usually have a particle size of 0.05 to 5
I! m, preferably 0.1 to 1/4+, is used, but when producing small particle size toner,
Particle size 0.8. It is desirable to use the following magnetic particles: Moreover, the magnetic material is contained in 10 parts by weight of the monomer composition.
The content is preferably in the range of 60 parts by weight.

Further, these magnetic materials may be treated with a surface treatment agent such as a silane coupling agent or a titanium coupling agent, or an appropriate reactive resin.

In this case, although it depends on the surface area of the magnetic particles or the density of hydroxyl groups present on the surface, the amount of surface treatment agent is usually 5 parts by weight or less, preferably 0.1 to 100 parts by weight, based on 100 parts by weight of the magnetic material.
A treatment amount of 3 parts by weight provides sufficient dispersibility in the polymerizable composition, and does not adversely affect the physical properties of the toner.

The toner of the present invention may contain a polarity control agent if necessary. Polarity control agents that can be used include: That is, as negative charge control agents, metal complexes of monoazo dyes, nitrohumic acid and its salts, salicylic acid, naphthoic acid, metal complexes of dicarboxylic acids such as C01Cr and Fe, sulfonated copper phthalocyanine pigments, nitro groups, and halogens are used. These include introduced styrene oligomers, chlorinated paraffins, and melamine resins. In addition, as positive charge control agents, Sumisol Black AR (Susumu Chemical, oil-soluble dye), Oil Black HBB (Orient Chemical, C, 1, 26150, C, 1, Solvent Black 3), Nigrosine, Mikethrene Blue R5N (Mitsui Toatsu, C,,I.

69800, C,1, Bat Blue 4), Ceres Blue R (Bayer AG, C,1,61500, C,1, Solvent Blue 8).

Varifast Blue 1605 (Orient Chemical, oil-soluble dye, C, I, 74180), Oil Blue 2N (Orient Chemical, oil-soluble dye C, 1,61555), Lurafix Bin B (manufactured by BASF, C, 1,11115, C
, I, Disbirds Red 13), Lurafix Blue FFR (manufactured by BASF, C, 1, 61505, C, 1,
Disperse Blue 3), Lulafix Bink FF3
B (8ASFll, C,1,62015, C,1, Disbird's Red 11), etc.

〔Example〕

Hereinafter, the present invention will be explained in more detail with reference to the following examples, but the present invention is not limited thereto.
Note that all parts are parts by weight.

(Production example 1 of suspension polymerized particles) Styrene monomer 75 parts n-
Butyl acrylate monomer 25 parts A100 (manufactured by Mitsubishi Kasei) 8 parts in carbon black The above polymerizable monomer mixture was dispersed for 24 hours using a ball mill.
After mixing, 1.5 parts of azobisisobutylnitrile was dissolved in this dispersion. on the other hand.

Potassium iodide 0.3 parts, polyvinyl alcohol 8.0 parts
1 part was dissolved in 400 parts of ion-exchanged water to prepare an aqueous medium.

Add the monomer composition to this and add the TK homomixer (
1 at 1 rotation speed of 7000 rpm using
Stirred for 0 minutes. After one polymerization was completed, four of these suspensions and dispersions were transferred to a rosetteable flask and polymerized for 7 hours at a rotation speed of 9 rpm and a temperature of 70° C. in a nitrogen atmosphere.

The generated particles were collected by repeated washing and filtration, and dried. The volume average particle size of these particles is approximately 7.3. Met.

(Production Example 2 of Suspension Polymerized Particles) Styrene monomer 80 parts n-butyl acrylate monomer 20 parts chromium-containing azo dye 3 parts The above polymerizable monomer mixture was dispersed and mixed for 24 hours using a ball mill, and then this dispersion was prepared. 1.5 parts of azobisisobutylnitrile was dissolved in the solution. On the other hand, an aqueous medium was prepared by dissolving 0.3 parts of potassium iodide and 8.0 parts of polyvinyl alcohol in 400 parts of ion-exchanged water. The above monomer composition was added to the mixture and stirred for 10 minutes at a rotational speed of 9000 rpm using a TK homomixer (Tokushu Kika Kogyo Division). Four of these suspended dispersions were transferred to a separable flask and polymerized for 7 hours under a nitrogen atmosphere at a rotation speed of 9 Orpm and a temperature of 70°C. After the completion of one polymerization, the generated particles were repeatedly washed and filtered to collect them.
Dry. The volume average particle size of these particles is 6.1. (Example 1) 1.5 parts of an organic acid having a fluorinated carbon group represented by the above formula (1-1) was dispersed in 60 parts of isopropyl alcohol, and the particles obtained in Production Example 1 were dispersed. 100 parts were spray coated. The particles were dried under reduced pressure at 50° C. for 5 hours to obtain a toner treated with an organic acid having a fluorinated carbon group.

This toner is coated with silicone resin and has an average particle size of approximately 1
For 100 parts of spherical ferrite carrier of 100p,
3 parts were added and stirred for 30 minutes in a ball mill pot to obtain a developer (two-component developer).

Using this developer, high temperature (30℃, 85%RH)
) and low temperature, low humidity (10°C, 15% RH) environment using a commercially available electrophotographic copying machine (Ricoh Co., Ltd. 11FT5510), the density of each image was high in both environments, and there was no background smudge. No sharper images were obtained.

The toner charge amount in both environments is high temperature and high temperature -17.9μC/
g, and -19.6 μC/g at low temperature and low humidity, with almost no change.

Further, when a 10,000 copy test was conducted at room temperature (20° C., 65% RH), the initial high image quality was maintained even after 10,000 copies, and there was almost no change in the amount of charge.

(Example 2) Except that an organic acid having a fluorinated carbon group represented by the above formula (l-5) was used instead of an organic acid having a fluorinated carbon group represented by the above formula (1-1), A toner was prepared in the same manner as in Example 1. A developer was prepared in the same manner as in Example 1, and an environmental test and continuous copy test were conducted using FT5510.

As shown in Table 1, the results were extremely good in both moisture resistance and durability.

(Comparative Example 1) 100 parts of the particles obtained in Production Example 1 were spray-coated with 60 parts of isopropyl alcohol, and then dried under reduced pressure at 50° C. for 5 hours to obtain a toner. A developer was prepared using this toner in exactly the same manner as in Example 1, and its moisture resistance and durability were examined. As a result, at low temperatures and low humidity, sharpness was good and the image quality was high, but at high temperatures and high humidity, sharpness decreased and background smear occurred. When the amount of charge of the toner was examined in both environments, as shown in Table 1, the amount of charge was decreased in high humidity. In addition, as a result of a continuous copy test, good image quality was obtained initially, but as the number of copies increased, background smudge became more severe.

(Example 3) A toner was prepared in exactly the same manner as in Example 1, except that particles obtained in Production Example 2 were used instead of particles obtained in Production Example 1. A developer was prepared in the same manner as in Example 1, and an environmental test and a 20,000 copy test were conducted using FT5510. As shown in Table 1, the results were very good in both moisture resistance and durability.

(Example 4) A toner was prepared in exactly the same manner as in Example 2, except that particles obtained in Production Example 2 were used instead of particles obtained in Production Example 1. Hereinafter, a developer was prepared in the same manner as in Example 1, and tested in exactly the same manner as in Example 3. As shown in Table 1, the results were extremely good in both moisture resistance and durability.

(Example 5) 1.5 parts of an organic acid having a fluorinated carbon group represented by the above formula (1-8) was dispersed in 60 parts of methyl alcohol, and this was sprayed onto 100 parts of the particles obtained in Production Example 2. Coated. The particles were dried under reduced pressure at 50° C. for 8 hours to obtain a toner treated with an organic acid having a fluorinated carbon group. A developer was prepared using this toner in exactly the same manner as in Example 1, and the same tests as in Example 1 were conducted. The results are shown in Table 1.
As shown in the figure, both moisture resistance and durability were extremely good.

(Comparative Example 2) A toner was prepared in exactly the same manner as in Comparative Example 1, except that the particles of Production Example 2 were used instead of the particles obtained in Production Example 1. A test was conducted using this toner in the same manner as in Example 3. As a result, the initial images at room temperature had good sharpness and high image quality, but as shown in Table 1, moisture resistance and
Durability was also not good.

(Example 6) In place of 165 parts of the organic acid having a fluorinated carbon group represented by the above formula (I-1), 2 parts of an organic acid having a fluorinated carbon group represented by the above formula (If-2) was used. Other than that,
A toner was prepared in the same manner as in Example 1.

Hereinafter, a developer was prepared in the same manner as in Example 1, and FT55
10 was used to conduct environmental tests and continuous copy tests. As shown in Table 2, the results were extremely good in both moisture resistance and durability.

(Example 7) An organic acid having a fluorinated carbon group represented by the above formula (If-16) was used instead of 1.5 parts of an organic acid having a fluorinated carbon group represented by the above formula (If-16). Other than that,
A toner was prepared in the same manner as in Example 6. A developer was prepared in the same manner as in Example 6, and an environmental test and a continuous copy test were conducted using FT551O. As shown in Table 2 (for comparison, the results of Comparative Examples 1 and 2 are also shown in the table), both moisture resistance and durability were very good.

(Example 8) A toner was prepared in exactly the same manner as in Example 6, except that particles obtained in Production Example 2 were used instead of particles obtained in Production Example 1. A developer was prepared in the same manner as in Example 6, and an environmental test and a 20,000 copy test were conducted using FT5510. As shown in Table 2, the results were extremely good in both moisture resistance and durability.

(Example 9) A toner was produced in exactly the same manner as in Example 7, except that particles obtained in Production Example 2 were used instead of particles obtained in Production Example 1. A developer was prepared in the same manner as in Example 6 and tested in exactly the same manner as in Example 8. As shown in Table 2, the results were extremely good in both moisture resistance and durability.

(Example 10) 2 parts of an organic acid having a fluorinated carbon group represented by the above formula (II-18) was dispersed in 60 parts of methyl alcohol, and this was spray applied to 100 parts of the particles obtained in Production Example 2. . The particles were dried under reduced pressure at 50° C. for 8 hours to obtain a toner treated with an organic phosphoric acid compound having a fluorinated carbon group. A developer was prepared using this toner in exactly the same manner as in Example 6, and the same tests as in Example 6 were conducted. As shown in Table 2, the results were extremely good in both moisture resistance and durability.

〔Effect of the invention〕

The toner for developing electrostatic images of the present invention is produced by dispersing a polymer monomer and a colorant in an aqueous phase containing a dispersion stabilizer, and then subjecting the resulting suspension polymerization to suspension polymerization using a specific fluorinated carbon group. Since the film is treated with an organic acid having the following properties, moisture resistance and durability can be improved, and higher image quality can be achieved.

Claims (3)

[Claims] (1) Suspension polymerized particles obtained by dispersing at least a polymerizable monomer and a colorant in an aqueous phase containing a dispersion stabilizer and carrying out suspension polymerization are treated with an organic acid having a fluorinated carbon group. A toner for developing electrostatic images characterized by: (2) Suspension polymerized particles obtained by dispersing at least a polymerizable monomer and a colorant in an aqueous phase containing a dispersion stabilizer and carrying out suspension polymerization have the following general formula Rf-X or (RfO)_m-Ar- X_w (where m = 1 to 3, w = 1 to 3, Rf is CF_2(CY_2)n [however, n = 0 to 9, Y is hydrogen or fluorine atom, and each Y
may be the same or different. ], Ar is a divalent aliphatic hydrocarbon group or aromatic hydrocarbon group, and X is a carboxyl group, a sulfonic acid group or a hydroxyl group. ) A toner for developing an electrostatic image, characterized in that it is treated with an organic acid having a fluorinated carbon group represented by: (3) Suspension polymerized particles obtained by dispersing at least a polymerizable monomer and a colorant in an aqueous phase containing a dispersion stabilizer and carrying out suspension polymerization have the following general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ ( However, n = 1 to 3, m = 0 to 2, R is -ORf or -Ar-ORf [However, Ar is 2
a valent aliphatic hydrocarbon group or an aromatic hydrocarbon group,
Rf is a fluorinated carbon group. ] Q is oxygen, a hydroxyl group, or a C_1 to C_4 alkoxy group. ) A toner for developing an electrostatic image, characterized in that it is treated with an organic phosphoric acid compound having a fluorinated carbon group represented by: