JP3219316B2 - Electrophotographic developing toner - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a toner used for developing an electric latent image or a magnetic latent image in an electrophotographic method, an electrostatic printing method, and the like. And a toner for electrophotographic development that hardly affects developer characteristics such as charging characteristics even after long-term use in a developing device.

[0002]

2. Description of the Related Art In the case of a dry method, an electrostatic image formed by an electrophotographic method, an electrostatic printing method, an electrostatic recording method, etc. is generally developed with a dry toner mainly containing a binder resin and a colorant, and then copied. Transferred and fixed on paper. There are various methods for fixing a toner image, but a heat roller fixing method is widely used because of its high thermal efficiency and high-speed fixing. When high-speed fixing is performed by such a heat fixing method, the toner is required to have good low-temperature fixability (or a low fixing minimum temperature), and therefore, a binder resin having a low softening point is used. You. However, when the low softening point resin is contained in the toner, a part of the toner image adheres to the surface of the heat roller at the time of fixing, and the toner image is transferred onto copy paper to cause a background stain (so-called “offset phenomenon”). ) And the winding phenomenon (especially when the temperature of the heat roller is low) is likely to occur.

[0003] As means for preventing these phenomena, Japanese Patent Application Laid-Open No. 51-143333 and Japanese Patent Application Laid-Open No.
No. 52, JP-A-58-97056, JP-A-60-24
In publications such as No. 7250, it is proposed to add a solid silicone varnish, a higher fatty acid, a higher alcohol, various waxes and the like as a release agent. Nothing showing offset resistance and wrap resistance is known. Specifically, conventional polyolefin waxes such as low molecular weight polyethylene and low molecular weight polypropylene have good offset resistance, but do not have sufficient low-temperature fixability. Moreover, since the conventional release agent has poor dispersibility in the binder resin, a phenomenon in which the release agent is released from the toner and adheres to the photoconductor and the developing sleeve during development (so-called "filming phenomenon") is caused. In many cases, carrier contamination due to spent toner also occurred, and it was difficult to stably form high-quality images over a long period of time.

However, it is known that it is effective to use a polyester resin in order to maintain low-temperature fixability. However, with the conventional developer, the charge control agent in the toner peels off after long-term use and contaminates the carrier surface, making it impossible to obtain a stable charge amount. It was difficult to form a high-quality image due to the following reasons. In order to impart a negative charge to the toner, a technique using a metal-containing complex salt dye disclosed in JP-B-45-26478 or a calix (n) allene compound disclosed in JP-A-2-201378 may be used. Although the method of containing is known, it is difficult to obtain a stable charge amount for a long period of time unless the method of use is optimized.

[0005]

SUMMARY OF THE INVENTION It is an object of the present invention to provide a toner for electrophotographic development which has a sufficient offset resistance at the time of fixing, has a low minimum fixing temperature, and does not cause winding of a fixing roller. It is. Another object of the present invention is to provide a toner which is free from background smear and toner scattering, has high fidelity equivalent to the initial image even during continuous use, and is suitable for high-speed fixing.

[0006]

SUMMARY OF THE INVENTION The present invention relates to a toner for electrophotographic development mainly comprising a binder resin, a release agent, a charge control agent and a colorant, wherein the toner contains a polyester resin as the binder resin. And a release agent containing at least one selected from the group consisting of carnauba wax having a free fatty acid having an acid value of 5 or less, a montan ester wax, a rice wax having an acid value of 10 to 30 and a sasol wax. And a charge control agent characterized by containing at least one compound represented by the following general formula (I).

Embedded image (However, X and Y are each an integer, and when n = X + Y, n is 4 to 8. R ¹ is a hydrogen atom and has 1 carbon atom.)
5 alkyl or ^{_{- (CH 2) mCOOR 21 (}} R 21 represents a hydrogen atom or a lower alkyl group, m is an integer of 1 to 3) is. R ² is a hydrogen atom, a halogen atom,
An alkyl group having 1 to 12 carbon atoms which may have branching;
Aralkyl _{group, -NO 2, -NH 2, -N} (R 22) 2 (R
²² is a lower alkyl ^{_{group), - SO 3 R 23 (}} R 23 is a hydrogen atom), phenyl group which may have a substituent group or -Si,
(CH ₃ ) ₃ . R ³ and R ⁴ represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 3 carbon atoms, —NH ₂ , or —N
(R ²⁴ ) ₂ (R ²⁴ is a lower alkyl group). R ⁵ is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R ¹¹ is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or — (CH ₂ ) p
COOR ³¹ (R ³¹ represents a hydrogen atom or a lower alkyl group, and p represents an integer of 1 to 3). R ¹² represents a hydrogen atom, a halogen atom, or a branched carbon atom having 1 to 1 carbon atoms.
12 alkyl group, an aralkyl group, -NO _2, -NH _{2,
^{-N (R 32) 2 (R}} 32 is a lower alkyl group), - SO ₃ R ³³
(R ³³ is a hydrogen atom), a phenyl group which may have a substituent, or —Si (CH ₃ ) ₃ . R ¹³ and R ^{14 each} represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 3 carbon atoms,
H ₂ or —N (R ³⁴ ) ₂ (R ³⁴ is a lower alkyl group). R ¹⁵ is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. )

In the present invention, the toner can be used by mixing it with a carrier. In this case, the toner is mixed with a carrier obtained by coating a core material with a silicone resin so that the toner can be used for a longer period of time. The same charging property and image quality can be obtained.

The charge control agent represented by the above general formula (I) and used in the toner of the present invention is called a calix (n) allene compound, which imparts charge stability to the long-term use of the toner and environmental changes. . This compound is synthesized in high yield from phenol and formaldehyde as raw materials, particularly when a strong alkali is used.

Specific examples of the compounds include those shown in Table 1 below, but are not limited thereto.

[Table 1- (1)]

[Table 1- (2)]

The charge control agent is added in an amount of 0.5 to 15 parts by weight, preferably 1 to 5 parts by weight, based on the whole toner.
If the amount is less than this range, a sufficient amount of negative charge cannot be imparted to the toner.If the amount is more than this range, the charge control agent detaches from the toner surface during continuous use in the developing device, and the amount of charge increases. May change.

The binder resin used in the toner of the present invention is at least a polyester resin,
In particular, if a polyester resin synthesized from a monomer containing a bisphenoldiol-type alcohol and a polycarboxylic acid as the main components is used, the resistance to PVC (plasticizer resistance) is obtained.
And good toner can be obtained without impairing the color of the color material of the color toner. Of course, the fixability at low temperatures is also good. The diol component in the polyester resin is represented by the following general formula (II)

Embedded image (However, R ⁴¹ is an alkylene group having 2 to 4 carbon atoms, x and y
Is an integer and the average of the sum is 2 to 16. ). On the other hand, as the polyvalent carboxylic acid, the following general formula (III) or (IV)

Embedded image (However, R ⁵¹ is a saturated or unsaturated hydrocarbon group having 4 to 20 carbon atoms.)

Embedded image (However, R ⁵² and R ⁵³ are a saturated or unsaturated hydrocarbon group having 4 to 20 carbon atoms). In these polyester resins, the compound represented by the general formula (II) is suitably from 1 to 50 mol%, and the compound represented by the general formula (III) or (IV) is suitably from 10 to 30 mol%.

In the present invention, the polyol component and the polycarboxylic acid component are usually mixed in an inert gas atmosphere for one hour.
A polyester resin can be prepared by condensation polymerization at a temperature of 80 to 250 ° C.

The free fatty acid-type carnauba wax used as a mold release agent in the toner of the present invention is obtained by removing free fatty acids from carnauba wax as a raw material, and thus has an acid value of 5% or less. In addition, the diameter of the dispersed particles in the binder resin is finer than that of the conventional carnauba wax and is 1 μm or less, so that the dispersibility is improved.

The montan-based ester wax is refined from minerals, becomes microcrystals like carnauba wax, has a dispersed particle diameter of 1 μm or less in the binder resin, and has improved dispersibility. In the case of montan ester wax, the acid value is particularly preferably 5 to 14.

The oxidized rice wax of the present invention is obtained by subjecting rice bran wax to air oxidation. The acid value is preferably from 10 to 30, and if it is less than 10, the fixing lower limit temperature rises and the low-temperature fixability becomes insufficient. If it is more than 30, the cold offset temperature rises and the low-temperature fixability also becomes insufficient.

Sasol wax is Sasol wax H1, H2, A1, A2, A3, A manufactured by Sasol.
4, A6, A7, A14, C1, C2, SPRAY3
0, SPRAY40, etc. can be used.
H2, SPRAY30 and SPRAY40 are preferred because of their excellent low-temperature fixation and storage stability.

The above-mentioned waxes may be used alone or in combination. The above-described good results can be obtained by incorporating 1 to 15 parts by weight, preferably 2 to 10 parts by weight of the whole toner.

The coloring agents used in the present invention include carbon black, lamp black, iron black, ultramarine blue, aniline blue, phthalocyanine blue, phthalocyanine green, Hansa Yellow G, rhodamine 6G lake, calco oil blue, chrome yellow, and quinacridone. Any conventionally known dyes and pigments such as benzidine yellow, rose bengal and triallylmethane dyes can be used alone or in combination. The amount of these colorants to be used is generally 1 to 30% by weight, preferably 3 to 20% by weight, based on the binder resin.

Among the colorants used in the present invention, particularly desirable ones are C.I. I. Pigment Red 48.

Embedded image (Here, when X = Ba, CI Pigment Red 48: 1 When X = Ca, CI Pigment Red 48: 2, when X = Sr, CI Pigment Red 48 : 3 When X = Mn, CI Pigment Red 48: 4
It is. )

As the red colorant, C.I. I. When CI Pigment Red 48 is used, C.I. I. Pigment Red 57: 1, C.I. I. Pigment Red 112,
C. I. Pigment Red 122, C.I. I. Advantageously, at least one solvent red 49 (both of which are also infrared colorants) is used in combination.

Embedded image

Embedded image

Embedded image

Embedded image

Note that C.I. I. Solvent Red 57:
1, C.I. I. Solvent Red 112, C.I. I. Solvent Red 122 and C.I. I. At least one red colorant selected from Solvent Red 49; I. Pigment Red 48 to measure the charge stabilizer of the toner. I. Pigment Red 48 and the other C.I. I. When the compounding ratio (weight ratio) with Solvent Red 57: 1 or the like is preferably 9: 1 to 1: 9, the charge amount of the red toner can be further stabilized.

The toner of the present invention further contains a magnetic material and can be used as a magnetic toner. Examples of magnetic materials contained in the magnetic toner include iron oxides such as magnetite, hematite, and ferrite; metals such as iron, cobalt, and nickel; and aluminum, cobalt, copper, lead, magnesium, tin, zinc, and antimony of these metals. ,
Examples include metal alloys such as beryllium, bismuth, cadmium, calcium, manganese, selenium, titanium, tungsten, and vanadium, and mixtures thereof. These ferromagnetic materials preferably have an average particle size of about 0.1 to 2 μm, and are contained in the toner in an amount of about 20 to 200 parts by weight, particularly preferably 100 parts by weight, per 100 parts by weight of the resin component. 40 to 150 parts by weight per part.

Further, the toner of the present invention may optionally contain additives. Examples of the additive include a lubricant such as Teflon and zinc stearate or a polishing agent such as cerium oxide and silicon carbide; a fluidity imparting agent such as colloidal silica and aluminum oxide; a caking inhibitor; or carbon black and tin oxide. And the like.

The toner of the present invention may be used as a one-component developer, or may be mixed with a carrier and used as a two-component developer. As the carrier, any of those known in the art can be used, but a carrier having a core material coated with a silicone resin is particularly preferable.

The carrier core particles coated with the silicone resin may be those conventionally known, for example, iron,
Ferromagnetic metals such as cobalt and nickel: alloys and compounds such as magnetite, hematite and ferrite: glass beads and the like. The average particle size of these core particles is usually 10 to 1000 μm, preferably 30 to 500 μm.

The amount of the silicone resin used is usually 1 to 10% by weight based on the carrier core particles. The silicone resin used in the present invention may be any of the conventionally known silicone resins, for example, KR261, KR271, K
R272, KR275, KR280, KR282, KR
285, KR251, KR155, KR220, KR2
01, KR204, KR205, KR206, SA-
4, ES1001, EA1001N, ES1002T,
KR3093 or Toray Silicone SR2100, S
R2101, SR2107, SR2110, SR210
8, SR2109, SR2115, SR2400, SR
2410, SR2411, SH805, SH806A,
SH840 or the like is used.

As a method for forming the silicone resin layer, the silicone resin may be applied to the surface of the carrier core particles by a spraying method, an immersion method, or the like, as in the prior art. Since the surface energy of the silicone resin-coated carrier is low, it is possible to extremely reduce the fusion of the toner to the surface by long-term stirring or the like in the developing device.

[0028]

EXAMPLES The present invention will be described more specifically with reference to examples, but the present invention is not limited to these examples. All parts here are parts by weight.

Example 1 81 parts of a polyester resin (number average molecular weight = 5000, weight average molecular weight = 55000, Tg = 62 ° C.) 4 parts of a free fatty acid type carnauba wax (acid value 2) 4 parts carbon black (manufactured by Mitsubishi Carbon Co., Ltd.) 44) 12 parts Exemplified compound (1) 2 parts After sufficiently stirring and mixing a mixture of these compositions in a Henschel mixer, a mixture of about 4 at a temperature of 80 to 110 ° C by a roll mill.
After heat-fusing for 0 minutes and cooling to room temperature, the obtained kneaded material was pulverized and classified to obtain a toner having a particle size of 5 to 20 μm. Three parts of the toner were mixed with 97 parts of a 150-250 mesh iron oxide powder carrier (TEFV manufactured by Nippon Iron Powder Co., Ltd.) using a ball mill to obtain a two-component developer. The toner charge amount is-
It was 20 μc / g. Next, the developer was set on a plain paper copier (FT-4530, manufactured by Ricoh Co., Ltd.) equipped with a Teflon-coated roller as a fixing roller, and a continuous copy test was performed at a heat roller temperature of 130 ° C., which revealed an offset and winding phenomenon. Good images were obtained in the initial stage and after 100,000 copies, and no filming on the photoreceptor or the developing sleeve was observed. When a hot offset, a cold offset, a winding occurrence temperature, and a fixing lower limit temperature were measured as a fixing test, good results were obtained as shown in Table 2 below. Further, when the toner spent of the developer after 100,000 sheets was measured, no toner spent was observed.

Example 2 Instead of 4 parts of carbon black, C.I. I. Pigment Red 48: 1 was used in the same manner as in Example 1 except that 7 parts of Pigment Red were used, a two-component developer was used, and a continuous copy test was performed. The results are as shown in Table 2, and good results were obtained as in Example 1.

Comparative Examples 1 and 2 Instead of the carnauba wax of the free fatty acid type in Example 1, a low molecular weight polypropylene (660 manufactured by Sanyo Chemical Industries, Ltd.) was used.
A developer was prepared in the same manner as in Examples 1 and 2 except that P) was used, and a continuous copy test was performed. As a result, a winding phenomenon occurred and a good image was not obtained.

Example 3 Polyester resin (same as in Example 1) 85 parts Montan ester wax (acid value: 12.0) 3 parts Carbon black (# 44, manufactured by Mitsubishi Carbon Corporation) 9 parts Exemplary compound (2) 5 parts A mixture of these compositions was sufficiently stirred and mixed in a Henschel mixer in the same manner as in Example 1, and then mixed with a roll mill at 80 to 1%.
Melted at a temperature of 10 ° C. for about 40 minutes, cooled to room temperature,
The obtained kneaded material was pulverized and classified to obtain a toner having a particle size of 5 to 20 μm. 3.5 parts of this toner coated with a silicone resin (SR-2410: manufactured by Toray Silicone Co., Ltd.)
96.5 parts of an iron oxide powder carrier of 0 to 250 mesh was mixed with a ball mill to obtain a two-component developer. The charge amount of the toner was -18 μc / g. Using this developer, a continuous copy test was performed in the same manner as in Example 1.
Good results were obtained as in Example 1. In addition, the fixing property was good as shown in Table 2 below.

Example 4 Instead of 9 parts of carbon black, C.I. I. Pigment Red 48: 1 and 4 parts of C.I. I. Pigment Red 57:
A toner was prepared in exactly the same manner as in Example 3 except that two parts of No. 1 were used, and a continuous copy test was carried out on a two-component developer. The results were as shown in Table 2, and good results were obtained as in Example 3.

Example 5 The same procedure as in Example 1 was carried out except that the oxidized rice wax having an acid value of 15 was used in place of the carnauba wax of the free fatty acid type in Example 1, and the charge control agent was changed to Exemplified Compound (3). Thus, a developer was obtained. Next, a continuous copy test was performed using this developer in the same manner as in Example 1. As a result, good results were obtained as in Example 1. In addition, the fixing property was good as shown in Table 2 below.

Example 6 Oxidation 1 was used in place of the montan ester wax of Example 3.
Oxidized rice wax, 9 parts of carbon black instead of C.5 I. Pigment Red 48: 1 and 4 parts of C.I.
I. Pigment Red 112, and a toner was prepared in exactly the same manner as in Example 3 except that Exemplified Compound (3) was used instead of Exemplified Compound (2). Tested. The results were as shown in Table 2, and good results were obtained as in Example 3.

Comparative Examples 3 and 4 A developer was prepared in the same manner as in Examples 3 and 4 except that the montan ester waxes of Examples 3 and 4 were not used, and a continuous copy test was performed. Was good, but the winding phenomenon occurred, and no good image was obtained.

Comparative Examples 5 and 6 A developer was prepared in the same manner as in Examples 1 and 2, except that a styrene acrylic resin (SBM-73: manufactured by Sanyo Chemical Co., Ltd.) was used instead of the polyester resin of Examples 1 and 2. When a continuous copy test was performed, the minimum fixing temperature was high and the fixability was insufficient, and no good image was obtained.

Example 7 In place of the polyester resin of Example 1, another polyester resin (number average molecular weight = 5300, weight average molecular weight = 5)
1000, glass transition point = 59.5 ° C.), the same as in Example 1, except that carnauba wax having a free fatty acid type having an acid value of 4 was used, and the exemplified compound (4) was used as a charge control agent. Thus, a developer was obtained. When a continuous copy test was performed, good results were obtained as in Example 1. In addition, the fixing property was good as shown in Table 2 below.

Example 8 C.I. I. A developer was obtained in exactly the same manner as in Example 7 except that 3 parts of Pigment Red 122 was added. When a continuous copy test was performed, good results were obtained as in Example 1. The fixability of this product is shown in Table 2 below.
As shown in FIG.

Examples 9 and 10 Sasol wax H1 manufactured by Sasol was used in place of carnauba wax in Examples 7 and 8, and Exemplified compound (5) was used in place of Examples 7 and 8 as a charge control agent. Other than the above, a developer was obtained in the same manner as in Examples 7 and 8. Next, a continuous copy test was performed on this developer in the same manner as in Examples 7 and 8, and good results were obtained as in Examples 7 and 8. In addition, the fixing property was good as shown in Table 2 below.

Example 11 Polyester resin (number average molecular weight = 5200, weight average molecular weight = 55000, Tg = 62 ° C.) 85 parts Oxidized rice wax (acid value 12.0) 3 parts Carbon black (# 44 manufactured by Mitsubishi Carbon Corporation) 10 parts Exemplified compound (6) 2 parts A mixture of these compositions was prepared in the same manner as in Example 1 for 5 to 20 µm.
m was obtained. Three parts of the toner were mixed with 97 parts of a 100 to 250 mesh ferrite carrier coated with a silicone resin (SR-2411, manufactured by Toray Silicone Co., Ltd.) in a ball mill to obtain a two-component developer. Note that the charge amount of the toner was -19 μc / g.
Next, a continuous copy test was performed using this developer in the same manner as in Example 1. As a result, good results were obtained as in Example 1. In addition, the fixing property was good as shown in Table 2 below.

Example 12 Instead of 10 parts of carbon black, C.I. I. Pigment Red 48: 1, 7 parts of C.I. I. Solvent Red 49
Was used in the same manner as in Example 11 except that three parts were used to obtain a two-component developer. The charge amount of the toner was −21 μc / g. Next, a continuous copy test was performed using this developer in the same manner as in Example 1. As a result, good results were obtained as in Example 1. In addition, the fixing property was good as shown in Table 2 below.

Comparative Example 7 A developer was prepared in the same manner as in Example 1 except that polypropylene oxide (manufactured by Sanyo Chemical Industries, Ltd.) was used in place of the carnauba wax of the free fatty acid type in Example 1, and a continuous copy test was performed. As a result, a winding phenomenon occurred, and a good image was not obtained. As shown in Table 2 below, the fixability was sufficient at low temperature, but was not at a practical level due to occurrence of hot offset.

Comparative Examples 8 and 9 A developer was prepared in the same manner as in Examples 1 and 2 except that the chromium oxynaphthoate complex was used in place of the charge control agent of Examples 1 and 2, and a copy image was produced. However, fogging occurred in the background portion of the image, and a good image was not obtained.

Example 13 A developer was prepared in the same manner as in Example 1 except that Exemplified Compound 7 was used in place of the charge control agent of Example 1, and a copy image was obtained. A good image was obtained even after copying. However, the initial charge amount is -17.
-13 μc / g after 100,000 copies against μc / g
And a tendency to slightly decrease was observed.

Example 14 C. of Example 2 I. Pigment Red 48: 1 instead of C.I. I. Pigment Red 239 was used to prepare a developer in the same manner as in Example 2, and a copy image was obtained. No abnormality was found in the initial image, but after printing 100,000 sheets, Fog occurred on the background portion, and it was difficult to obtain a good image.

[Table 2] Offset occurrence temperature: The toner image transferred onto the copy paper is fixed by the Teflon-coated roller while the heating temperature of the roller is sequentially increased, and the operation of fixing the toner image under the conditions of a nip width of the roller of 4 mm and a linear velocity of 250 mm / sec is repeated. Is determined, the lowest temperature at this time is defined as a cold offset generation temperature, and the highest temperature is defined as a hot offset generation temperature. Winding occurrence temperature: Using a so-called solid black original, the toner is transferred to almost the entire surface of the copy paper, and the fixing operation is repeated in the same way as the measurement of the offset occurrence temperature, except that the heating temperature of the roller is gradually reduced. Then, determine the temperature at which the copy paper is wound around the roller. Fixing lower limit temperature: Fixing is performed in the same manner as in the measurement of the offset occurrence temperature, and the temperature at which the toner fixing rate by the clock meter reaches 70% is obtained.

The dry toner of the present invention has (1) sufficient offset resistance and wrap resistance, (2) can be fixed at a low temperature, can be fixed at high speed, and (3) has a binder of a release agent. Good dispersibility in resin; therefore, less toner filming on the photoreceptor and developing sleeve during development; no carrier contamination by spent toner; stable for a long time; and (4) sufficient negative chargeability And an advantage that a high quality image can be formed.

Continued on the front page (72) Inventor Fumio Kondo 1-3-6 Nakamagome, Ota-ku, Tokyo Inside Ricoh Company (72) Inventor Chiharu Mochizuki 1-3-6 Nakamagome, Ota-ku, Tokyo Stock Company Inside Ricoh (72) Inventor Yasutaka Iwamoto 1-3-6 Nakamagome, Ota-ku, Tokyo Inside Ricoh Company (72) Inventor Toshiki Minatani 1-3-6 Nakamagome, Ota-ku, Tokyo Inside Ricoh Company (56) References JP-A-1-109360 (JP, A) JP-A-3-5764 (JP, A) JP-A-3-139664 (JP, A) JP-A-1-238671 (JP, A) JP-A-1-238672 (JP, A) JP-A-60-254153 (JP, A) JP-A-61-273555 (JP, A) JP-A-3-179458 (JP, A) JP-A-2-201378 (JP JP, A) JP-A-3-237468 (JP, A) JP-A-2-301770 (JP, A) JP-A-63-173066 (JP, A) JP-A-63-247758 (JP, A) Hei 3-220564 (JP, ) (58) investigated the field (Int.Cl. ^7, DB name) G03G 9/08

Claims (5)

(57) [Claims] 1. A toner containing a binder resin, a release agent, a charge control agent and a colorant as main components, wherein the toner contains a polyester resin as a binder resin, and a release agent having an acid value of 5 or less as a release agent. It contains at least one member selected from the group consisting of free fatty acid type carnauba wax, montan ester wax, oxidized rice wax having an acid value of 10 to 30 and sasol wax, and further has the following general formula (I) as a charge control agent: A toner for electrophotographic development comprising at least one compound represented by the formula: Embedded image (However, X and Y are each an integer, and when n = X + Y, n is 4 to 8. R ¹ is a hydrogen atom and has 1 carbon atom.)
5 alkyl or ^{_{- (CH 2) mCOOR 21 (}} R 21 represents a hydrogen atom or a lower alkyl group, m is an integer of 1 to 3) is. R ² is a hydrogen atom, a halogen atom,
An alkyl group having 1 to 12 carbon atoms which may have branching;
Aralkyl _{group, -NO 2, -NH 2, -N} (R 22) 2 (R
²² is a lower alkyl ^{_{group), - SO 3 R 23 (}} R 23 is a hydrogen atom), phenyl group which may have a substituent group or -Si,
(CH ₃ ) ₃ . R ³ and R ⁴ represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 3 carbon atoms, —NH ₂ , or —N
(R ²⁴ ) ₂ (R ²⁴ is a lower alkyl group). R ⁵ is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R ¹¹ is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or — (CH ₂ ) p
COOR ³¹ (R ³¹ represents a hydrogen atom or a lower alkyl group, and p represents an integer of 1 to 3). R ¹² represents a hydrogen atom, a halogen atom, or a branched carbon atom having 1 to 1 carbon atoms.
12 alkyl group, an aralkyl group, -NO _2, -NH _{2,
^{-N (R 32) 2 (R}} 32 is a lower alkyl group), - SO ₃ R ³³
(R ³³ is a hydrogen atom), a phenyl group which may have a substituent, or —Si (CH ₃ ) ₃ . R ¹³ and R ^{14 each} represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 3 carbon atoms,
H ₂ or —N (R ³⁴ ) ₂ (R ³⁴ is a lower alkyl group). R ¹⁵ is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. ) 2. The method according to claim 1, wherein the colorant is C.I. I. 2. The electrophotographic developing toner according to claim 1, which is Pigment Red 48. 3. The method according to claim 1, wherein the colorant is C.I. I. Pigment Red 48 and C.I. I. Pigment Red 57: 1, C.I.
I. Pigment Red 112, C.I. I. Pigment Red 49 and C.I. I. 2. The electrophotographic developing toner according to claim 1, wherein the toner is used in combination with at least one pigment red 122. 4. The electrophotographic developing toner according to claim 1, wherein the toner is used by mixing with a carrier. 5. The electrophotographic developing toner according to claim 1, wherein the core material is used by being mixed with a carrier coated with a silicone resin.