JPH10298167A - Triazine-based compound and toner for electrophotography containing the same compound - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject new compound having a substituent group which is a specific substituted amino, etc., being colorless, not containing a heavy metal, capable of developing good rising property of static electrification, stability with the passage of time and environmental stability and producing stable toner and useful as a toner for a electrophotography. SOLUTION: This compound of the formula [R2 is phenyl or benzyl; X is OH, a halogen or a group of the formula NR1 R2 (R1 is benzyl;)], e.g. 2-(N,N- dibenzylamino)-4,6-dihydroxy-1,3,5-triazine. The compound of the formula, when it is a monoamino substituent, is obtained by dissolving cyanuric chloride into a water-soluble aprotic solvent or a mixed solvent of the solvent with water, dropping 1 equivalent weight of the corresponding amine compound to the solution at <=5 deg.C, reacting the amine compound with cyanuric chloride while keeping pH to weakly acidic property and as necessary, hydrolyzing the resultant compound.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a triazine compound and an electrophotographic toner containing the same, which is used for developing an electrostatic latent image in electrophotography, electrostatic recording and the like. .

[0002]

2. Description of the Related Art In an image forming process such as electrostatic recording and electrostatic photography utilizing static electricity, a photoconductive substance such as phthalocyanine and other organic pigments, selenium, cadmium sulfide, and amorphous silicon is coated on a base material such as aluminum and paper. In the process of forming an electrostatic latent image on a photoreceptor obtained by applying the toner on a photoreceptor by an optical signal, and in a two-component developing method, colored fine particles adjusted to 5 to 50 μm, which is called toner, Carrier (iron powder, ferrite powder, etc.) is charged by contact,
The one-component developing method includes a process in which a toner is directly charged and then applied to an electrostatic latent image to be visualized.
Note that the toner needs to be provided with a charge corresponding to the polarity of the electrostatic latent image formed on the photoreceptor, that is, any of positive and negative charges.

[0003] Colored fine particles generally called toner contain a binder resin and a coloring material as essential components, and are further formed of magnetic powder or the like as required. As a method for imparting charge to the toner, the charge characteristics of the binder resin itself can be used without using a charge control agent. However, in this case, the stability over time of charging and the moisture resistance are poor, and good image quality cannot be obtained. Therefore, a charge control agent is usually added for the purpose of holding the charge of the toner and controlling the charge.

[0004] The quality characteristics required of the toner include excellent chargeability, fluidity, fixability, and the like. These quality characteristics are greatly affected by the charge control agent used in the toner. .

The charge control agents conventionally added to toners include: 1) 2: 1 type metal-containing complex dyes as colored negative charge control agents (eg, JP-B-45-26478, JP-B-41-201)
53) Phthalocyanine pigment (for example, JP-A-52-4593)
1) Also, examples of colorless negative charge control agents include metal complexes of aromatic dicarboxylic acids (eg, JP-B-59-7384),
Metal complexes of salicylic acid (eg, JP-A-57-10494)
0) or a charge control agent described in JP-A-61-3149, etc.

2) Nigrosine dyes, triphenylmethane dyes, various quaternary ammonium salts (Journal of the Institute of Electrostatics, 1980, Vol. 4, No. 3, P-144) as positive charge control agents,
Organic tin compounds such as dibutyltin oxide (eg, Japanese Patent Publication No. 57-29704) are known. Toner containing these as a charge control agent has quality characteristics such as chargeability and stability over time required for the toner. Is not fully satisfied.

For example, 2: 1 known as a negative charge control agent
Although the toner containing the type metal-containing complex dye has a certain level of charge, the 2: 1 type metal-containing complex dye generally has a disadvantage of poor dispersibility in a binder resin. Therefore, the toner is not uniformly distributed in the binder resin, and the distribution of the charge amount of the obtained toner is extremely poor in sharpness, and the obtained image has low gradation and poor image forming ability.

Further, the 2: 1 type metal-containing complex salt dye has a drawback that it can be used only for a toner having a limited hue centering on black, and cannot be practically used as a charge control agent for a color toner. Furthermore, it has the disadvantage of containing metals from the viewpoint of environmental safety.

An example of a near-colorless negative charge control agent is a metal complex of an aromatic dicarboxylic acid.
This product has a drawback that it cannot be completely colorless and has a drawback in its dispersibility. As a colorless negative charge control agent having relatively good charging performance, a metal complex of salicylic acid can be mentioned (JP-A-57-10494).
0) It contains heavy metals, and its safety to the environment is questionable. JP-A-61-3149 and JP-A-63-38 are colorless and heavy metal-free negative charge control agents.
Compounds introduced in 958 and compounds disclosed in JP-A-2-201378 are known. However, these compounds have a drawback that the charge rising speed is slow and the charge amount is insufficient. The properties are inadequate. Nigrosine-based dyes and triphenylmethane-based dyes, which are known as positive charge control agents, are themselves colored and therefore can be used only for toners having a limited hue, mainly black. There is a disadvantage that the stability over time for continuous copying is not good. Further, conventional quaternary ammonium salts have the disadvantage that when formed into toner, the stability over time due to insufficient moisture resistance is poor, and a high-quality image is not obtained by repeated use.

[0010]

SUMMARY OF THE INVENTION An object of the present invention is to provide an electrophotographic toner which has excellent charge rising characteristics, excellent stability over time of charging and environmental stability, exhibits stable properties at the time of toner production, and does not contain heavy metals. .

[0011]

Means for Solving the Problems The present inventors have made intensive efforts to solve the above-mentioned problems, and as a result, by incorporating a triazine-based compound having a specific structure into an electrophotographic toner, the toner is obtained. The inventors have found that the charging characteristics are greatly improved, and have completed the present invention.

That is, the present invention provides: (1) a triazine compound represented by the following formula (1):

[0013]

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(In the formula (1), X represents a hydroxyl group, a halogen atom or an arbitrary substituent selected from —NR ₁ R ₂ , wherein R ₁ is a benzyl group, R ₂ is a benzyl group or a phenyl group. (2) In the compound of the formula (1), X represents a hydroxyl group or -N
The triazine compound according to the above item (1), which is R ₁ R ₂ (3) In the compound of the formula (1), both the R ₁ and R ₂ are benzyl groups. (4) In the compound of the formula (1), X is a hydroxyl group or -N
An _{R 1 R 2, R 1,} R 2 are both triazine compound according to item (1) is a benzyl group (5) above (1) 1 to a compound according to any one of (4) (6) The electrophotographic toner according to (5), wherein the compound according to any one of (1) to (4) is contained in an amount of 0.1 to 10% by weight based on a binder resin. Related to the electrophotographic toner.

[0015]

DETAILED DESCRIPTION OF THE INVENTION The present invention will be described in detail. The compound of the formula (1) acts as a charge control agent, but it has good compatibility with the binder resin, and the toner containing the compound has a high specific charge amount and has good stability over time. Even when the toner is stored for a long time, a clear image is stably provided in the image formation of electrostatic recording. Further, since it has a colorless negative charging performance, it can produce both black negatively charged toner and color toner. In addition, since it does not contain heavy metals, it is highly safe for the environment. Further, when a toner is prepared by a suspension polymerization method or an emulsion polymerization method, there is no polymerization inhibiting action by heavy metals as seen in a metal-containing charge control agent, so that a toner can be stably produced. . When the compound of the formula (1) is contained in a resin or the like, it can be used as a light stabilizer, a deterioration inhibitor, an antioxidant, an ozone deterioration inhibitor,
It can be used as a curing accelerator for epoxy resins, epoxy resin-acid anhydride compositions, rubbers and the like, and also as an ultraviolet absorber.

Specific examples of the compound of the formula (1) to be contained in the toner as a charge control agent in the present invention include the following compounds (Compound Examples (1) to (8)), but are not limited thereto. It is not something to be done.

[0017]

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[0018]

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[0019]

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The triazine-based compound of the present invention shown in the above example is prepared by dissolving cyanuric chloride in a water-soluble aprotic solvent such as acetone, MEK, dioxane, DMF, or a mixed solvent thereof with water, followed by primary condensation. When it is desired to obtain a compound, 1 equivalent of the corresponding amine compound is added dropwise to this solution at a temperature of preferably 5 ° C. or lower under cooling, and the hydrochloric acid resulting from the condensation is preferably treated with an alkali such as caustic soda, sodium bicarbonate or triethyleneamine. Is obtained by reacting while neutralizing so that the pH keeps a weak acidity.The secondary condensate is further added with one equivalent of the corresponding amine compound, and the reaction temperature is raised from room temperature to 60 ° C. It is obtained by reacting hydrochloric acid generated as a result of the condensation with an alkali such as caustic soda, sodium bicarbonate, triethylamine or the like, preferably in the same manner as the primary condensation, while preferably neutralizing the pH so as to maintain a weak acidity. Further, the tertiary condensate can be obtained by similarly reacting at a higher reaction temperature, preferably at a reflux temperature. The obtained primary condensation and secondary condensation dichlorides and monochlorides are heated and hydrolyzed in an alkaline agent such as caustic soda, and then neutralized by adding an acid such as hydrochloric acid or sulfuric acid. To obtain a hydroxy compound.

As a method for producing a toner containing the compound of the formula (1), a mixture comprising the compound of the formula (1), a colorant, a binder resin and the like can be mixed by heating using a heating kneader or a two-roller. After kneading the binder resin under melting with a suitable device, and then cooling and solidifying the mixture, it is crushed to a particle size of 3 to 20 μm by a crusher such as a jet mill or a ball mill through a coarse crushing step, and then subjected to an airflow classifier or the like. A method obtained by classification, a method in which a colorant, a binder resin and a compound of the formula (1) are dissolved in a solvent (eg, acetone,
A solution obtained by dissolving or dispersing in methanol or the like, stirring, throwing into water, reprecipitating or directly filtering and drying, and then pulverizing or disintegrating to a particle size of 3-20 μm with a pulverizer such as a ball mill. The compound of (1), the monomer of the colorant and the binder resin are uniformly suspended in water, and the monomer is polymerized in fine particles with stirring to form a precipitate. The precipitate is filtered, washed with water, There is a method of drying to obtain a fine particle powder, and classifying the powder to obtain a target having a particle size of 3 to 20 μm. Also, a soft particle containing a low-melting resin for pressure fixing such as a binder, a coloring component, a magnetic material, and the like. The core material (core particles) may be used as an outer shell material of a microcapsule toner having a form covered with a hard outer shell having a protective function and a charge control function. Further, a colored fine particle containing no charge control agent is prepared by the above method,
Next, the compound of the formula (1) can be fixedly added to the particle surface alone or together with an external additive such as colloidal silica by a mechanochemical method or the like.

In these cases, the binder resin component is usually 9
9 to 65%, more preferably 98.5 to 83%, the colorant is 0.5 to 20%, more preferably 5 to 15%, and the charge control agent is 0.1 to 10%, more preferably 0.5 to 3%. (All are weight%, the same applies hereinafter). In addition, if necessary, an anti-offset agent such as low molecular weight polypropylene may be added in an amount of several weight%.

Examples of the colorant that can be used in the electrophotographic toner of the present invention include carbon black, ultramarine, iron black, activated carbon, copper oxide, manganese dioxide, graphite, zinc yellow, cadmium yellow, yellow iron oxide, and minerals. Fast yellow,
Inorganic pigments such as nickel titanium yellow, red yellow lead, molybdenum orange, red iron oxide, cadmium red, manganese purple, titanium oxide, zinc sulfide, chrome green, chromium oxide, and antimony white; Pigment Yellow 1, C
I. Pigment Red 9, CI. Pigment Blue 1
5. Aniline black, naphthol yellow S, benzidine yellow GR, quinoline yellow lake, anthrapyrimidine yellow, Hansa yellow G, permanent yellow NC
G, pyrazolone orange, indanthrene brilliant orange GK, pyrazolone red, brilliant carmine 6B, rhodamine lake B, quinacridone, alizarin lake, thioindigo red, thioindigo maroon, brilliant carmine 3B, methyl violet lake, dioxazine violet, aniline blue Organic pigments such as metal-free phthalocyanine blue, phthalocyanine blue, fast sky blue, indanthrene blue BC, phthalocyanine green, malachite green lake, and final yellow green G; Solvent Yellow 93, CI. Solvent Red 146,
CI. Solvent Blue 35, CI. Disperse Yellow 42, CI. Disperse Red 59, CI. Disperse Blue 81, CI. Solvent Red 49, CI. Solvent Red 52, CI. Solvent Red 109,
CI. Basic Red 12, CI. Basic Red 1, CI. Direct Red 1, CI. Acid Red 1, CI. Basic Red 1, CI. Direct Red 4, CI. Modant Red 30, CI. Direct Blue 2, CI. Acid Blue 9, CI. Basic Blue 3, CI. Basic Blue 5, CI. Acid Blue 15, CI. Known colorants such as oil-soluble dyes such as Modant Blue 7 (CI is an abbreviation for Color Index, the same applies hereinafter) and the like can be mentioned.

Examples of the binder resin include polystyrene, styrene-methacrylic acid copolymer, styrene-methacrylic acid ester copolymer, styrene-acrylic acid copolymer, styrene-acrylic acid ester copolymer, and styrene-acrylonitrile copolymer. Polymer, acrylic resin, styrene-maleic acid copolymer, polyvinyl chloride, polyvinyl acetate, epoxy acrylate resin, olefin resin,
A polyester resin, a polyurethane resin, an epoxy resin or the like can be used alone or as a mixture.

Further, the compound of the formula (1) and the monomer of the colorant and the binder resin are uniformly suspended in water, and the monomer is polymerized in fine particles under stirring to form a precipitate. When the product is filtered, washed with water, and dried to obtain a fine-grained powder, and then classified to obtain a toner having a particle size of 3 to 20 μm, a monomer of the above resin is used. Vinyl aromatic hydrocarbon monomers such as styrene, α-methylstyrene, vinyltoluene, chlorostyrene, ethylstyrene, divinylbenzene, acrylic acid, methacrylic acid, methyl acrylate, ethyl acrylate, butyl acrylate, acrylic acid 2-ethylhexyl, octyl acrylate, phenyl acrylate, methyl methacrylate, ethyl methacrylate, butyl methacrylate, 2-ethylhexyl methacrylate, Monomers of acrylic compounds such as octyl methacrylate and phenyl methacrylate, acrylonitrile, methacrylonitrile, monocarboxylic acids having a double bond such as acrylamide, maleic acid, methyl maleate, butyl maleate, dimethyl maleate,
Dicarboxylic acids such as phthalic acid, succinic acid, terephthalic acid, ethylene, propylene, butylene, vinyl methyl ketone, vinyl hexyl ketone, vinyl methyl ether,
Vinyl monomers such as vinyl isobutyl ether, ethylene glycol, diethylene glycol, triethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol, 1,4-butanediol, 1,6
-Hexanediol, bisphenol A, hydrogenated bisphenol A, polyoxyethylenated bisphenol A
And isocyanates such as 1,4-tetramethylene diisocyanate, ethylamine, butylamine, ethylenediamine, 1,4-diaminobenzene, 1,4-diaminobutane, monoethanolamine, etc. And epoxy compounds such as diglycidyl ether, ethylene glycol diglycidyl ether, bisphenol A glycidyl ether, and hydroquinone diglycidyl ether. These can be used alone or in combination.

Further, the electrophotographic toner of the present invention contains fine particles of a fluidizing agent such as silicon oxide (colloidal silica), aluminum oxide and titanium oxide, an anti-fogging agent such as mineral oil, and various magnetic materials for a magnetic one-component system. Alternatively, a conductivity imparting agent such as iron powder and zinc oxide may be added as necessary. In the electrophotographic toner obtained by the present invention, in a one-component system such as a non-magnetic one-component or a magnetic one-component, the toner itself is charged by a charging blade or a charging roller, and in a two-component system, for example, 125 to 200 mesh Weight ratio of carrier (iron powder, ferrite powder, or coated carrier obtained by coating silicone resin, acrylic resin, fluororesin, etc. on ferrite powder) and, for example, 3-8: 97-92 (toner: carrier) The developer is used in a developing step in electrophotography by mixing with a developer, charging the developer, and charging the developer.

The toner for electrophotography according to the present invention has sharper charge amount distribution, better charge stability over time, better moisture resistance, better dispersibility in a binder resin, and the like as compared with a toner using a conventional charge control agent. Excellent and has high charging performance. As a result, it is characterized in that an image with extremely high gradation without fog is obtained and the repetitive image forming ability is extremely good. Further, since the charge control agent itself is colorless and does not contain a metal, it is characterized in that a clear image that does not impair the original color of the coloring material is obtained and that the safety for the environment is high.

[0028]

The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples. In the examples, parts are by weight unless otherwise specified.

Example 1 Cyanuric chloride (8 parts) was dissolved in acetone (180 parts), cooled to 5 ° C. or lower, and dibenzylamine (8, 6 parts) dissolved in acetone (4, 6 parts) was added dropwise under cooling for 1 hour. Stir for 3 hours. 25.7 parts of a 6.9% aqueous solution of caustic soda was added dropwise over 1.5 hours, and the mixture was stirred at room temperature for 2.5 hours.
Further, 67 parts of 10.4% caustic soda was added, the temperature was raised to 60 ° C., and the mixture was stirred for 6 hours. After cooling to room temperature, 81.4 parts of a 2N aqueous hydrochloric acid solution was added dropwise to adjust the pH to 2, followed by filtration, washing with water, and drying to obtain 12.2 parts of the compound of the compound example (1) as colorless crystals.

Example 2 10.0 parts of cyanuric chloride was dissolved in 180 parts of dioxane, cooled to 10 ° C., 32.1 parts of dibenzylamine was added dropwise in 30 minutes, and after completion of the addition, the mixture was stirred at room temperature for 5 hours. .
Thereafter, 41.8 parts of a 20.7% aqueous sodium carbonate solution was added dropwise, and the mixture was heated under reflux for 7 hours. After cooling to room temperature, water 13
1.3 parts were added, filtered, washed with water and dried at 70 ° C. to obtain 33.3 parts of compound (2) as colorless crystals. mp. 181.5 ° C (DSC:
Ti)

Example 3 Cyanuric chloride (8.4 parts) was dissolved in acetone (171 parts), and dibenzylamine (18.0 parts) was added dropwise over 20 minutes while cooling with ice.
Thereafter, the mixture is stirred at room temperature for 40 minutes, and 38.7 parts of a 16.3% aqueous potassium carbonate solution is dropped in 40 minutes. The temperature is raised to 40 ° C., the mixture is stirred for 1 hour, the heating is stopped, and the mixture is left to cool and stir. The crystals were filtered, washed with water, and dried to obtain 21.8 parts of the compound (3) as colorless crystals. mp. 10
2.3 ° C (DSC: Ti)

Example 4 Styrene-butyl acrylate copolymer (binder) 100 parts Low molecular weight polypropylene 5 parts Carbon black (colorant) 8 parts Compound 2 of compound example (1) obtained in Example 1 2 parts of the above composition The mixture was melt-mixed with a kneader adjusted to 105 to 140 ° C., and then cooled and solidified. Next, after coarsely pulverized by a rotoplex coarse pulverizer, fine pulverization is performed by a jet mill pulverizer, and further classification is performed by an airflow classifier to obtain a black toner having a particle size of 5 to 20 μ (median particle size of 11 μ). Was.

To 100 parts of the toner thus obtained, 0.3 part of colloidal silica was externally added using a Henschel mixer. The obtained externally added toner was mixed with a silicon-coated ferrite carrier of about 125 mesh at a weight ratio of 3:97 (toner: carrier) to obtain a developer A.

Using the developer A thus obtained, a charge stability test (charge amount aging stability test, charge amount aging stability test) was carried out. The results shown in Table 1 below were obtained.

[0035]

[Table 1] Table 1 Charge amount aging stability test (unit, -μC / g) Time (min) 1 5 15 30 60 120 Developer A 11.0 11.3 11.3 10.8 10.8 13.5 Charge amount humidity resistance aging stability test (unit,- μC / g) Time (min) 15 15 30 60 120 Developer A 10.0 10.0 11.6 10.3 10.1 12.2 Decay rate 9.1%

As described above, even after the developer A is exposed to high humidity, a sufficient charge can be obtained as usual,
The change in the charge was not abrupt over time, and the charge stability was extremely excellent.

The charging stability test was performed according to the following method. ○ Electric charge aging stability test A developer (a mixture of a toner and a carrier) was weighed in a plastic container, and was charged with a ball mill at 30 rpm for 1 hour for 100 hours.
The remaining one hour is contact-charged by a ball mill at rpm. At that time, sampling is performed every time, and the charge amount of the toner is measured by a blow-off method. ○ Electric charge humidity resistance aging stability test In the same manner as the electrification aging stability test, the toner and carrier were weighed in a poly container, the container was opened, and the container was opened at 35 ° C., 8
The container is left under the condition of 5% RH for 20 hours, the container is covered, and sampling is performed every hour in the same manner as in the above test, and the charge amount of the toner is measured by a blow-off method. At this time, the charge amount one minute after each is defined as the initial charge amount and the initial charge amount after the high humidity test. Here, the attenuation rate was calculated by the following equation. Decay rate = (initial charge amount without high humidity treatment−initial charge amount after high humidity treatment) / initial charge amount without high humidity treatment × 100 (%)

Example 5 Styrene-butyl acrylate copolymer (binder) 100 parts Low molecular weight polypropylene 5 parts Carbon black (colorant) 8 parts Compound 2 of compound example (2) obtained in Example 2 2 parts of the above composition The mixture was melt-mixed with a kneader adjusted to 105 to 140 ° C., and then cooled and solidified. Next, after coarsely pulverized by a rotoplex coarse pulverizer, fine pulverization is performed by a jet mill pulverizer, and further classification is performed by an airflow classifier to obtain a black toner having a particle size of 5 to 20 μ (median particle size of 11 μ). Was.

To 100 parts of the obtained toner, 0.3 parts of colloidal silica was externally added using a Henschel mixer. The obtained externally added toner was mixed with a silicon-coated ferrite carrier of about 125 mesh and 3:97 (toner: carrier).
To obtain a developer B.

Using the obtained developer B, a charge stability test (charge amount aging stability test, charge amount humidity aging stability test)
Was carried out, and the results in Table 2 below were obtained. Further, when copying was performed by a copying machine using this developer B, a clear black image was obtained with excellent gradation.

[0041]

[Table 2] Table 2 Stability test of charge amount over time (unit, -μC / g) Time (min) 1 5 15 30 60 120 Developer B 13.5 13.7 13.2 13.3 12.8 13.2 Stability test of charge amount over time (unit,- μC / g) Time (min) 1 15 15 30 60 120 Developer B 12.6 12.8 12.5 12.5 13.9 13.1 Decay rate 6.7%

As described above, the developer B was sufficiently charged as usual even after being exposed to high humidity, and there was little change in the charge over time and the charge stability was extremely excellent. .

Example 6 Styrene-butyl acrylate copolymer (binder) 100 parts Low molecular weight polypropylene 5 parts Carbon black (colorant) 8 parts Compound 2 of compound example (3) obtained in Example 3 The mixture was melt-mixed with a kneader adjusted to 105 to 140 ° C., and then cooled and solidified. Next, after coarsely pulverized by a rotoplex coarse pulverizer, fine pulverization is performed by a jet mill pulverizer, and further classification is performed by an airflow classifier to obtain a black toner having a particle size of 5 to 20 μ (median particle size of 11 μ). Was.

To 100 parts of the obtained toner, 0.3 parts of colloidal silica was externally added using a Henschel mixer. The obtained externally added toner was mixed with a silicon-coated ferrite carrier of about 125 mesh and 3:97 (toner: carrier).
To obtain a developer C.

Using the obtained developer C, a charge stability test (charge amount aging stability test, charge amount humidity resistance aging stability test)
The results shown in Table 3 below were obtained.

[0046]

[Table 3] Table 3 Stability test of charge amount over time (unit, -μC / g) Time (min) 1 5 15 30 60 120 Developer C 11.7 11.8 10.8 12.5 10.8 13.7 Stability test of charge amount over time (unit,- μC / g) Time (min) 15 15 30 60 120 Developer C 9.3 10.5 10.3 10.1 10.8 11.8 Decay rate 20.5%

As described above, after the developer C was exposed to high humidity, a sufficient charge was obtained in the same manner as usual, and there was little change in the charge over time and the charge stability was extremely excellent. .

[0048]

The toner for electrophotography obtained by the present invention has a sharper charge distribution, moisture resistance and stability over time than toners using conventional charge control agents, and has high charging performance. ing. As a result, it is characterized in that an image having extremely high gradation is obtained and the repetitive image forming ability is extremely good. Also, the charge control agent itself is essentially colorless,
Because the dispersibility to the binder resin is very good,
It is characterized in that any colorant can be selected according to the hue required for the color toner, and that the original hue of the dye or pigment is not hindered at all. Furthermore, the use of a charge control agent that does not contain a metal is also characterized by high safety to the environment.

Claims (6)

[Claims] A triazine compound represented by the following formula (1): (In the formula (1), X represents a hydroxyl group, a halogen atom or an arbitrary substituent selected from —NR ₁ R ₂ , wherein R
₁ represents a benzyl group, and R ₂ represents a benzyl group or a phenyl group, respectively. ) 2. The triazine compound according to claim ₁ , wherein X is a hydroxyl group or -NR ₁ R ₂ in the compound of the formula (1). 3. The triazine compound according to claim ₁ , wherein in the compound of the formula (1), both R ₁ and R ₂ are benzyl groups. 4. The triazine compound according to claim 1, wherein in the compound of the formula (1), X is a hydroxyl group or —NR ₁ R ₂ , and R ₁ and R ₂ are both benzyl groups. 5. An electrophotographic toner comprising at least one compound according to claim 1. Description: 6. The electrophotographic toner according to claim 5, wherein the compound according to claim 1 is contained in an amount of 0.1 to 10% by weight based on the binder resin.