JPS61213855A - Electrostatic charge image developing toner - Google Patents

Abstract

PURPOSE:To obtain a toner uniform in triboelectrification amt., easy in its control, and durable for long storage by incorporating a specified triazine deriv. CONSTITUTION:The triazine deriv. is represented by formula I in which R1-R3 are each H or an electron donative group and each is optionally same or different. As the mode of adding it, both of an internal addition mode of uniformly mixing it into the toner or encapsulating it and mixing the capsules into the toner, and an external addition mode can be adopted. In the case of internal addition, it is added in an amt. of 0.1-40pts.wt., preferably, 1-10pts.wt. per 100pts.wt. of the binder resin, and in the case of external addition, it is added, preferably, in an amt. of 0.01-10pts.wt. per 100pts.wt. of the resin, and as the binder resin, such as, polystyrene and paraffin wax, are used alone or in a combination. As the colorant, carbon black, disazo pigments, and other conventionally known dyes and pigments are used alone or in a combination.

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a new toner for developing electrostatic images in electrophotography, electrostatic recording, electrostatic printing, and the like.

[Prior Art] Conventionally, various electrophotographic methods have been described in US Pat. However, they essentially provide a uniform electrostatic charge on a photoconductive insulator layer, form an electrostatic latent image by irradiating the insulator layer with a light image, and then convert the latent image into a photoconductive layer using the technique. The image is developed and visualized using a fine powder called toner, and after the powder image is transferred to paper or the like as necessary, it is fixed by heat, pressure, solvent vapor, or the like.

The developing methods applied to these electrophotographic methods include:
Broadly speaking, there are dry development methods and wet development methods. The former method is further divided into a method using a two-component developer and a method using a -component developer. Two-component developing methods include a magnetic brush method using an iron powder carrier, a cascade method using a bead carrier, a fur brush method using fur, etc., depending on the type of carrier for conveying the toner.

In addition, those belonging to the -component type development method include a powder cloud method in which toner particles are sprayed, and a contact development method (contact development, or (also referred to as toner development), jumping development method in which toner particles are not brought into direct contact with the electrostatic latent image surface, but are charged and flown toward the latent image surface by the electric field of the electrostatic latent image; and magnetic conductive method. There is the MagneDry method, which develops by bringing a toner into contact with the electrostatic latent image surface.

Conventionally, toners used in these development methods are fine powders in which dyes and pigments are dispersed in natural or synthetic resins. Finely pulverized particles of about 1 to 30 JL are used as toner. In addition, magnetic toners containing magnetic particles such as gnetite instead of or in addition to the dyes or pigments described above are used. In the case of a system using a so-called two-component developer, the toner is usually mixed with carrier particles such as glass beads and iron powder. Further, the toner is made to have a positive or negative charge depending on the polarity of the electrostatic latent image to be developed.

In order to make the toner hold an electric charge, it is also possible to use the triboelectricity of the resin that is a component of the toner, but since the toner's chargeability is small with this method, the image obtained by development is prone to fogging and is unclear. Become something. Therefore, in order to impart desired triboelectrification properties to toners, dyes and pigments that impart electrostatic properties, as well as charge control agents, are added.

Charge control agents known in the art today include the following:

(1) Things that control the toner to be positively charged Nigrosine, azine dyes containing an alkyl group having 2 to 18 carbon atoms (Japanese Patent Publication No. 1827/1983), basic dyes (e.g. C, 1, B
agic Yellow 2 (C, I. 41000)
,G,1. Ba5ic Yellow 3, C, 1
, Ba5ic Red 1 (G, 1. 45180)
, C, T,, Ba5ic Red 9
(C, I.

42500), C, 1, Basic Violet
1 (C, I-42535), C, 1, Ba5ic
Violet 3 (C-1,42555)C,
1, BasicViolet 10 CC, L
45170), C, L Ba5ic Violet
14 (C, 1, 42510), C01, Ba5
ic Blue 1 (C, 1°42025),
C, r, Ba5ic Blue 3 (C
,I. 51005), C, I.

Bs1c Blue 5 (CA, 4214G)
, C, I, Ba5ic Blue7 (C, 1, 4
2595), C, 1, Ba5ic Blue 9
(C, I.

52015), G, 1. Ba5ic Blue 2
4 (C, 1, 52030), C, LBasic B
lue 25 (C,L 52025), C,1
,Ba5ic Blue213 (C-1,4404
5) , C,L Ba5ic Green
1 (C, I.

42040), C, 1, Ba5ic Green 4
(C,1,42000) ,C,r,42510
．． C, 1,45170, etc., lake pigments of these basic dyes (lake-forming agents include phosphotungstic acid, phosphomolybdic acid, phosphotungsten-molybdic acid,
Tannic acid, lauric acid, gallic acid, ferricyanide, ferrocyanide, etc.), C,1,5olv
ent Black 3 (C,!, 28150),
Hansa Yellow G (C, 1, 11880), C, 1
, MordlantBlack 11. C, I, Pi
gment Black 1, Gilt Night, Asphalt, etc.

Quaternary ammonium salt 1 For example, benzylmethyl-hexadecyl ammonium chloride, decyl-trimethylammonium chloride, organic tin compounds such as dibutyltin oxide, metal salts of higher fatty acids, inorganic fine powders such as glass, mica, zinc oxide, etc., EDTA, Polyamine resins such as metal complexes of acetylacetone, bivalent polymers containing amine 7 groups, and condensation polymers containing amino groups.

(2) A device that controls toner to be negatively charged
No. 0153, No. 43-27598, No. 44-8397
Metal complex salts of monoazo dyes described in No. 45-28478.

Metal complexes of salicylic acid, naphthoic acid, guicarboxylic acid such as Go, Cr, Fe, etc. described in Japanese Patent Publication No. 55-42752, Japanese Patent Publication No. 58-41508, Japanese Patent Publication No. 59-7384, Japanese Patent Publication No. 59-7385, etc. , sulfonated copper phthalocyanine pigments, nitro groups, styrene oligomers with halogens introduced, chlorinated paraffins, melamine resins, etc.

However, as mentioned above, the use of conventional charge control agents still has many problems that need to be improved. That is,
Many of these charge control agents are derived from dyes and pigments, and generally have complex structures, inconsistent properties, poor stability, and strong coloring properties. Recently, there are some products that have been proposed that are different from the above-mentioned ones, but none of them exceeds dye- and pigment-based ones in terms of overall performance, and although they have many disadvantages as listed below, In most cases, dye and pigment-based charge control agents are used.

In other words, these charge control agents are usually added to a thermoplastic resin, which is also a binder resin, and are contained in a toner prepared through processes such as hot melt dispersion, pulverization, and classification. In the process, the above-mentioned dye and pigment-based charge control agents often cause problems. For example, as mentioned above, these charge control agents have poor stability as substances, decompose during hot kneading, and mechanical It is easy to decompose or change in quality due to physical impact, friction, changes in temperature and humidity conditions, etc., and it is easy to cause a phenomenon in which charge controllability is deteriorated, and toners containing these dyes and pigments as charge control agents cannot be used in copying machines for development. Then, as the number of copies increases, the charge control agent decomposes or changes in quality, which may cause deterioration of the toner during repeated copying operations.

Furthermore, since it is extremely difficult to uniformly disperse these charge control agents in thermoplastic resins, they pose the fatal problem of causing differences in the amount of frictional charge between toner particles obtained by pulverization. have. For this reason, various methods have been used to achieve more uniform dispersion.
Basic nigrosine dyes are used by forming salts with higher fatty acids in order to improve their compatibility with thermoplastic resins.
Dispersion products of unreacted fatty acids or salts are often exposed on the toner surface and contaminate the carrier or toner carrier, causing a decrease in toner fluidity, fog, and a decrease in image density. There is. Alternatively, in order to improve the dispersion of these charge control agents into the resin, a method has also been adopted in which charge control agent powder and resin powder are mechanically pulverized and mixed in advance and then hot melt-kneaded. However, the inherent poor dispersion cannot be avoided, and at present, sufficient uniformity of charge has not yet been obtained for practical use.

Moreover, most of the substances generally known as charge control agents have a dark color, and there is a problem in that they cannot be incorporated into bright chromatic color developers.

In addition, many charge control agents are hydrophilic, and due to poor dispersion in these resins, when pulverized after melting and mixing,
The dye is exposed on the toner surface.

Therefore, when using toner under high humidity conditions, these
Since the charge control agent is wood-philic, it has the disadvantage that high-quality images cannot be obtained.

In this way, when conventional charge control agents are used in toner,
Variations occur in the amount of charge generated on the surface of toner particles between toner particles, between toner and carrier, or between toner and a toner carrier such as a sleeve,
Problems such as development fog, toner scattering, carrier contamination, etc. are likely to occur, and these problems become noticeable when copying is repeated many times, resulting in a result that is practically unsuitable for copying machines.

Furthermore, under high humidity conditions, the transfer efficiency of toner images decreases significantly, and many of them become unusable. Even at room temperature, when the toner is stored for a long period of time, it often undergoes deterioration due to the instability of the charge control agent used and becomes unusable due to poor charging properties.

Furthermore, when conventional charge control agents are used in toner, long-term use may cause the charge control agents to adhere to the surface of the photoreceptor or promote toner adhesion, adversely affecting latent image formation (
There are many things that have a negative effect on the cleaning process of a copying machine, such as the filming phenomenon), those that cause scratches on the surface of the photoreceptor or cleaning members such as cleaning blades, and those that accelerate wear of the members.

Furthermore, when conventional charge control agents are used in toners, many of them have a large effect on the thermal melting properties of the toners and reduce fixing performance. In particular, there are some that worsen high-temperature offset performance, increase the clinging of transfer paper to the roller during heat roll fixing, and shorten the durable life of the roller.

As described above, conventional charge control agents have many drawbacks.
There is a strong demand in the technical field to improve these.
Although many improved techniques have been proposed so far, the reality is that no one has yet been found that is comprehensively satisfactory for practical use.

[Problems to be Solved by the Invention] An object of the present invention is to provide a new technique for toner charge control that overcomes these problems. The amount of triboelectric charge between the toner and the carrier, between the toner and the toner carrier such as a sleeve in the case of -component development is stable, and the distribution of the amount of triboelectricity is sharp and uniform, and the charge is suitable for the developing system used. The objective is to provide a developer whose amount can be controlled.

Still another object is to develop a developer that is faithful to the latent image and to perform the transfer, that is, without toner adhesion in the background area during development, without fogging or toner scattering around the edges of the latent image. High image density can be obtained,
To provide a developer with good halftone reproducibility.

Still another object is to provide a developer that maintains its initial characteristics even when the developer is used continuously over a long period of time, and that causes no toner aggregation or change in charging characteristics.

Another objective is to develop a developer that reproduces stable images that are not affected by changes in temperature and humidity, especially a developer that has high transfer efficiency and does not cause scattering or transfer dropouts during transfer at high or low humidity. On offer.

Still another object is to provide a bright chromatic developer.

Still another object is to provide a developer with excellent storage stability that maintains its initial characteristics even during long-term storage.

Still another object is to provide a developer that does not stain, abrade, or scratch the electrostatic latent image surface and is easy to clean.

Still another object is to provide a developer that has good fixing properties, particularly a developer that does not have problems such as high-temperature offset.

[Means and effects for solving the problems] The present invention is an electrophotographic toner used for developing electrostatic images, and is a developer containing a triazine derivative represented by the following general formula CI.

(However, in the formula, R1, R21R3 represent a hydrogen atom or an electron-donating group, and may be the same or different.) The present inventors have discovered that the compound represented by the general formula [I] It has been found that it is a high-quality charge control agent that is stable over a period of one hour, has low hygroscopicity, and provides a developer with excellent electrophotographic properties when included in a developer.

In general formula [I], RI + R2e R3 is a hydrogen atom or -NH2, -NHR, -NR2 (wherein R represents an alkyl group, an aryl group, a substituted aryl group, an aralkyl group, or a substituted aralkyl group) Amino group or substituted amino group represented by; alkoxy group; linear or branched alkyl group or substituted alkyl group; -N
HCOR (R represents an alkyl group or an aralkyl group)
Electron-donating groups such as an amide group represented by:

Typical specific examples of the compound represented by the general formula [I] include the following.

[Compound example] G2. Various methods for synthesizing H5 triazine are known, for example, J, Am, Chew, Sac, 7B, [
2゜(11354); J, Chew, Sa
c., 1947. 154: C, A,, 4
3゜238 (1949); C, A,, 45
．． 2513. (1951); J, Org.
.

Chew, 1, 11B2 (1952)
; Chem-Ber,', Gie, 1885
(1954); 5science, 121. Elf
(11355) and others.

For example, compound example (1) is synthesized by the reaction of cyanuric chloride and plluidine.

Generally, the above compound is preferably used for toner preparation as a particle size having an average diameter in the range of 10 to 0.01 JL, particularly 2 to 0.1 JL.

The toner of the present invention can be obtained by blending the above triazine derivative into a toner (colored fine powder) containing a binder resin and a colorant as essential components. Either a so-called internal addition form in which the toner is encapsulated uniformly or in a capsule form, or an external addition form in which the toner is mixed and adhered to the toner can be adopted.

When internally added, the amount of triazine derivative used is determined by the type of binder resin, the presence or absence of additives used as necessary, and the toner manufacturing method including the dispersion method.
Although not generally limited, it is preferably used in an amount of 0.1 to 40 parts by weight (more preferably 1 to 10 parts by weight) per 100 parts by weight of the binder resin.

When externally added, it is preferably 0.01 to 10 parts by weight per 100 parts by weight of the resin.

Note that, if necessary, a conventionally known charge control agent may be used in combination with the charge control agent of the present invention.

As the binder resin for the toner, monopolymers of styrene and its substituted products such as polystyrene, poly p-chlorostyrene, and polyvinyltoluene; styrene-p-chlorostyrene copolymer, styrene-propylene copolymer, and styrene-p-chlorostyrene copolymer;
Vinyltoluene copolymer, styrene-vinylnaphthalene copolymer, styrene-methyl acrylate copolymer, styrene-ethyl acrylate copolymer, styrene-butyl acrylate copolymer, styrene-octyl acrylate copolymer, Styrene-methyl methacrylate copolymer, styrene-ethyl methacrylate copolymer, styrene-butyl methacrylate copolymer, styrene-α-chloromethyl methacrylate copolymer, styrene-acrylonitrile copolymer, styrene-vinylmethyl Ether copolymer, styrene-vinylethyl ether copolymer, styrene-vinyl methyl ketone copolymer, styrene-butadiene copolymer, styrene-isoprene copolymer, styrene-acrylonitrile-indene copolymer, methyl y-- y Styrenic copolymers such as Ray 7m copolymer and styrene-maleate ester copolymer: polymethyl methacrylate, polybutyl methacrylate, polyvinyl chloride, polyvinyl acetate, polyethylene, polypropylene, polyester, polyurethane, polyamide, epoxy Resin, polyvinyl butyral, polyacrylic acid resin, rosin, modified rosin, terpene resin, phenol resin, aliphatic or alicyclic hydrocarbon resin, aromatic petroleum resin, chlorinated paraffin, paraffin wax, etc. Can be used in combination.

In particular, as binder resins suitable for pressure fixing, the following can be used alone or in combination.

Polyolefin (low molecular weight polyethylene, low molecular weight polypropylene, polyethylene oxide, polytetrafluoroethylene, etc.), nipoxy resin, polyester resin, styrene-butadiene copolymer (monomer ratio 5-30:95-70)
, olefin copolymers (ethylene-acrylic acid copolymer, ethylene-acrylic acid ester copolymer, ethylene-
Methacrylic acid copolymer, ethylene-methacrylic acid ester copolymer, ethylene-vinyl chloride copolymer, Ethyre 7
-vinyl acetate copolymer, ionomer resin), polyvinylpyrrolidone, methyl vinyl ether-maleic anhydride copolymer, maleic acid-modified phenol resin, phenol-modified terpene resin.

Colorants include carbon black, lamp black,
Iron black, ultramarine blue, nigrosine dye, aniline blue, phthalocyanine blue, phthalocyanine clean, Hansa yellow G, rhodamine 8Glz-ki, calco oil blue, chrome yellow, quinacridone, pendzini yellow, rose bengal, triallylmethane dye, monoazo, disazo Conventionally known dyes and pigments such as dyes and pigments may be used alone or in combination. Furthermore, the toner of the present invention can further contain a magnetic material and be used as a magnetic toner. Examples of the magnetic material contained in the magnetic toner of the present invention include iron oxides such as magnetite and ferrite; iron oxides such as iron, cobalt, and nickel; metals or aluminum of these metals,
Examples include alloys of metals such as cobalt, copper, lead, magnesium, tin, zinc, antimony, beryllium, bismuth, cadmium, calcium, manganese, selenium, titanium, tungsten, vanadium, and mixtures thereof.

These ferromagnetic materials preferably have an average particle size of about 0.1 to 2 IL, and are contained in the toner in an amount of about 20 to 200 parts by weight per 100 parts by weight of the resin component, particularly preferably about 100 parts by weight of the resin component. 40 to 150 parts by weight.

Further, the toner of the present invention may be mixed with additives other than those mentioned above, if necessary. Examples of additives include Teflon,
A lubricant such as zinc stearate, or an abrasive such as cerium oxide or silicon carbide, or a fluidity agent such as colloidal silica or aluminum oxide, an anti-caking agent, or a conductivity agent such as carbon black or tin oxide. or a fixing aid such as low molecular weight polyethylene.

To prepare the toner for developing an electrostatic image according to the present invention, the triazine derivative charge control agent according to the present invention is combined with the above-described binder resin, a pigment or dye as a coloring agent, and optionally a magnetic material. The pigments or dyes are dispersed or mixed in a ball mill or other mixer, and then melted and kneaded using a heat kneader such as a heated roll, niegu, or extruder to make the resins compatible with each other. Dissolve, cool and solidify, then crush and classify to obtain an average particle size of 5.
~20 liters of toner can be obtained. Alternatively, the material can be obtained by dispersing the material in a binder resin solution and then spray-drying it, or by mixing the specified material with the monomers that should constitute the binder resin to form an emulsified suspension and then polymerizing it. , polymerization method to obtain toner, toner manufacturing method, and other methods can be applied.

Furthermore, as described above, the toner of the present invention can also be obtained by externally adding a charge control agent to a toner that has been formed by removing all or part of the charge control agent.

Toners prepared by these methods can be used for developing to visualize electrostatic images in electrophotography, electrostatic recording, electrostatic printing, etc. by any conventionally known means.

[Example] The present invention will be explained in more detail below with reference to Examples.

Example 1 Carbon black (Mitsubishi Cloud 44) 10 parts Low molecular weight polyethylene wax 2 parts Compound of Example (1) 2 parts The above materials were thoroughly mixed in a blender and then kneaded with two rolls heated to 150°C. After the kneaded material is left to cool naturally, it is roughly pulverized using a cutter mill, then pulverized using a pulverizer using a jet stream, and further classified using an air classifier to obtain a fine powder with a particle size of 5 to 20 l. Obtained.

A developer was prepared by kneading 5 parts of the above toner to 100 parts of iron powder carrier having an average particle size of 50 to 80 rounds.

Further, the amount of triboelectric charge of the toner in the developer was measured by a conventional blow-off method.

Next, by a conventionally known electrophotographic method,
A negative electrostatic image was formed, and this was powder-developed using the above-mentioned developer using a magnetic brush method to create a toner image, which was transferred to plain paper and heat-fixed. The resulting transferred image has a density of 1.3
4, which was sufficiently high, and a good image with high resolution was obtained with no fogging and no toner scattering around one image. Transfer images were continuously created using the above developer and their durability was examined, and the transferred images after 30,000 copies were also completely dull compared to the initial images.

Further, during durability, the above-mentioned filming phenomenon related to toner on the photoreceptor was not observed at all, and no problems were found in the cleaning process. Also, there were no problems during the fusing process at this time, and at the end of the 30,000-sheet durability test, the fusing machine was observed, and there were no scratches or damage to the rollers, and there was almost no dirt from offset toner, so there were no practical problems at all. Ta.

In addition, when the environmental conditions were set to 35°C and 85%, the image density was 1.27, a value that was almost unchanged from normal temperature and humidity, and clear images were obtained without fogging or scattering, and the durability was 30,000 yen. There was almost no change up to the 0th order 15
When a transferred image was obtained at a low temperature and low humidity of 10% at a temperature of 10%, the image density was as high as 1.30, solid black was developed and transferred extremely smoothly, and the image was excellent with no voids or hollow spots. Durability was carried out under these environmental conditions, and although copies were made continuously and intermittently, the density variation was ±0.2 up to po and ooo sheets, which was sufficient for practical use.

Comparative Example 1 A developer was obtained in the same manner as in Example 1, except that 2 parts of nigrosine dye (Nigrosine Base EX, manufactured by Orient Chemical Industry Co., Ltd.) was used instead of 2 parts of the compound in Example (1) above, and developed and
Transfer and fixing were performed to obtain an image in the same manner.

At room temperature and humidity, there was little fog, but the image density was low at 1.08, line drawings were scattered, and solid black was noticeably rough. Durability was examined and the density decreased to 0.83 after 30,000 sheets.

Also, during the durability test, the toner material formed a film in the form of thin stripes on the surface of the photoreceptor before and after the photoreceptor, and appeared as lines on the image. This is so-called filming, and is thought to be due to the charge control agent changing the lubricity of the toner powder.

Furthermore, during durability, the fixed image tended to get caught up in the fixing roller during the fixing process, and there was difficulty in peeling it off from the roller.

When an image was obtained under conditions of 35° C. and 85%, the image density was as low as 0.88, and fogging, scattering, and roughness increased. Transfer efficiency was also low.

When an image was obtained under the conditions of 15° C. and 10%, the image density was as low as 0.81, and there was severe scattering, fogging, and roughness, and transfer omissions were noticeable. I tried to take continuous images, but 3
After about 0,000 sheets, the density became 0.53, making it impractical.

Example 2 A developer was obtained in the same manner as in Example 1 except that 3 parts of the compound of Example (2) was used instead of 2 parts of the compound of Example (1) above,
Development, transfer, and fixing were performed to obtain an image in the same manner.

The detailed results are shown in Tables 1 and 2, and satisfactory results almost the same as in Example 1 were obtained.

Example 3 A developer was obtained in the same manner as in Example 1, except that 2 parts of the compound of Example (3) was used instead of 2 parts of the compound of Example (1),
Development, transfer, and fixing were performed to obtain an image in the same manner.

The detailed results are shown in Tables 1 and 2, and almost the same satisfactory results as in Example 1 were obtained.

Example 4 A developer was obtained in the same manner as in Example 1, except that 2 parts of the compound of Example (4) was used instead of 2 parts of the compound of Example (1),
Development, transfer, and fixing were performed to obtain an image in the same manner.

The detailed results are shown in Tables 1 and 2, and almost the same satisfactory results as in Example 1 were obtained.

Example 5 Triiron tetroxide EPT-500 (Toda Kogyo type) 80 parts Low molecular weight polypropylene wax 2 parts Compound of Example (1) 2 parts The above materials were thoroughly mixed in a blender and then kneaded with two rolls heated to 150°C. did. After allowing the mixture to cool naturally, it is roughly pulverized using a cutter mill, then pulverized using a pulverizer using a jet stream, and further classified using an air classifier to obtain a fine powder with a particle size of 5 to 20μ. Ta.

Next, hydrophobic colloidal silica R was added to 100 parts of the fine powder.
0.4 part of -972 (manufactured by Nippon Aerosil Co., Ltd.) was mixed in a sample mill to prepare a -component magnetic toner.

When this toner was applied to a commercially available copying machine (trade name NP-150Z, manufactured by Canon ■) and an image was produced, good results almost the same as those of Example 1 were obtained.

Example 6 In Example 5, instead of 2 parts of the compound of Example (1),
A developer was obtained in the same manner as in Example 5, except that 3 parts of the compound of Example (2) was used, and an image was obtained in the same manner by performing development, transfer, and fixing.

The detailed results are shown in Tables 1 and 2, and almost the same satisfactory results as in Example 5 were obtained.

Example 7 In Example 5, instead of 2 parts of the compound of Example (1),
A developer was obtained in the same manner as in Example 5, except that 2 parts of the compound of Example (3) was used, and an image was obtained in the same manner by performing development, transfer, and fixing.

The detailed results are shown in Tables 1 and 2, and almost the same satisfactory results as in Example 5 were obtained.

Comparative Example 2 In Example 5, 2 parts of dimethylbenzylhexadecyl ammonium chloride was used instead of 2 parts of the compound of Example (1).
A developer was obtained in the same manner as in Example 5, except that the developer was used, and an image was obtained in the same manner. At room temperature and humidity, there is little fog, but the image density is 0.
．． At 81, the line drawings were scattered and the solid black was noticeably rough. I checked the durability, but the density was 0 after 30,000 sheets.
．． It dropped to 48.

Furthermore, the above-mentioned filming phenomenon during durability and problems in the fixing process were almost the same as those in Comparative Example 1, and were undesirable.

When an image was obtained under conditions of 35° C. and 85%, the image density was as low as 0.72, and fogging, scattering, and roughness increased, making it unusable. Transfer efficiency was also low. When an image was obtained under the conditions of 15° C. and 10%, the image density was as low as 0.73, and there was severe scattering, fogging, roughness, and transfer omissions were noticeable. I tried to take continuous images, but
At the time of 30,000 sheets, the density was 0.58, making it impractical.

Example 8 Copper phthalocyanine blue pigment 5 parts Low molecular weight polypropylene wax 2 parts Compound of Example (1)
Two parts of the above materials were thoroughly mixed in a blender and then kneaded with two rolls heated to 150°C. After the kneaded material was left to cool naturally, it was roughly pulverized using a cutter mill, then pulverized using a pulverizer using a jet stream, and further classified using an air classifier to obtain a fine powder with a particle size of 5 to 20 IL. Ta.

Further, the amount of triboelectric charge of the toner was measured by a conventional blow-off method.

Next, 50 g of carrier iron powder having a particle size of 50 to 80 JL was mixed with 100 parts of the toner to prepare a developer.

This developer was put into a developer container 1 of a developing device shown in FIG. 1, and a developing operation was performed. That is, in this device, at the lower opening of the container 1.

A cylindrical toner carrier 2 made of stainless steel with a roughened surface was housed so as to substantially close this, and was rotated in the direction of arrow a at a circumferential speed of 88 W/sec. On the other hand, an iron blade 3 whose tip is placed 200 layers from the sleeve surface is placed at the outlet on the downstream side in the rotational direction of the sleeve 2 of the container 1, and a fixed magnet 4 is placed inside the sleeve 2. The N pole, which is the main magnetic pole, was arranged so that the angle θ between the line connecting this and the center of the sleeve and the center of the sleeve and the tip of the blade 3 was 30°. Under these conditions, as the sleeve 2 rotates, a magnetic brush 5 is formed in the container 1 by the carrier iron powder contained in the developer, and this magnetic brush 6 absorbs the toner distributed preferentially above the magnetic brush 5. 6 and sleeve 2
The toner circulates along the periphery of the sleeve 2 under the container 1 while being supplied to the surface of the sleeve 2, and forms a thin layer IB of toner on the surface of the sleeve 2 that has passed through the blade 3.

In this example, the thickness thus formed is approximately 80I.
Due to the thin toner layer of the L layer, the developing area (nearest area) faces each other at an interval of approximately 300 p, m and has a width of approximately 80 mm1/
A negative electrostatic image of -800V and -1500V in the dark area was developed on a conventional drum 7 rotating in the direction of the arrow at a peripheral speed of seconds. At this time, a bias voltage having a frequency of 800 Hz, a peak-to-peak value of 1.4 KV, and a center value of 1,300 V was applied between the sleeve 2 and the photosensitive drum 7 by the power source 8.

When the image was printed in this way, a good image with a bright blue color was obtained, and even after printing 1500 images, the toner/carrier ratio was 10 parts to 150 parts. No change in image density was observed, and good images were obtained even after printing up to 30,000 sheets while replenishing toner.

Normal temperature-normal humidity (25°C, 80%
The evaluation results under various environmental conditions of high temperature (RH), high temperature (35° C., 85% RH), and low temperature and humidity (15° C., 10% RH) are summarized in Tables 1 and 2 below.

The evaluation results of each example and comparative example are shown in Tables 1 and 2.

[Effects of the Invention] As described above, the toner of the present invention containing the above compound as a charge control agent has a uniform amount of frictional charge between toner particles, and the amount of charge can be easily controlled. In addition, the toner is extremely stable as it does not change in quality during use and the amount of triboelectric charge does not vary or decrease. This eliminates problems such as development fog, toner scattering, and contamination of electrophotographic materials and copying machines, as described above, and also reduces toner aggregation, clumping, and low-temperature fluidity during storage, which were major problems in the past. It is a toner that can be stored for a long time without causing any problems, and the toner image has excellent abrasion resistance, fixing properties, and adhesion properties.

These excellent effects of the toner are further magnified when used in a repetitive transfer copying system in which the operations of charging, exposure, development, and transfer are successively repeated. Further, since there is little color tone disturbance caused by the charge control agent, it is possible to form color images with excellent colors when used as a color electrophotographic toner.

[Brief explanation of drawings]

1 is a schematic cross-sectional view of an example of a developing device suitable for applying the toner according to the present invention. l...developer container, 2...toner carrier, 3...
Doctor blade, 4... Fixed magnet, 5... Magnetic brush, 6... Toner, 7... Electrostatic latent image carrier, 16
...Thin layer toner.

Claims (1)

[Scope of Claims] An electrophotographic toner for developing electrostatic images, which is characterized by containing a triazine derivative represented by the following general formula [I]. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [I] (However, in the formula, R_1, R_2, and R_3 represent hydrogen atoms or electron-donating groups, and may be the same or different.)