JP2755943B2 - Toner for developing electrostatic images - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial applications]   The present invention relates to a toner for developing an electrostatic image, and more particularly,
Is used in electrophotography, electrostatic recording, electrostatic printing, etc.
The present invention relates to a toner for developing an electrostatic image. [Conventional technology and problems]   Conventional electrophotographic methods include U.S. Pat.
No. 297691, No. 2357809, etc.
The photoconductive insulating layer is uniformly charged, and then the layer is
Expose and dissipate the charge on the exposed area
To form an electrostatic latent image,
Attach fine powder with colored charge called toner
Visualization (development process)
After transferring the visible image to a transfer material such as transfer paper (transfer
Process), heating, pressure or other suitable fixing method.
(Fixing step).   As a developing method applied to these electrophotographic methods, etc.
Are roughly classified into a dry development method and a wet development method. former
Are two-component developer and one-component developer
There are two ways to use the agent. For two-component development method
It belongs to the type of system that transports toner.
Magnetic brush using magnetic powder carrier utilizing magnetic force
Method, cascade with somewhat coarse bead carriers
Method, using glass fiber instead of carrier particles
Fur brush method.   Conventionally, toner applied to these developing methods
Of dyes, pigments, etc. in natural or synthetic thermoplastics
Fine powder in which a colorant is dispersed is used. For example,
Coloring agents in binder resins such as polystyrene and polyester
And the dispersion of various additives described below to about 1-30μ
Finely pulverized particles are used as toner. Lord
Magnet is a magnetic toner used in one-component developers.
What contains magnetic particles such as netite is used
Have been. On the other hand, in the case of a method using a two-component developer,
The toner is usually a carrier such as glass beads, iron powder, etc.
Used as a mixture with particles. Also, the toner is developed
Positive or negative charge depending on the polarity of the electrostatic latent image
Is required.   To maintain the desired charge on the toner, the carrier
-And the surface material or the friction of the resin that is a component of the toner
Although triboelectricity can be used, this method alone
Low toner chargeability or quickly reaches desired charge amount
The image obtained by development is easy to fog and
It will be clear. Therefore, the desired amount of triboelectric
Dyes that can be charged to quickly apply
And charge control agents.
ing.   For positive charging, electron donating dye such as nigrosine dye
It is effective, and negative toner
Tolerable organic complexes are widely used.   Nigrosine dye has poor dispersibility in resin.
Also used in denaturation with oleic acid and stearic acid
Many.   In addition, for positive toner, Isol Black,
Aliphatic amine, quaternary ammonium salt, quaternary ammonium
Feschwaltz
HBW, Sudan Teak Schwarz BBC, Brilliant Spies
Lit, zaponschwarz X, solvent red etc.
Yes, colloidal silica, aliphatic
Metal salt, monoazo dye metal complex salt, chlorinated paraffin, salt
Polyester, Spiron Black (Hodogaya Chemical
Made), Balifast Black, Orie
Chromogen Schwarz ETCO, Azo Oil
Black, etc., but generally copper phthalocyanine
Aminated with a substituent or chromium-containing metal
A dimer with a toro group is utilized.   Many of these charge control agents are generated from dyes and pigments.
And generally have complex structures, many of which have strong coloring.
ing.   Color dyes cannot be used with color toners.
In addition to the above-mentioned use of triboelectricity of resin,
Electric control agents are being studied. For example, quaternary ammonium
System, dehydration condensate of ortho-position amine and dicarboxylic acid,
Vinyl pyridine, vinyl pyrazine, etc. are used.
None of the pigment-based products exceeded the overall performance.
In most cases, dyes are used unsatisfactorily.   These are usually added to the thermoplastic resin and hot melt kneaded
And pulverize it to adjust it to an appropriate particle size if necessary.
Used.   However, these dyes as charge control agents
Has a complex structure, inconsistent properties and poor stability
There are many things. In addition, decomposition during heat kneading, mechanical shock, friction
Rubbing, easy to decompose or change due to changes in temperature and humidity conditions,
A phenomenon in which charge controllability lowers easily occurs.   Therefore, these dyes were included as charge control agents.
Developing toner using a copier increases the number of copies
As a result, the charge control agent decomposes or degrades, causing
May cause deterioration.   In addition, these charge control agents are uniformly dispersed in the thermoplastic resin.
Because it is extremely difficult to disperse, it was obtained by grinding
Fatal cause of difference in triboelectric charge between toner particles
Problems. For this reason, conventionally, the dispersion is more even.
Various methods for doing so have been implemented. For example, salt
Basic nigrosine dye improves compatibility with thermoplastics
It is used as a salt with higher fatty acids to
Often, unreacted fatty acid or salt dispersion products
-Exposed on the surface, carrier or toner carrier
Contamination, lowering of toner fluidity, fogging and image density
Cause. Or these loads
In order to improve the dispersion of the charge control agent in the resin,
Mechanical powder and resin powder are mechanically pulverized and mixed and then melted.
A method of melt-kneading is also known. However, the original dispersion
Benignity cannot be avoided, and the charge level is still sufficient for practical use.
The longevity of the developer is not complete.
There is no present.   In addition, substances generally known as charge control agents are
Many are chromatic or dark, vivid desired chromatic
The problem is that it cannot be contained in the developer.
You.   Many charge control agents are hydrophilic, and these resins
Due to poor dispersion inside, after melt kneading, when crushed,
Exposed on the toner surface. Therefore, toner under high humidity conditions
When used, these charge control agents are hydrophilic
Therefore, it has a disadvantage that a high quality image cannot be obtained.   Thus, when a conventional charge control agent is used in a toner,
Between toner particles or between toner and carrier
In the process of generating triboelectric charging between layers, toner particles
The amount of charge generated on the surface varies, causing development fog,
Obstacles such as toner scattering and carrier contamination are likely to occur. Ma
Octopus failure is a phenomenon that becomes noticeable when copying many times.
Which results in a result that is virtually unsuitable for copiers.   Furthermore, under high humidity conditions, the transfer efficiency of toner images
Is remarkably reduced, and many of them cannot withstand use. Normal temperature and normal humidity
Even when the toner is stored for a long period of time,
Deteriorated due to the instability of the charged control agent
In many cases, it becomes unusable due to poor sex.   Furthermore, when a conventional charge control agent is used in toner,
Charge control agent adheres to photoreceptor surface
Or promotes toner adhesion and adversely affects latent image formation.
(Filming phenomenon),
It may cause scratches on cleaning members such as
Copying, such as to improve the wear of the member
Few have a bad effect on the machine cleaning process
I don't.   Furthermore, when a conventional charge control agent is used in toner,
Has a significant effect on the thermal melting characteristics of
There are many things. Also deteriorated high-temperature offset performance
The transfer paper to the rollers.
Increases the sticking property, and the toner adheres to the roller,
In some cases, the durability of the roller is reduced.   Thus, the conventional charge control agents have many disadvantages.
There is a strong demand in the art to improve these.
And many improvements have been proposed so far.
However, there is still something that is practically satisfactory overall
Not in.   An object of the present invention is to provide a toner package that overcomes the above problems.
It is to provide a new technology of electric control.   Another object of the present invention is to provide a method between toner particles or with toner.
In the process of generating triboelectric charging between carriers, etc.
-The amount of triboelectric charge is stable, and the rise of triboelectric charge is
It is quick, and the charge amount is suitable for the developing system used.
It is to provide a controllable developer.   Still another object is to perform development and transfer faithfully to a latent image.
Developer, that is, in the background area during development.
Toner around the edge of fog or latent image
High image density without toner scattering
An object of the present invention is to provide a developer with good reproducibility of halftone.   Still another object is to use the developer continuously for a long time.
In this case, the initial characteristics are maintained, and toner aggregation and charging characteristics change.
It is an object of the present invention to provide a developer with high efficiency of toner consumption without any modification.   Still other purposes are not affected by changes in temperature and humidity
Developer that reproduces stable images, especially at high and low humidity
High transfer efficiency without scattering or missing during transfer
To provide a new developer.   Still another object is to provide a developer having good fixing properties,
Another object of the present invention is to provide a developer free from problems such as high-temperature offset.   Yet another object is to provide vivid chromatic developers.
You.   Still another purpose is to maintain the initial properties even after long-term storage
Another object of the present invention is to provide a developer having excellent storage stability.   Still another object is to make the electrostatic latent image surface dirty or worn.
Easy cleaning process without scratches or scratches
In providing an imaging agent. [Means for solving the problem]   The present invention relates to an electrophotographic toner used for developing an electrostatic image.
Wherein at least a binder resin, a coloring agent and the following general formula
Contain a compound having the structural unit represented by (I)
And a toner for developing electrostatic images characterized by the following.
You.   AR₁-B-R_{1 p}                      (I) (However, A is a compound residue having a phenol group.         B is a group represented by the following general formula (II)         R₁Is a methylene or ethylene group         R_TwoIs an alkylene group having 1 to 8 carbon atoms or aryl
Len group         R_Three, R_FourIs hydrogen atom, alkyl having 1 to 8 carbon atoms
Group, aryl group, aminoalkyl group, aralkyl group or
Represents a cyclic alkyl group, R_ThreeAnd R_FourAre linked to form a ring
Also good         p is a number from 1 to 200         r is 0 or an integer of 1 to 3)   Compound having a phenol group represented by A in the above formula
Specific examples of the residue include residues of the compounds shown below.
Can be   Phenol, cresol, ethylphenol, n-p
Propyl phenol, isopropyl phenol, n-butyl
Phenol, sec-butylphenol, tert-butyl
Phenol, sec-amylphenol, isopentyl
Enol, hexylphenol, octylphenol
Any alkyl phenol; chlorophenol, bromophenol
Halogenated phenols such as phenols; p-cyclohexyl
Luphenol, phenylphenol, tolylphenol
Arylphenols such as 2,3-xylenol, 3,4-
Xylenol, 2,5-xylenol, 2,3-diethylphenol
Phenol, 3,4-diethylphenol, 2,5-diethylphenol
Nol, 2,3-diisopropylphenol, 3,4-diiso
Propylphenol, 2,5-diisopropylphenol
2,3-dichlorophenol, 3,4-dichlorophenol
Disubstituted phenols such as bisphenol A, bisphenol
Nord F, 1,1,2,2-tetrakis (4-hydroxyphene)
Nyl) ethane, 4,4 '-[1,4-phenylenebis (1-meth
Tylethylidene)] bisphenol, α, α ', α "-
Tris (4-hydroxyphenyl) -1,3,5-triiso
Polyphenols such as propylbenzene; and cateco
, Resorcin, hydroquinone, phloroglysin, 1,
Polyhydric phenols such as 2,4-trihydroxybenzene,
Nobola obtained by condensing the above phenols with formalin
Check polyphenol, p-hydroxystyrene and
Phenol polymers such as copolymers with lyl esters.   Compound having a structural unit represented by the above general formula (I)
Representative examples include the following. (Polyhydroxystyrene polymer and piperazine
Formalin condensate)   In the present invention, the structural unit represented by the general formula (I)
At least at room temperature is solid
It is more preferable that the softening point is more than 50 ℃
is there. Long-term storage of liquids or compounds with low softening points at room temperature
Or the compound may bleed on the surface of powder toner during use.
Out, electrical deterioration occurs, and developer and photoreceptor
Changes in the image by causing filming etc.
It is to exert.   Compound having a structural unit represented by the above general formula (I)
As a method of incorporating the toner into the toner,
There is a method of adding and a method of adding externally. If you want to add
The amount of these compounds used depends on the type of binder resin and
Toner production including the presence and absence of additives used and dispersion method
It is determined by the method and is uniquely limited
It is not, but preferably for 100 parts by weight of binder resin
0.1 to 20 parts by weight (more preferably 0.5 to 10 parts by weight)
Used in   When externally added, the above compound has a softening point of 100 ° C or lower.
The above is preferable, and the particle size is also preferably 10 μm or less. The amount of addition
0.01 to 10 parts by weight is desirable for 100 parts by weight of the resin.   Further, a conventionally known charge control agent is combined with the charge control agent of the present invention.
It can be used in combination with the charge control of the present invention.
A plurality of agents may be used in combination.   Colorants used in the present invention include carbon black.
Black, lamp black, iron black, ultramarine, nigrosine dye,
Nirin blue, phthalocyanine blue, phthalocyanine
Green, Hansa Yellow G, Rhodamine 6G, rake,
Calco oil blue, chrome yellow, quinacridone,
Benzidine yellow, rose bengal, triallyl meta
Conventionally known dyes, monoazo dyes, disazo dyes and pigments
Any dyes and pigments can be used alone or in combination
it can.   The binder resin used in the present invention is polystyrene.
, Poly-p-chlorostyrene, polyvinyltoluene
Any styrene and its substituted homopolymer; styrene-p
-Chlorostyrene copolymer, styrene-propylene copolymer
Coal, styrene-vinyltoluene copolymer, styrene-
Vinyl naphthalene copolymer, styrene-methyl acrylate
Copolymer, styrene-ethyl acrylate copolymer,
Tylene-butyl acrylate copolymer, styrene-acryl
Octyl acrylate copolymer, styrene-methyl methacrylate
Copolymer, styrene-ethyl methacrylate copolymer,
Tylene-butyl methacrylate copolymer, styrene-ac
Rilonitrile copolymer, styrene-vinyl methyl ether
Copolymer, styrene-vinyl ethyl ether copolymer
Body, styrene-vinyl methyl ketone copolymer, styrene
-Butadiene copolymer, styrene-isoprene copolymer
Body, styrene-acrylonitrile-indene copolymer,
Styrene-maleic acid copolymer, styrene-maleic acid
Styrene-based copolymers such as ester copolymers;
Methacrylate, polybutyl methacrylate, polysalt
Vinyl chloride, polyvinyl acetate, polyethylene, polypropylene
Ren, polyester, polyurethane, polyamide, epo
Xy resin, polyvinyl butyral, polyacrylic acid resin
Fat, rosin, modified rosin, terpene resin, phenol tree
Fat, aliphatic or alicyclic hydrocarbon resin, aromatic petroleum tree
Fat, chlorinated paraffin, paraffin wax, etc.
Can be used alone or in combination.   Further, the toner of the present invention is used as a two-component developer.
In some cases, it is used by mixing with a carrier powder.   Known carriers that can be used in the present invention
Are all usable, for example, iron powder, ferrite powder,
Magnetic powder such as nickel powder, glass beads, etc.
Surface treated with resin, etc.
Powders obtained by melting and kneading the material with the binder resin and pulverizing
It is.   Further, the toner of the present invention further contains a magnetic material so that
Can also be used as a nailer. Magnetic toner of the present invention
The magnetic materials contained therein include magnetite, hemata,
Iron oxides such as iron and ferrite, iron, cobalt, nickel
Metals such as aluminum or aluminum
, Copper, lead, magnesium, tin, zinc, antimony
, Beryllium, bismuth, cadmium, calcium,
Manganese, selenium, titanium, tungsten, vanadium
Metal alloys and mixtures thereof.   These magnetic materials have an average particle size of about 0.1 to 2μ.
It is desirable that the amount contained in the toner is a resin component
About 20 to 200 parts by weight, particularly preferably resin, per 100 parts by weight
It is 30 to 50 parts by weight based on 100 parts by weight of the component.   Further, the toner of the present invention may contain additives as necessary.
Is also good. As additives, for example, Teflon, stearin
Lubricants such as zinc oxide, or cerium oxide, silicon carbide
Abrasives, such as colloidal silica, titanium oxide
Fluidity-imparting agents such as tin and aluminum oxide, caking
Inhibitors or, for example, carbon black, tin oxide, etc.
Conductivity imparting agent, or low molecular weight polyethylene, low content
And fixing aids such as polypropylene.   Before preparing the electrostatic image developing toner according to the present invention,
Charge control agent having a structural unit represented by general formula (I)
As vinyl or non-vinyl thermoplastic resin and colorant
Pigments or dyes, magnetic materials, additives, etc.
Mix well with a mill or other mixer
Using a heat kneader such as a tool, kneader, extruder, etc.
After melting, kneading and mixing the resins with each other and cooling and solidifying
Pulverizing and classifying to obtain toner having an average particle size of 8 to 15μ
Can be.   Alternatively, after dispersing the material in the binder resin solution,
Drying, or forming a binder resin
After mixing the desired material with the monomer to be made into an emulsified suspension
Polymerization method to obtain toner by polymerization
Can be applied.   The toners produced by these methods are conventionally known.
Means for electrophotography, electrostatic recording, electrostatic printing, etc.
All that can be used for development to visualize the packed image
This produces the following excellent effects.   That is, the amount of triboelectric charge of the toner particles is stable, and
The quantity is easy to control. In addition, it changes during use and the amount of triboelectric charge is reduced.
Extremely stable toner without variation or reduction
It is. For this reason, as described above, image fog and toner
Remove obstacles such as dust, contamination of electrophotographic photosensitive materials and copiers
And the toner of the present invention is extremely excellent.
For example, toner agglomeration and lumps during storage, which were major disadvantages in the past
No long-term storage without phenomena such as denaturation and low-temperature flow
A toner, and abrasion resistance, fixability and
Excellent adhesion.   The excellent effects of such a toner are charging, exposure, development,
Transfer type copying system that repeats the transfer and transfer operations continuously
When used for
You. Furthermore, since there is no color hindrance caused by the charge control agent,
Excellent color by using as a child photo toner
A color image can be formed. 〔Example〕   Hereinafter, the present invention will be described specifically with reference to Examples.
Does not limit the invention in any way. In addition, the following
All parts in the formulations are parts by weight. Example 1   Styrene / butyl acrylate (30/20) copolymer   (Weight average molecular weight w: about 300,000) 100 parts   Carbon black (Mitsubishi^#44) 10 copies   2 parts of low molecular weight polypropylene wax   Compound (1) 4 parts   After mixing the above materials well in a blender, heat to 150 ° C.
And kneaded with two rolls. After allowing the kneaded material to cool naturally,
After coarse pulverization with a termill, fine pulverization using a jet stream
Pulverized using an air classifier, and further classified using an air classifier.
A fine powder having a diameter of 5 to 20 μ was obtained.   The fine powder is used for 100 parts of an iron powder carrier having an average particle size of 50 to 80 μ.
Powder was mixed at a ratio of 5 parts to prepare a developer.   Then on the OPC photoreceptor by a conventionally known electrophotographic method,
A negative electrostatic charge image is formed, and this is
Create a toner image by powder development using the lash method and transfer it to plain paper
And heat-fixed. The transfer image obtained has a sufficiently high density
No fogging and no toner scattering around the image
A good image with high resolution was obtained. High fixing strength
Significant improvements were seen. Continuous transfer using the above developer
An image was created and the durability was checked.
The image is also comparable to the initial image.
Was.   Also, at the time of durability, the above-mentioned film related to the toner
No cleaning phenomenon was observed and what was the problem in the cleaning process?
I couldn't find anything. At this time, trouble in the fixing process
No, observe the fuser at the end of the 50,000-sheet endurance test
However, roller scratches and damage were not seen, offset
Almost no toner contamination and no practical problems
Was.   Table 1 summarizes the image evaluation results under the normal environment.   When the environmental conditions were 35 ° C and 85%, the image density was
The value is almost the same as normal temperature and normal humidity.
Clear images can be obtained without scattering, and durability is up to 50,000 sheets.
There was almost no change. Next, at 15 ℃, 10% low temperature and low humidity
When the transferred image was obtained, the image density was sufficiently high.
Black is also developed and transferred very smoothly,
There was no excellent picture. Endurance was performed under these environmental conditions
Was copied continuously and intermittently, but still up to 50,000
, The concentration fluctuation was within ± 0.2, which was practically sufficient. Comparative Example 1   Instead of 4 parts of compound (1), a nigrosine dye (origin)
Using 4 parts of Nigrosine Base EX) manufactured by Ent Kagaku Kogyo
In the same manner as in Example 1, a developer was obtained, developed, transferred, and fixed.
And an image was obtained in the same manner.   Table 1 shows the image evaluation results under the normal environment.
At normal humidity, fog is low, but image density is low at 1.00 and line drawings
Splattered, the solid black was noticeably rough. Check durability
However, the density decreased to 0.80 at 50,000 sheets. Toner consumption
20% more than in Example 1 with a total consumption of up to 50,000 sheets
won.   Also, at the time of durability, from around 10,000 sheets on the photoreceptor surface, toner material
The film forms a thin streak film and forms a line on the image.
It was broken. This is called filming
Charge control agent changed the lubricity of toner powder
It is thought.   Transfer efficiency was 80% or more at the initial stage, but 30,000 sheets
At that time, it dropped to 60%.   During endurance, the fixed image is spread on the fixing roller during the fixing process.
Tends to be entangled, and the fixing roller surface becomes dirty.
This was conspicuous, and the peelability of the roller was difficult. Again
There was a lot of dirt inside, and there was also a problem with the scattering of toner.   When the image was obtained under the conditions of 35 ° C and 85%, the image density was 1.
Although there was no problem with 35, it splattered and the roughness increased.
Was. Transfer efficiency was low and toner consumption increased.   When the image was obtained under the conditions of 15 ° C and 10%, the image density was
As low as 0.90, splattering, fog, and rough transcribe are severely transferred.
The tear was noticeable. Continuous image output, but about 30,000 sheets
The concentration became 0.53 by degree, and it became impractical. Example 2   Use 5 parts of compound (2) instead of 4 parts of compound (1)
Other than that, a developer was obtained in the same manner as in Example 1, and development and transfer were performed.
Copying and fixing were performed, and an image was obtained in the same manner.   The detailed results are shown in Table 1, and the results are almost the same as in Example 1.
The results were quite satisfactory. Example 3   Use 4 parts of compound (5) instead of 4 parts of compound (1)
Other than that, a developer was obtained in the same manner as in Example 1, and development and transfer were performed.
Copying and fixing were performed, and an image was obtained in the same manner.   The detailed results are shown in Table 1, and the results are almost the same as in Example 1.
The results were quite satisfactory. Example 4   Use 4 parts of compound (6) instead of 4 parts of compound (1)
Other than that, a developer was obtained in the same manner as in Example 1, and development and transfer were performed.
Copying and fixing were performed, and an image was obtained in the same manner.   The detailed results are shown in Table 1, and the results are almost the same as in Example 1.
The results were quite satisfactory. Example 5   Styrene-butyl acrylate (80/20) copolymer   (Weight average molecular weight w: about 300,000) 100 parts   Iron trioxide EPT-500 (made by Toda Kogyo) 60 parts   2 parts of low molecular weight polypropylene wax   Compound (3) 4 parts   Mix the above materials in a blender and heat to 150 ℃
And kneaded with two rolls. After allowing the kneaded material to cool naturally,
After coarse pulverization with a termill, fine pulverization using a jet stream
Pulverized using an air classifier, and further classified using an air classifier.
A fine powder having a diameter of 5 to 20 μ was obtained.   Copier using this toner with commercially available one-component toner
Table 1 shows the results obtained by applying (using OPC photoreceptor) images.
As shown in the figure, almost the same good results as in Example 1 were obtained.
Was. Example 6   In Example 1, styrene / butyl acrylate
Polyester resin (polyoxyethylene) instead of polymer
Bisphenol A, polyoxypropylene bispheno
A, terephthalic acid, trimellitic anhydride, tetrap
Polycondensates of lophenyl succinic anhydride; Ring and ball softening point 145
° C) except that a developer was obtained in the same manner as in Example 2.
Image, transfer and fixing were performed to obtain an image in the same manner.   The detailed results are shown in Table 1, but almost the same as in Example 2.
Results were obtained. Comparative Example 2   In Example 1, instead of 4 parts of compound (1),
Zirmethyl-hexadecyl ammonium chloride 4 parts
A developer was obtained in the same manner as in Example 5 except that
I got   Table 1 shows the image evaluation results under the normal environment.
At normal humidity, fog is small, but image density is low at 0.90 and line drawings
Splattered, the solid black was noticeably rough. Check durability
However, the density decreased to 0.48 at 30,000 sheets.   In addition, the filming phenomenon at the time of durability and the problem in the fixing process.
Comparative Example 1 with respect to the title, transfer efficiency, and toner consumption.
It was almost as bad.   The image density was the first when the image was obtained under the conditions of 35 ° C and 85%.
Although the period was 1.35, there was no problem.
Yellowtail, splatters, roughness increase, and it cannot withstand use
It was. The transfer efficiency was also low. 15 ℃, 10% condition
Image density was as low as 0.70,
, Fog, and gasket were very noticeable. Communicating
The continuous image output was performed, but the density was 0.50 at 10,000 sheets.
It became impractical. Example 7   100 parts of the same polyester resin as in Example 6   Copper phthalocyanine blue pigment 5 parts   2 parts of low molecular weight polypropylene wax   Compound (1) 4 parts   Mix the above materials in a blender and heat to 150 ° C.
And kneaded with two rolls. After allowing the kneaded material to cool naturally,
-Fine crusher using jet stream after coarse crushing with a mill
And then classify using an air classifier.
A fine powder of 5-20 μ was obtained.   Next, a carrier iron powder having a particle size of 50 to 80 μm is added to 5 parts of the fine powder.
100 parts were mixed to obtain a developer.   Using this developer, image formation was performed in the same manner as in Example 1.
However, a good image exhibiting a vivid blue color was obtained.
After that, image was output up to 300 million sheets while supplying toner.
However, a good image was obtained.   Table 1 summarizes the image evaluation results under the normal environment. 〔The invention's effect〕   The effects obtained by the present invention are as follows. (1) Development and transfer faithful to latent images can be performed, and long-term
Maintains initial properties even when used continuously for
Is a developer having no change in aggregation and charging characteristics. (2) A stable image that is not affected by changes in temperature and humidity
Images can be reproduced, and vivid chromatic images can be obtained
It is a developer. (3) Stain, rub, or scratch the electrostatic latent image surface
Easy-to-clean cleaning process and fixing properties
Excellent developer, especially with high temperature offset
is there.

   ────────────────────────────────────────────────── ─── Continuation of front page    (72) Inventor Kazuhiko Okabe               1334 Minato, Wakayama-shi Kao Corporation Wakayama Lab               Inside the office                (56) References JP-A-61-124954 (JP, A)                 JP-A-58-171060 (JP, A)                 JP-A-61-124958 (JP, A)                 JP-A-62-67563 (JP, A)

Claims (1)

(57) [Claims] At least a binder resin, a colorant and the following general formula (I)
A toner for developing an electrostatic charge image, comprising a compound having a structural unit represented by the formula: AR ₁ -BR _{1 p} (I) (where A is a compound having a phenol group and residue B is a group represented by the following general formula (II) R ₁ is a methylene group or an ethylene group R ₂ is an alkylene group having 1 to 8 carbon atoms or an arylene group R ₃ and R ₄ are a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group, an aminoalkyl group, an aralkyl group or Represents a cyclic alkyl group, R ₃ and R ₄ may combine to form a ring, p is a number from 1 to 200, r is 0 or an integer from 1 to 3, and When the compound having the structural unit represented by the general formula (I) is internally added to the toner, the content of the compound having the structural unit represented by the general formula (I) is 0.1 to 100 parts by weight based on 100 parts by weight of the binder resin. 2. The toner according to claim 1, wherein the amount is 20 parts by weight.