JP3531308B2 - Method for producing toner composition and toner composition - Google Patents

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a charge control agent for toner used in electrophotography, electrostatic recording and the like and a method for producing a toner composition.

[0002]

2. Description of the Related Art As developers used in electrophotography and the like, two-component developers composed of a carrier and a toner and one-component developers requiring no carrier (magnetic toner or non-magnetic toner) are known. ing. And, conventionally, charge control agents such as nigrosine dyes, triphenylmethane dyes, and quaternary ammonium salt compounds have been known as those for imparting a charge to a developer. (1) To increase the charging speed of the toner (2) To stabilize the charge maintaining property of the toner (3) To make the distribution of the charge amount of the toner uniform (4) To reduce the environmental dependence of the toner charge amount ( 5) The carrier and the charging member are not contaminated by the charge control agent in the toner. (6) The charge control agent is safe for the environment and the body as a toner material. (7) The charge control agent used for color toner is For example, it may not impair the color of the toner.

In order to meet these demands, various charge control agents have been proposed in the past, for example, JP-A-6-23607.
No. 1 discloses a specific quaternary ammonium salt compound. However, the toner using the conventional charge control agent has a large change in image density during continuous copying of the copying machine, the toner is contaminated in the copying machine as the number of copies increases, and the copy gradation property, etc. There was a problem such as deterioration of image quality.

[0004]

Therefore, the first aspect of the present invention
The purpose of is to provide a charge control agent having functions and the like required for toner. A second object of the present invention is to provide a method for producing a charge control agent and a toner composition capable of obtaining a toner having stable image quality such as copying when continuously used and less in-machine contamination and excellent in durability performance. .

[0005]

As a result of various investigations by the present inventors, a crystalline compound having specific thermal analysis characteristics was used as a charge control agent, and the particle size and bulk of the charge control agent were adjusted to a specific range. The present invention has been accomplished by finding that the above problems can be solved by using it as a raw material for toner. That is, the gist of the present invention is to provide resins, colorants, and charge control agents.
Mixing, kneading, cooling and solidifying, pulverizing, and classifying raw materials containing
In the method for producing a toner composition, the average particle size of the resin is
The particle size is 30 to 3000 μm, the charge control agent is a crystalline compound having one endothermic peak by thermal analysis, and the average particle size is 20 μm or less and the bulk is 2.5 ml.
/ G or more, a method for producing a toner composition
Exists in the law .

[0006]

BEST MODE FOR CARRYING OUT THE INVENTION The charge control agent of the present invention is a crystalline compound among various known charge control agents, and a thermal analysis endothermic peak derived from the compound (for example, an endothermic peak derived from crystal water is There is one, and the average particle size (D
c) is 20 μm or less and the bulk (ρ) is 2.5 ml
/ G or more is preferable. Those having two or more endothermic peaks are easily affected by the kneading temperature when the toner is manufactured by the melt kneading method, and the charge imparting property to the toner is greatly affected, and the toner charge amount is stably controlled. It is difficult and not preferable. If the average particle size (Dc) and bulk (ρ) of the charge control agent are out of the above ranges, the toner characteristics are deteriorated, the image quality is not stable, and contamination inside the machine occurs, which is not preferable. The average particle diameter (Dc) and bulk (ρ) are each preferably 15 μm or less and 2.7 ml / g or more. The average particle diameter (Dc) of the charge control agent is 3 times or less, preferably 2 times or less, particularly preferably 1 times or less of the average particle diameter (Dt) of the toner particles. If the amount is 3 times or more, the charge control agent is not sufficiently dispersed in each toner particle, the toner charge distribution becomes broad, and the amount of low-charge or reverse-polarity toner increases, resulting in poor toner charging characteristics and poor image quality. It is not preferable because it easily causes contamination in the machine.

Further, it is preferable that one crystalline compound is present at a position where the thermal analysis endothermic peak (Tp) is higher than the flow end temperature (Te). When the temperature is lower than the flow end temperature (Te), the charge control agent is decomposed during melt-kneading, and a crystalline substance partially or wholly becomes amorphous, which hinders the toner charging function, which is not preferable. The temperature of the melt-kneaded product is appropriately determined depending on the materials used, the kneader, etc.
Usually, it is set to a temperature higher than the flow end temperature (Te) of the resin used. The temperature of the melt-kneaded product may be measured with a commercially available thermometer for the kneaded product at the exit of the kneading machine. When the temperature of the melt-kneaded product is lower than the flow end temperature (Te), the charge control agent, the colorant and other internal additives in the toner are not well dispersed, which causes fog and toner scattering, which is not preferable. The crystalline compound in the present invention may be any compound having a crystal structure to the extent that an endothermic peak is observed in thermal analysis, and does not necessarily mean that the entire compound has a crystal structure. The crystalline compound of the charge control agent is preferably a quaternary ammonium salt compound, and examples thereof include compounds represented by the following general formula (I).

[0008]

[Chemical 2]

(In the formula, R ¹ , R ² , R ³ and R ⁴ each represent a hydrogen atom, an alkyl group which may have a substituent, or an aralkyl group which may have a substituent. , A represents an aromatic ring residue which may have a substituent) A methyl group is a specific example of R ¹ , R ² , R ³ and R ⁴ .
Ethyl group, n-propyl group, iso-propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group,
Alkyl groups such as tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, hexadecyl group, heptadecyl group, stearyl group, nonadecyl group, eicosyl group, docosyl group, tetracosyl group; hydroxyl group substituted alkyl group, halogen group substituted alkyl group, alkoxyl group substituted alkyl group A substituted alkyl group such as aralkyl group; aralkyl group such as benzyl group and phenethyl group;
Examples of the substituted aralkyl group include a lower alkyl group-substituted aralkyl group, a nitro group-substituted aralkyl group, and a halogen group-substituted aralkyl group. Among them, an alkyl group having 16 or less carbon atoms which may have a substituent, a benzyl group, a lower group An alkyl group-substituted benzyl group, a nitro group-substituted benzyl group, and a halogen group-substituted benzyl group are preferable. Among them, the alkyl group is preferably an unsubstituted alkyl group having 16 or less carbon atoms. Further, the carbon number of the alkyl group is preferably 12 or less, and it is particularly preferable that R ² , R ³ and R ⁴ are the same group.

A represents an aromatic ring residue which may have a substituent, and examples thereof include an arylene group such as a phenylene group, a naphthylene group and an anthrylene group, and a phenylene group and a naphthylene group are particularly preferable. These may have a substituent, and examples of the substituent include an alkyl group, a hydroxyl group, an amino group and a halogen group, and a hydroxyl group is particularly preferable. Of the compounds represented by the above general formula (I), specific examples of the compounds suitable for use in the present invention include the compounds represented by the following structural formulas, but are not limited to these. Absent. Exemplified compound

[0011]

[Table 1]

[0012]

[Table 2]

[0013]

[Table 3]

[0014]

[Table 4]

[0015]

[Table 5]

[0016]

[Table 6]

[0017]

[Table 7]

The compound represented by the above general formula (I) can be used in the present invention regardless of its production method, and an example of its specific production method will be described below. The compound represented by the general formula (I) is generally represented by the general formula (II)

[0019]

[Chemical 3]

A halogenated quaternary ammonium salt compound represented by the formula (wherein X represents halogen such as chlorine or bromine) is represented by the general formula (III)

[0021]

[Chemical 4]

(Wherein A represents the same meaning as in the general formula (I), Y represents an alkali metal such as sodium or potassium) and water or alcohol, for example, 5
It can be obtained by heating at about 0 to 70 ° C. and reacting.

The content of the charge control agent in the toner of the present invention is 0.01 to 2 with respect to 100 parts by weight of the binder resin.
0 parts by weight is preferable, 0.05 to 15 parts by weight is more preferable, and 0.1 to 10 parts by weight is particularly preferable. If the content of the charge control agent is too small, the charge amount is low and the desired charge amount cannot be obtained, and if it is excessive, the charge control agent liberated from the toner imparts the charge to the toner carrier such as the carrier and the developing blade. Contamination of members and the like becomes severe, and in any case, image quality is deteriorated, which is not preferable.

The charge control agent of the present invention may be used alone or in combination of two or more kinds. Further, other charge control agents may be used in an amount that does not interfere. The charge control agent and manufacturing method of the present invention are preferably for a positively chargeable toner composition. In order to obtain the average particle diameter (Dc) and bulk (ρ) of the charge control agent of the present invention, it is preferable to adjust them by mechanical means. For example, during the synthesis of the charge control agent, crystals are finely powdered. After precipitating, the particles may be crushed or crushed by a crusher and classified by a wind classifier or the like to adjust the particle size. Considering productivity, handleability, etc., it is preferable to pulverize and classify the charge control agent fine powder crystals by a pulverizer equipped with an air classifier. Examples of the crusher equipped with such a wind force classifying mechanism include New Cosmomizer manufactured by Nara Machinery Co., Ltd., SK-Jet Oh Mill manufactured by Seishin Enterprise Co., Ltd., and ACM Pulverizer manufactured by Hosokawa Micron Corporation. There is.

Each test method of the charge control agent used in the present invention will be described below. [Particle size distribution] The particle size distribution is measured by a dry method using a laser diffraction type particle size distribution measuring device (model: HEROS & RODOS) manufactured by Sympatech in Germany under the following conditions. Average particle size (D
c) was read from the measurement data.

Dispersion method: fluid dispersion unit ・ Dispersion air pressure: 3 bar ・ Dispersion nozzle: 120 bar ・ Lens focal length: 500mm ・ Measurement time: 3 seconds

[Endothermic peak (Tp)] The peak position was determined from the endothermic curve measured by a differential thermal analyzer (DTA-40 manufactured by Shimadzu Corporation) under the conditions of a heating rate of 10 ° C./min. The peak temperature is the melting point.

[Bulk (ρ)] Charge control agent weight (Wc) 5 g
A glass graduated cylinder (inner diameter 21 mm, height 220
mm) and tapping 5 times from a position of 10 cm in height, the volume (Vc) is read from the graduated cylinder scale on the powder surface, and the volume (ρ) is calculated by the following formula. ρ (ml / g) = Vc (ml) / Wc (g)

As the resin used in the present invention, known types suitable for toner can be used. Examples of the styrene-based resin (styrene or a styrene-substituted homopolymer or copolymer) include polystyrene, chloropolystyrene, poly-α-methylstyrene, styrene-chlorostyrene copolymer, and styrene-propylene copolymer. , Styrene-butadiene copolymer, styrene-vinyl chloride copolymer, styrene-vinyl acetate copolymer, styrene-acrylic acid ester copolymer (styrene-methyl acrylate copolymer, styrene-ethyl acrylate copolymer , Styrene-butyl acrylate copolymer, styrene-octyl acrylate copolymer and styrene-phenyl acrylate copolymer), styrene-methacrylic acid ester copolymer (styrene-methyl methacrylate copolymer, styrene- Ethyl methacrylate copolymer, styrene-methac Le butyl acrylate copolymer and styrene - phenyl methacrylate copolymer), styrene -α- chloromethyl acrylate copolymers, and styrene - acrylonitrile - there are acrylic acid ester copolymer.

Furthermore, the cross-linking binder resins described in JP-B-51-23354 and JP-A-50-44836, or JP-B-55-6895 and JP-B-63-32180 are described. The non-crosslinked binder resin which has been used can also be used.

As the polyester resin, a known saturated resin,
It can be arbitrarily used from unsaturated ones, and the composition is composed of a polyhydric alcohol and a polybasic acid, and at least one of the polyhydric alcohol and the polybasic acid optionally contains a trifunctional or higher polyfunctional component. It is obtained by polymerizing a monomer composition. Examples of the epoxy resin include a general-purpose epoxy resin of a polycondensate of bisphenol A and epichlorohydrin, a modified epoxy resin modified with carboxylic acid, phenol, diarylsulfonamide, etc., and an epoxy resin in which a phenol resin and an epoxy resin are blended. is there.

As other resins, vinyl chloride resin, rosin-modified maleic acid resin, phenol resin, polyethylene resin, polypropylene resin, ionomer resin, polyurethane resin, silicone resin, ketone resin, ethylene-ethyl acrylate copolymer, xylene resin, There are polyvinyl butyral resin, polycarbonate resin and the like.

Examples of resins preferably used in the present invention include styrene resins, saturated or unsaturated polyester resins and epoxy resins. Further, the resin is not limited to being used alone, and two or more kinds can be used in combination. As the resin used in the present invention, a resin containing a styrene resin as a main component (preferably 50% or more) is particularly preferable.

The flow softening temperature (Tm) of the resin is 8
The temperature is preferably about 0 to 150 ° C, more preferably about 90 to 140 ° C. If the temperature is lower than 80 ° C, the fixing temperature on the paper is low and good, but hot offset is likely to occur, and the toner is easily crushed inside the developing tank, resulting in a spent phenomenon in which the toner adheres to the carrier surface and the doctor blade. However, there is a problem in that the charging characteristics are deteriorated and the durability performance of the developer is deteriorated. On the other hand, if it is higher than 150 ° C., there are problems such as a high fixing temperature on paper and poor toner pulverizability.

The glass transition temperature (Tg) of the resin is preferably about 45 ° C. or higher. If the temperature is lower than 45 ° C., the toner will be hard to agglomerate or stick when left at a high temperature of 40 ° C. for a long time, resulting in poor storage stability. In addition, it is easy to generate toner aggregates in the external addition process, and it is easy to generate aggregates by adhering to the screen, side wall, etc. of the sieving device. Furthermore, when the toner is used for a long time in the developing device, However, there is a problem in use such as sticking to parts such as the bearing and the spike control plate.

The average particle size (Dr) of the resin is 30 to
It is preferably about 3000 μm, more preferably 50 to 2000 μm, and the main peak (Pr) of the particle size distribution is 200.
It should be at a position of 0 μm or less, and even 1000 μm
It should be located below. If the average particle size is less than 30 μm, the mixing property with materials other than the resin is poor, the fluidity at the time of feeding the raw materials is poor, and the miscibility at the time of kneading is poor. It is not preferable because it is likely to occur. Further, when the main peak is located at a position larger than 2000 μm, the raw material is likely to be ubiquitous and the toner composition is not uniform, which is not preferable. The resin may be produced by a known production method, for example, in the case of a styrene resin, it may be produced by solution polymerization, suspension polymerization, bulk polymerization, emulsion polymerization or the like, and if necessary, a low molecular weight substance and a high molecular weight substance. The polymerization method may be different, and when the predetermined particle size of the resin cannot be obtained in the production stage, the resin may be crushed or pulverized by a known mechanical means.

Each test method for the resin used in the present invention will be described below. [Flow end temperature (Te) and flow softening temperature (T
m)] Flow tester (CFT- manufactured by Shimadzu Corporation)
500), the sample 1g, the nozzle 1mm × 10mm
Of the die, a load of 30 kg, a preheating time of 50 ° C. for 5 minutes, and a temperature rising rate of 3 ° C./minute. The temperature at which the flow ends is the flow end temperature (Te), The temperature at the midpoint is defined as the flow softening temperature (Tm).

[Glass transition temperature (Tg)] A transition (inflection) start portion of a curve measured by a differential thermal analyzer (DTA-40 manufactured by Shimadzu Corporation) at a heating rate of 10 ° C./min. Tangent to the glass transition temperature (T
g).

[Particle size distribution] Laser diffraction type particle size distribution measuring device (model HEROS & GRA
It is measured by the dry method under the following conditions.・ Dispersion type unit: Vertical descent type dispersion unit ・ Lens focal length: 2000mm ・ Measurement time: 2 seconds

As the colorant used in the present invention, known pigments and dyes may be used. For example, carbon black,
Iron black, titanium oxide, zinc white, alumina white, calcium carbonate, ultramarine blue, navy blue, phthalocyanine blue, phthalocyanine green, malachite green, lake red C, Hansa yellow G, rhodamine dye, chrome yellow, quinacridone magenta, benzidine yellow, rose. Colorants such as Bengal, triallylmethane dyes, anthraquinone dyes, monoazo and disazo dyes and pigments may be used alone or in combination of two or more, and black, red, blue, green,
Any color such as brown, magenta, and cyan can be obtained.

The content of the colorant may be an amount sufficient to color the toner so that a visible image can be formed by development, and for example, 1 to 25 parts by weight, preferably 100 parts by weight of the resin. 3 to 20 parts by weight is suitable. In order to disperse the colorant more uniformly, a method of pretreatment by a masterbatch method or a method of treating the surface of the colorant with a dispersion improving agent such as surface soap may be carried out, if necessary.

If desired, other internal additives may be used alone or in combination as an auxiliary agent. For example, known low-molecular-weight olefin polymers as releasing agents, metal soaps as lubricants, and magnetite as magnetic powders. Examples thereof include powder / ferrite powder, organic / inorganic filler, and the like. An example of the toner production flow of the present invention will be described with reference to FIG. 1, but the present invention is not limited to the following description as long as the gist thereof is not exceeded.

[Raw Material Mixing Step] In this step, the raw material resin, colorant and charge control agent are mixed. The mixing of these materials may be performed by stirring and mixing with a known mixing device, and examples of the mixing device include a double cone mixer, a V-type mixer, a drum-type mixer, a super mixer, a Henschel mixer, and a Nauta mixer. . In order to preferably operate the present invention, a high-speed rotary blade mixer that has a stirring blade that rotates at high speed inside at the time of mixing and gives a shearing action to materials is preferable, for example, a super mixer or a Henschel mixer. . With such a mixing device,
Toner charging characteristics are improved, image stability during continuous copying is improved, and toner contamination is reduced. Although this mechanism has not been clarified, it is presumed that the charge control agent is well dispersed in the toner and the toner charging characteristics are improved.

[Kneading Step] As a kneading device for melt-kneading the above mixture, either a batch type or a continuous type may be used, but in view of productivity, a uniaxial or biaxial continuous kneader may be used. For example, KTK twin screw extruder manufactured by Kobe Steel, TEM twin screw extruder manufactured by Toshiba Machine Co., Ltd., twin screw extruder manufactured by KCK, PCM twin screw extruder manufactured by Ikegai Iron Works, Kuriyama Seisakusho. A twin-screw extruder manufactured by Co. and a co-kneader manufactured by Bus Co. are preferable.

[Cooling and solidifying step] After kneading, the kneaded material is rolled by two rolls or the like, cooled by air cooling or water cooling with a belt cooler, a drum cooler or the like, and solidified by a cooling and solidifying step. [Pulverizing step] The pulverizing step usually includes a coarse pulverizing step and a fine pulverizing step. In the coarse pulverizing step, the kneaded product after cooling is coarsely pulverized by a crusher, a hammer mill, a feather mill, etc., and in the fine pulverizing step, a jet mill. Finely pulverize with a high-speed rotor rotary mill or the like, and pulverize to a predetermined toner particle size stepwise.

[Classification step] After crushing, inertia classification type elbow jet, centrifugal classification type microplex, D
The toner is classified with an S separator or the like, and the average particle size is 3 to 1
5 μm toner is obtained. To obtain high image quality, the average particle size of the toner is preferably 3 to 10 μm, more preferably 3 to 8 μm.
In the present invention, the smaller the toner particle size, the more effective it is.
The coarse toner powder generated in the classification step may be returned to the crushing step, and the fine powder generated may be returned to the mixing step of the toner raw materials for reuse.

[External Addition Step] The classified toner and various known external additives are mixed in a predetermined amount, and the mixture is preferably stirred and mixed by a high-speed stirrer such as a Henschel mixer or a super mixer that gives a shearing force to the powder.

As the external additive, various known inorganic or organic external additives can be used. In particular, in order to improve the fluidity of the toner and suppress the cohesiveness, titania, silica, alumina, zinc oxide, and oxidation are used. Inorganic fine powder such as magnesium is suitable. The mixing amount of the external additive depends on the external additive to be used and the average particle size and particle size distribution of the toner particles.
0.01 to 15 parts by weight, more preferably 0.
1 to 10 parts by weight is suitable. If the mixing amount is less than 0.01 parts by weight, there is no fluidity improving effect and the storage stability performance at high temperature is poor, and if the mixing amount is more than 15 parts by weight, filming occurs on the photoconductor due to some external additives released Undesirably, or it accumulates inside the developing tank and causes problems such as deterioration of the charging function of the developer.

[Sieving step] The externally added toner is screened by a Sato type vibrating screen, a gyro shifter, a centrifugal classifier, etc. for the purpose of removing foreign matters, coarse toner particles, and freed external additives. To be done.

[Filling Step] A container such as a bottle or a cartridge, an aluminum bag, a plastic bag or the like is filled with a predetermined amount of toner. The obtained toner is a one-component developer that does not use a carrier (a magnetic one-component toner containing a magnetic substance such as magnetite, or a non-magnetic one-component toner containing no magnetic substance), or iron powder, ferrite, or magnetite. , A two-component developer mixed with a magnetic carrier such as a magnetic resin carrier.

[0051]

By using the toner charge control agent and the method for producing a toner composition of the present invention, a toner in which the charge control agent and the like are uniformly dispersed can be obtained, and the image quality is excellent even when repeatedly copied. It provides a great industrial benefit by providing a toner with stable quality and less contamination in the machine.

[0052]

EXAMPLES The present invention will be described in more detail below with reference to examples. In the following examples, "parts" simply means "parts by weight". The charge control agent is quaternary ammonium salt compound No. Using (8), X of the compound
X-ray diffraction analysis system P manufactured by Philips
As a result of carrying out with W-1700, it had a crystal structure as shown in FIG. Further, the results of differential thermal analysis of the compound are shown in FIG. 3, and there was one endothermic peak and the melting point (Mp) was 199 ° C.

Example 1 Resin a Styrene / n-butyl acrylate = 82/18 100 parts [Tm = 134 ° C., Te = 153 ° C., Tg = 63 ° C., Dr = 97 μm] Charge control agent a Compound No. (8) 2 parts [Tp = 199 ° C., Dc = 8.0 μm, ρ = 3.3 ml / g] -Colorant carbon black MA-100 (Mitsubishi Chemical Co., Ltd.) 6 parts-Polypropylene wax 550P (Sanyo Kasei Co., Ltd.) Co., Ltd. 1 part Polyethylene wax PE130 (Hoechst Co.) 1 part was mixed with a Henschel mixer for 15 minutes, and an outlet kneaded material temperature of 176 was obtained using a continuous extruder (Ikegai PCM type).
Average particle diameter (Dt) after kneading at ~ 178 ° C, crushing and classification
10 μm (Coulter Coulter Counter TA-
(Measured in II) was obtained. To 100 parts of this powder, 0.15 part of silica (R972 of Nippon Aerosil Co., Ltd.) and magnetite powder (EPT-1000 of Toda Kogyo Co., Ltd.).
A black toner was obtained by stirring and mixing 3 parts. This toner 4
Particle diameter of 100 parts and surface coated with silicone resin
Stir 96 parts of Cu-Zn-ferrite carrier of μm
A developer was prepared by mixing. This developer was used as an organic photoconductor as a photoconductor and was equipped with a urethane blade cleaning type cleaning mechanism at a copying speed of 40 sheets / min (Sharp SF-8870) to produce 30,000 durable copies. The results are shown in Table 2. The image density was high and stable from the beginning to the end, the fog was low, the image quality was stable, and there was no contamination inside the machine due to toner scattering.

Examples 2 and 3 Toners and developers were prepared in the same manner as in Example 1 except that the charge control agents shown in Table 2 were changed to the charge control agents shown in Table 2.
The results of durability actual copying are shown in Table 2. The image characteristics were good from the beginning to the end.

Comparative Examples 1, 2 and 3 Toners and developers were prepared in the same manner as in Example 1 except that the charge control agents shown in Table 2 were changed to the charge control agents shown in Table 2.
The results of durability actual copying are shown in Table 2. However, it was not preferable because the image density change in the photographic mode was large and there was contamination inside the machine due to toner scattering.

Explanation of terms in Table 2 [Normal mode] A mode in which development is performed at a photoreceptor surface potential Dc-700V and a bias voltage Dc-200V. [Photo mode] A mode in which development is performed at a photoreceptor surface potential Dc-500V and a bias voltage Dc-200V.

[Image Density Change Width] The difference between the maximum value and the minimum value of the image density measured by a Macbeth reflection densitometer (manufactured by Sakata Inx Co., Ltd.) for the black portion copied for every 5,000 sheets is defined as the image density change width. . [Fog] The whiteness of each copy of 5,000 sheets was measured for Hunter whiteness with a color difference meter (Nippon Denshoku Industries Co., Ltd.), and the difference in Hunter whiteness before and after copying was taken as the fog.

[Toner Scattering Amount] After copying 30,000 sheets, the toner deposited on the bottom of the developing tank was sampled, and the collected weight was weighed to obtain the toner scattering amount.

[0059]

[Table 8]

[0060]

[Brief description of drawings]

FIG. 1 Example of toner manufacturing flow

2 is a quaternary ammonium salt compound No. X-ray diffraction result of (8)

FIG. 3 Quaternary ammonium salt compound No. Differential thermal analysis result of (8)

─────────────────────────────────────────────────── ─── Continuation of the front page (56) Reference JP-A-6-3860 (JP, A) JP-A-4-125655 (JP, A) JP-A-6-186779 (JP, A) JP-A-3- 157670 (JP, A) JP 4-204855 (JP, A) JP 1-238673 (JP, A) (58) Fields investigated (Int.Cl. ⁷ , DB name) G03G 9/087-9 / 097

Claims (5)

(57) [Claims] 1. A resin, a colorant, and a charge control agent are contained.
The raw materials to be mixed, kneaded, solidified by cooling, crushed, and classified
In the method for producing a ner composition, the average particle size of the resin is
30 to 3000 μm, the charge control agent is a crystalline compound having one endothermic peak by thermal analysis, and the average particle size is 20 μm or less and the bulk is 2.5 ml / g or more. A method for producing a toner composition, comprising: 2. The charge control agent is a quaternary ammonium chloride.
The toner composition according to claim 1, wherein the toner composition is a substance.
Method of manufacturing things. 3. The charge control agent is represented by the general formula (I): (In the formula, R ¹ , R ² , R ³ , and R ⁴ each represent a hydrogen atom, an alkyl group which may have a substituent, or an aralkyl group which may have a substituent, and A represents according to claim 1 or 2, wherein the substituted is a compound represented by the also represents an aromatic ring residue)
Method for producing toner composition . The average particle diameter of wherein said charge control agent, a toner composition according to any one of claims 1 to 3, equal to or less than 3 times the average particle diameter of the toner composition after classification Manufacturing method. 5. The manufacturing method according to claim 1.
A toner composition obtained by a method.