JP2003177576A - Electrostatic charge image developing toner - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an excellent electrostatic charge image developing toner having such durability and stability that neither increase of surface stain (fog) of a white background nor lowering of image density is caused when the toner is repeatedly used in a copying machine, a printer or the like and neither increase of fog nor scattering in a machine is caused even if the toner undergoes a change with time when it is allowed to stand in a hot environment. <P>SOLUTION: In the electrostatic charge image developing toner comprising at least a binding resin, a colorant and a charge controlling agent, the charge controlling agent is a compound of formula (1) (where R is a 5-25C saturated or unsaturated monovalent aliphatic group). <P>COPYRIGHT: (C)2003,JPO

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an electronic copying machine in which an image is formed by utilizing an electrophotographic method, an electrostatic recording method, etc.
The present invention relates to an electrostatic charge image developing toner used for developing an electrostatic latent image in a laser beam printer or the like.

[0002]

2. Description of the Related Art Conventionally, as a method of developing an electrostatic latent image formed on an electrostatic charge image bearing member such as an electrophotographic photosensitive member or an electrostatic recording member, fine toner is generally classified into an electrically insulating liquid. There are known two methods, a method using a dispersed liquid developer (wet developing method) and a method using a toner in which a colorant or magnetic powder is dispersed in a binder resin (dry developing method). In the dry development method, a method of using a two-component developer containing carrier particles and a toner and a method of using a one-component developer containing only a toner are known.

The electrostatic image developing toner used in these dry developing methods usually uses a styrene resin or a polyester resin as a binder resin, and a colorant such as a dye or a pigment is kneaded and cooled. After that, it is manufactured through a crushing and classification process. The particle size of the toner for developing an electrostatic charge image is usually about 1 to 30 μm. In the case of magnetic toner, magnetic powder such as magnetite is further used.
Further, as the carrier particles used in the two-component developer, glass beads, iron powder, ferrite, magnetite, etc., which are optionally coated with a resin, are used.

The electrostatic image developing toner as described above is required to hold positive or negative charges depending on the polarity of the electrostatic latent image to be developed. In order to retain the electric charge in the electrostatic image developing toner, the triboelectrification property of the toner components such as the binder resin and the colorant can be utilized, but this alone usually has a small charge amount and a stable polarity. Therefore, the image obtained by the development is easily fogged and becomes unclear. Therefore, a substance called a charge control agent is generally added to the toner in order to impart desired charging characteristics to the toner.

Typical examples of conventional charge control agents include:
For imparting a positive charging property to the toner, for example, a basic dye such as a triarylmethane dye, a nigrosine dye (Japanese Patent Publication No. 48-25669), and a quaternary ammonium salt (Japanese Patent Laid-Open No. 57-119364). Gazette), organotin oxide (Japanese Patent Publication No. 57-29704), and polymers having an amino group, such as electron donating substances, which impart negative chargeability to the toner, such as metal complexes of monoazo dyes and aromatic hydroxy compounds. Examples thereof include metal-containing dyes such as carboxylic acid metal compounds and chromium-containing organic dyes (copper phthalocyanine green, chromium-containing monoazo dyes).

In recent years, as a photoreceptor for an electrophotographic copying machine or a printer, a photoreceptor using an organic photoreceptor has become popular, and a positively chargeable toner is required as a developer for a copying machine using the organic photoreceptor. Has been. However, many of the positively chargeable charge control agents used for producing this positively chargeable toner are hydrophilic, and the charge amount is likely to decrease under high humidity conditions, while the charge amount decreases under high humidity conditions. Many of them do not have a problem that the charge amount becomes unnecessarily high under low humidity. In addition, there are many cases where the positively chargeable charge control agent suffers from deterioration due to heat when the toner is left at a high temperature for a long period of time, resulting in increased fog and scattering in the machine. For example, the Nigrosine dye is
Although it has high charging performance, the amount of charge on the toner becomes excessively high due to its very strong positive charging property, and the image density may decrease as the number of copies increases. Conditions required as a charge control agent It's hard to get anything that satisfies you. Further, the quaternary ammonium salt is
Due to its low charge imparting ability, fog may increase and scattering may occur in the machine as the number of copies increases under high temperature and high humidity. Furthermore, deterioration often occurs when left at high temperature and high humidity.

Further, triarylmethane dyes such as methyl violet, crystal violet, methyl violet base, and crystal violet base are
Although it exhibits excellent positive chargeability, it often has problems in water resistance or oil resistance and is practically difficult to use as a toner. If the water resistance is poor, the environmental stability will be poor, and the charge amount will decrease, especially in high humidity, causing fog to increase and scattering in the machine. Further, these dyes are eluted from the toner and cause image contamination. On the other hand, if the oil resistance is poor,
When using silicone oil etc. in the fixing unit,
When the toner melts, these dyes elute and cause color contamination of the fixing unit and the image.

[0008]

As described above, the triarylmethane dyes are relatively excellent positive charge control agents, but they also have various problems. Solving these problems, it is excellent in water resistance and oil resistance, has a moderately high amount of charge and is stable, has little dependency on temperature and humidity during development, and does not deteriorate toner properties due to being left at high temperature and high humidity. There is a demand for a positively chargeable charge control agent having excellent dispersibility in respect to the toner, excellent development characteristics and excellent durability, and a positively chargeable toner containing the same.

An object of the present invention is to provide a positively chargeable electrostatic image developing toner having excellent characteristics which does not have the above problems, that is, friction between a toner and a carrier and between a toner and a toner carrier such as a developing sleeve. It is an object of the present invention to provide a toner for developing an electrostatic charge image having a high charge amount, which is stable, is not affected by temperature and humidity, and can form a stable toner image, which has a positive chargeability.

Another object of the present invention is to provide a toner for developing a positively chargeable electrostatic image, which has a stable triboelectric charge amount even when the number of copies increases and does not cause fog or toner scattering in the machine. Is.

Another object of the present invention is to provide a positively chargeable electrostatic charge image developing toner capable of forming a clear image without fog in which a charge control agent is uniformly dispersed in the toner. That is.

A further object of the present invention is to provide a positively chargeable electrostatic image developing toner which does not deteriorate in toner characteristics due to thermal stress during toner storage.

As a result of intensive studies, the present inventors have found that C.I.
I. Solvent Violet 8 and 6 to 2 carbon atoms
The present invention has been accomplished by finding that the above object can be achieved by using a compound consisting of six saturated or unsaturated fatty acids as a charge control agent.

[0014]

That is, the first aspect of the present invention is to provide an electrostatic image developing toner containing at least a binder resin, a colorant, and a charge control agent, wherein the charge control agent is represented by the following general formula (1). The present invention relates to a toner for developing an electrostatic charge image, which contains a compound represented by the formula.

[Chemical 3] (Wherein, R represents a monovalent aliphatic group, saturated or unsaturated C ₅ ~C _25.)

The second invention is characterized in that the content of the compound represented by the general formula (1) is 0.1 to 10 parts by weight with respect to 100 parts by weight of the binder resin. The electrostatic charge image developing toner according to the first aspect of the present invention.

In a third aspect of the invention, the compound represented by the general formula (1) has a volume average particle size of 0.5 to 40 μm.
The present invention is the electrostatic charge image developing toner according to the first or second invention.

A fourth invention is the electrostatic image developing toner according to any one of the first to third inventions, wherein the toner has a positive charging property.

The fifth invention is the electrostatic image developing toner according to any one of the first to fourth inventions, wherein the toner is a non-magnetic toner.

The sixth invention is the electrostatic image developing toner according to any one of the first to fourth inventions, wherein the toner is a magnetic toner.

The seventh aspect of the present invention relates to C.I. of structural formula (2).
I. A toner for developing an electrostatic charge image comprising a compound obtained by reacting Solvent Violet 8 with a fatty acid represented by the following general formula (3).

[Chemical 4] (Wherein, R represents a monovalent aliphatic group, saturated or unsaturated C ₅ ~C _25.)

The present invention will be described in more detail below. Good as a positive charge control agent for electrostatic image developing toner,
The compound of the present invention is obtained by converting methyl violet represented by the structural formula (4) into a base group by using alkali metal hydroxide to form C.I. I. Solvent Viol
After obtaining et 8, it is a compound represented by the general formula (1) obtained by further reacting with a fatty acid represented by the general formula (3).

[Chemical 5] Specifically, methyl violet is added little by little to hard water of 50 to 70 ° C. to completely dissolve it, and the mixture is stirred while keeping the temperature warm. To convert. It may be taken into consideration that the base conversion is a reaction in which about 1 part by mole of the alkali hydroxide solution is used with respect to 1 part by mole of methyl violet. To confirm the end point of basing, it can be determined that the reaction solution was dropped on the filter paper, and when the bleeding disappeared, the end point was determined to be the base. At the end point of base formation, the dropping of the alkali hydroxide solution is stopped, the reaction solution is sufficiently stirred, suction filtration is performed, and the mixture is washed with water. After washing with water, the product remaining on the filter paper was dried to remove water with a dryer, and then C.I. I.
Solvent Violet 8 is obtained. Furthermore, 1 mol part of the fatty acid represented by the general formula (3) is 120 to
After melting at 140 ° C., C.I. I. Solvent V
1 mole part of iolet 8 is added little by little and mixed uniformly at a molar ratio of 1: 1. After that, 150-17
The temperature of the mixture is raised to 0 ° C., the mixture is sufficiently stirred to react, and then allowed to cool to room temperature to obtain the compound of the present invention.

In designing the compound of the present invention, it is necessary to fully select the above-mentioned fatty acid as a raw material in the selection. That is, those having a large molecular weight tend to have strong lipophilicity, excellent compatibility, wettability, and good dispersibility and distribution in the binder resin. On the other hand, those having a small molecular weight tend to have low resistance. Although the cause is not clear, in the case of unsaturated fatty acid, the larger the number of double bonds, the weaker the positive charging property tends to be.

Further, it is essential that the charge control agent has good water resistance and oil resistance. If the water resistance is poor, the charge control agent will elute from the toner under high humidity, making it impossible to impart good charge to the toner. Further, the image may be contaminated due to elution. On the other hand, if the oil resistance is poor, the charge control agent will elute in the fixing step or the like using silicone oil, which will contaminate the fixing member and also the copy image. For water resistance, 5
It can be confirmed by adding 500 mg of the charge control agent sample to 0 cc of water and visually confirming the solubility. The oil resistance can be confirmed by adding 500 mg of the charge control agent sample to 50 cc of silicone oil and visually confirming the solubility. The water resistance and oil resistance of the compound of the present invention were confirmed by these methods.

The fatty acid which can be used in the present invention is preferably a saturated or unsaturated fatty acid having 6 to 26 carbon atoms. Examples of saturated fatty acids include caproic acid,
Caprylic acid, capric acid, lauric acid, myristic acid,
Palmitic acid, stearic acid, arachidic acid, behenic acid, lignoceric acid, cerotic acid and the like can be used. Examples of unsaturated fatty acids include decylenic acid, dodecylenic acid, palmitoleic acid, oleic acid, ricinoleic acid, petroselinic acid, vaccenic acid, linoleic acid, linolenic acid, eleostearic acid, licanoic acid, parinaric acid, tariphosphoric acid, gadoleic acid. Acids, arachidonic acid, cetoleic acid, erucic acid, ceracoleic acid and the like can be used. Saturated or unsaturated fatty acids having 16 to 22 carbon atoms are preferable. Stronger positive electrification than this, dispersibility in the binder resin, good distributability, water resistance, oil resistance and the like are particularly stearic acid, palmitic acid, oleic acid, It is preferred to use linoleic acid. On the other hand, valeric acid, propionic acid, acetic acid, etc., which have less than 6 carbon atoms, are soluble in water, so these fatty acids and C.I. I. Solvent
The compound consisting of Violet 8 has poor water resistance,
It is difficult to use it as a charge control agent.

C. I. Solvent Violet
Although t 8 shows good positive chargeability, it has poor oil resistance and is difficult to use as a charge control agent for toner. However, water resistance and oil resistance can be improved by reacting with a saturated fatty acid or unsaturated fatty acid having 6 to 26 carbon atoms. The compound of the present invention obtained here is excellent in both water resistance and oil resistance, and has very stable positive charging property.

The compound of the present invention is ground by a grinder,
It can be used more effectively by adjusting to a desired particle size distribution. As the type of crusher, an airflow collision type crusher such as a jet mill, a turbo mill, KTM, MV
A mechanical impact type crusher such as M is used. A good particle size distribution for the charge control agent of the present invention is 0.5 in terms of volume average particle size.
˜40 μm, more preferably 1-20 μm
Good to be. If the particles having a particle size larger than 40 μm are contained, it becomes difficult to disperse the charge control agent in the binder resin, and it becomes impossible to disperse the charge control agent in the toner. In addition, the content of the charge control agent per toner particle becomes uneven, which causes an increase in fog and scattering in the machine. On the other hand, when the particles having a particle size smaller than 0.5 μm are used, the dispersion in the binder resin is good,
The specific surface area of the charge control agent becomes large, and the toner is excessively charged, the charge amount increases, and the image density decreases.

The amount of the compound of the present invention used in the toner for developing an electrostatic image varies depending on the kind of the binder resin used,
Usually, 0.1 to 10 parts by weight, preferably 0.5 to 5 parts by weight, and more preferably 0.
8 to 3 parts by weight.

In the electrostatic image developing toner of the present invention, as the charge control agent, other charge control agents may be used in addition to the compound of the present invention for the purpose of finely adjusting the charge control of the toner. . As such a charge control agent, any known charge control agent which has been known to be capable of imparting a positive chargeability to a toner may be used, and among them, a nigrosine dye or Quaternary ammonium salts are preferred.

As the constituent components of the toner for developing an electrostatic image of the present invention, a binder resin and a colorant, which are known materials constituting the toner, are used in addition to the charge control agent of the present invention. When a magnetic toner is obtained, a magnetic powder is further used. When a magnetic powder is used, the magnetic powder may be used as a coloring agent. Therefore, in the present invention, the colorant also includes magnetic powder. If necessary, a releasing agent, a lubricant, a fluidity improving agent, an abrasive, a conductivity-imparting agent, an image peeling preventing agent, etc. are internally or externally added to the electrostatic image developing toner.

Specific examples of the binder resin used in the toner of the present invention include styrene-based polymers such as polystyrene, poly-p-chlorostyrene, and homopolymers of substituted styrenes such as polyvinyltoluene. Styrene-p-chlorostyrene copolymer, styrene-propylene copolymer, styrene-vinyltoluene copolymer, styrene-vinylnaphthalene copolymer, styrene-acrylic copolymer, styrene-α-chloromethacrylic acid methyl ester Copolymer, styrene-vinyl methyl ether copolymer,
Styrene-vinyl ethyl ether copolymer, styrene-
Vinyl methyl ketone copolymer, styrene-butadiene copolymer, styrene-isoprene copolymer, styrene-acrylonitrile-indene copolymer, styrene-dimethylaminoethyl acrylate copolymer, styrene diethylaminoethyl acrylate copolymer, styrene- Styrene-based copolymers such as butyl acrylate-diethylaminoethyl methacrylate copolymer, cross-linked styrene-based copolymers, etc .; polyester resins such as aliphatic dicarboxylic acids, aromatic dicarboxylic acids, aromatic dialcohols, diphenols Polyester resin having a monomer selected from the structural units as a structural unit, cross-linked polyester resin, etc .; other polyvinyl chloride, phenol resin, modified phenol resin, malein resin, rosin modified maleic resin, polyvinyl acetate Silicone resins, polyurethane resins, polyamide resins, epoxy resins, polyvinyl butyral, rosin, modified rosin, terpene resin, xylene resin, aliphatic or aliphatic hydrocarbon resins, and petroleum resins.

Examples of the acrylic monomer used in the styrene / acrylic copolymer include acrylic acid and methacrylic acid, methyl acrylate, ethyl acrylate, butyl acrylate, dodecyl acrylate, octyl acrylate. , 2-ethylhexyl acrylate, phenyl acrylate, methyl methacrylate, ethyl methacrylate,
Examples thereof include (meth) acrylic acid esters such as butyl methacrylate and octyl methacrylate, and examples of monomers that can be used with these include acrylonitrile, methacrylonitrile, acrylamide, maleic acid, and maleic acid such as butyl maleate. Acid half ester or diester, vinyl acetate, vinyl chloride,
Examples thereof include vinyl ethers such as vinyl methyl ether, vinyl ethyl ether, vinyl propyl ether and vinyl butyl ether, and vinyl ketones such as vinyl methyl ketone, vinyl ethyl ketone and vinyl hexyl ketone.

As the cross-linking agent used for producing the above-mentioned cross-linked styrenic polymer, compounds mainly having two or more unsaturated bonds can be mentioned, and specific examples thereof include divinylbenzene and divinyl. Aromatic divinyl compounds such as naphthalene; Carboxylic esters having two or more unsaturated bonds such as ethylene glycol diacrylate and ethylene glycol dimethacrylate; Divinyl compounds such as divinylaniline, divinyl ether, divinyl sulfide and divinyl sulfone; and unsaturated The compounds having three or more bonds can be used alone or in combination. The cross-linking agent is used in an amount of 0.01 to 10% by weight, preferably 0.05 to 5% by weight, based on 100 parts by weight of the binder resin.

These resins can be used alone or in combination of two or more kinds. Of these resins, styrene polymers and polyester resins are preferable because they exhibit particularly excellent charging characteristics. The molecular weight distribution measured by GPC (gel permeation chromatography) has at least one peak in the region of 1x10 ³ to 5x10 ⁴ and at least one peak or shoulder in the region of 10 ⁵ or more. Such a molecular weight can be obtained by using a styrene-based copolymer that has the above-mentioned styrene-based copolymer, further two or more kinds of resins, for example, a combination of the styrene resin and a styrene-acrylic copolymer or a combination of two or more kinds of styrene-acrylic copolymers. A resin composition having a distribution is preferable from the viewpoint of toner pulverizability and fixing property.

Further, when the pressure fixing method is used, a binder resin for pressure toner can be used. Examples of such resins include polyethylene, polypropylene, polymethylene, polyurethane elastomer, ethylene-ethyl acrylate copolymer, styrene-isoprene copolymer, linear saturated polyester, paraffin and other waxes.

As the colorant that can be used in the toner for developing an electrostatic image of the present invention, any of the colorants known to be used in the production of conventional toners can be used. Examples thereof include fatty acid metal salts, various carbon blacks, phthalocyanine-based, rhodamine-based, quinacridone-based, triarylmethane-based, anthraquinone-based, azo-based and diazo-based dyes and pigments. These may be used alone or in admixture of two or more.

The magnetic powder used in the toner for developing an electrostatic charge image of the present invention is any powder such as alloys and compounds containing a ferromagnetic element, which are conventionally used in the production of magnetic toners. Good. Examples of these magnetic powders include iron oxide such as magnetite, maghemite, and ferrite, or a compound of a divalent metal and iron oxide, metals such as iron, cobalt, and nickel, or aluminum, cobalt, copper, and lead of these metals. , Magnesium, tin, zinc, antimony, beryllium, bismuth, cadmium,
Examples thereof include powders of alloys of metals such as calcium, manganese, selenium, titanium, tungsten and vanadium, and mixtures thereof. These magnetic powders preferably have an average particle size of 0.1 to 2 μm, more preferably 0.1 to 0.5 μm. The content of the magnetic powder in the toner is
The amount is about 20 to 200 parts by mass, preferably 40 to 150 parts by mass with respect to 100 parts by mass of the thermoplastic resin. Further, the saturation magnetization of the toner is preferably 15 to 35 emu / g (measurement magnetic field: 1 kilo Oersted).

The toner of the present invention can be mixed with a carrier and used as a two-component developer. The carrier that can be used with the toner of the present invention may be any conventionally known carrier. Examples of the carrier that can be used include magnetic powder such as iron powder, ferrite powder, nickel powder, glass beads, and the like, or those whose surface is treated with a resin or the like. As the resin coating the carrier surface,
Styrene-acrylic acid ester copolymer, styrene-methacrylic acid ester copolymer, acrylic acid ester copolymer, methacrylic acid ester copolymer, fluorine-containing resin, silicone-containing resin, polyamide resin, ionomer resin, polyphenylene sulfide resin, etc. Or a mixture of these. Among these, a fluorine-containing resin and a silicone-containing resin are particularly preferable because they rarely form spent toner.

The particle size of the toner for developing an electrostatic charge image of the present invention is
Weight average particle diameter is 1 to 30 μm, preferably 3 to 15 μm
Is desirable. In particular, 12 to 60% by number of toner particles having a particle size of 5 μm or less are contained, and 8 to 12.
1 to 33% by number of toner particles having a particle size of 7 μm are contained, and 2.0% of toner particles having a particle size of 16 μm or more are contained.
It is contained in an amount of not more than 5% by weight, and the weight average particle diameter of the toner is 4 to 10
Those having a thickness of μm are more preferable from the viewpoint of developing characteristics. The particle size distribution of the toner can be measured using, for example, a Coulter counter.

In the toner of the present invention, known additives such as a releasing agent, a lubricant, a fluidity improving agent, an abrasive, a conductivity-imparting agent, an image peeling preventing agent, etc., which are used in the production of the toner, may be added, if necessary. The agent may be added internally or externally, and examples of these additives include mold release agents such as low molecular weight polyethylene, low molecular weight polypropylene, microcrystalline wax, carnauba wax, sazol wax, and paraffin wax. Wax-like substances such as, for example, are usually added to the toner in an amount of about 0.5 to 5% by weight. Further, as the lubricant, polyvinylidene fluoride, zinc stearate and the like, as the fluidity improver, silica produced by a dry method or a wet method,
Aluminum oxide, titanium oxide, silicon-aluminum co-oxide, silicon-titanium co-oxide, and those obtained by subjecting these to a hydrophobic treatment are used as polishing agents, and silicon nitride, cerium oxide, silicon carbide, strontium titanate, tungsten carbide, carbonic acid, etc. Examples of the conductivity-imparting agent include calcium and those obtained by hydrophobizing them, and carbon black, tin oxide and the like. Further, fine powder of a fluorine-containing polymer such as polyvinylidene fluoride is preferable from the viewpoints of fluidity, abradability, charge stability and the like.

In the present invention, hydrophobized silica, hydrophobized aluminum oxide, hydrophobized silicon-aluminum co-oxide or hydrophobized silicon-titanium co-oxide fine powder is excluded. It is preferably used as an additive. Examples of the hydrophobic treatment of the silica fine powder include treatment with a silane coupling agent such as silicone oil, dichlorodimethylsilane, hexamethyldisilazane, and tetramethyldisilazane. Also,
It is preferable to use positively charged silica having a positive triboelectric charge with respect to the iron powder carrier when measured by the blow-off method. In order to obtain this positively charged silica, it may be treated with a silicone oil having an organo group having at least one nitrogen atom in its side chain or a nitrogen-containing silane coupling agent. The amount of the silica fine powder subjected to the hydrophobic treatment is 0.01 per weight of the developer.
-20%, preferably 0.03-5%.

The toner according to the present invention can be manufactured by a conventionally known toner manufacturing method. Generally, the toner constituent material as described above is prepared by a ball mill,
After thoroughly mixing with a mixer such as a Henschel mixer, knead well using a heat kneader such as a heat roll kneader or a single-screw or twin-screw extruder, and after cooling and solidifying, mechanically using a crusher such as a hammer mill. It is preferable to roughly pulverize, then finely pulverize with a jet mill or the like, and then classify. After further classification, it is preferable to use the external additive after thoroughly mixing it with a mixer such as a Henschel mixer. However, the method for producing the toner is not limited to this method, and other toner constituent materials are dispersed in the binder resin solution and then spray-dried, that is, a method for producing a toner by a so-called microcapsule method, and a binder. Other methods, such as a polymerization method in which a predetermined material is mixed with a monomer forming a resin and emulsion or suspension polymerization is performed to obtain a toner, can be adopted.

The toner for developing an electrostatic charge image of the present invention is preferably developed for any method or apparatus for forming a dry toner image by utilizing conventionally known electrophotography, electrostatic recording or electrostatic printing. It can be used as a toner.

[0043]

The present invention will be described in more detail with reference to the following examples, but the embodiments of the present invention are not limited to these examples.

Production Example of Charge Control Agent Production Example 1 To 8000 g of hard water at 60 ° C., 385 g of methyl violet was added little by little and dissolved. After stirring for 15 minutes while keeping warm, 1
A 0% aqueous sodium hydroxide solution was added over about 30 minutes to base methyl violet. The base decision is N
o. 2 The end point was the point where the bleeding of the reaction solution disappeared by instilling it on filter paper. At this time, the sodium hydroxide aqueous solution used for basification was 373 g. After basification, the mixture is stirred for 5 minutes, suction filtered, washed with 2500 g of water, and the filter residue is dried at 50 ° C. for 18 hours, then 70
Dried for 5 hours at 285 ° C. and 285 g of C.I. I. Solvent
Violet 8 was obtained. Further, 213.0 g of stearic acid was placed in the stainless steel tray, and the stainless steel tray was heated to 130 ° C. with a heater to dissolve the stearic acid. After that, C.I. I. Solvent Violet
8,281.0g was added little by little and mixed uniformly. After setting the heater temperature to 160 ° C., the mixture was stirred for 10 minutes and then allowed to cool to room temperature. After that, the charge control agent 1 having a volume average particle size of 7.6 μm is pulverized by a pulverizer (jet mill).
Got

[Chemical 6]

Production Example 2 A charge control agent 2 having an average particle size of 7.6 μm was obtained in the same manner as in Production Example 1 except that palmitic acid was used instead of stearic acid.

[Chemical 7]

Production Example 3 A charge control agent 3 having an average particle size of 7.5 μm was obtained in the same manner as in Production Example 1 except that oleic acid was used instead of stearic acid.

[Chemical 8]

Production Example 4 A charge control agent 4 having an average particle size of 7.7 μm was obtained in the same manner as in Production Example 1 except that linoleic acid was used instead of stearic acid.

[Chemical 9]

Production Example 5 A charge control agent 5 having an average particle size of 7.5 μm was obtained in the same manner as in Production Example 1 except that caproic acid was used instead of stearic acid.

[Chemical 10]

Production Example 6 A charge control agent 6 having an average particle size of 7.6 μm was obtained in the same manner as in Production Example 1 except that cerotic acid was used instead of stearic acid.

[Chemical 11]

Comparative Production Example 1 The C.I. I. Solvent Viol
Et 8 was crushed by a crusher (jet mill) to have an average particle size of 7.6.
It was pulverized to μm.

Comparative Production Example 2 A charge control agent 7 having an average particle size of 7.5 μm was prepared in the same manner as in Production Example 1 except that valeric acid was used instead of stearic acid.
Got

[Chemical 12]

[0052]

[Table 1]

Example 1 Styrene-n-butyl acrylate copolymer 87.5 parts by weight carbon black 8 parts by weight Charge control agent 12 parts by weight Polypropylene wax 2 parts by weight Polyethylene wax 0.5 parts by weight The above materials were mixed with a Henschel mixer. After uniformly mixing, the mixture was put into a twin-screw heating kneader, kneaded, and extruded was cooled at room temperature and coarsely crushed with a hammer mill to obtain chips.
Next, this was finely pulverized with a turbo mill pulverizer, introduced into a classifier, and a portion having an average particle size of 11.5 μm was taken out as fine powder for toner. Next, with respect to 100 parts by weight of this fine powder for toner, positively chargeable hydrophobic silica fine powder 0.
3 parts by weight, and tungsten carbide fine powder 0.4
By weight, the mixture was mixed with a Henschel mixer to obtain a positively chargeable non-magnetic toner. 4 parts of the obtained toner was mixed with 100 parts of a carrier coated with a silicone resin having an average particle size of 100 μm using a ball mill to prepare a developer. Next, using this toner and developer, a commercially available copying machine FP773
5 (manufactured by Matsushita Electric Transmission Co., Ltd.), high temperature and high humidity (30 ° C, 85%
The live-action test was performed under the environment of (RH). At this time, the toner is placed in a drier to accelerate the confirmation of heat deterioration and to identify it.
The mixture was heated under the conditions of ° C and 72 hours. When the obtained toner and developer were used, fogging was small even after actual copying of 50,000 sheets, the image density was stable, and neither toner scattering in the machine nor image stain was observed. The image densities at the initial copying and 50,000 copying were 1.39 and 1.38, respectively, and the fog at the initial copying and 50,000 copying were 0.5 and 0.4, respectively.
Met.

The image density is measured by using a Macbeth photometer and may be 1.35 or more. The fogging was performed by measuring the reflectance with a photo bolt. A value of 1.2% or less is a good value. The toner scattering inside the machine was performed by confirming whether the scattered toner was present on the transfer charger of the copying machine. When the toner scattering is seen on the transfer charger, the image stain is generated accordingly.

Examples 2 to 6 and Comparative Examples 1 to 4 Instead of using the charge control agent 1 used in Example 1, Table 2
The same evaluation as in Example 1 was carried out except that the charge control agent described in 1. was used. The results are shown in Table 3.

[0056]

[Table 2]

Example 7 Styrene-n-butyl acrylate copolymer 55.5 parts by weight Magnetic iron oxide 40 parts by weight Charge control agent 12 parts by weight Polypropylene wax 2 parts by weight Paraffin wax 0.5 parts by weight are mixed with a Henschel mixer. After that, put into a twin-screw heating kneader, knead, and cool the extruded one at room temperature,
Coarse crushing with a hammer mill gave chips. Then, this is pulverized with a turbo mill pulverizer and introduced into a classifier to obtain 10μ.
A portion having an average particle size in m was taken out as a fine powder for toner. To 100 parts by weight of this toner fine powder, 0.25 parts by weight of silica hydrophobized with silicone oil was added and mixed with a Henschel mixer to obtain a positively chargeable magnetic toner, and this toner was heated with time. I checked. The heat aging test was carried out by placing the toner in a dryer at 50 ° C. for 72 hours.
After leaving it to stand for a while to accelerate the heat deterioration, it was used to remove 23 by using a commercially available copying machine (copying machine NP4145 manufactured by Canon Inc.).
It was based on continuous continuous shooting of 50,000 sheets at an environmental condition of 50 ° C. The image densities at the initial copying and 50,000 copying were 1.42 and 1.39, respectively, and the fog at the initial copying and 50,000 copying were 0.4 and 0.5, respectively, which were not particularly changed. Furthermore, there was no scattering of toner particles inside the machine after copying 50,000 sheets, and there was no stain on the obtained image.

Examples 8 to 12 and Comparative Examples 5 to 8 Instead of using the charge control agent 1 used in Example 7, Table 3
The same evaluation as in Example 7 was carried out except that the charge control agent described in 1 was used. The results are shown in Table 3.

[0059]

[Table 3]

[0060]

As described above, by using the compound of the present invention as a charge control agent for a toner for developing an electrostatic charge image, a toner for developing an electrostatic charge image in which a charge control agent is uniformly dispersed can be obtained. This toner has a good image density from the initial stage and can obtain a fog-free copy image, and the image density does not decrease even when a large number of copies are piled up, and the electrostatic charge image of the present invention can be obtained. It is possible to obtain a good toner which does not change with time due to heating and does not change in characteristics due to heat stress during storage or transportation of the toner before or after purchase.

Claims (7)

[Claims] 1. An electrostatic charge image developing toner containing at least a binder resin, a colorant and a charge control agent, wherein the charge control agent is a compound represented by the following general formula (1). Toner for charge image development. [Chemical 1] (Wherein, R represents a monovalent aliphatic group, saturated or unsaturated C ₅ ~C _25.) 2. The electrostatic charge according to claim 1, wherein the content of the compound represented by the general formula (1) is 0.1 to 10 parts by weight with respect to 100 parts by weight of the binder resin. Toner for image development. 3. The toner for developing an electrostatic image according to claim 1, wherein the compound represented by the general formula (1) has a volume average particle size of 0.5 to 40 μm. 4. The toner for developing an electrostatic charge image according to claim 1, wherein the toner has a positive charging property. 5. The toner for developing an electrostatic charge image according to claim 1, wherein the toner is a dry non-magnetic toner. 6. The toner for developing an electrostatic charge image according to claim 1, wherein the toner is a dry magnetic toner. 7. C.I. of structural formula (2) I. Solvent
A toner for developing an electrostatic image, comprising a compound obtained by reacting Violet 8 with a fatty acid represented by the general formula (3). [Chemical 2] (Wherein, R represents a monovalent aliphatic group, saturated or unsaturated C ₅ ~C _25.)