JP3313871B2 - Toner for electrostatic image development - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a toner for developing an electrostatic image containing a specific compound.

[0002]

2. Description of the Related Art In an electrophotographic image forming process, an electrostatic latent image is formed on an inorganic photoreceptor such as selenium, a selenium alloy, cadmium sulfide, amorphous silicon, or an organic photoreceptor using a charge generating agent and a charge transporting agent. It is developed with a toner, transferred to paper or a plastic film, and fixed to obtain a visible image.

[0003] The photoreceptor has a positive charging property and a negative charging property depending on its configuration. When a printed portion is left as an electrostatic latent image by exposure, it is developed with a reverse-charging toner, while the printed portion is discharged. When reverse development is performed, development is performed with the same sign charging toner. A toner is composed of a binder resin, a colorant and other additives. In general, a charge control agent is used to impart desirable frictional charging characteristics (charging speed, charging level, charging stability, etc.), stability over time, and environmental stability. Is used. The characteristics of the toner are greatly affected by the charge control agent.

In the case of a color toner, a light-colored, preferably colorless, charge control agent which does not affect the hue is required. These light-colored or colorless charge control agents include, for example, Japanese Patent Publication No. 55-4 for negatively chargeable toners.
No. 2752, JP-A-61-69073, metal complex salt compounds of hydroxybenzoic acid derivatives described in JP-A-61-221756 and the like.
No. 541, etc., metal salts of aromatic dicarboxylic acids, JP-A-61-141453, JP-A-62
Metal complex salt compounds of anthranilic acid derivatives described in JP-A-94856 and the like, organoboron compounds described in U.S. Pat. There are biphenol compounds and the like. Japanese Patent Application Laid-Open Nos. 57-119364 and 58-9
There are quaternary ammonium salt compounds described in JP-A-154-154 and JP-A-58-98742.

[0005] However, these charge control agents are chromium compounds of which environmental concerns are a concern, cannot be completely colorless, or have a low charge-providing effect, and are mostly reverse-charged toners. There were drawbacks such as poor dispersibility and poor compound stability, and none of them had satisfactory performance as a charge control agent.

[0006]

DISCLOSURE OF THE INVENTION The present invention provides a compound having good stability, good dispersibility in a binder resin, no deterioration during toner production, and a charge characteristic due to friction under various environmental conditions. An object of the present invention is to provide a toner which always provides a good and high-quality image stably.

[0007]

Means for Solving the Problems The present inventors have found a colorless and stable compound which has good dispersibility with a binder resin and can impart good charging characteristics to a toner. As a result, an excellent toner was invented.

That is, the present invention provides the following general formula (1)

[0009]

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[Wherein R ₁ has a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a hydroxyl group, an alkoxyl group having 1 to 8 carbon atoms, an amino group, an alkylamino group having 1 to 8 carbon atoms or a substituent. Represents a phenyl group which may be substituted, and R ₂ represents an alkyl group having 4 to 12 carbon atoms which may have a substituent,

[0011]

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(R ₃ is a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a hydroxyl group, an alkoxyl group having 1 to 8 carbon atoms, a halogen atom, a nitro group, an amino group, a carbamoyl group, an alkylamino group, a carboxyl group, 1-8 carbon atoms
Represents an ester group or an acetyl group, m represents an integer of 1 to 5), or represents a heterocyclic compound containing a nitrogen or oxygen atom, and n represents an integer of 4 to 8], or the following general formula (2 )

[0013]

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[In the formula, R ₄ represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, and R ₅ represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a hydroxyl group, and a phenyl which may have a substituent. A group, an alkoxyl group having 1 to 8 carbon atoms, an amino group or an alkylamino group having 1 to 8 carbon atoms, wherein R ₆ is a hydrogen atom, an alkyl group having 1 to 12 carbon atoms which may have a substituent, or The following general formula

[0015]

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(R ₇ is a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a hydroxyl group, an alkoxyl group having 1 to 8 carbon atoms, a halogen atom, a nitro group, an amino group, a carbamoyl group, an alkylamino group, a carboxyl group, 1-8 carbon atoms
Represents an ester group or an acetyl group, m 'represents an integer of 1 to 5), or a heterocyclic compound containing a nitrogen or oxygen atom, and n' represents an integer of 4 to 8]. And a toner for developing an electrostatic image.

The compounds represented by the general formulas (1) and (2) contained in the toner for electrostatic charge development of the present invention are produced by a known synthesis method.

The present invention basically comprises a binder resin, a colorant and the compound represented by the general formula (1) or (2) according to the present invention. The mixture is kneaded under melting of the binder resin by a heating and mixing apparatus, and after kneading, cooling, coarse pulverization, fine pulverization, a method of obtaining by classification, dissolving these mixtures in a solvent, atomizing by spraying, drying, How to classify and get
There is a method in which a colorant or a charge controlling agent represented by the general formula (1) or (2) is dispersed in the suspended monomer particles to obtain a polymer by a polymerization method.

As the binder resin, polystyrene,
Styrene-methacrylate copolymer, styrene-
Propylene copolymer, styrene-butadiene copolymer,
Acrylic resin, styrene-maleic acid copolymer, olefin resin, polyester, epoxy resin, polyurethane resin, polyvinyl butyral, and the like can be used alone or in combination.

As a coloring agent, carbon black is generally used for a black toner, and the following coloring agents can be used for a color toner. As the yellow colorant, C.I. I. Pigment Yellow 1, C.I. I.
Pigment Yellow 5, C.I. I. Pigment Yellow 1
2, C.I. I. Azo organic pigments such as CI Pigment Yellow 17, inorganic pigments such as loess or C.I. I. Solvent Yellow 2, C.I. I. Solvent Yellow 6, C.I. I. Solvent Yellow 14, C.I. I. Solvent Yellow 19
Such as oil-soluble dyes, etc.

Examples of the magenta colorant include C.I. I. Pigment Red 57, C.I. I. Azo pigments such as CI Pigment Red 57: 1, C.I. I. Pigment Violet 1, C.I.
I. Xanthene pigments such as CI Pigment Red 81;
I. Pigment Red 87, C.I. I. Butt Red 1,
C. I. Thioindigo pigments such as CI Pigment Violet 38 or C.I. I. Solvent Red 19, C.I. I. Solvent Red 49, C.I. I. Oil-soluble dyes such as Solvent Red 52,

Cyan colorants include C.I. I. Triphenylmethane pigments such as C.I. Pigment Blue 1; I. Pigment Blue 15, C.I. I. Phthalocyanine pigments such as CI Pigment Blue 17 or C.I. I. Solvent Blue 2
5, C.I. I. Solvent Blue 40, C.I. I. Known colorants such as oil-soluble dyes such as Solvent Blue 70 can be used.

Specific examples of the compound according to the present invention which can be used as a charge control agent include the following.

Compound No (1)

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Compound No. (2)

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Compound No. (3)

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Compound No (4)

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Compound No (5)

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Compound No (6)

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Compound No. (7)

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Compound No. (8)

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Compound No (9)

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Compound No. (10)

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Compound No. (11)

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Compound No. (12)

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Compound No (13)

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Compound No (14)

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Compound No (15)

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Compound No (16)

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Compound No (17)

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Compound No (18)

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Compound No (19)

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Compound No (20)

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Compound No (21)

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Compound No (22)

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Compound No (23)

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Compound No (24)

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Compound No (25)

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Compound No (26)

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Compound No (27)

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Compound No (28)

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Compound No (29)

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Compound No (30)

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Compound No (31)

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Compound No (32)

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Compound No (33)

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Compound No (34)

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In the toner, a photoreceptor
For the purpose of protecting the carrier, improving the fluidity of the toner, adjusting the thermal, electrical, and physical properties, adjusting the resistance, adjusting the softening point, and improving the fixing property, for example, hydrophobic silica, metal soap, a fluorine-based surfactant, Dioctyl phthalate, wax, tin oxide, conductive zinc oxide and the like are used as needed.

When the toner of the present invention is used as a two-component developer, the carrier may be a binder type carrier of fine glass beads, iron powder, ferrite powder, resin particles in which magnetic particles are dispersed, or a polyester resin. Fluorinated resin,
A resin-coated carrier coated with an acrylic resin, a silicon resin, or the like is used. Further, the toner of the present invention shows excellent performance even when used as a one-component toner.

[0060]

The present invention will be described below in detail with reference to examples. Parts in Examples are parts by weight.

Example 1 1 part of (Compound No. (9)), 5 parts of carbon black, and 94 parts of styrene-ethylhexyl methacrylate copolymer were kneaded by a heating and mixing apparatus, cooled, and coarsely ground by a hammer mill. After finely pulverizing with a jet mill, classify it 1
A black toner of 0 to 12 μm was obtained. This toner was mixed with an iron powder carrier at a weight ratio of 4 to 100 and shaken. As a result, the toner was negatively charged, and the charge was -23 μc / g as measured by a blow-off powder charge meter. When an image was produced using a modified commercial copying machine using this toner, clear images were obtained at the initial stage and after 10,000 copies.

Example 2 1 part of Compound No. (16), 5 parts of carbon black,
Styrene-ethylhexyl methacrylate copolymer 94
The mixture was kneaded with a heating and mixing device, cooled, and coarsely ground with a hammer mill. After finely pulverized by a jet mill, the mixture was classified to obtain a black toner of 10 to 12 μm. This toner was mixed with an iron powder carrier at a weight ratio of 4 to 100 and shaken. As a result, the toner was negatively charged, and the charge was -18 μc / g as measured by a blow-off powder charge meter.
When an image was produced using a modified commercial copying machine using this toner, clear images were obtained at the initial stage and after 10,000 copies.

Example 3 One part of (Compound No. (9)), 5 parts of a copper phthalocyanine oil-soluble dye, Spiron Blue 2BNH (a product of Hodogaya Chemical Industry Co., Ltd.), and 94 parts of a styrene-butyl methacrylate copolymer were heated. Kneading with a mixing device,
After cooling, it was coarsely ground with a hammer mill. After finely pulverizing with a jet mill, the mixture was classified to obtain a blue toner of 10 to 12 μm. This toner was mixed with an iron powder carrier at a weight ratio of 4 to 100 and shaken. As a result, the toner became negatively charged.
It was 25 μc / g. When an image was produced using a modified commercial copying machine using this toner, clear images were obtained at the initial stage and after 10,000 copies.

Example 4 1 part of (Compound No. (9)), 5 parts of carbon black, and 94 parts of a styrene-ethylhexyl methacrylate copolymer were kneaded by a heating and mixing apparatus, cooled, and coarsely ground by a hammer mill. After finely pulverizing with a jet mill, classify it 1
A black toner of 0 to 12 μm was obtained. This toner was mixed with a silicon coating carrier at a weight ratio of 4 to 100, and the toner was negatively charged when shaken. The charge amount was -15 μm as measured by a blow-off powder charge amount measuring device.
c / g. When an image was produced using a modified commercial copying machine using this toner, clear images were obtained at the initial stage and after 10,000 copies.

Example 5 1 part of (Compound No. (6)), 5 parts of carbon black and 94 parts of styrene-ethylhexyl methacrylate copolymer were kneaded by a heating and mixing apparatus, cooled, and coarsely ground by a hammer mill. After finely pulverizing with a jet mill, classify it 1
A black toner of 0 to 12 μm was obtained. This toner was mixed with an acrylic coating carrier at a weight ratio of 4 to 100, and shaken. As a result, the toner was negatively charged.
c / g. When an image was produced using a modified commercial copying machine using this toner, clear images were obtained at the initial stage and after 10,000 copies.

Example 6 One part of (Compound No. (31)), 60 parts of magnetic iron powder and 100 parts of a styrene-acrylic copolymer were kneaded by a heating and mixing apparatus, cooled, and coarsely ground by a hammer mill. After finely pulverized by a jet mill, the mixture was classified to obtain a black toner of 10 to 12 μm. When an image was produced using a modified commercial copying machine using this one-component toner, a clear image could be obtained at the initial stage and after 10,000 copies.

Examples 7 to 13 The same procedures as in Example 1 were carried out except for using the compounds shown in Table 1 in place of the compound No. (9) in Example 1, to obtain the results shown in Table 1.

[0068]

[Table 1]

[0069]

The toner containing the compound of the present invention as a charge control agent has good environmental resistance and stability over time. As a result, the toner for developing a high-quality electrostatic image is free from copy contamination. Further, since the charge control agent itself is white or substantially colorless (does not affect the coloring of the colorant), it is possible to select an arbitrary colorant according to the hue required for the color toner. It is also characterized in that it does not hinder the original hue of dyes and pigments.

──────────────────────────────────────────────────続 き Continued on front page (58) Field surveyed (Int.Cl. ⁷ , DB name) G03G 9/097 CA (STN)

Claims (1)

(57) [Claims] [Claim 1] The following general formula (1) ... (1) wherein R ₁ is a hydrogen atom, an alkyl group having 1 to 12 carbon atoms,
A hydroxyl group, an alkoxyl group having 1 to 8 carbon atoms, an amino group, an alkylamino group having 1 to 8 carbon atoms or a phenyl group which may have a substituent, and R ₂ may have a substituent An alkyl group having 4 to 12 carbon atoms, or the following general formula: (R ₃ is a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a hydroxyl group, an alkoxyl group having 1 to 8 carbon atoms, a halogen atom, a nitro group, an amino group, a carbamoyl group, an alkylamino group, a carboxyl group, Represents an ester group or an acetyl group of -8, m represents an integer of 1-5), or represents a heterocyclic compound containing a nitrogen or oxygen atom;
Represents an integer of 4 to 8], or the following general formula (2): (2) wherein R ₄ represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, R ₅ represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms,
A hydroxyl group, a phenyl group which may have a substituent, an alkoxyl group having 1 to 8 carbon atoms, an amino group or 1 to carbon atoms;
8 represents an alkylamino group, and R ₆ represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms which may have a substituent, or the following general formula: (R ₇ is a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a hydroxyl group, an alkoxyl group having 1 to 8 carbon atoms, a halogen atom, a nitro group, an amino group, a carbamoyl group, an alkylamino group, a carboxyl group, Represents an ester group or an acetyl group of -8, and m 'represents an integer of 1-5),
Or represents a heterocyclic compound containing a nitrogen or oxygen atom,
n 'represents an integer of 4 to 8].