JPH07104519A - Toner for developing electrostatic charge image - Google Patents

Abstract

PURPOSE:To prevent deterioration at the time of producing a toner and to obtain a toner having satisfactory triboelectric chargeability under various environmental conditions and always stably giving an image having high image quality by incorporating a specified compd. CONSTITUTION:This toner consists of a resin binder, a colorant and a compd. represented by the formula, wherein each of X and X' is H, lower alkyl, lower alkoxy or halogen, X and X' may be the same as or different from each other each of (m) and (m') is an integer of 1-3, each of R and R' is a halogen, R and R' may be the same as or different from each other, each of (n) and (n') is an integer of 1-3 and A is an optionally substd. 4-40C aliphatic ammonium ion. The compd. represented by the formula causes no environmental problem and has satisfactory stability as a colored compd. and improved dispersibility to the resin binder.

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 charge 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, or amorphous silicon, or an organic photoreceptor using a charge generating agent and a charge transporting agent. After being formed, it is developed with toner, transferred to paper or a plastic film, and fixed to obtain a visible image.

The photosensitive member has a positive charging property and a negative charging property depending on its constitution. When the printing portion is left as an electrostatic latent image by exposure, it is developed with a toner of opposite sign charging, while the printing portion is discharged. When reversal development is carried out, the development is carried out with a toner having the same sign. A toner is composed of a binder resin, a colorant and other additives, but is generally a charge control agent in order to impart desirable triboelectrification characteristics (charging speed, charging level, charging stability, etc.), temporal stability and environmental stability. Is used. The characteristics of the toner are greatly affected by this charge control agent.

Negative charging toner is used in the case of developing with the opposite sign charging toner using the positive charging photosensitive member and in the case of reversal development using the negative charging photosensitive member. In this case, the negative charging toner is used. A sex charge control agent is used.

Examples of the charge control agent include, for example, Japanese Patent Laid-Open No. 61-61.
-101558, JP-A-61-155463, JP-A-61-155464, etc., azo metal complex salt compounds, JP-B-55-42752, JP-A-61-69073, etc. Described metal complex salt compound of hydroxybenzoic acid derivative, JP-A-57-111
Aromatic dicarboxylic acid metal salt compounds described in JP-A No. 541 and the like, JP-A-61-141453 and JP-A-62.
-94856, etc., metal complex salt compounds of anthranilic acid derivatives, USP-4767688,
There are organic boron compounds described in JP-A-1-306861 and the like, and biphenol compounds described in JP-A-61-3149.

However, these charge control agents have drawbacks such as chromium compounds, which may cause environmental problems, compounds which are designated as dangerous substances, and poor stability of the compounds. Further, when a toner is prepared by using these charge control agents, there are disadvantages such as a large amount of reversely charged toner, or a low image density due to a low initial charge imparting effect, or a large amount of toner scattering and fogging. None of the charge control agents had satisfactory performance.

[0007]

The present invention is an iron compound having no fear of environmental problems, has good stability as a colored compound, has good dispersibility in a binder resin, and does not deteriorate during toner production. In other words, the present invention provides a toner having good charging characteristics by friction even under various environmental conditions and constantly providing a high quality image stably.

[0008]

DISCLOSURE OF THE INVENTION The inventors of the present invention have found a stable colored compound which has good dispersibility with a binder resin and can impart good charging characteristics to a toner. The present invention has led to the invention of excellent toners.

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

[0010]

[Chemical 2]

[Wherein X and X'represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a halogen atom,
X and X'may be the same or different, m and m'represent an integer of 1 to 3, R and R'represent a halogen atom, and R and R'are the same. may be the or different, n and n'represents an integer of 1 to 3, a represents an aliphatic ammonium ion represented by C ₄ -C ₄₀ carbon atoms (including substituted aliphatic ammonium ions). ] The present invention relates to a toner for developing an electrostatic charge image, which comprises a compound represented by

The present invention basically comprises a binder resin, a colorant and a compound represented by the general formula (1) according to the present invention. As a method for producing the toner of the present invention, a mixture of these is used. Method of obtaining by kneading, cooling, coarsely pulverizing, finely pulverizing, and classifying after melting the binder resin with a heating and mixing device, dissolving these mixtures in a solvent, atomizing by spraying, drying, and classifying And a method in which the colorant or the compound represented by the general formula (1) is dispersed in the suspended monomer particles and obtained by a polymerization method.

As the binder resin, polystyrene,
Styrene-methacrylic acid ester copolymer, styrene-
Propylene copolymer, styrene-butadiene copolymer,
Acrylic resins, styrene-maleic acid copolymers, olefin resins, polyesters, epoxy resins, polyurethane resins, polyvinyl butyral, etc. can be used alone or in combination.

As a colorant, for black toner, black dyes or pigments such as carbon black, black titanium oxide, ferrosoferric oxide, spirit black and nigrosine are generally used, phthalocyanine, rhodamine B lake, quinacridone and poly. Non-black dyes or pigments such as tungstophosphoric acid, induslen blue, and sulfonamide derivatives can be used.

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

Compound No. (1)

[Chemical 3]

Compound No (2)

[Chemical 4]

Compound No. (3)

[Chemical 5]

Compound No (4)

[Chemical 6]

Compound No. (5)

[Chemical 7]

Compound No. (6)

[Chemical 8]

Compound No. (7)

[Chemical 9]

Compound No. (8)

[Chemical 10]

Compound No. (9)

[Chemical 11]

Compound No. (10)

[Chemical 12]

Compound No. (11)

[Chemical 13]

Compound No. (12)

[Chemical 14]

Compound No (13)

[Chemical 15]

Compound No (14)

[Chemical 16]

Compound No. (15)

[Chemical 17]

Compound No. (16)

[Chemical 18]

Compound No. (17)

[Chemical 19]

Compound No. (18)

[Chemical 20]

Compound No (19)

[Chemical 21]

Compound No (20)

[Chemical formula 22]

Further, the toner may be used as an additive in the toner.
For the purpose of carrier protection, toner fluidity improvement, thermal / electrical / physical property adjustment, resistance adjustment, softening point adjustment, and fixability improvement, hydrophobic silica, metal soap, fluorine-based surfactant, Dioctyl phthalate, wax, tin oxide, conductive zinc oxide and the like are used if necessary.

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

[0038]

EXAMPLES The present invention will be specifically described below with reference to examples. Parts in the examples represent parts by weight.

Example 1 1 part of Exemplified Compound (1), 5 parts of carbon black, 2 parts of low molecular weight polypropylene, and 92 parts of styrene-ethylhexyl methacrylate copolymer were kneaded by a heating mixer, and after cooling, coarsely crushed with a hammer mill. did. It was finely pulverized with a jet mill and then classified to obtain a black toner of 10 to 12 μm. After this toner was externally added, it was mixed with an iron powder carrier in a weight ratio of 4: 100, and when shaken, the toner was negatively charged, and when measured with a blow-off powder charge amount measuring device, the charge amount was −. It was 25 μc / g. When an image was produced using a modified commercial copying machine using this toner, a clear image having no fog could be obtained at the initial stage and after copying 10,000 sheets.

Example 2 1 part of Exemplified Compound (2), 5 parts of carbon black, 2 parts of low molecular weight polypropylene, and 92 parts of styrene-ethylhexyl methacrylate copolymer were kneaded by a heating mixer, and after cooling, coarsely crushed with a hammer mill. did. It was finely pulverized with a jet mill and then classified to obtain a black toner of 10 to 12 μm. After this toner was externally added, it was mixed with an iron powder carrier in a weight ratio of 4: 100, and when shaken, the toner was negatively charged, and when measured with a blow-off powder charge amount measuring device, the charge amount was −. It was 22 μc / g. When an image was produced using a modified commercial copying machine using this toner, a clear image having no fog could be obtained at the initial stage and after copying 10,000 sheets.

Example 3 1 part of Exemplified Compound (3), 5 parts of carbon black, 2 parts of low molecular weight polypropylene, and 92 parts of polyester resin were kneaded by a heating mixer, cooled, and coarsely crushed by a hammer mill. After finely pulverizing with a jet mill, classify 10
12 μm black toner was obtained. After this toner was externally added, it was mixed with an iron powder carrier in a weight ratio of 4: 100, and when shaken, the toner was negatively charged, and when measured with a blow-off powder charge amount measuring device, the charge amount was −. 25 μc
/ G. When an image was produced using a modified commercial copying machine using this toner, a clear image having no fog could be obtained at the initial stage and after copying 10,000 sheets.

Example 4 1 part of Exemplified Compound (4), 5 parts of carbon black, 2 parts of low molecular weight polypropylene, and 92 parts of styrene-ethylhexyl methacrylate copolymer were kneaded by a heating mixer, cooled, and coarsely crushed with a hammer mill. did. It was finely pulverized with a jet mill and then classified to obtain a black toner of 10 to 12 μm. This toner was externally added and then mixed with a silicon coating carrier at a weight ratio of 4 to 100, and when shaken, the toner was negatively charged, and the charge amount measured by a blow-off powder charge amount measuring device was −17 μc / It was g. When an image was produced using a modified commercial copying machine using this toner, a clear image having no fog could be obtained at the initial stage and after copying 10,000 sheets.

Example 5 1 part of Exemplified Compound (1), 40 parts of magnetic iron powder, 2 parts of low molecular weight polypropylene, and 57 parts of styrene-ethylhexyl methacrylate copolymer were kneaded by a heating mixer, cooled, and then coarsely cut by a hammer mill. Crushed. After finely pulverized with a jet mill, it was classified to obtain a black toner of 10 to 12 μm. After externally adding the toner, the toner was mixed with a ferrite carrier and shaken, so that the toner was negatively charged. When this toner was put into a developing machine for a one-component toner of a modified copying machine and an image was produced, a clear image having no fog could be obtained.

Examples 6 to 10 The results shown in Table 1 were obtained in the same manner as in Example 1 except that the compound shown in Table 1 was used instead of the compound example (1) of Example 1.

[0045]

[Table 1]

Comparative Example 1 Instead of the exemplified compound (1), the following formula

[0047]

[Chemical formula 23]

A toner was prepared by using the compound represented by the same procedure as in Example 1 and the image was evaluated. As a result, fog was recognized in the initial stage, and the image density was reduced after copying 10,000 sheets.

Comparative Example 2 Instead of the exemplified compound (1), the following formula was used.

[0050]

[Chemical formula 24]

A toner was prepared by using the compound shown by the same procedure as in Example 1 and the image was evaluated. Fogging was observed in the initial stage, and the image density was decreased after copying 10,000 sheets.

Comparative Example 3 Instead of the exemplified compound (1), the following formula was used.

[0053]

[Chemical 25]

A toner was prepared by using the compound represented by the same procedure as in Example 3 and the image was evaluated. Fogging was observed in the initial stage, and the image density was reduced after 10,000 copies.

[0055]

As described above, according to the toner of the present invention, in the toner containing at least the binder resin, the colorant and the charge control agent, the charge control agent is represented by a specific chemical formula having no environmental problem. It is an iron compound that is used as a colored compound, has good stability as a colored compound, has good dispersibility in a binder resin, has good charging characteristics due to friction even under various environmental conditions, and constantly provides high-quality images in a stable manner. Give the effect of providing.

The toner of the present invention is suitable for electrophotography, electrostatic recording,
It can be applied to toners used in copiers, printers, facsimiles and the like using methods such as magnetic recording.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Kayoko Watanabe 45 Miyukigaoka, Tsukuba City, Ibaraki Prefecture Hodogaya Chemical Industry Co., Ltd. Tsukuba Research Institute

Claims (1)

[Claims] 1. The following general formula: [Wherein X and X'represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a halogen atom, X and X'may be the same or different, and m and m'are 1
To R3 and R'represent a halogen atom, R and R'may be the same or different, and n
And n'represent an integer of 1 to 3, A is a carbon number of C ₄
An aliphatic ammonium ion represented by C ₄₀ (including a substituted aliphatic ammonium ion) is shown. ] A toner for developing an electrostatic charge image, comprising a compound represented by