JPH06301240A - Toner - Google Patents

Abstract

PURPOSE:To provide a toner contg. a colorless electric charge controlling agent having electric charge controlling ability effective to a polymerized toner. CONSTITUTION:This toner contains at least one kind of electric charge controlling agent represented by formula I, II or III. In the formulae I-III, Ph is optionally substd. phenyl, A is Al, Zn or B, each of R1-R3 is 1-18C alkyl, R4 is 1-18C alkylene and X is sulfonic acid amido or carboxylic acid amido.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION This invention relates to toners for developing electrostatic latent images in electrophotography.

[0002]

2. Description of the Related Art In electrophotography, a method is generally used in which a latent image formed on a photoconductor is made visible by a powder developer (toner) and then fixed on a substrate (for example, paper) by heat or pressure. Is. As such an electrophotographic developer, a two-component developer comprising a mixture of a toner in which a colorant is dispersed in a natural resin or a synthetic resin and a carrier of iron powder or ferrite powder is used. Further, a one-component developer in which a coloring agent and a magnetic material are mixed with a natural resin or a synthetic resin is used.

A two-component developer adheres toner charged by friction with a carrier to an electrostatic latent image to achieve development, and a one-component developer functions similarly to this instead of the carrier. Toner charged by friction with the brush-shaped or plate-shaped friction member develops the electrostatic latent image. Toners must be maintained in the desired polarity by either positive or negative development of the photoconductor, for which a charge control agent is generally added.

On the other hand, in order to improve the image quality, the particle size of the toner is being reduced, and as a manufacturing method thereof, a so-called polymerized toner obtained by reacting a monomer dispersed in a protective colloid aqueous solution is noted. Has been done. However, there are very few charge control agents applicable to polymerized toners, and moreover, there are many colored substances such as alloy dyes, and therefore their use in color toners is limited. This property is particularly remarkable in a charge control agent that is negatively charged.

[0005]

SUMMARY OF THE INVENTION The present invention relies on providing a toner that is a colorless negative charge control agent that includes a charge control agent that is applicable to polymerized toners.

[0006]

That is, the present invention has the formula:

[Chemical 2] (Wherein Ph is a substituted or unsubstituted phenyl group, A is aluminum, zinc or boron, and R ₁ , R ₂ and R _{3 are}
Represents an alkyl group having 1 to 18 carbon atoms, and R ₄ has 1 carbon atom
To 18 alkylene groups, and X represents a sulfonic acid amide group or a carboxylic acid amide group. And a toner containing at least one charge control agent.

The toner is generally a resin powder composed of a colorant and a binder resin, and includes a pulverized toner for crushing the resin molding and a polymerized toner formed by a method such as suspension polymerization or emulsion polymerization. However, the charge control agent of the present invention can be used in any type of toner.

The binder resin in any type of toner is generally known, for example, styrene resin,
Styrene-acrylate resins, styrene-butadiene resins, acrylate resins, polyester resins, polyamide resins, polyamine resins, ammonium resins, ethylene resins, phenolic resins, epoxy resins or combinations thereof are conceivable.

The colorant to be blended in the toner may be of any type conventionally used in toners, such as phthalocyanine blue, quinacridone, azo pigments, and Reiki type pigments (carmine). 6B), carbon black, Rhodamine G and the like. The amount of these colorants blended can vary greatly depending on the purpose and type of toner, but is, for example, 0.2 to 20% by weight, and particularly 2.0 to 12% by weight.

The charge control agent of the present invention is very suitably used for a polymerized toner which can be polymerized by dispersing a binder monomer in a protective colloid aqueous solution such as suspension polymerization, emulsion polymerization or interfacial polymerization. Monomers for obtaining the above types of binding resins are also known, for example vinyl aromatic compounds.
(For example, styrene, α-methylstyrene), vinyl ester (for example, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate), polyfunctional isocyanate, acid chloride or a mixture thereof. .

The charge control agent of the present invention comprises compounds (I) to (II
Any of I) or mixtures thereof can be used. In the above formula of the compound, Ph is a substituted or unsubstituted phenyl group, and examples of the substituent that may be present on the phenyl group include an alkyl group having 1 to 18 carbon atoms and a carbon number of 1 to 1
8 alkoxy group, halogen, halogenated alkyl group
(C1-18) and the like. Specific examples of the Ph group include methylphenyl, t-butylphenyl, stearylphenyl, methoxyphenyl, chlorophenyl,
Examples include trifluoromethylphenyl and the like.

A is a metal element and is selected from the group consisting of aluminum, zinc or boron. R _{1 to} R ₃ may be the same or different and each is an alkyl group having 1 to 18 carbon atoms. R _{1 to} R ₄ are alkylene groups having 1 to 18 carbon atoms, preferably ethylene group, propylene group, butylene group and the like.

Specific examples of the above compound (I) include:

[Chemical 3] Is mentioned.

The above charge control agent is used in relation to the toner weight.
The amount is 0.01 to 10% by weight, preferably 0.1 to 5% by weight. If the amount is less than 0.01% by weight, the charge control agent ability is poor, and if the amount is more than 10% by weight, the volume resistance value is lowered, which causes inconvenience such as decrease in charge amount over time.

In the toner of the present invention, various additives can be blended in addition to the above resin binder, colorant and charge control agent. Examples of such additives include release agents
(For example, polypropylene wax, silicone oil, etc.) and fluorescent substances (eg pyrene perylene, etc.) are mentioned.

[0016]

The charge control agent of the present invention is colorless and is a charge control agent which can act extremely effectively on the polymerized toner, and the toner containing it has high charging characteristics.

[0017]

EXAMPLES The present invention will be described in more detail by way of examples. The invention should not be construed as limited to these examples.

Example 1 Ingredients By Weight Isophorone Diisocyanate Main Component 45 Polyurethane (Tg: 28 ° C.) Butyl Acetate 15 Carmine 6B 10 Charge Control Agent of Compound Example 1 below 2.5 m-Tetramethylxylene diisocyanate 40

[0019]

[Chemical 4]

The pigment dispersion paste containing the above components was emulsified in an aqueous solution of polyvinyl alcohol and a cellulosic protective colloid, and diamine and then monoamine were added thereto to complete the interfacial polymerization. This was centrifuged and dried to obtain a toner.

Example 2 Instead of the charge control agent of the compound example (1), the following compound example (2)
A toner was prepared in the same manner as in Example 1 except that the toner was prepared using the charge control agent described in 1.

[0022]

[Chemical 5]

Example 3 Instead of the charge control agent of the compound example (1), the following compound example (3)
A toner was prepared in the same manner as in Example 1 except that the above charge control agent was used.

[0024]

[Chemical 6]

Comparative Example 1 The following compound example (4) was used instead of the charge control agent of compound example (1).
A toner was prepared in the same manner as in Example 1 except that the above charge control agent was used.

[0026]

[Chemical 7]

Example 4 Component parts by weight Toluene diisocyanate-based polyurethane (Tg: 34 ° C.) 40 Styrene 50 2-Ethylhexyl acrylate 10 Legal 330R (carbon black) 10 Compound example (2) charge control agent 2.5 V -59 (azo polymerization initiator) 1.8

The pigment dispersion paste containing the above components was emulsified in an aqueous solution of polyvinyl alcohol and a cellulosic protective colloid, and the polymerization was completed at 75 ° C./6 hours. This was centrifuged and dried to obtain a toner.

Comparative Example 2 The following compound example (5) was used instead of the charge control agent of compound example (2).
A toner was prepared using the charge control agent of.

[0030]

[Chemical 8]

Comparative Example 3 The following compound example (6) was used instead of the charge control agent of compound example (2).
A toner was prepared in the same manner as in Example 4 except that the above charge control agent was used.

[0032]

[Chemical 9]

Experimental Example 1 Using the above toner, the environmental dependence of the charge amount of the toner and the amount of the opposite polarity toner by the charge distribution measurement were measured. The measurement method is as follows: (1) Charge amount is 15 ℃ / 8% RH and 35 ℃ / 8
The toner left for 24 hours in an environment of 0% RH and the ferrite carrier were mixed in a weight ratio of 3/97, and the mixture was measured by a blow-off method. (2) Reverse polarity toner amount is 15 ° C / 8% created in (1)
The charge distribution was measured with a q / d meter using the toner / carrier mixture at RH and determined from the results.

[0034]

[Table 1]

From the above results, it can be seen that the toner using the charge control agent of the present invention exhibits good environmental stability and charge distribution.

Claims (1)

[Claims] 1. The formula: (Wherein Ph is a substituted or unsubstituted phenyl group, A is aluminum, zinc or boron, and R ₁ , R ₂ and R _{3 are}
Represents an alkyl group having 1 to 18 carbon atoms, and R ₄ has 1 carbon atom
To 18 alkylene groups, and X represents a sulfonic acid amide group or a carboxylic acid amide group. ) A toner containing at least one charge control agent represented by