JPH03134672A - Toner for electrophotography - Google Patents

Abstract

PURPOSE:To obtain the toner which forms sharp images and allows continuous use by incorporating a specific comps. as a charge control agent into the toner and using the colorless charge control agent which has high mechanical friction and impact stability and temp. and humidity stability. CONSTITUTION:The charge control agent has the high mechanical friction and impact stability and temp. and humidity stability and is colorless and, therefore, when the compd. expressed by formula I is incorporated into this agent, the electrophotographic toner which forms the sharp images and allows continuous use is obtd. In the formula, R1: a hydrogen atom or alkyl group, R2: an aryl group, aryloxy group, acyl group, aryloxycarbonyl group, acyloxy group, sulfonyl group, alkoxysulfonyl group, aryloxysulfonyl group, sulfonyl oxy group, alkylamide group, aminoacyl group, sulfoneamide group, aminosulfonyl group, cyano group, aralkyl group, alicycle (including a condensed ring), m: 1 to 4, M: bivalent metal.

Description

DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a toner for developing electrostatic latent images in electrophotography.

(Prior art) In electrophotography, a latent image is formed on a photoconductor made of a photoconductive material, etc., and this is developed with a powder developer to make it visible. The most common method is to establish Developers for such electrophotography include natural resins or synthetic resins, colorants, charge control agents,
A two-component developer consisting of a mixture of toner with a fluidizing agent dispersed therein and a carrier such as iron powder or ferrite powder, and a natural resin or synthetic resin, a coloring agent, a charge control agent, a fluidizing agent, and a magnetic material. It can be broadly classified into one-component type developer.

A two-component developer achieves development by attaching charged toner to an electrostatic latent image through friction with a carrier. Conventionally, a one-component developer uses this instead of a carrier. Toner is known that is charged by friction with a brush-like or plate-like friction member that has the same function as that of a brush-like or plate-like friction member. Toners that are charged by friction have become known. The photoconductor layer can be positively or negatively charged so that exposure under the original produces a positive or negative electrostatic latent image. Depending on the polarity of this electrostatic latent image, the developing toner remains positive or negative.

In order to keep the toner charged, it has been proposed to utilize the triboelectricity of the resin, which is the main component of the toner, but this method has a small charge on the toner and a large solid surface resistance value, so The resulting image is prone to fogging and becomes unclear. Therefore, in order to impart desired triboelectric charging properties to the toner, it has been attempted to add charge-imparting dyes, pigments, and even charge control agents, and these techniques are now in practical use in this technical field.

(Problems to be Solved by the Invention) However, these dyes and pigments used as charge control agents have complex structures and lack stability, such as mechanical friction and impact, changes in temperature and humidity conditions, and electrical resistance. It is easily decomposed or altered by impact, light irradiation, etc., and the charge adjustment ability is easily lost. One essential flaw is that, being a colored material, it violates the requirement that toners with a specific hue require a charge control agent that can be considered colorless or substantially colorless. .

(Means for Solving the Problems) The present inventors have developed a toner material that has good dispersibility with the resin component, has thermal stability up to a temperature that allows sufficient melt-kneading, and is colorless. They discovered a compound that can impart a negative charge to the toner and invented an excellent toner.

That is, the present invention relates to the general formula (I) (wherein R1 represents a hydrogen atom or an alkyl group, and R2
is an aryl group, an aryloxy group, an acyl group, an aryloxycarbonyl group, an acyloxy group, a sulfonyl group,
It represents an alkoxysulfonyl group, an aryloxysulfonyl group, a sulfonyloxy group, an alkylamido group, an aminoacyl group, a sulfonamide group, an aminosulfonyl group, a cyano group, an aralkyl group, and an alicyclic ring (including fused rings), and m is 1.2 .3 or 4, and M represents a divalent metal. )
This is an electrophotographic toner characterized by containing a compound represented by the following as a charge control agent.

The compound represented by general formula (I) will be explained in detail. Examples of the alkyl group for R1 include a methyl group, ethyl group, n-butyl group, 15O-amyl group, n-dodecyl group, n-octadecyl group, and cyclohexyl group. Examples of the aryl group of R2 include a substituted or unsubstituted phenyl group, α-naphthyl group, etc., and examples of the aryloxy group include a substituted or unsubstituted phenoxy group, α-naphthoxy group, etc. Examples of the acyl group include substituted or unsubstituted acetyl groups, benzoyl groups, etc., examples of the aryloxycarbonyl group include substituted or unsubstituted phenoxycarbonyl groups, and examples of the acyloxy group include substituted or unsubstituted acetoxy groups, Examples include benzoxy group. Examples of sulfonyl groups include mesyl group, butylsulfonyl group, substituted or unsubstituted phenylsulfonyl group, etc. Examples of alkoxysulfonyl group include butoxysulfonyl group, and examples of aryloxysulfonyl group include substituted or unsubstituted phenoxysulfonyl group. Examples of the sulfonyloxy group include a mesyloxy group and a substituted or unsubstituted phenylsulfonyloxy group. Examples of the alkylamido group include a propionylamino group, and examples of the aminoacyl group include a butylaminocarbonyl group and a substituted or unsubstituted anilinocarbonyl group. The sulfonamide group has
Examples of the aminesulfonyl group include a mesylamino group, a substituted or unsubstituted phenylsulfonylamino group, and examples of the aminesulfonyl group include a hexylaminosulfonyl group and a substituted or unsubstituted anilinosulfonyl group. Aralkyl groups include substituted or unsubstituted benzyl groups, α-phenethyl groups, cumyl groups, etc., and alicyclic groups include substituted or unsubstituted cyclohexyl groups, which may be fused to a benzene ring. .

Further, examples of M include Mgt, Ca1Zn, etc., which are divalent metals.

Specific examples of the compound represented by general formula (I) are shown below.

In addition, compound No. is used in common in Examples.

Compound no.

Compound No., Structural formula %formula% formula Compound no.

3 0 4 5 2 6 Compound no.

Structural formula % Formula % Structural formula 0 Compound (I) used as the charge control agent of the present invention can be prepared, for example, by adding the following general formula (II) 8 (wherein R1, R2 and m are the same as compound (I)) to an alkaline aqueous solution. It can be easily obtained by dissolving the compound and adding a divalent metal salt.

Incidentally, the amount of the compound represented by general formula (I) added to the toner component is generally 0.1 to 10 parts by weight, preferably 0.5 to 5 parts by weight, based on 100 parts by weight of the resin. Make it contain.

In addition to the compound of the above general formula (I), the toner of the present invention includes:
In consideration of adhesion, preservability, fluidity, crushability, etc., one or more of the known toner resins such as styrene resin, styrene-acrylic resin, styrene-butadiene resin, epoxy resin, polyester resin, paraffin wax, etc. A mixture of several types is used. As the coloring agent, many known dyes and pigments can be used, and examples of those which are particularly excellent as toners for color copying include benzidine yellow, quinacridine, copper phthalocyanine blue, and copper phthalocyanine green.

The toner of the present invention is typically mixed with a carrier to provide a two-component developing agent, but can of course also be used as a one-component developing agent.

(Example) Hereinafter, the present invention will be explained in detail with reference to Examples.

Note that parts in the examples represent parts by weight.

Disaster 110 A mixture of 100 parts of styrene resin, 6 parts of carbon black, and 2 parts of compound No. 1 is uniformly premixed using a ball mill to prepare a premix. Next, the mixture was heated and melted and kneaded, cooled, and then coarsely pulverized using a vibration mill and further finely pulverized using a jet mill to obtain a black toner. The particle size of this black toner was 8 to 15 μm.

A developer was prepared by mixing 95 parts of iron powder carrier with 5 parts of the obtained toner. The initial blow-off charge amount of this developer was -19.5 μC/g.

When a toner image was formed using this developer on a commercially available selenium drum using a magnetic brush development method, a clear image without capri was obtained. With this toner, no deterioration in copy quality was observed even after continuous copying of 100 sheets.

100 parts of styrene-acrylic copolymer resin, yellow dye (C
, I, Disbirds Yellow 33) 6 parts, Compound No.
The initial blow-off charge amount of the developer prepared in the same manner as in Example 1 using 2 parts of the compound shown in , 3 was -20.4.
It was μC/g.

When copies were made using this developer in the same manner as in Example 1, clear yellow images without fog were obtained. With this toner, no deterioration in copy quality was observed even after 10,000 continuous copies were made.

Disaster IL13 Styrene-n-butyl methacrylate copolymer resin 10
0 parts, red dye (C, I, Pigment Red 12) 8
A blend of 1 part and 2 parts of the compound designated as Compound N004 was treated in the same manner as in Example 1 to obtain a red toner. The developer prepared from the obtained red toner in the same manner as in Example 1 had an initial blow-off charge amount of -28.3 μC/g.

When copies were made using this developer in the same manner as in Example 1, clear red images without fog were obtained. With this toner, no deterioration in copy quality was observed even after continuous copying of too many copies.

A blend of 100 parts of a polyester resin, 6 parts of a blue dye (C, 1, Pigment Blue 15), and 2 parts of a compound represented by compound N005 was treated in the same manner as in Example 1 to obtain a blue toner. The initial blow-off charge amount of the developer prepared from the obtained blue toner in the same manner as in Example 1 was -25.7 μC.
/g.

When copies were made using this developer in the same manner as in Example 1, clear blue images without fog were obtained. With this toner, no deterioration in copy quality was observed even after 10,000 continuous copies were made.

Instead of compound No. 1, compound No.
A black toner was obtained in the same manner as in Example 1 except that the compound shown in No. 08 was used. The developer prepared from the obtained black toner in the same manner as in Example 1 had an initial blow-off charge amount of -24.8 μC/g.

1 ball 1” Instead of the compound shown in compound No. 33, compound No.
A yellow toner was obtained in the same manner as in Example 2 except that the compound shown in No. 11 was used. The developer prepared from the obtained yellow toner in the same manner as in Example 1 had an initial blow-off charge amount of -22.4 μC/g.

1 ball 1j Compound No. Instead of the compound shown in 4, compound No.
A red toner was obtained in the same manner as in Example 3 except that the compound shown in No. 17 was used. The initial blow-off charge amount of the developer prepared from the obtained red toner in the same manner as in Example 1 was -22.4 μC/g.
A blue toner was obtained in the same manner as in Example 4 except that the compound shown in No. 20 was used. The developer prepared from the obtained blue toner in the same manner as in Example 1 had an initial blow-off charge amount of -20.7 μC/g.

(Effects of the Invention) The charge control agent used in the present invention has excellent mechanical friction and impact stability, temperature and humidity stability, and is colorless, so it is an electrophotographic toner that provides clear images and can be used continuously. was gotten.

Claims (1)

[Claims] The following general formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, R_1 represents a hydrogen atom or an alkyl group, and R
_2 is an aryl group, an aryloxy group, an acyl group, an aryloxycarbonyl group, an acyloxy group, a sulfonyl group, an alkoxysulfonyl group, an aryloxysulfonyl group, a sulfonyloxy group, an alkylamide group, an aminoacyl group, a sulfonamide group, an aminosulfonyl group , cyano group, aralkyl group, alicyclic ring (including fused rings),
m is 1, 2, 3 or 4, and M represents a divalent metal. ) A toner for electrophotography, characterized in that it contains a compound represented by the following formula as a charge control agent.