JP2764606B2 - Toner for developing electrostatic images - Google Patents

Description

The present invention relates to a toner for developing an electrostatic latent image in electrophotography, electrostatic recording, electrostatic printing, and the like.

(Prior Art) An electrostatic latent image can be visualized by adhering toner by its electrostatic attraction, and is fixed by heat or a solvent, and in some cases, pressure. In addition to the developer, a powder developer is widely and generally used.

This powder developer is composed of a mixture of a fine particle powder called a toner in which a colorant, a charge control agent, a fluidizing agent, etc. are dispersed in a natural resin or a synthetic resin, and a fine iron powder or a glass powder called a carrier. Colorant, charge control agent, fluidizing agent for natural developer or synthetic resin,
It can be broadly classified into a one-component developer consisting only of a fine particle powder toner in which ferrite or the like is dispersed.

The two-component developer charges the toner by friction with the carrier, is visualized by attaching to the electrostatic latent image, and further develops by fixing the image. The one-component developer charges the toner by friction with a brush-like or plate-like friction member instead of a carrier and attaches the toner to the electrostatic development. Some toners are charged by mutual friction. These developing toners maintain a positive or negative charge depending on the polarity of the electrostatic latent image to be developed.

To maintain the charge of the toner, it has been proposed to utilize the triboelectricity of the resin, which is the main component of the toner.However, in this method, the charge of the toner is small and the solid surface resistance is large. The resulting image is easily fogged and unclear. For this reason, in order to maintain a necessary charge, a dye or pigment for giving a charge and a charge control agent are added.

(Problems to be Solved by the Invention) However, conventional charge control agents generally have a complicated structure and poor stability, and are decomposed or deteriorated by heat, mechanical friction and impact, changes in temperature, humidity conditions, and the like. hand,
Function as a charge control agent is likely to be lost. Further, since the substance itself is a colored substance, it is suitable for the toner of the color tone, but is not suitable for the toner of a different color tone. Further, since it is difficult to uniformly disperse the particles in a thermoplastic resin, there is a disadvantage that a difference occurs in the triboelectric charge between toner particles obtained by pulverization. There have been several proposals to improve the disadvantages of these charge control agents, and different types of compounds have been proposed, but none have been found to be totally satisfactory.

(Means for Solving the Problems) The present inventors have found that the compatibility with a thermoplastic resin is good, the thermal stability is higher than the resin melting temperature, and a uniform and sufficient charge is imparted to toner particles. A colorless compound which does not impair the color characteristics of the coloring substance of the color toner composition has been found, and the present invention has been completed.

That is, the toner of the present invention has the following general formula (I) (In the formula, M and R ₁ represent the same meaning as described above.)
Is an electrostatic image developing toner containing an imide compound represented by the formula:

The imide compound represented by the general formula (I) used in the present invention is a compound represented by the following general formula (II) (provided that
In the formula, R ₁ has the same meaning as described above. ) Can be reacted with a hydroxide by a conventional method to obtain a high yield.

The hydroxide used in the above reaction is, for example, lithium hydroxide, sodium hydroxide, potassium hydroxide and the like.

Specific examples of the imide metal complex represented by the general formula (I) are shown below. The compound No. used here is commonly used also in Examples.

In addition to the imide compound represented by the general formula (I), the toner of the present invention may be made of a styrene resin, a styrene-acrylic resin, a styrene-butadiene resin in consideration of adhesiveness, storage properties, fluidity, pulverizability, and the like. , An epoxy resin, a polyester resin, a paraffin wax, or a mixture of one or more. As the coloring agent, many known dyes and pigments can be used, and particularly preferable ones include bengara, benzidine yellow, quinacdrine, copper phthalocyanine blue, and copper phthalocyanine green.

In the present invention, the amount of the imide compound represented by the general formula (I) added to the toner composition is generally 0.1 to 10 parts by weight, preferably 0.5 to 5 parts by weight, per 100 parts by weight of the resin. Let it be included.

The toner containing the imide compound of the present invention is mixed with a carrier to provide a two-component developer, but can also be used as a one-component developer.

Hereinafter, the present invention will be described in detail with reference to examples. In addition, the part in an Example represents a weight part.

Example 1 29.4 parts of phthalimide, 13 parts of potassium hydroxide and 300 parts of water were dissolved and heated to 80 ° C. Thereafter, stirring was continued for 2 hours, and then cooled to room temperature. The water is distilled off and the residue is
Drying under reduced pressure at 60 ° C. provided 30 parts of an imide compound of compound No. 1 as a colorless powder.

Styrene-acrylic copolymer resin 100 parts, carbon black 12 parts, imide compound synthesized as described above
1.5 parts were mixed well, melted by heating, cooled, and finely pulverized with a jet mill to obtain a black toner. From this black toner, a clear image without fog was obtained, and a good copied image with no change even after repeated use over a long period of time was obtained.

Example 2 35 parts of dimethylphthalimide and 13 parts of potassium hydroxide were added to water
It was dissolved in 300 parts and heated to 80 ° C. Thereafter, stirring was continued for 2 hours, and then cooled to room temperature. Water was distilled off, and the residue was dried under reduced pressure at 50 to 60 ° C. to obtain 34 parts of an imide compound of Compound No. 2 as a colorless powder.

100 parts of a styrene-acrylic copolymer resin, 7 parts of benzidine yellow, and 1.5 parts of the imide compound synthesized as above are mixed well, heated and melted, cooled, and then finely pulverized by a jet mill to obtain a yellow toner. I got From this yellow toner, a clear image without fog was obtained, and a good copied image with no change even after repeated use over a long period of time was obtained.

Example 3 57 parts of tetrachlorophthalimide and 13 parts of potassium hydroxide were dissolved in 300 parts of water, and heated to 80 ° C. Thereafter, stirring was continued for 2 hours, and then cooled to room temperature. Distill off the water,
The residue was dried under reduced pressure at 50-60 ° C to give compound No. 3 as a colorless powder.
56 parts of the imide compound were obtained.

100 parts of a styrene-acrylic copolymer resin, 6 parts of copper phthalocyanine green, and 1.5 parts of the imide compound synthesized as above are mixed well, heated and melted, cooled, and finely pulverized by a jet mill to obtain a green toner. I got From this green toner, a clear image without fogging was obtained, and a good copied image with no change even after repeated use over a long period of time was obtained.

Example 4 38.4 parts of 4-nitrophthalimide and 13 parts of potassium hydroxide were dissolved in 300 parts of water, and heated to 80 ° C. Thereafter, stirring was continued for 2 hours, and then cooled to room temperature. Distill off the water,
The residue was dried under reduced pressure at 50-60 ° C. to give compound N as a colorless powder.
39 parts of imide compound of o.4 were obtained.

100 parts of a styrene-acrylene copolymer resin, 6 parts of copper phthalocyanine blue, and 1.5 parts of the imide compound synthesized as described above are mixed well, heated and melted, cooled, and finely pulverized by a jet mill to obtain a blue toner. I got From this blue toner, a clear image without fog was obtained, and a good copied image with no change even after repeated use over a long period of time was obtained.

Example 5 29.4 parts of phthalimide and 8.4 parts of lithium hydroxide were dissolved in 300 parts of water and heated to 80 ° C. Thereafter, stirring was continued for 2 hours, and then cooled to room temperature. The water is distilled off and the residue is
Drying under reduced pressure at 60 ° C. gave 26 parts of a colorless powder of the imide compound.

Styrene-acrylic copolymer resin 100 parts, carbon black 12 parts, imide compound 1.5 synthesized as described above
The resulting mixture was heated and melted, cooled, and then finely pulverized with a jet mill to obtain a black toner. From this black toner, a clear image without fog was obtained, and a good copied image with no change even after repeated use over a long period of time was obtained.

Example 6 35 parts of dimethylphthalimide and 8.4 parts of lithium hydroxide were dissolved in 300 parts of water and heated to 80 ° C. Thereafter, stirring was continued for 2 hours, and then cooled to room temperature. The water was distilled off, and the residue was dried under reduced pressure at 50 to 60 ° C. to give Compound No. 19 as a colorless powder.
Thus, 31 parts of the imide compound were obtained.

Styrene-acrylic copolymer resin 100 parts, benzidine yellow 7 parts, and imide compound 1.
Five parts were mixed well, melted by heating, cooled, and finely pulverized with a jet mill to obtain a yellow toner. From this yellow toner, a clear image without fog was obtained, and a good copied image with no change even after repeated use over a long period of time was obtained.

Example 7 39 parts of naphthalene-1,8-dicarboxylic acid imide and 8.4 parts of lithium hydroxide were dissolved in 300 parts of water, and heated to 80 ° C. Thereafter, stirring was continued for 2 hours, and then cooled to room temperature.
Water was distilled off, and the residue was dried under reduced pressure at 50 to 60 ° C. to obtain 36 parts of an imide compound as a colorless powder.

Styrene-acrylic copolymer resin 100 parts, carbon black 12 parts, imide compound 1.5 synthesized as described above
The resulting mixture was heated and melted, cooled, and then finely pulverized with a jet mill to obtain a black toner. From this yellow toner, a clear image without fog was obtained, and a good copied image with no change even after repeated use over a long period of time was obtained.

Example 8 9,10-dihydroanthracene-9,10-endo-αβ-
54.6 parts of succinic anhydride, 8.4 parts of lithium hydroxide and water 3
The mixture was dissolved in 00 parts and heated to 80 ° C. Thereafter, stirring was continued for 2 hours, and then cooled to room temperature. Distill water and remove residue
Drying under reduced pressure at 50 to 60 ° C. gave 48 parts of a colorless powder of the imide compound.

100 parts of a styrene-acrylic copolymer resin, 6 parts of copper phthalocyanine blue, and 1.5 parts of the imide compound synthesized as described above are mixed well, heated and melted, cooled, and finely ground by a jet mill to obtain a blue toner. I got From this blue toner, a clear image without fog was obtained, and a good copied image with no change even after repeated use over a long period of time was obtained.

Example 9 39 parts of naphthalene-1,8-dicarboxylic acid imide and 8.6 parts of sodium hydroxide were dissolved in 300 parts of water, and heated to 80 ° C.
Thereafter, stirring was continued for 2 hours, and then cooled to room temperature. Pour into 300 parts of water, filter the precipitated solid, and
Drying under reduced pressure at 40 ° C. gave 40 parts of a colorless powder of the imide compound.

Styrene-acrylic copolymer resin 100 parts, carbon black 12 parts, imide compound 1.5 synthesized as described above
The resulting mixture was heated and melted, cooled, and then finely pulverized with a jet mill to obtain a black toner. From this black toner, a clear image without fog was obtained, and a good copied image with no change even after repeated use over a long period of time was obtained.

Example 10 9,10-Dihydroanthracene-9,10-endo-αβ-
54.6 parts of succinic anhydride and 8.6 parts of sodium hydroxide are added to D
It was dissolved in 60 parts of MF and heated to 80 ° C. Thereafter, stirring was continued at 80 ° C. for 2 hours, and then cooled to room temperature. 300 parts of water was added, the precipitated solid was separated by filtration, and dried under reduced pressure at 50 to 60 ° C. to obtain 55 parts of a colorless powder of the imide compound.

100 parts of a styrene-acrylic copolymer resin, 6 parts of copper phthalocyanine green, and 1.5 parts of the imide compound synthesized as above are mixed well, heated and melted, cooled, and finely pulverized by a jet mill to obtain a green toner. I got From this green toner, a clear image without fogging was obtained, and a good copied image with no change even after repeated use over a long period of time was obtained.

(Effect of the Invention) The charge control agent used in the present invention is excellent in mechanical friction and impact stability, temperature and humidity stability, etc. and is colorless, so that an electrophotographic toner with a clear image and continuous use can be obtained. was gotten.

──────────────────────────────────────────────────続 き Continuation of the front page (56) References JP-A-63-58355 (JP, A) JP-A-55-65962 (JP, A) JP-A-60-178460 (JP, A) JP-A 62-58460 205108 (JP, A) JP-A-1-202760 (JP, A) (58) Fields investigated (Int. Cl. ⁶ , DB name) G03G 9/08 344

Claims (1)

(57) [Claims] 1. A compound represented by the following general formula (I) (Wherein, M represents an alkali metal or ammonium ion, and R ₁ represents R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ are hydrogen or an alkyl group having 1 to 18 carbon atoms, halogen, -NO ₂ or -SO ₃ H, which may be the same or different, and R ₁₀ is -CH _2- , R ₁₁ , R ₁₂ and R ₁₃ are hydrogen or a carbon atom having 1 to
5 alkyl groups, which may be the same or different. A toner for developing an electrostatic image, comprising an imide compound represented by the formula: