JPH0251165A - Magenta color toner composition - Google Patents

Abstract

PURPOSE:To obtain a distinct picture image of Magenta color contg. no fog and to improve color fastness of the picture image by incorporating a specified anthraquinone dye into a binder resin. CONSTITUTION:A color toner is obtd. by incorporating pref. 0.1-10pts.wt. compd. expressed by formula I into a binder resin. In formula I, R is an H atom, halogen atom, alkyl group, alkoxy group, alkoxyalkyl group, alkoxyalkoxy group, aralkyl group, alkoxycarbonyl group, or alkyl carboxy group. Thus, a toner compsn. having high miscibility in molten state is obtd. Its practical value is increased because the toner compsn. contains a Magenta dye having high light fastness and provides picture images having a stable image density when it is used for continuous copy in a repetitive development.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a color toner, particularly a negatively charged color toner composition for electrostatic charge development.

Conventionally, electrostatic printing, electrophotography, and the like are well-known methods for forming visible images by developing electrical latent images with color toners. Generally, a photoconductive material is used to form an electrical latent image on a photoconductive photoreceptor by various means, and the latent image is then developed with toner to obtain a visible image; After transferring the powder image to paper or the like as necessary, it is fixed by heating, pressure, solvent vapor, etc. to obtain a visible image.

To obtain a multicolor image, a document is exposed to light using a color separation filter, and the above steps are repeated multiple times using color toners such as yellow, magenta, and cyan to create a color image.

As a toner for developing an electrical latent image, conventionally used particles are particles obtained by dispersing a coloring agent in a binder resin such as polystyrene and pulverizing the particles to about 0.1 to 50 microns. This color toner is usually mixed with a carrier material such as glass beads or iron powder and used to develop an electrical latent image.

(Prior Art and Problems to be Solved by the Invention) These color toners are required to have various physical and chemical properties as shown below.

(1) The triboelectric properties of color toners are not affected by temperature changes.

(2) The density obtained changes due to collision between color toner particles and carrier particles due to repeated development for continuous use, and mutual deterioration of those particles and the photosensitive plate, or
The background density must not increase and reduce the quality of the copy.

(3) If an attempt is made to increase the density of a copied image by increasing the amount of color toner adhering to the surface of the photosensitive plate having a latent image, the background density will usually increase, so the so-called fog phenomenon must not occur.

(4) Do not lose transparency when layering multiple colors.

(5) Each color toner needs to have excellent melt compatibility.

(6) In order to accurately reproduce the original, it is necessary to have good spectral reflection characteristics.

At present, many of the known color toners do not fully satisfy the above-mentioned required characteristics, and improvements are currently desired.

(Means for Solving the Problems) The present invention has been made through intensive studies to solve the problems of the above-mentioned color toners, and has been developed to have excellent melt compatibility, and furthermore, to provide an image density that can be obtained by continuous copying through repeated development. The present invention was completed by discovering a stable magenta dye with good light fastness.

That is, the present invention has the following - pattern hole (1) (in the formula,
R is a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an alkoxyalkyl group, an alkoxyalkoxy group,
Indicates an aralkyl group, an alkoxycarbonyl group, or an alkylcarboxy group. ) is a magenta color toner composition for electrostatic charge development, characterized by containing a dye represented by:

Specific examples of R in formula (1) include halogen atoms such as hydrogen atom, chlorine atom, fluorine atom, and bromine atom, methyl group, ethyl group, propyl group, isobutyl group, t-butyl group, n- Alkyl groups such as octyl group, methoxy group, ethoxy group, n-propoxy group, alkoxy group such as n-hexyloxy group, methoxymethyl group, methoxyethyl group, ethoxyethyl group, n-propoxyethyl group, n-butoxyethyl group Alkoxyalkyl groups such as groups, alkoxyalkoxy groups such as methoxymethoxy groups, ethoxyethyl groups, ethoxyethoxy groups, benzyl groups, phenethyl groups,
Examples include aralkyl groups such as γ-phenylpropyl group, alkoxycarbonyl groups such as methoxycarbonyl group, ethoxycarbonyl group, and n-propoxycarbonyl group, and alkylcarboxy groups such as acetyloxy group, ethylcarboxy group, and n-propylcarboxy group. .

The compound of general formula (1) is 1-amino-2-chloro-4
-Easily obtained by reacting hydroxyanthraquinone and dihydroxybenzenes in a polar solvent in the presence of a base such as potassium carbonate.

As a method for producing a color toner using the magenta coloring matter of the present invention, a color toner is prepared by preferably containing 0.1 to 10 parts by weight of the compound of formula (I) in a binder resin. Obtainable.

Hereinafter, the constituent components of the color toner of the present invention will be explained in detail.

A particularly important component of the color toner is the anthraquinone compound represented by the general formula (1) described above.

The amount of these pigments added for magenta color toners depends on the chargeability of the binder resin, the chargeability of the auxiliary added colorant or additive, and the compatibility with the binder resin or dispersion. Since it is determined by the method etc., it is not limited uniformly, but generally speaking, it is desirable to use it in a range of about 0.1 to 10 (wt%) based on the binder resin.

All known binder resins can be used as the binder resin for the color toner of the present invention, such as polystyrene,
Monopolymers of styrene and its substituted products such as polyP-chlorostyrene and polyvinyltoluene, styrene-vinylnaphthalene copolymers, styrene-methyl acrylate copolymers, styrene-ethyl acrylate copolymers, styrene-
Butyl acrylate copolymer, styrene-octyl acrylate copolymer, styrene-methyl methacrylate copolymer, styrene-ethyl methacrylate copolymer, styrene-
Butyl methacrylate copolymer, styrene-α-chloromethyl methacrylate copolymer, styrene-acrylonitrile copolymer, styrene-vinyl methyl ether copolymer, styrene-vinyl ethyl ether copolymer, styrene-vinyl methyl ketone copolymer Polymers, styrenic copolymers such as styrene-butadiene copolymers, styrene-isoprene copolymers, styrene-acrylonitrile-indene copolymers, styrene-maleic acid copolymers, styrene-maleic acid ester copolymers, Methyl methacrylate, polybutyl methacrylate, polyvinyl chloride, polyvinyl acetate, polyethylene, polypropylene, polyester, polyurethane, polyamide, polyvinyl butyral, polyacrylic acid resin, rosin, modified rosin, terpene resin, phenolic resin, aliphatic or alicyclic resin Hydrocarbon resins, aromatic petroleum resins, chlorinated paraffins, paraffin waxes, etc. can be used alone or in combination.

Further, as a carrier agent for a developer, for example, iron,
Magnetic substances such as cobalt and nickel, alloys and mixtures thereof, or coatings on the surfaces thereof.

(Function) Conventional toners have had problems such as poor light fastness of copies, generation of capri phenomenon, and poor melt compatibility, but the toner composition of the present invention has excellent melt compatibility. However, the dye has a stable magenta color and good light fastness, and the image density obtained by continuous copying through repeated development is extremely valuable in practice.

(Example) Hereinafter, the present invention will be explained in more detail with reference to Examples. The compounds used were produced by conventional methods.

The light resistance of Examples 1 to 17 was determined after 60 hours of irradiation using a fetometer (carbon arc lamp) at 63°C.

5 parts of I-amino-4-hydroxy-2-(p-hydroxyphenyl) anthraquinone, 95 parts of toner resin [styrene-acrylic acid ester copolymer; trade name: Hymer TB-1000F (manufactured by Kaku Kasei Co., Ltd.]) After mixing and pulverizing in a ball mill, the mixture is heated to 150° C., melt-mixed, cooled, coarsely pulverized using a hammer mill, and then finely pulverized using an air jet type pulverizer. The toner is further classified to select 1 to 20 microns.

For 10 parts of this toner, carrier iron powder (trade name, E
90 parts of F V250/400 (Japanese iron powder type) were uniformly mixed to prepare a developer. Using this developer, a dry plain paper electrophotographic copying machine (product name, NP-5000; Canon)
When copying was carried out using a copying machine (manufactured by K. K.), a clear magenta image with no fog was obtained. Moreover, the light resistance of the copy was also good and was grade 6.

Examples 2 to 17 Using the dyes shown in Table 1, in exactly the same manner as in Example 1,
A high performance color toner composition was obtained.

(Leaving space below) Example Table-1 General formula (1) Substitution position of hydroxyl group -cp p-(CJ)3C p-C,It, O m-C21150CHz p~(CLL+C p-CJ50Czl140 0-C6115CH2CH2 O-CH3COO - Br O-(CH3) 3C o-C,H,0 O-C1l:lOc2H4 m-C61iSC)12 m-CIhOCo Light resistance (effect of the invention) Copying was possible using the developer using each dye in the example. The images produced using this method have a clear magenta color with no fog, and have good light resistance. However, the images copied using developers using the respective dyes in the comparative examples have poor light resistance. It is found that the compatibility between the toner and the resin is poor, and capri occurs.

In addition, if the dye of formula (+) is used as a polymerizable dye by reacting with vinyl isocyanate, for example, and copolymerized with styrene, methyl acrylate, etc., the dye resin covalently bonded in the resin can be purified. can be easily carried out, and an excellent color toner composition can be obtained.

Patent applicant Mitsui Toatsu Chemical Co., Ltd.

Claims (1)

[Claims] In the binder resin, there are general formulas (I) ▲mathematical formulas, chemical formulas, tables, etc.▼(I) (wherein R is a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an alkoxyalkyl 1. A magenta color toner composition for electrostatic charge development, comprising an anthraquinone dye represented by the following formula: alkoxyalkoxy, aralkyl, alkoxycarbonyl, or alkylcarboxy group.