JPH0336553A - Electrophotographic magenta toner - Google Patents

Abstract

PURPOSE:To obtain a superior toner capable of satisfying the requirements of various characteristics in good balance by using a compound represented by a specified structural formula. CONSTITUTION:The binder resin contains the compound represented by formula I in which R<1> is H, optionally substituted alkyl, such phenyl, or such allyl; K is an aniline type coupling component; and n is 0, 1, or 2, thus permitting the obtained toner to satisfy the requirements as the characteristics of the color toner in good balance, especially to be excellent in spectral reflectance characteristics, and good in electric chargeability characteristics, and to always form stable images.

Description

DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a color toner for electrophotography, and more particularly to a magenta toner for electrophotography containing a specific compound.

(Prior art) The electrophotographic method is described in U.S. Patent No. 2297/97,
I2-239/θ Publication Button and Special Publication Shoda 3-2117'
Generally, an electrostatic latent image is formed on a photoreceptor containing a photoconductive material by various means, and then the latent image is powdered with toner. After developing it as an image and transferring the powder image to paper etc. as necessary,
It is fixed by heating, pressure, solvent vapor, etc.

However, in recent years, electrostatic latent images of originals are formed by exposing them to spectral light, which is then developed with colored toners to obtain colored copies, or by superimposing copies of each color. A color copying method for obtaining full-color copied images has been put into practical use, and color toners such as yellow, magenta, and cyan, which are made by dispersing dyes and/or pigments of each color in a binder resin, have been manufactured. .

The toner used is made by dispersing coloring agents such as dyes and pigments in a resin such as polyester and finely pulverizing the particles to about 30 μm. It is used by mixing with a carrier material such as casing or fur.

(Problems to be Solved by the Invention) However, with conventional color toners, it has been difficult to satisfy the various performances required of color toners.

In other words, conventional color toners (1) lack light transmittance, making color reproduction difficult when overprinting multiple colors; and overprinting (OHP).
When creating transparencies and ranges, good transmission images cannot be obtained.

(2) Good hue and color cannot be obtained because the spectral reflection characteristics are not good.

(3) Due to insufficient fastness to light and heat, the color of the copied image fades during storage.

(4) Due to the low affinity between dyes and pigments and binder resin,
The dyes and pigments migrate to the photoreceptor, reducing its performance.

(5) Due to poor charging characteristics, the color balance deteriorates as the number of copies increases, and defects such as capri density changes occur on images.

Such problems were occurring.

Therefore, as a result of intensive studies to solve these problems, the present inventors found that by using a compound represented by a specific structural formula, the above problems could be solved and the various required characteristics could be satisfied in a well-balanced manner. The present invention was achieved based on the knowledge that it is possible to obtain a toner with a high temperature.

(Means for Solving the Problem) That is, the gist of the present invention is that the following -
A magenta toner for electrophotography is characterized by containing a compound represented by a pattern (1).

(In the formula, R1 represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, or an allyl group, and K represents an anion-based coupling component.n
is an integer 0. / or represents ko. ) (Function) The present invention will be explained in detail below.

The compound represented by the above-mentioned -Momonana (1) used in the present invention will be specifically explained.

In general formula (I), the aniline-based coupling component represented by () refers to any monovalent group derived from aniline or its derivative; Among the compounds represented by 1), the following -Momona (II) R1! alkyl group 5 represents a substituted or unsubstituted phenyl group or allyl group, R4 represents a hydrogen atom, a lower alkyl group, a substituted or unsubstituted alkoxy group or a halogen atom,
R5 represents hydrogen, a lower alkyl group, a formylamino group, a substituted or unsubstituted alkylcarbonylamino group, a benzoylamino group, a substituted or unsubstituted alkoxycarbonylamino group, or a halogen atom). Particularly advantageous are those having a coupling component of .

The compound represented by the above-mentioned pattern (I) used in the present invention can be produced by a known method disclosed in JP-A-57-90OSS, for example, but the magenta toner for electrophotography of the present invention Examples of compounds that can be used include Rt, R2, R3, R4 and R5 in general formula (n).
The following can be mentioned.

As the alkyl group represented by R', & and R3,
Examples include C1 to C6 linear or branched alkyl groups, and examples of substituted alkyl groups include co-hydroxyethyl group, 3-hydroxybrobyl group, terhydroxybutyl group, nihydroxy-probyl group, etc. Hydroxy-substituted alkyl groups, carboxy-substituted alkyl groups such as carboxymethyl, 2-carboxyethyl and 3-carboxypropyl groups, cyano-substituted alkyl groups such as 2-cyanoethyl and cyanomethyl groups, and amino such as 4-amino-ethyl groups. Substituted alkyl group 1.2-1'roloethyl group, 3-chloropropyl group, dichloropropyl group,
Co, Co,, 2-To IJ Halogen atom-substituted alkyl groups such as fluoroethyl groups, phenyl-substituted alkyl groups such as Hensyl group, p-chlorobenzyl group, niphenylethyl group, niemethoxyethyl group, niethoxyethyl group,
Ni (n) propoxyethyl group, ' (iso) propoxyethyl group, Ni (n) butoxyethyl group, Ni (
iso) butoxyethyl group, ni(=-ethylhexyloxy)ethyl group, 3-methoxypropyl group, methoxybutyl group, co-methoxyglobyl group, etc., alkoxy-substituted alkyl group, ni(λ-methoxyethoxy)ethyl group , ni(2-ethoxyethoxy)ethyl group, λ-(
(n) propoxyethoxy)ethyl group, 2-(2
-(iso)propoxyethoxy)-ethyl group, 2-(
2-(n)butoxyethoxy)ethyl group, λ-(2-(
iso)butoxyethoxy)ethyl group, X-(, Z-(
Alkoxyalkoxy substituted alkyl groups such as X-ethylhexyloxy)ethoxy)ethyl group, substituted alkyl groups such as 2-allyloxyethyl group, niphenoxyethyl group, nibenzyloxyethyl group, niacetyloxyethyl group, 4-propionyl group Oxyethyl group 1.2-
(n) Butyryloxyethyl group,! -(iso)butyryloxyethyl group, acyloxy-substituted alkyl group such as trifluoroacetyloxyethyl group, methoxycarbonylmethyl group, ethoxycarbonylmethyl group, (n
) propoxycarbonylmethyl group, (iso) propoxycarbonylmethyl group, (n) butoxycarbonylmethyl group, (iso) butoxycarbonylmethyl group, nee-ethylhexyloxycarbonylmethyl group, benzyloxycarbonylmethyl group, furfuryloxycarbonylmethyl group group, tetrahydrofurfuryloxymethyl group, methoxycarbonylethyl group, λ-ethoxycarbonylethyl group, 2-(n) 7'ropoxycarbonylethyl group, '-(iso)propoxycarbonylethyl group, ni(n) butoxy carbonylethyl group 1,2
Substituted or unsubstituted alkoxycarbonyl-substituted alkyl groups such as -(iso)butoxycarbonylethyl group, col(nietherhexyloxycarbonyl)ethyl group, neepenzyloxycarbonylethyl group, 2-yyl7lylcarbony, ruethyl group, etc. , λ-methoxycarbonyloxyethyl group, coethoxycarbonyloxyethyl group, -2-(n)propoxycarbonyloxyethyl &
, 2-(iso)propoxycarbonyloxyethyl group, 2-(n)butoxycarbonyloxyethyl group, x
-(iso)butoxycarbonyloxyethyl group, a
Substituted or unsubstituted alkoxycarbonyloxy-substituted alkyl groups such as -(2-ethylhexyloxycarbonyloxy)ethyl group, 2-benzyloxycarbonyloxyethyl group, 2-furfuryloxycarbonyloxyethyl group, furfuryl group , a heterocyclic-substituted alkyl group such as a tetrahydronyl7lyl group, etc.O al , Substituted phenyl groups represented by R2 and R3 include, for example, as a substituent, -C, -C, linear or branched alkyl groups, etc. Those with chain alkyl groups, those with C1 to C4 linear or branched alkoxy groups, those with halogen atoms such as fluorine atoms, chlorine atoms, bromine atoms, nitro groups, cyano groups, etc. Examples include things that you have.

Examples of the halogen atom among the substituents represented by R5 include a fluorine atom, a chlorine atom, and a bromine atom, and examples of the lower alkyl group include a linear or branched alkyl group of 01 to C4. Examples of the substituted or unsubstituted alkylcarbonylamino group include those in which the alkyl group is a C3-C4 linear or branched alkyl group, and those in which the alkyl group is a trifluoromethyl group. Examples of the substituted alkoxycarbonylamino group include those in which the alkoxy group is a C1 to C4 linear or branched alkoxy group, furfuryloxy group, benzyloxy group, or tetrahydrofurfuryloxy group. It will be done.

Among the substituents represented by R4, examples of the rogen atom include a fluorine atom, a chlorine atom, a bromine atom,
Examples of lower alkyl groups include C1 to C4 linear or branched alkyl groups, and examples of substituted or unsubstituted alkoxy groups include C4 to C8 linear or branched alkoxy groups, cochloro, etc. ethoxy group, comethoxyethoxy group, 2-ethoxyethoxy group, co(n
) Propoquine ethoxy group,! -(iso)propoxyethoxy group, '(n)butoxyethoxy group, J-
Examples include (iso)butoxyethoxy group, cophenoxyethoxy group, copenzyloxyethoxy group, cofurfuryloxyethoxy group, kochitrahydrofurfuryloxyethoxy group, furfuryloxy group, and tetrahydrofurfuryloxy group.

Particularly advantageous among the above-mentioned groups represented by R+ are C, -C, linear or branched alkyl groups,
Cyanoethyl group, cyanomethyl group, Hensyl group, Coffenylethyl group 1.2-(C.

-C4 alkoxy)ethyl group, C1-C4 alkoxycarbonylmethyl group, 1,2-(C,-04 flukoxycarponyl)ethyl group, and allyl group.

Among the above groups represented by R2 and R3, particularly preferred are C1 to C6 linear or branched alkyl groups, cohydroxyethyl groups, cocyanoethyl groups, cochloroethyl groups, benzyl group, λ-phenylethyl group, 2-CC, ~C4 alkoxy)ethyl group, 4-
Allyloxyethyl group, copenzyloxyethyl group,
Examples include a-(C1-C4 alkoxycarbonyl)ethyl group, coacetyloxyethyl group, 2-(C1-C4 alkoxycarbonyloxy)ethyl group, and allyl group.

Among the above-mentioned groups represented by R5, particularly preferred are a hydrogen atom, a methyl group, a formylamino group, an acetylamino group, a trifluoromethylcarbonylamino group, and the like.

Particularly advantageous among the above groups represented by R4 include methyl group, methoxy group, and hydrogen atom.

More specific examples of the compound represented by the above-mentioned -Momona (I) include those shown in Table/.

The coloring agent to be contained in the magenta toner of the present invention is not limited to the specific examples listed above, but it is also possible to use a mixture of two or more of the compounds represented by the above-mentioned pattern (1). It is possible. Further, compounds other than these compounds may be used in combination as a coloring agent, as long as the favorable effects produced by using the compounds are not impaired. Furthermore, the compound can be mixed with toners of other colors and used for color improvement.

On the other hand, the binder resin for the magenta toner of the present invention can be selected from a wide range including known ones, but colorless and transparent ones are preferred, such as polystyrene,
Chloropolystyrene, poly-α-methylstyrene, styrene-chlorostyrene copolymer, styrene-propylene copolymer, stele/-butadiene copolymer, styrene-
Vinyl chloride copolymer, styrene-vinyl acetate copolymer,
Styrene-maleic acid copolymer, styrene-acrylic acid ester copolymer (styrene-methyl acrylate copolymer, styrene-ethyl acrylate copolymer, styrene-butyl acrylate copolymer, styrene-octyl acrylate) copolymers and styrene-phenyl acrylate copolymers), styrene-methacrylic acid ester copolymers (styrene-methyl methacrylate copolymers, styrene-phenyl acrylate copolymers, etc.)
ethyl methacrylate copolymer, styrene-butyl methacrylate copolymer, styrene-phenyl methacrylate copolymer, etc.), styrene-α-methyl chloroacrylate copolymer, and stele/-acrylonitrile-acrylic acid ester copolymer Styrenic resins (unipolymer or copolymer containing styrene or styrene substitutes), vinyl chloride resin, rosin-modified maleic acid resin, phenol resin, epoxy resin, polyester resin, low molecular weight polyethylene, low molecular weight polypropylene, etc. Ionomer resins, polyurethane resins, silicone resins, ketone resins, ethylene-ethyl acrylate copolymers, xylene resins, polyvinyl butyral resins, etc. are particularly preferred for use in the present invention! Examples of suitable resins include styrene resins, saturated or unsaturated polyester resin buttons, and epoxy resins. Moreover, the above resins are not limited to being used alone, but can also be used in combination of two or more.

The total amount of the above coloring agent added to the toner is desirably 30 parts by weight based on 700 parts by weight of the binder resin, particularly preferably θ, S -/θ parts by weight. If the amount added is too small, the coloring effect as a magenta color will be poor, and if the amount added is too large, the fixing properties will tend to be poor.

The charge control of the toner may be performed using the binder resin or dye/pigment itself, but if necessary, a charge control agent that does not cause problems in color reproduction may be used in combination. As the positive charge control agent, a basic/electron-donating substance such as a double ammonium salt, and as the negative charge control agent, acidic or electron-withdrawing substances such as metal chelates or gold-containing dyes may be selected and used as appropriate. good.

The amount of the charge control agent to be added should be determined by taking into consideration conditions such as the chargeability of the binder resin, the manufacturing method including the amount and dispersion method of the colorant, and the chargeability of other additives. A suitable amount is 0.7 to 70 parts by weight.

These charge control agents may be used by being mixed into the binder resin, or may be used in the form of being attached to the surface of the toner particles.

Furthermore, the electrical properties of the toner can be controlled by adding solid electrolytes, polymer electrolytes, charge transfer complexes, conductors such as metal oxides such as tin oxide, semiconductors, ferroelectric materials, magnetic materials, etc. O In addition, it is also possible to add various auxiliary agents such as plasticizers and release agents to the toner for the purpose of adjusting thermal properties, physical properties, etc. The appropriate amount of addition is θ, / to /θ parts by weight based on 100 parts by weight of the binder resin.

Furthermore, toner particles include TiO2, Al2O3, 5102
The fluidity and agglomeration resistance of the toner can be improved by adding fine powders such as these and coating the surfaces of the toner particles. The amount added is the binder resin io
It is preferably o, i to /θ parts by weight relative to θ parts by weight.

Various conventional toner manufacturing methods can be applied to the toner manufacturing method of the present invention. For example, the following example can be given as a boat fishing manufacturing method.

A ball mill, a V-type mixer,
Uniformly disperse using an S-type mixer, Henschel mixer, etc.

Next, the dispersion is melt-kneaded using a double-arm kneader, a pressure kneader-extruder roll mill, or the like. The mixed material is pulverized using a pulverizer such as a hammer mill, cutter mill, jet mill, or ball mill, and the resulting powder is further classified using an air classifier.

The resulting color toner can be mixed with a carrier and used as a developer for electrophotographic copying. As the carrier, it is preferable to use a magnetic material such as a known iron powder carrier or ferrite carrier, or a carrier coated on the surface thereof in an amount of 70 parts to 100 parts per part of toner.

(Examples) The present invention will be described in more detail below with reference to Examples, but the present invention is not limited to the following Examples unless the gist thereof is exceeded. In addition, "parts" in each example and comparative example shall represent "parts by weight."

(Example/) Unsaturated polyester resin /θθ part Compound A/ in Table 7 3 parts Zinc salicylate complex compound 7 parts The above materials were melt-kneaded using a heated roll mill, and after cooling, coarsely ground using a hammer mill. Then, it was pulverized using an air jet type pulverizer.

The resulting fine powder was classified to select particles with a particle size of ~2 μm to obtain a magenta toner. 6 parts of this magenta toner was added to 100 parts of iron powder and mixed in a V-type mixer to prepare a developer.

When this developer was used for copying with a dry plain paper electrophotographic copying machine, there was no capri, the spectral reflection characteristics were good, and clear images were obtained. Furthermore, when 20,000 copies were continuously made using this developer, there was no deterioration in the quality of the copied images.

The image density at the initial stage of copying and after 20,000 copies is i, lIs and/or 93, and the charge amount of this toner is 1/2 at the beginning of copying and after 20,000 copies.
The charge amount was 3 μc/g and -76.2 μc/g, and the amount of charge was stable.

(Example 2) Example 2 was carried out in exactly the same manner as Example 2, except that a styrene-n-butyl acrylate copolymer was used instead of the unsaturated polyester resin, and the same results as Example 2 were obtained.

(Example 3) Example 3 was carried out in exactly the same manner as in Example 3, except that compounds AJ and ? in the table 1 were used for the compound ^/ in Table 1 (1). Equivalent results were obtained.

(Example D) AI in the table/instead of the compound in AI in the table/in the table above
The same procedure as in Example 1 was carried out except that compound No. 2 was used, and the same results as in Example 2 were obtained.

(Example was carried out in exactly the same manner as in Example/, except that a compound of CoO was used in / in the above table/instead of the compound in AI in the above table/in /, and the same result as in Example/ was obtained. Obtained.

(Effects of the Invention) As explained above, the magenta toner for electrophotography of the present invention has
It satisfies the properties required of a color toner in a well-balanced manner, and among others, has excellent spectral reflection properties and good charging properties, so that stable images can always be obtained.

Applicant: Mitsubishi Kasei Corporation Representative Patent Attorney Naga Kagawa Others/names

Claims (1)

[Claims] (1) A magenta toner for electrophotography, characterized in that a binder resin contains a compound represented by the following general formula (I). ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, R^1 represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, or an allyl group, and K is an aniline-based Represents a coupling component.n
represents an integer 0, 1 or 2. )