JPH0341473A - Cyan toner for electrophotography - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

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 cyan toner for electrophotography containing a specific compound.

(Prior art) Electrophotography is covered by US Patent No. 229749/No., Special Publication Showa 4
As disclosed in various publications such as T-Ko-23910 Publication Sameyo and Tokko Shoke No. 3-, 2-Gukugza Publication, electrostatic charge is generally transferred onto a photoreceptor containing a photoconductive material by various means. A latent image is formed, and then the latent image is developed as a powder image with toner, and if necessary, the powder image is transferred to paper or the like, and then fixed by heat, pressure, solvent vapor, or the like.

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. Color copying methods for obtaining full-color copied images have 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 is made by dispersing coloring agents such as dyes and pigments in a resin such as polyester and finely pulverizing the particles to a size of about 1 to 308 m. It is used by mixing with a carrier material such as fur.

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

In other words, with conventional color toners, (1) due to insufficient light transmittance, color reproduction becomes difficult when multiple colors are overprinted, and overhead project (OHP)
), a good transmitted image 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 resins, dyes and pigments transfer to sensitization and degrade their performance.

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

Such problems were occurring.

Therefore, the present inventors conducted intensive studies to solve these problems, and as a result, by using a compound represented by a 5% constant structural formula, the above problems were solved and various required properties were satisfied in a well-balanced manner. The present invention was achieved by learning that an excellent toner can be obtained.

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

IN I-11 ((wherein, R represents a hydrogen atom, a substituted or unsubstituted alkyl group, a cycloalkyl group, an allyl group, or a substituted or unsubstituted phenyl group, and X represents a cyano group or an alkoxycarbonyl group) ) (Function) The present invention will be described in detail below.

To specifically explain the compound represented by the above-mentioned (I) used as a colorant in the present invention, in the formula, R
Examples of the alkyl group represented by include C1 to C8 linear or branched alkyl groups, and examples of substituted alkyl groups include cohydroxyethyl group, 3
Hydroxypropyl group, hydroxybutyl group, 4-
hydroxy-substituted alkyl groups such as hydroxypropyl groups;
Carboxy-substituted alkyl groups such as carboxymethyl group, 2-carboxyethyl group, 3-carboxypropyl group; 4
-Cyano-substituted alkyl groups such as cyanethyl group and cyanomethyl group; Amino-substituted 5 alkyl groups such as 4-anoethyl group; u-10 loethyl group, 3-chloropropyl group, 4-chloropropyl group, 2.2. Halogen-substituted alkyl groups such as 2-tolynefluoroethyl group; phenyl-substituted alkyl groups such as benzyl group, ρ-chlorobenzyl group, and 4-phenylethyl group; 4-methoxyethyl group, 4-ethoxyethyl group, -2( r+l propoxyethyl group, 4-(iso)phenylethyl group, a-(n,
l-butoxyethyl group 1.2-(iso)butoxyethyl group, 4(,2-ethylhexyloxy)ethyl group, 3-
Alkoxy-substituted alkyl groups such as methoxyfurovir group, y-methoxybutyl group, 4-methoxypropyl group; p-(
,2-methoxyethoxy)ethyl group, -2(-2-ethoxyethoxy)ethyl group 1.2- (2-(nlpropoxyethoxynoethyl group 1,!-(,2-C15o)
70 poxyethoxynoethyl group, ;2-(,2(n)
butoxyethoxy)ethyl group, 2- (2-(iso)
butoxyethoxy]ethyl group 1,: x -(,2-(+
Alkoxyalkoxy substitution such as 2-ethylhexyloxynoethoxy)ethyl group - Alkyl group; Substituted alkyl group such as allyloxyethyl group, niphenoxyethyl group, nibenzyloxyethyl group; 4-acetyloxyethyl group, -27 'ropionyloxyethyl group, di(1)butyryloxyethyl group,
Acyloxy-substituted alkyl groups such as 2-(jso)butyryloxyethyl group, x-trifluoroacetyloxyethyl group; methoxycarbonylmethyl group, ethoxycarbonylmethyl group, (n) propoxycarbonylmethyl group,
(iso) propoxycarbonylmethyl group, (rl
) butoxycarbonylmethyl group, (iso)butoxycarbonylmethyl group, nee ethylhexyloxycarbonylmethyl group, benzyloxycarbonylmethyl group,
furfuryloxycarbonylmethyl group, tetrahydrofurfuryloxycarbonylmethyl group, 4-methoxycarbonylethyl group, 2-ethoxycarbonylethyl group, co(nl propoxycarbonylethyl group, u-(is
o,) propoxycarbonylethyl group, 2-(nl butoxycarbonylethyl group, a-(iso,)butoxycarbonylethyl M1-2 (-2-ethylhexyloxycarbonylethyl group, 4-benzyloxycarbonylethyl group) , a substituted or unsubstituted alkoxycarbonyl-substituted alkyl group such as 4-furfuryloxycarbonylethyl group; 4-methoxycarbonyloxyethyl group, 2-ethoxycarbonyloxyethyl group i-2(
nl propoxycarbonyloxyethyl group, -2-(i
so) propoxycarbonyloxyethyl group i 2
(nl butoxycarbonyloxyethyl group, 2-
(iso)butoxycarbonyloxyethyl group, 2-
(Jethylhexyloxycarbonyloxy)ethyl group, copenzyloxycarbonyloxyethyl group, 4-
Substituted or unsubstituted alkoxycarbonyloxy-substituted alkyl groups such as a furfuryloxycarbonyloxyethyl group; heterocyclic-substituted alkyl groups such as a furfuryl group and a tetrahydrofurfuryl group; and the like.

Examples of the cycloalkyl group represented by R include a cyclopentyl group and a cyclohexyl group.

Furthermore, all substituted phenyl groups represented include those having a C1-CB linear or branched alkyl group as a substituent, and C1-C4 linear or branched alkoxy groups. Examples include those having a group, those having a halogen atom such as a fluorine atom, a chlorine atom, and a bromine atom, and those having a nitro group, a cyano group, and a trifluoromethyl group.

Of all the groups represented, particularly advantageous are C1
~C8 linear or branched alkyl group, C3~
C8 alkoxy-substituted alkyl group, benzyl group, niphenylethyl group, allyl group, phenyl group, 0-1! Jru group L m-)lyl group, p-)! , 1 group, etc.

The alkoxycarbonyl group represented by X is,
For example, those having a linear or branched alkyl group of 01 to C8 may be mentioned.

More specific examples of the compounds represented by the above-mentioned -monana (I) include, for example, the compounds shown in Table 7.

= 9 Table 10 - Continued from Table 1 These dyes can be produced by known methods, but for example, when X is a cyan group in the above-mentioned -Momona (I), the following -Momona (II) , 1 (wherein R represents the same meaning as above) can be easily obtained by reacting with KCN or Na CN in water or N,N-dimethylformamide. In the above-mentioned -Momona (I), when X is an alkoxycarbonyl group, a compound represented by the following -Momona (, In,) (in the formula, R represents the same meaning as above) is added to the corresponding alcohol, e.g. It can be obtained by adding an acid catalyst such as sulfuric acid and carrying out an esterification reaction E.k.

12- The colorant to be contained in the cyan toner of the present invention is not limited to the specific examples listed above;
It is also possible to use a mixture of λ or more of the compounds represented by the above-mentioned -Momona (, I, l).Also, as long as the favorable effects produced by using the compound are not impaired, other compounds than these compounds may be used. The compound may also be used as a coloring agent.Furthermore, the compound can be mixed with toners of other colors and used to improve the color.

On the other hand, the binder resin for the cyan toner of the present invention can be selected from a wide range including known ones.
Colorless and transparent materials are preferred, such as polystyrene, chloropolystyrene, poly-α-methylstyrene, styrene-chlorostyrene copolymer, styrene-propylene copolymer, styrene-butadiene copolymer, and styrene-vinyl chloride copolymer. , styrene-vinyl acetate copolymer, styrene-maleic acid copolymer, styrene-acrylic acid ester copolymer (styrene-methyl acrylate copolymer, styrene-3-ethyl acrylate copolymer, styrene-acrylic acid copolymer) butyl copolymer, styrene-octyl acrylate copolymer, styrene-phenyl acrylate copolymer, etc.), styrene-methacrylate copolymer (styrene-methyl methacrylate copolymer, styrene-ethyl methacrylate copolymer, etc.) styrene-based resins such as styrene-butyl methacrylate copolymers, styrene-phenyl methacrylate copolymers, etc.), styrene-α-methyl chloroacrylate copolymers, and styrene-acrylonitrile-acrylic ester copolymers. styrene or styrene-substituted monopolymer or copolymer), vinyl chloride resin, rosin-modified maleic acid resin, phenol resin, epoxy resin 5 polyester resin, low molecular weight polyethylene, low molecular weight polypropylene, iO/-r-mllllL Polyurethane resin, silicone resin, ketone resin. There are ethylene-ethyl acrylate copolymers, xylene resins, polyvinyl butyral resins, etc., but 1 is used in the present invention.
Particularly preferred resins include styrene resins, saturated or unsaturated polyester resins, and epoxy resins. However, the above resins are not limited to being used alone, but four or more types can also be used in combination.

The total amount of the colorant added to the toner is desirably from O, I to 30 parts by weight, and particularly desirably from O, S to IO, based on 100 parts by weight of the binder resin. If the amount added is too small, the cyan coloring effect will be poor, and if it is too large, the fixing properties will 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 chargeability control agent, a basic/electron-donating substance such as a Q-class ammonium salt may be used, and as the negative chargeability control agent, an acidic or electron-withdrawing substance such as metal chelates or gold-containing dyes may be appropriately selected and used. good.

The amount of the charge control agent to be added should be determined after considering 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. resin io.

0.0% by weight. /~10 parts by weight is appropriate.

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. .

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 amount added is o, i to i based on ioo parts by weight of the binder resin.

Parts by weight are appropriate.

Furthermore, the toner particles have T 102, A ]203.81
By adding fine powders such as 02 and coating the surfaces of toner particles, it is possible to improve the fluidity and agglomeration resistance of the toner. The amount added is preferably o, i to IO parts by weight per 100 parts by weight of the binder resin.

Various conventional toner manufacturing methods can be applied to the toner manufacturing method of the present invention, and examples of general manufacturing methods include the following.

1. First, mix the resin and colorant (additives such as a charge control agent may be added in some cases) using a ball mill, type mixer,
Uniformly disperse using an S-type mixer, Henschel mixer, etc.

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

The resulting color toner can be mixed with a carrier and used as a developer for electrophotographic copying. As the button and carrier, it is recommended to use a magnetic material such as a known iron powder carrier or ferrite carrier, or a material coated on the surface thereof in an amount of 10 to 10 parts per 7 to 7 parts 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 as long as the gist thereof is not exceeded. In addition, in each example and comparative example, "part"
The term "parts by weight" refers to "parts by weight."

(Example/) 100 parts of unsaturated polyester resin
3 parts of the compound of table/f 7 parts of zinc salicylate complex compound The above materials were melted and kneaded using a hot roll, and after cooling, coarsely ground using a hammer mill.
Then, it was pulverized using an air jet type pulverizer.

The obtained fine powder was classified to select particles having particle sizes ranging from 3 to λSμ to obtain a cyan toner. 6 parts of this cyan toner was added to 10 parts of iron powder and mixed in a type 2 mixer to prepare a developer.

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

The image density at the initial copy and after copying too many sheets is /, '13, and 8 l/3, and in the past, the charge amount of this toner was 1/+ at the initial copying stage and after copying 40,000 sheets.
! , 0 μc/y and −/s, y μc/f, and the amount of charge was stable.

(Example 4) The same procedure as in Example 1 was obtained except that a styrene n-butyl acrylate copolymer was used as the glue 9 of the unsaturated polyester resin, and the same results as in Example 1 were obtained.

(Example 3) The same Table 7 A, / g of the compound of the same table 29
Example 1 was carried out in exactly the same manner as in Example 1, except that the compound was used, and the same results as Example 1 were obtained.

(Example q) The same procedure as in Example 1 was obtained except that the compound in Table 1 A/g was replaced with the compound in Table 30, and the same results as in Example 1 were obtained. .

(Example S) When the same procedure as in Example 1 was carried out except that the compound shown in Table 1 A/g was used as a substitute for the compound shown in Table 1 A/g, the same results as in Example 1 were obtained. Ta.

(Effects of the Invention) As explained above, the cyan toner for electrophotography of the present invention satisfies the properties required for a color toner in a well-balanced manner, and among others, has excellent spectral reflection properties, good charging properties, and is always stable. An image is obtained.

Applicant: Mitsubishi Kasei Corporation Representative Patent Attorney Hase 1 other person

Claims (1)

[Claims] (1) A cyan toner for electrophotography, which contains a compound represented by the following general formula (I) in a binder resin. ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・・・・(
I) (In the formula, R represents a hydrogen atom, a substituted or unsubstituted alkyl group, a cycloalkyl group, an allyl group, or a substituted or unsubstituted phenyl group, and X represents a cyano group or an alkoxycarbonyl group.)