JP3003297B2 - Toner for developing electrostatic images - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an electrostatic image developing toner used in an electronic copying machine or the like.

[0002]

2. Description of the Related Art In a developing step, a developer used in an electronic copying machine or the like is once adhered to an image carrier such as a photoreceptor on which an electrostatic image is formed, and then is exposed to light in a transfer step. After being transferred from the body to the transfer paper, it is fixed on the copy paper surface in a fixing step. At this time, as a developer for developing an electrostatic image formed on the latent image holding surface, a two-component developer composed of a carrier and a toner and a one-component developer (magnetic toner) not requiring a carrier are used. It has been known. Conventionally, a charge controlling agent such as a nigrosine dye, a quaternary ammonium salt, a metal-containing complex dye, a coating agent for a carrier, and the like have been known as ones that impart a chargeability to the developer.

[0003]

However, these conventional charge-imparting agents do not always have a sufficient effect of imparting the chargeability, and in particular, the effect changes with time, so that copy contamination due to continuous copying occurs and the copy quality is reduced. There was a problem that it decreased.

[0004]

The inventors of the present invention have conducted intensive studies to provide a high-quality toner for developing an electrostatic charge image which is less likely to cause copy stains even after a lapse of time.
It has been found that by incorporating a compound having a specific structure into the toner, these problems can be solved.
The present invention has been reached. That is, the gist of the present invention is to provide a toner for developing an electrostatic image, which comprises at least one metal compound of a pamoic acid compound in a toner for developing an electrostatic image comprising at least a resin and a colorant. Exists.

Hereinafter, the present invention will be described in detail. In the present invention, the pamoic acid-based compound is a compound in which a substituted or unsubstituted hydroxynaphthalenecarboxylic acid is dimerized with a methylene chain as represented by the following general formula (I) or (II).

[0006]

Embedded image In the formula, one of R and R 'represents a hydroxyl group and the other represents a hydrogen atom, and both do not become a hydroxyl group or a hydrogen atom. X and X 'each represent an arbitrary substituent such as a hydrogen atom, an alkyl group, an amino group or an alkoxy group.

Specific examples of the substituents X and X 'include a hydrogen atom: an alkyl group such as a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group and a tert-butyl group: an amino group. And an alkyl-substituted amino group; and an alkoxy group such as a methoxy group and an ethoxy group. The metal compound of the pamoic acid compound in the present invention,
It means a product obtained by reacting the pamoic acid compound with a metal-imparting agent, and is not clear as a structural formula, but as a metal complex, or a metal salt, a carboxyl group and / or a hydroxyl group of the pamoic acid compound. It is presumed that each metal atom is bonded in various bonding states such as an ionic bond, a coordinate bond and a covalent bond. Ti, Zr, Si, Fe, Z
n, Cu, Al, Cr, Ni, Co and the like. Various known methods can be adopted as the synthesis method. For example, when the metal is Ti, Zr, Si or the like, the pamoic acid compound and the metal are heated at 50 to 120 ° C. in a solvent such as toluene or dioxane. It is obtained by reacting an imparting agent. Specific examples of the metal imparting agent include tetraisopropoxytitanium, tetra-n-butoxytitanium, tetraisopropoxyzirconium, and tetraisopropoxysilane. The metal is Fe, Zn, Cu, Al, C
In the case of r, Ni, Co, etc., it is obtained by reacting in an aqueous solution. Examples of the metal imparting agent include iron sulfate, zinc chloride, copper sulfate, aluminum chloride, chromium sulfate, nickel chloride, and cobalt chloride. The metal compounds of these pamoic acid compounds have good charging performance,
It has the advantage of excellent thermal stability.

Specific examples of suitable toners for inclusion in the toner for electrostatic images of the present invention include, but are not limited to, the following. Exemplified compound (1) 4,4'-methylenebis (3-hydroxy-2-
2: 1 compound of naphthalenecarboxylic acid) and Ti (2) 4,4′-methylenebis (3-hydroxy-2-
2: 1 compound of naphthalenecarboxylic acid) and Zr (3) 4,4′-methylenebis (3-hydroxy-2-
2: 1 compound of naphthalenecarboxylic acid) and Si (4) 4,4′-methylenebis (3-hydroxy-7-
2: 1 compound of methyl-2-naphthalenecarboxylic acid) and Ti (5) 4,4′-methylenebis (3-hydroxy-7-
2: 1 compound of methyl-2-naphthalenecarboxylic acid) and Si

(6) 4,4'-methylenebis (7-ethyl-3-hydroxy-2-naphthalenecarboxylic acid) and T
2: 1 compound of i (7) 4,4'-methylenebis (3-hydroxy-7-
Propyl-2-naphthalene carboxylic acid) and Zr 2: 1
Compound (8) 2: 1 compound of 4,4'-methylenebis (7-butyl-3-hydroxy-2-naphthalenecarboxylic acid) and Si (9) 4,4'-Methylenebis (7-amino-3-hydroxy- 2: 1 compound of 2-naphthalenecarboxylic acid) and Ti (10) 2: 1 compound of 4,4′-methylenebis (7-amino-3-hydroxy-2-naphthalenecarboxylic acid) and Zr
Compound

(11) 4,4'-methylenebis (3-hydroxy-7-methoxy-2-naphthalenecarboxylic acid)
And a 2: 1 compound of Ti and (12) 4,4′-methylenebis (3-hydroxy-7
-Methoxy-2-naphthalenecarboxylic acid) and Zr 2:
1 compound (13) 4,4′-methylenebis (7-ethoxy-3-
Hydroxy-2-naphthalenecarboxylic acid) and Si:
1 compound (14) 4,4′-methylenebis (3-hydroxy-2
-Naphthalenecarboxylic acid) and Fe 1: 1 compound (15) 4,4'-methylenebis (3-hydroxy-7
1-methyl-2-naphthalenecarboxylic acid) and Fe
Compound

(16) 1: 1 of 4,4'-methylenebis (3-hydroxy-2-naphthalenecarboxylic acid) and Zn
Compound (17) 1: 1 of 4,4′-methylenebis (7-ethyl-3-hydroxy-2-naphthalenecarboxylic acid) and Zn
Compound (18) 4,4′-methylenebis (3-hydroxy-2
-Naphthalenecarboxylic acid) and 1: 1 compound of Cu (19) 1: 1 compound of 4,4'-methylenebis (7-butyl-3-hydroxy-2-naphthalenecarboxylic acid) and Cu
Compound (20) 4,4′-methylenebis (3-hydroxy-2
-Naphthalenecarboxylic acid) and Al 1: 1 compound

(21) 1: 1 compound of 4,4'-methylenebis (7-amino-3-hydroxy-2-naphthalenecarboxylic acid) and Al (22) 4,4'-methylenebis (3-hydroxy-2
-Naphthalenecarboxylic acid) and 1: 1 compound of Cr (23) 4,4'-methylenebis (3-hydroxy-7
-Methoxy-2-naphthalenecarboxylic acid) and Cr:
1 compound (24) 4,4′-methylenebis (3-hydroxy-2
-Naphthalene carboxylic acid) and 1: 1 compound of Ni (25) 4,4'-methylenebis (3-hydroxy-7
-Methyl-2-naphthalene carboxylic acid) and Ni 1: 1
Compound

(26) 1: 1 of 4,4'-methylenebis (3-hydroxy-2-naphthalenecarboxylic acid) and Co
Compound (27) 4,4′-methylenebis (3-hydroxy-7
-Propyl-2-naphthalenecarboxylic acid) and Co:
1 compound (28) 4,4′-methylenebis (1-hydroxy-2
-Naphthalenecarboxylic acid) and Ti 2: 1 compound (29) 4,4′-methylenebis (1-hydroxy-2
-Naphthalenecarboxylic acid) and Zn: 1: 1 compound (30) 4,4′-methylenebis (1-hydroxy-2
-Naphthalenecarboxylic acid) and Fe 1: 1 compound

(31) 1: 1 of 4,4'-methylenebis (1-hydroxy-2-naphthalenecarboxylic acid) and Al
Compound (32) 3,3′-methylenebis (2-hydroxy-1
-Naphthalenecarboxylic acid) and 2: 1 compound of Ti (33) 1: 1 of 3,3′-methylenebis (7-ethyl-2-hydroxy-1-naphthalenecarboxylic acid) and Zn
Compound (34) 3,3′-methylenebis (2-hydroxy-1
-Naphthalenecarboxylic acid) and a 1: 1 compound of Cu (35) 3,3′-methylenebis (2-hydroxy-1
-Naphthalenecarboxylic acid) and a 1: 1 compound of Ni (36) 3,3′-methylenebis (2-hydroxy-1
-Naphthalenecarboxylic acid) and Al 1: 1 compound

The resin component that can be used in the present invention includes:
Various known ones can be used. For example, there are a styrene resin, a styrene acrylic copolymer resin, a polyester resin, an epoxy resin, a resin mixture thereof, and a resin having an amino group in an alkyl side chain. The content of the metal compound of the pamoic acid-based compound in the toner is as follows.
The amount is preferably 0.1 to 20 parts by weight, more preferably 0.5 to 15 parts by weight, based on 00 parts by weight. If the content of the metal compound of the pamoic acid compound is too small, the effect of improving the chargeability is not improved, and if it is excessive, the quality of the toner is deteriorated, which is not preferable.

The colorant used in the present invention is not particularly limited as long as it has been conventionally used. To obtain a black toner, carbon black or the like is used. Further, in the toner of the present invention, apart from the metal compound of the pamoic acid compound, other charge control agents including known ones, for example, nigrosine dye, quaternary ammonium salt, metal-containing complex Compounds and the like may be contained. In addition, additives such as a low-molecular-weight olefin polymer and finely divided silica may be added as a toner component of the present invention in order to improve fixability and fluidity.

The toner may be produced by kneading the above components in a kneader or the like, cooling, pulverizing and classifying.
In addition to the two-component developer, the toner of the present invention can be applied to a so-called one-component developer (magnetic toner) such as an encapsulated toner, a polymerized toner, and a magnetite-containing toner. The average particle size of the toner is preferably 5 to 20 μm. The carrier for forming the developer by mixing with the toner of the present invention is not particularly limited, but is preferably a ferrite-based or magnetite-based iron powder having an average particle diameter of 10 to 200 μm. There is no particular limitation on any particle size.
In this case, a so-called coating carrier coated with a fluorine-based resin or the like can be used for the purpose of improving durability during continuous use. Iron powder can also be used. These carriers are preferably used in an amount of 5 to 100 parts by weight based on 1 part by weight of the toner.

[0018]

EXAMPLES Hereinafter, the present invention will be described in more detail by way of examples, but the present invention is not limited to the following examples unless it exceeds the gist thereof. In the following examples, “parts” simply means “parts by weight”. Example 1 Styrene-based resin (SBM-600, manufactured by Sanyo Chemical Co., Ltd.) 100 parts Carbon black (# 44, manufactured by Mitsubishi Kasei Co., Ltd.) 10 parts Exemplified compound (1) 1 part The above materials were blended, kneaded, pulverized and classified. Average particle size 11
A μm black toner was obtained. 5 parts of this toner was mixed with 100 parts of a ferrite carrier having an average particle size of about 100 μm,
By stirring, a developer was prepared. The charge amount of the toner measured by the blow-off method was −25.0 μc / g. Then, when 1000 continuous sheets of A4 size paper were continuously photographed with a copying machine using selenium as a photoreceptor, a stable and clear copy was always obtained.

Comparative Example 1 The procedure of Example 1 was repeated, except that Exemplified Compound (1) was not used as the charge control agent. The density of the image decreased as the number of actual shots increased, and the resulting image was of low quality. It was something. Example 2 The procedure of Example 1 was repeated, except that 2 parts of the exemplified compound (2) was used as the charge control agent. As a result, a good copy was obtained as in Example 1. Example 3 Except that 1 part of Exemplified Compound (4) was used instead of Exemplified Compound (1) as a charge controlling agent, the same procedure as in Example 1 was carried out, and a good copy was obtained as in Example 1. Was done. Example 4 Except that 3 parts of Exemplified Compound (7) was used instead of Exemplified Compound (1) as a charge controlling agent, the same procedure as in Example 1 was carried out, and a good copy was obtained as in Example 1. Was done. Example 5 Except that 2 parts of Exemplified Compound (10) was used instead of Exemplified Compound (1) as a charge control agent, the same procedure as in Example 1 was carried out, whereby a good copy was obtained.

Example 6 The procedure of Example 1 was repeated, except that 2 parts of the compound (11) was used instead of the compound (1) as a charge controlling agent. A copy was obtained. Example 7 The same procedure as in Example 1 was carried out except that 3 parts of the exemplary compound (14) was used instead of the exemplary compound (1) as a charge control agent. Example 8 The same procedure as in Example 1 was carried out except that 2 parts of Exemplified Compound (16) was used instead of Exemplified Compound (1) as a charge controlling agent, whereby a copy similar to that of Example 1 was obtained. Example 9 The same procedure as in Example 1 was carried out except that 3 parts of Exemplified Compound (20) was used instead of Exemplified Compound (1) as a charge controlling agent, whereby a copy similar to that of Example 1 was obtained. Example 10 The same procedure as in Example 1 was carried out except that 3 parts of Exemplified Compound (30) was used instead of Exemplified Compound (1) as a charge controlling agent, whereby a copy similar to that of Example 1 was obtained. Example 11 Except that 4 parts of Exemplified Compound (33) was used instead of Exemplified Compound (1) as a charge controlling agent, the same procedure as in Example 1 was carried out, and a copy similar to that of Example 1 was obtained.

[0021]

The toner for developing an electrostatic image of the present invention is a high-quality toner for developing an electrostatic image, which has high chargeability and is stable over time, and does not cause copy stains or the like due to continuous copying.

──────────────────────────────────────────────────続 き Continuation of the front page (56) References JP-A-4-3076 (JP, A) JP-A-61-267058 (JP, A) JP-A-3-83071 (JP, A) JP-A-1- 113762 (JP, A) (58) Field surveyed (Int. Cl. ⁷ , DB name) G03G 9/08 CA (STN)

Claims (1)

(57) [Claims] 1. An electrostatic image developing toner comprising at least a resin and a colorant, comprising at least one metal compound of a pamoic acid compound.