JP3264002B2 - Charge control agent for toner and 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 a toner for developing an electrostatic image and a charge control agent for the toner, which are used in an electronic copying machine or the like.

[0002]

2. Description of the Related Art In a developing process, 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 process. 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 coating agent for a carrier, and the like have been known as ones which impart a chargeability to a developer.

[0004]

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.

[0005]

The inventors of the present invention have conducted intensive studies to provide a high-quality electrostatic image developing toner which is less likely to cause copy stains and the like even after a lapse of time. It has been found that these problems can be solved by incorporating a compound having the formula (1) into the toner, and the present invention has been achieved. That is, the gist of the present invention is to provide a toner for developing an electrostatic image containing at least a resin and a colorant, comprising at least one compound represented by the following general formula (I). Exists in toner for image development. Another gist of the present invention is represented by the following general formula (I).
The toner charge control agent to be used.

[0006]

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[Wherein R ¹ , R ² and R ³ are each
R ³ represents an alkyl group having 2 to 14 carbon atoms which may have a substituent, or R ¹ and R ² represent a methyl group;
Represents an alkyl group having 6 to 14 carbon atoms which may have a substituent or a benzyl group which may have a substituent; R ⁴ represents a halogen atom or an alkyl group having 1 to 8 carbon atoms; A represents an aromatic ring residue which may have a substituent. Hereinafter, the present invention will be described in detail.

The toner for developing an electrostatic image of the present invention is characterized by containing one or more compounds represented by the general formula (I). In the general formula (I), specific examples of R ¹ , R ² and R ³ include an alkyl group having 1 to 24 carbon atoms; and an aralkyl group such as a benzyl group, a phenethyl group and a furfuryl group. As a substituent on these, a cycloalkyl group having 5 to 12 carbon atoms;
An alkenyl group; a hydroxyl group; an amino group; a mono- or dialkylamino group; an alkoxy group such as a methoxy group, an ethoxy group, a propoxy group and a butoxy group; a halogen group such as chlorine, bromine and fluorine;

R ¹ , R ² and R ³ are preferably methyl, ethyl, propyl, butyl, hexyl, octyl, decyl, lauryl, myristyl, cetyl, stearyl, benzyl. No. R ⁴ represents a halogen atom or an alkyl group having 1 to 8 carbon atoms;
Particularly, a chloro atom or an alkyl group having 1 to 4 carbon atoms is preferable. In the present invention, an ammonium salt having a cation component represented by the general formula (II) or (III) is used.

[0010]

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In the formula, R ⁷ represents an alkyl group having 6 to 14 carbon atoms such as an octyl group, a decyl group, a lauryl group, a myristyl group, a cetyl group, a stearyl group, or a benzyl group;
R ⁸ represents an alkyl group having 2 to 14 carbon atoms such as a butyl group, a hexyl group, an octyl group, a decyl group or a lauryl group. R ⁴ represents a halogen atom or an alkyl group having 1 to 8 carbon atoms.

When a substituent such as R ⁴ is present in the benzyl group, water solubility is reduced, and a salt exchange reaction in water is easily performed. Also, it has excellent moisture resistance as a toner. A is an aromatic ring residue which may have a substituent, for example, a phenylene group, a naphthylene group, and an anthrylene group, and a naphthylene group is particularly preferable. Examples of the substituent include an alkyl group, particularly a lower alkyl group, a halogen atom, a hydroxyl group or an amino group, and a hydroxyl group is particularly preferable.

Specific examples of the compounds represented by the general formula (I) which are suitable for inclusion in the toner for developing an electrostatic image of the present invention include a cation represented by the following structural formula, Combinations can be mentioned, but not limited to these. Illustrative compounds

[0014]

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[0015]

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[0016]

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[0017]

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The compound represented by the general formula (I) can be used in the present invention regardless of the production method. An example of the specific production method will be described below. The compound represented by the general formula (I) is generally, for example, a compound represented by the following general formula (II)

[0019]

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(Wherein A has the same meaning as in general formula (I), and Y represents an alkali metal such as sodium or potassium), and reacted by heating at about 70 ° C. in water or alcohol. Can be As the resin component usable in the present invention, various known resin components suitable for the toner for developing an electrostatic image can be used. For example, styrene-based resins, styrene-acrylic copolymer resins, polyester-based resins, epoxy-based resins, and mixed resins thereof, and those having an amino group in the alkyl side chain, and the like are available.

The content of the compound represented by formula (I) in the toner is preferably 0.1 to 20 parts by weight, more preferably 0.5 to 3 parts by weight, based on 100 parts by weight of the resin. . If the content of the compound represented by the general formula (I) is too small, the effect of improving the chargeability cannot be expected, and if it is excessive, the quality of the toner deteriorates, which is not preferable. The colorant used in the present invention is not particularly limited as long as it is conventionally used, and carbon black or the like is used to obtain a black toner. Further, since the compound represented by the general formula (I) is usually white, it may be contained in a color toner of blue, red, yellow or the like. In this case, a coloring agent composed of a dye or pigment of a corresponding color is used.

The content of the colorant is preferably 3 to 20 parts by weight based on 100 parts by weight of the resin. Further, in addition to the compound represented by the general formula (I), the toner of the present invention may contain other charge control agents including known ones such as a nigrosine dye, a quaternary ammonium salt, and a polyamine resin. May be included.

Other components of the toner of the present invention include:
In order to improve fixability and fluidity, additives such as a low molecular weight olefin polymer and finely divided silica may be added. As a method for producing the toner, the above components may be kneaded in a kneader or the like, cooled, pulverized and classified. 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 carrier having an average particle diameter of 10 to 200 μm. in this case,
A so-called coating carrier coated with a silicone-based resin, a fluorine-based resin, a chlorine-containing resin, or the like can be used for the purpose of improving durability during continuous use.
Further, other known carriers such as iron-based and magnetite-based carriers 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.

[0025]

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

[Table 1] Styrene-based resin 100 parts (manufactured by Sanyo Chemical Co., Ltd., trade name: SBM-600) Carbon black 10 parts (manufactured by Mitsubishi Kasei Co., Ltd. # 44) Exemplified compound (C1) (A5) 2 parts Compounding the above materials Knead, pulverized and classified, average particle size 11μ
m of black toner was obtained. 5 parts of this toner and an average particle size of about 1
00 μm fluororesin-coated carrier 100
And the resulting mixture were mixed and stirred to prepare a developer. Next, when this developer was actually photographed with a copying machine using an organic photoconductor as a photoreceptor, a clear copy with less background stains, so-called fog, was obtained.

Example 2 The procedure was the same as in Example 1 except that 2 parts of the exemplified compound (C5) (A6) was used instead of 2 parts of the exemplified compound (C1) (A5) as the charge controlling agent. However, Example-1
A good copy was obtained in the same manner as described above.

Example 3 Except that 2 parts of Exemplified Compound (C10) (A5) was used instead of 2 parts of Exemplified Compound (C1) (A5) as a charge controlling agent, the same procedure as in Example 1 was carried out. A good copy was obtained as in Example-1.

Example 4 The procedure was the same as in Example 1 except that 2 parts of Exemplified Compound (C11) (A5) was used instead of 2 parts of Exemplified Compound (C1) (A5) as a charge controlling agent. Example 1
A good copy was obtained in the same manner as described above.

Example -5 The same procedure as in Example 1 was carried out except that 2 parts of the exemplified compound (C12) (A5) was used instead of 2 parts of the exemplified compound (C1) (A5) as a charge controlling agent. Example 1
A good copy was obtained in the same manner as described above.

Example -6 The same procedure as in Example 1 was carried out except that 2 parts of Exemplified Compound (C13) (A5) was used instead of 2 parts of Exemplified Compound (C1) (A5) as a charge controlling agent. Example 1
A good copy was obtained in the same manner as described above.

Example -7 Except that 3 parts of the exemplified compound (C15) (A5) was used instead of 2 parts of the exemplified compound (C1) (A5) as the charge controlling agent, the procedure was the same as in Example 1. Example-
Good copies were obtained as in 1.

Example -8 The same procedure as in Example 1 was carried out except that 3 parts of the exemplified compound (C17) (A5) was used instead of 2 parts of the exemplified compound (C1) (A5) as the charge controlling agent. Example 1
A good copy was obtained in the same manner as described above.

Example -9 The same procedures as in Example 1 were carried out except that 2 parts of the exemplified compounds (C4) and (A6) were used instead of 2 parts of the exemplified compounds (C1) and (A5) as the charge controlling agent. A good copy was obtained as in Example-1.

Comparative Example 1 A developer was prepared and subjected to actual copying in the same manner as in Example 1 except that the exemplified compound (1) was not used as a material. As a result, a copy having a lot of fog and a poor copy quality was obtained. Was.

[0036]

The toner for developing an electrostatic image of the present invention is a high-quality toner for developing an electrostatic image, which does not cause stains on a copy in continuous copying.

──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Masako Takeuchi 1000 Kamoshita-cho, Midori-ku, Yokohama-shi, Kanagawa Prefecture Inside Mitsubishi Chemical Research Laboratory (72) Inventor Hirofumi Oda 370 Enzura, Chigasaki-shi, Kanagawa Prefecture Mitsubishi Chemical Corporation Chigasaki Office (56) References JP-A-4-294367 (JP, A) JP-A-62-2259 (JP, A) JP-A-4-57064 (JP, A) JP-A-4-37863 (JP, A) A) (58) Field surveyed (Int. Cl. ⁷ , DB name) G03G 9/08 CA (STN)

Claims (3)

(57) [Claims] 1. An electrostatic image developing toner comprising at least a resin and a colorant, comprising a compound represented by the following general formula (I). Embedded image [Wherein, R ¹ , R ² and R ³ each represent an alkyl group having 2 to 14 carbon atoms which may have a substituent, or R ¹ and R ² represent a methyl group, R ³ represents an alkyl group having 6 to 14 carbon atoms which may have a substituent or a benzyl group which may have a substituent; and R ⁴ represents a halogen atom or an alkyl group having 1 to 8 carbon atoms. And A represents an aromatic ring residue which may have a substituent. ] 2. A colorant is used in an amount of 3 to 100 parts by weight of the resin.
20 parts by weight of the compound represented by the formula (I) is 0.1% by weight.
2. The toner for developing an electrostatic image according to claim 1, comprising 1 to 20 parts by weight. 3. A charge control agent for toner represented by the general formula (I).