JP3264000B2 - 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 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 an electrostatic image developing toner containing at least a resin and a colorant, wherein at least one compound represented by the general formula (I) according to the above-mentioned claim 1 is used. The toner for developing an electrostatic image. Another aspect of the present invention provides a compound represented by the general formula:
It exists in the charge control agent for toner represented by (I). Less than,
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 following general formula (I).

[0007]

Embedded image

[Wherein, at least one of R _1, R _2, R ₃ and R ₄ represents a cyclic alkyl group;
Represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted aralkyl group, A represents an aromatic ring residue which may have a substituent, and n represents 1 or 2. ]
At least one of R _1, R _2, R ₃ and R ₄ is a cyclic alkyl group, and the cyclic alkyl group preferably has 5 to 7 carbon atoms, such as a cyclohexyl group, a cyclopentyl group, and a cycloheptyl group. And a cyclohexyl group is particularly preferred.

Other specific examples of R include methyl, ethyl, propyl, butyl, heptyl, hexyl, octyl, nonanyl, decyl, undecyl, dodecyl, tridecyl, and tetradecyl. Group,
C1-24 alkyl groups such as pentadecyl group, hexadecyl group, heptadecyl group and stearyl group; aralkyl groups such as benzyl groups; and substituted aralkyl groups such as lower alkyl-substituted benzyl groups, nitro-substituted benzyl groups and halogen-substituted benzyl groups. Preferably, at least one is a methyl group or a benzyl group. A represents an aromatic ring residue which may have a substituent, for example, a phenylene group, a naphthylene group, an anthrylene group,
Particularly, a naphthylene group is preferable. As the substituent for A, an alkyl group, particularly a lower alkyl group, a halogen atom, a hydroxyl group,
Alternatively, an amino group, a lower alkyl-substituted amino group and the like can be mentioned, and a hydroxyl group is particularly preferable. n is 1 or 2.

Among the compounds represented by the general formula (I),
Specific examples of compounds suitable for inclusion in the toner for developing an electrostatic image of the present invention include, but are not limited to, compounds represented by the following structural formulas.

Illustrative compounds (1) R ₁ ＲR ₂ ＣＨCH ₃ , R ₃ ＣC ₁₈ H ₃₇ , R ₄ = cyclohexyl, n = 1, A = p-hydroxybenzenesulfonate ion (2) R ₁ ＲR ₂ = CH ₃ , R ₃ = benzyl, R ₄ = cyclohexyl, n = 1, A = 1-naphthol-4-sulfonic acid ion (3) R ₁ = R ₂ = CH ₃ , R ₃ = C ₁₆ H ₃₃ , R ₄ = cyclohexyl, n = 1, A = 1-naphthol-4-sulfonate ion (4) R ₁ = R ₂ = CH ₃ , R ₃ = p-chlorobenzyl, R ₄ = cyclohexyl, n = 1, A = 1-naphthol-4-sulfonate ion _{(5) R 1 = R 2} = CH 3, R 3 = p- methylbenzyl, R ₄ = cyclohexyl, n = 1, A = 1-naphthol-4-sulfonic acid ion _{(6) R 1 = R 2} = CH 3, R 3 = C 14 H 29, R 4 = cyclopropyl Hexyl, n = 1, A = P- chlorobenzene - benzenesulfonate ion _{(7) R 1 = R 2} = CH 3, R 3 = C 18 H 37, R 4 = cyclohexyl, n = 1, A = p- toluene sulfonate ion _{(8) R 1 = R 2} = C 2 H 5, R 3 = p- nitrobenzyl, R ₄ = cyclohexyl, n = 1, A = 1- naphthol -
Le-4-sulfonic acid ion (9) R ₁ ＲR ₂ ＣC ₂ H ₅ , R ₃ = benzyl, R ₄ =
Cyclohexyl, n = 1, A = 1-naphthol-5-sulfonate ion (10) R ₁ = R ₂ = CH ₃ , R ₃ = benzyl, R ₄ =
Cyclohexyl, n = 1, A = 2-naphthol-6-sulfonate ion (11) R ₁ = R ₂ = CH ₃ , R ₃ = C ₁₆ H ₃₃ , R ₄ =
Cyclohexyl, n = 1, A = 2-naphthol-8-sulfonate ion (12) R ₁ = R ₂ = CH ₃ , R ₃ = C ₁₈ H ₃₇ , R ₄ =
Cyclohexyl, n = 2, A = m-benzenedisulfonate ion (13) R ₁ = R ₂ = CH ₃ , R ₃ = p-chlorobenzyl, R ₄ = cyclohexyl, n = 2, A = toluene-
3,4-disulfonate ion (14) R ₁ = R ₂ = CH ₃ , R ₃ = benzyl, R ₄ =
Cyclohexyl, n = 2, A = 1,2-dihydroxybenzene-3,5-disulfonic acid ion (15) R ₁ = R ₂ = CH ₃ , R ₃ = p-nitrobenzyl, R ₄ = cyclohexyl, n = 2 , A = 1,3-dihydroxybenzene-2,5-disulfonic acid ion (16) R ₁ = R ₂ = CH ₃ , R ₃ = benzyl, R ₄ =
Cyclohexyl, n = 2, A = 1,5-naphthalenedisulfonic acid ion (17) R ₁ ＝ R ₂ ＣC ₄ H ₉ , R ₃ ＣC ₈ H ₁₇ , R ₄
= Cyclohexyl, n = 2, A = 1,5-naphthalenedisulfonic acid ion (18) R ₁ = R ₂ = CH ₃ , R ₃ = p-chlorobenzyl, R ₄ = cyclohexyl, n = 2, A = 2- Naft
(6) R ₁ = R ₂ = CH ₃ , R ₃ = p-methylbenzyl, R ₄ = cyclohexyl, n = 2, A = 2-naphtho-
Le-6,8-disulfonic acid ion _{(20) R 1 = R 2} = CH 3, R 3 = C 18 H 37, R 4 =
Cyclohexyl, n = 2, A = 1,6-naphthalenedisulfonic acid ion (21) R ₁ = R ₂ = CH ₃ , R ₃ = -C ₁₆ H ₃₃ , R ₄
= Cyclohexyl, n = 2, A = 2,6-naphthalenedisulfonic acid ion (22) R ₁ = R ₂ = C ₂ H ₅ , R ₃ = benzyl, R ₄
= Cyclohexyl, n = 2, A = 3,6-naphthalenedisulfonic acid ion (23) R ₁ = R ₂ = C ₂ H ₅ , R ₃ = benzyl, R ₄
= Cyclohexyl, n = 2, A = 1-naphthol-3,
6-disulfonate ion (24) R ₁ = R ₂ = CH ₃ , R ₃ = benzyl, R ₄ =
Cyclohexyl, n = 2, A = 1-naphthol-4,8
-Disulfonic acid ion (25) R ₁ = R ₂ = CH ₃ , R ₃ = p-chlorobenzyl, R ₄ = cyclohexyl, n = 2, A = 3-amino-
1,5-naphthalene disulfonic acid ion _{(26) R 1 = R 2} = CH 3, R 3 = p- methylbenzyl, R ₄ = cyclohexyl, n = 2, A = 1- Amino -
8-naphthol-2,4-disulfonic acid ion (27) R ₁ ＲR ₂ ＣＨCH ₃ , R ₃ —C ₁₈ H ₃₇ , R ₄
= Cyclohexyl, n = 2, A = 1,8-dihydroxynaphthalene-3,6-disulfonic acid ion (28) R ₁ = R ₂ = CH ₃ , R ₃ = benzyl, R ₄ =
Cyclohexyl, n = 2, A = 3-amino-2,7-naphthalenedisulfonic acid ion

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)

[0013]

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(Wherein R ₁ , R ₂ , R ₃ and R ₄ have the same meanings as in formula (I), and X ⁻ represents a halogen group such as chlorine, bromine and the like). The salt compound is represented by the following general formula (III)

[0015]

Embedded image

Wherein A and n have the same meanings as in formula (I),
Y represents an alkali metal such as sodium or potassium)
And heated to about 60 ° C. in water or alcohol to cause a reaction.

The resin component that can be used in the present invention includes:
Various known toners suitable for the electrostatic image developing toner 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 1 to 1 part by weight, per 100 parts by weight of the resin.
5 parts by weight.

When the content of the compound represented by the general formula (I) is
If the amount is too small, the effect of improving the chargeability cannot be expected, and if the amount 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, blue, red,
It may be contained in a color toner such as yellow, and in this case, a colorant composed of a facial cleanser or the like 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 carrier having a core of ferrite 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 used in an amount of 5-1 to 1 part by weight of the toner.
It is preferable to use 00 parts by weight.

[0022]

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”.

Embodiment 1

Table 1 Styrene-based resin 100 parts (manufactured by Sanyo Chemical Co., Ltd., trade name: SBM-600) Carbon black 10 parts (Mitsubishi Kasei Co., Ltd. # 44) Exemplified compound (2) 2 parts

The above materials were mixed and kneaded, and crushed and classified to obtain a black fine powder having an average particle diameter of 11 μm. 5 parts of this toner and 100 parts of a fluororesin-coated carrier having an average particle size of about 100 μm 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 Except that 3 parts of Exemplified Compound (4) was used instead of 2 parts of Exemplified Compound (2) as a charge controlling agent, the procedure of Example 1 was repeated. A good copy was obtained in the same manner as described above.

Example 3 Except that 4 parts of Exemplified Compound (8) were used instead of 2 parts of Exemplified Compound (2) as a charge controlling agent, the procedure was the same as that of Example 1 and the same as Example 1. A good copy was obtained.

Example 4 The procedure of Example 1 was repeated except that 3 parts of Exemplified Compound (12) were used instead of 2 parts of Exemplified Compound (2) as a charge controlling agent. Good copies were obtained as well.

Example-5 Except that 2 parts of Exemplified Compound (16) was used instead of 2 parts of Exemplified Compound (2) as a charge controlling agent, the procedure was the same as in Example-1. Good copies were obtained as well.

Example -6 Example 1 was repeated except that 3 parts of Exemplified Compound (19) was used instead of 2 parts of Exemplified Compound (2) as a charge controlling agent. Good copies were obtained as well.

Example -7 The same procedure as in Example 1 was carried out except that 3 parts of Exemplified Compound (22) was used instead of 2 parts of Exemplified Compound (2) as a charge controlling agent. A good copy was obtained in the same manner as described above.

Example -8 The same procedure as in Example 1 was carried out except that 4 parts of Exemplified Compound (24) was used instead of 2 parts of Exemplified Compound (2) as a charge controlling agent. Good copies were obtained as well.

Example -9 The same procedure as in Example 1 was carried out except that 5 parts of Exemplified Compound (25) was used instead of 2 parts of Exemplified Compound (2) as a charge controlling agent. A good copy was obtained.

Example -10 The same procedure as in Example 1 was conducted except that 5 parts of Exemplified Compound (27) was used instead of 2 parts of Exemplified Compound (1) as a charge controlling agent. A good copy was obtained.

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 (2) was not used as a material. As a result, a copy having a lot of fog and a poor copy quality was obtained. Was.

[0035]

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 Enzo, Chigasaki-shi, Kanagawa Mitsubishi Co., Ltd. (56) References JP-A-4-264454 (JP, A) JP-A-4-170555 (JP, A) JP-A-4-328758 (JP, A) JP-A-4-306666 (JP, A A) U.S. Pat. No. 4,990,426 (US, A) U.S. Pat. No. 5,054,423 (US, A) (58) Fields investigated (Int. Cl. ⁷ , DB name) G03G 9/08 CA (STN)

Claims (4)

(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 [In the formula, at least one of R _1, R _2, R ₃ and R ₄ represents a cyclic alkyl group, and the other represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted aralkyl group, respectively. A represents an aromatic ring residue which may have a substituent, and n represents 1 or 2. ] 2. In the general formula (I), R ₄ is a cyclic alkyl group, and R _1, R ₂ and R ₃ are a substituted or unsubstituted alkyl group or a substituted or unsubstituted aralkyl group. 2. The electrostatic image developing toner according to item 1. 3. The 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.
The electrostatic image developing toner according to claim 1, comprising 1 to 20 parts by weight. 4. A toner charge control agent represented by the general formula (I).