JPH05197198A - Decolorizable toner - Google Patents

Abstract

PURPOSE:To improve light resistance by containing binding resin, a specific near infrared absorbing dye, and a decolorant specifying the combination ratio of a heat-resistant antioxidant to the binding resin. CONSTITUTION:A toner contains binding resin, a near infrared absorbing dye expressed by the formula I or the formula II, and a decolorant expressed by the formula III, and 0.05-30 pts.wt. of a heat-resistant antioxidant is combined to 100 pts.wt. of the binding resin. In the formula I, X indicates halogen ion or perchloric acid ion. In the formula II, R<1>-R<4> independently indicate hydrogen atom, hydrocarbon group, or hydrocarbon group containing hetero atom respectively, and Y indicates cation having the absorption characteristic in the near infrared region. In the formula III, R<5>-R<8> independently indicate alkyl group respectively, at least one of which is the alkyl group having the carbon number of 1-12, and R<9>-R<12> independently indicate hydrogen atom or alkyl group respectively. A toner having excellent light resistance during production and storage and having excellent light resistance of a formed image is obtained.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a decolorizable toner.
More specifically, it relates to a near-infrared erasable toner capable of visualizing an electric latent image or electric signal in an electrophotographic or electrostatic recording material.

[0002]

2. Description of the Related Art In recent years, the reuse and recycling of used paper has been reviewed to protect nature, especially to protect forest resources and reduce waste in urban areas. As part of this, the reuse of waste paper such as used copy paper, printed matter, and facsimile paper that has become unnecessary in the office of a company is being studied.

Therefore, a company has put a paper manufacturing company in a group, collects waste paper, melts it, reprocesses it as recycled paper, and reuses it, but these papers are generally regarded as trade secrets. Since most of the company's internal confidential documents are
It is extremely difficult to collect and recycle these papers at a paper manufacturing company outside the company, and since the recorded parts and printed parts of printed matter, copied matter, etc. cannot be easily erased, they can be incinerated or burned. It had to be crushed and discarded, and it was thought that it would be virtually impossible to reuse such papers. In addition, some studies have been conducted on the recycling of waste paper that has been crushed by shredders, but the strength of recycled paper manufactured using such crushed waste paper is generally low, so for example, information paper, etc. There was a drawback that it could not be used as.

[0004]

Therefore, as a result of intensive studies conducted by the present inventors in view of the above-mentioned prior art, the near infrared light erasable recording capable of absorbing, decomposing and erasing near infrared rays. The material has been found, and a decolorizable toner using such a recording material has been developed (Japanese Patent Application No. 2-194187).

When electrostatic copying is performed using the decolorizable toner, the image, print, etc. recorded on the copying paper can be erased only by irradiating the near infrared rays, and after the electrostatic copying, the electrostatic copying is performed again. This makes it possible to reuse the copy paper, and when discarding used copy paper, recorded images, prints, etc. can be erased by irradiation of near infrared rays. It is possible to prevent external leakage of the copy paper, and at the same time, it is possible to collect and reuse the copy paper.

However, since the rays of light which change the near-infrared absorbing dye and the decoloring agent contained in the decolorizable toner are contained in the sun rays, during the production and storage of the decolorizable toner. In addition, there is a drawback that the near infrared absorptive dye fades when exposed to natural light or when an image formed by the decolorizable toner is exposed to natural light.

The present invention has been made in order to solve the above drawbacks, and provides a decolorizable toner having excellent light resistance during production and storage, and further having excellent light resistance of formed images. The purpose is to

[0008]

Means for Solving the Problems That is, the present invention provides a binder resin, a compound represented by the general formula (I):

[0009]

[Chemical 4]

(Wherein X represents a halogen ion, a perchlorate ion, PF ₆ ⁻ , SbF ₆ ⁻ , OH ⁻ , a sulfonate ion or BF ₄ ⁻ ) or the general formula (II):

[0011]

[Chemical 5]

(In the formula, R ¹ , R ² , R ³ and R ⁴ are each independently a hydrogen atom, a hydrocarbon group or a hydrocarbon group containing a hetero atom; Y is a cation having an absorption characteristic in the near infrared region. A near-infrared absorbing dye represented by the general formula (III):

[0013]

[Chemical 6]

(In the formula, R ⁵ , R ⁶ , R ⁷ and R ⁸ are each independently an alkyl group, an aryl group, an allyl group, an aralkyl group, an alkenyl group, an alkynyl group, a silyl group,
A heterocyclic group, a substituted alkyl group, a substituted aryl group, a substituted allyl group, a substituted aralkyl group, a substituted alkynyl group, a substituted alkynyl group or a substituted silyl group, and R ⁵ , R ⁶ and R ⁷
And at least one of R ⁸ is an alkyl group having 1 to 12 carbon atoms; R ⁹ , R ¹⁰ , R ¹¹ and R ¹² are each independently a hydrogen atom, an alkyl group, an aryl group, an allyl group, an aralkyl group or an alkenyl. Group, an alkynyl group, a heterocyclic group, a substituted alkyl group, a substituted aryl group, a substituted allyl group, a substituted aralkyl group, a substituted alkenyl group or a substituted alkynyl group). , Heat resistant anti-aging agent for 100 parts by weight of resin for binding
The present invention relates to a decolorizable toner containing 0.05 to 30 parts by weight.

[0015]

OPERATION AND EXAMPLES The decolorizable toner of the present invention can be used even when it is exposed to natural light during production and storage of the decolorizable toner, and after image formation using the decolorizable toner. Since the fading due to the modification of the near-infrared absorbing dye contained in the decolorizable toner hardly occurs, the storage stability is excellent.

The decolorizable toner of the present invention has such excellent characteristics that low-molecular compounds are produced from various materials constituting the toner when exposed to natural light, and the low Although the molecular compound deteriorates the near-infrared absorbing dye, the blended heat-resistant anti-aging agent acts to suppress the formation of the low-molecular compound, and the near-infrared absorbing dye is modified even when directly exposed to natural light. It is considered to be caused by exhibiting the action of suppressing

The binder resin used in the decolorizable toner of the present invention is, for example, polystyrene resin represented by polystyrene or the like, polyester resin represented by saturated polyester or unsaturated polyester, epoxy resin or polymethyl resin. (Meth) acrylic resin represented by methacrylate, silicone resin, fluororesin, polyamide resin, polyvinyl alcohol resin, polyurethane resin, polyolefin resin, polyvinyl butyral resin, phenol formaldehyde resin, rosin-modified phenol formaldehyde resin However, the present invention is not limited to such examples. These binding resins are usually used alone or in admixture of two or more.

In the present invention, the binder resin may be blended with wax such as polyolefin wax and paraffin wax, if necessary. The amount of such a wax is 100% in order to sufficiently bring out the effect of adding the wax.
It is desirable that the amount is 0.1 part or more, preferably 0.5 part or more with respect to 1 part (part by weight, the same applies below). Since film formation tends to occur, it is desirable that the amount is 20 parts or less, preferably 10 parts or less, based on 100 parts of the binder resin.

In the present invention, the near infrared ray absorbing dye has the general formula (I):

[0020]

[Chemical 7]

(Wherein X represents a halogen ion, a perchlorate ion, PF ₆ ⁻ , SbF ₆ ⁻ , OH ⁻ , a sulfonate ion or BF ₄ ⁻ ) or the general formula (II):

[0022]

[Chemical 8]

(In the formula, R ¹ , R ² , R ³ and R ⁴ are each independently a hydrogen atom, a hydrocarbon group or a hydrocarbon group containing a hetero atom; Y is a cation having an absorption characteristic in the near infrared region. The one represented by (showing ions) is used.

Examples of the halogen ion include fluorine ion, chlorine ion, bromine ion and iodine ion, and examples of the sulfonate ion include CH ₃
SO ₃ ^- methyl sulfonic acid ion such as, FCH ₂ SO
^{_{3 -, F 2 CHSO 3 -}} , F 3 CSO 3 -, ClCH 2
^{_{SO 3 -, Cl 2 CHSO 3}} -, Cl 3 CSO 3 -, C
^{_{H 3 OCH 2 SO 3 -,}} (CH 3) 2 NCH 2 SO 3 -
Substituted methyl sulfonate ion such as, C ₆ H ₅ SO ₃ ^-
Phenylsulfonate ion such as CH ₃ C ₆ H ₄ SO
^{_{3 -, (CH 3) 2}} C 6 H 3 SO 3 -, (CH 3) 3 C
^{_{6 H 2 SO 3 -, HOC}} 6 H 4 SO 3 -, (HO) 2 C
^{_{6 H 3 SO 3 -, (}} HO) 3 C 6 H 2 SO 3 -, CH 3
^{_{OC 6 H 4 SO 3 -,}} C 6 H 4 ClSO 3 -, C 6 H 3
^{_{Cl 2 SO 3 -, C 6}} H 2 Cl 3 SO 3 -, C 6 HCl
^{_{4 SO 3 -, C 6 Cl}} 5 SO 3 -, C 6 H 4 FS
^{_{O 3 -, C 6 H 3}} F 2 SO 3 -, C 6 H 2 F 3 S
^{_{O 3 -, C 6 HF 4}} SO 3 -, C 6 F 5 SO 3 -, (C
Substituted phenyl sulfonate ion such as H ₃ ) ₂ NC ₆ H ₄ SO ₃ ⁻ may be used.

In the general formula (II), R ¹ , R
Specific examples of ² , R ³ and R ⁴ include, for example, hydrogen atom, alkyl group, aryl group, allyl group, aralkyl group, alkenyl group, alkynyl group, silyl group, heterocyclic group, substituted alkyl group, substituted aryl group, A substituted allyl group,
Examples thereof include a substituted aralkyl group, a substituted alkenyl group, a substituted alkynyl group and a substituted silyl group. Specific examples of preferable ones among these include, for example, hydrogen atom, phenyl group, anisyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-dodecyl group. , Cyclohexyl group, cyclohexenyl group, methoxymethyl group, methoxyethyl group, ethoxyphenyl group, toluyl group, t-butylphenyl group, fluorophenyl group,
Examples thereof include chlorophenyl group, diethylaminophenyl group, vinyl group, allyl group, triphenylsilyl group, dimethylphenylsilyl group, dibutylphenylsilyl group, trimethylsilyl group, piperidyl group, thienyl group and furyl group. Further, at least one of R ¹ , R ² , R ³ and R ⁴ is preferably an alkyl group having 1 to 12 carbon atoms, and more preferable alkyl group is, for example, n-butyl. Group, n-pentyl group, n-
Examples thereof include alkyl groups having 4 to 12 carbon atoms such as hexyl group, n-heptyl group, n-octyl group and n-dodecyl group.

Preferred examples of the near-infrared absorbing dye represented by the general formula (I) as Y include, for example, cyanine, triarylmethane, aminium, diimmonium, thiazine, xanthene, which have absorption characteristics in the near-infrared region. Examples include oxazine, styryl and pyrylium-based cationic dyes. As a typical example of such Y, for example,

[0027]

[Chemical 9]

[0028]

[Chemical 10]

And the like.

The amount of the near-infrared absorbing dye blended is 0.01 to 25 parts, preferably 0.1 to 100 parts by weight of the binder resin.
~ 15 copies. When the compounding amount of the near-infrared absorbing dye is less than the above range, sufficient coloring is not given to the obtained toner, and when it is more than the above range, the triboelectric charge unique to the obtained toner is obtained. May adversely affect quantity.

In the present invention, the general formula (II
I):

[0032]

[Chemical 11]

(Wherein R ⁵ , R ⁶ , R ⁷ and R ⁸ are each independently an alkyl group, an aryl group, an allyl group, an aralkyl group, an alkenyl group, an alkynyl group, a silyl group,
A heterocyclic group, a substituted alkyl group, a substituted aryl group, a substituted allyl group, a substituted aralkyl group, a substituted alkenyl group, a substituted alkynyl group or a substituted silyl group, and R ⁵ , R ⁶ and R ⁷
And at least one of R ⁸ is an alkyl group having 1 to 12 carbon atoms: R ⁹ , R ¹⁰ , R ¹¹ and R ¹² are each independently a hydrogen atom, an alkyl group, an aryl group, an allyl group, an aralkyl group or an alkenyl. Group, an alkynyl group, a heterocyclic group, a substituted alkyl group, a substituted aryl group, a substituted allyl group, a substituted aralkyl group, a substituted alkenyl group or a substituted alkynyl group).

Specific examples of the decoloring agent include tetramethylammonium n-butyltriphenylboron,
Tetramethylammonium n-butyltrianisyl boron, tetramethylammonium n-octyltriphenylboron, tetramethylammonium n-octyltrianisylboron, tetraethylammonium n-butyltriphenylboron, tetraethylammonium n-butyltrianisylboron, tetrabutyl Ammonium n-butyltriphenylboron, tetrabutylammonium n-butyltrianisylboron, tetraoctylammonium n-octyltriphenylboron, tetrabutylammonium
n-dodecyl triphenyl boron, trimethylhydrogen ammonium n-butyl triphenyl boron, triethyl hydrogen ammonium n-butyl triphenyl boron, tetrahydrogen ammonium n-butyl triphenyl boron, tetramethyl ammonium tetrabutyl boron, tetraethyl ammonium tetrabutyl boron,
Tetra n-butyl ammonium tetra n-butyl boron, tetramethyl ammonium tri n-butyl (triphenylsilyl) boron, tetraethyl ammonium tri n-butyl (triphenylsilyl) boron, tetrabutyl ammonium n-butyl (triphenylsilyl) boron , Tetramethylammonium tri-n-butyl (dimethylphenylsilyl) boron, tetraethylammonium tri-n-butyl (dimethylphenylsilyl) boron, tetrabutylammonium tri-n-butyl (dimethylphenylsilyl) boron, tetramethylammoniumn-octyldiphenyl ( Di-n-butylphenylsilyl) boron, tetraethylammonium n-octyldiphenyl (di-n-butylphenylsilyl) boron, tetrabutylammonium n-octyldiphenyl (di-n-butylphenyl) Silyl) boron, tetramethylammonium dimethylphenyl (trimethylsilyl) boron, tetraethylammonium dimethylphenyl (trimethylsilyl) boron, tetrabutylammonium dimethylphenyl (trimethylsilyl) boron, etc., and these decolorizers may be used alone or in combination of two or more. Used as a mixture.

The compounding amount of the decoloring agent cannot be unconditionally determined because it varies depending on the kind of the near-infrared absorbing dye, but usually 1 to 2500 parts per 100 parts of the near-infrared absorbing dye, Preferably, it is selected from the range of 5 to 1000 parts. When the compounding amount of the decoloring agent is less than the above range, the decoloring speed becomes slow, and when the compounding amount is more than the above range, the light resistance of the printing and image formed by using the obtained toner. It becomes less sexual and discolors and fades.

In the present invention, as described above, in order to prevent the fading of the near infrared absorptive dye in the decolorizable toner due to the irradiation of natural light, a heat resistant antioxidant is blended.

As the heat resistant anti-aging agent, the obtained decolorizable toner does not become contaminated when it is transferred and fixed on an image support such as paper, and white color such as copy paper is used. When it is applied to a sheet having a color, it is preferable to use a color close to white or a light color. Specific examples of such heat-resistant antioxidants include hydroquinone derivatives such as 2,5-di-t-amylhydroquinone, 2,5-di-t-butylhydroquinone, 2,5-dihydroquinone, and hydroquinone monoethyl ether. Systemic anti-aging agent;
1-oxy-3-methyl-4-isopropylbenzene, 2,6-t-
Butylphenol, 2,6-di-t-butyl-4-ethylphenol, 2,6-di-t-butyl-4-methylphenol, 2,6-di
-t-butyl-4-sec-butylphenol, butylhydroxyanisole, 2,6-di-t-butyl-α-dimethylamino
-p-cresol, 2- (1-methylcyclohexyl) -4,6-
Alkylated phenol-based and phenol derivative-based antiaging agents such as dimethylphenol, styrenated phenol, and alkylated phenol; 1,1,3-tris- (2-methyl-4)
-Hydroxy-5-t-butylphenyl) butane, 4,4'-
Butylidene bis- (3-methyl-6-t-butylphenol),
2,2-thiobis (4-methyl-6-t-butylphenol), n-
Octadecyl-3- (4'-hydroxy-3 ', 5'-di-t-
Butylphenyl) propionate and other hindered phenolic antioxidants; tris (nonylphenyl) phosphite, tris (mixed mono and di-nonylphenyl)
Phosphite, phenyldiisodecylphosphite, diphenylmono (2-ethylhexyl) phosphite, diphenylmonotridecylphosphite, diphenylisodecylphosphite, diphenylisooctylphosphite, diphenylphenylphosphite, triphenylphosphite, tris (tridecyl) ) Phosphite, phosphite-based antioxidants such as tetraphenyldipropylene glycol phosphite, 2,2-bis (4-hydroxyphenyl) propane, ethyl p-hydroxybenzoate,
There are non-contaminating heat-resistant anti-aging agents that hardly contaminate white copying paper such as n-propyl gallate, lauryl gallate, resorcinol, and diphenylamine. These heat-resistant anti-aging agents can be used alone or in combination. The above is mixed and used. Among these heat-resistant anti-aging agents, hydroquinone derivative anti-aging agents and phenol derivative anti-aging agents have good compatibility with styrene-based binder resins and significantly prevent deterioration of crystalline resins due to light rays. It is preferable because it has the property of

The amount of the heat resistant anti-aging agent to be blended is 0.05 to 30 parts, preferably 0.5 to 30 parts, relative to 100 parts of the binding resin.
It is 10 parts, more preferably 0.5 to 2 parts. When the amount of the heat-resistant antiaging agent is less than the above range, the effect of preventing fading of the near-infrared absorbing dye becomes insufficient, and when the amount exceeds the above range, no more is added. Increasing the quantity not only increases the cost, but also
The coloring property of the near-infrared absorbing dye becomes insufficient.

The decolorizable toner of the present invention contains a binder resin, a near-infrared absorbing dye, a decoloring agent and a heat resistant antiaging agent, and further includes, for example, a charge control agent, a magnetic powder, and a fluidizing agent. Agents, colorants, plasticizers, etc. may be appropriately mixed.

The method of preparing the decolorizable toner of the present invention includes a solution method and a melting method.

In the solution method, the near-infrared absorbing dye and the binder resin are dissolved and kneaded in an organic solvent, and a decolorizing agent,
A heat resistant anti-aging agent, wax if necessary, and other additives are mixed and melt-mixed, the organic solvent is removed from the obtained mixture, and then coarsely crushed with, for example, a hammer mill or a cutter mill, and then, for example, a jet mill, etc. Is finely pulverized to prepare a toner having an average particle size of about 5 to 30 μm.

In the melting method, a near-infrared absorbing dye is heated and melt-kneaded with a binder resin, and a decoloring agent, a heat-resistant anti-aging agent, and if necessary, a wax and other additives are added thereto. After kneading and cooling, the toner is prepared by finely pulverizing in the same manner as the solution method.

The decolorizable toner of the present invention thus obtained is printed and fixed on an image support made of, for example, paper, and then irradiated with near infrared rays by means such as a semiconductor laser, a halogen lamp and a light emitting diode. The printed part can be erased. Then, after the printed portion is erased, it is possible to print again by overlapping the erased portion again.

The decolorizable toner of the present invention is blended with a heat resistant anti-aging agent, and the presence of the heat resistant anti-aging agent suppresses the formation of a low molecular compound due to natural light, and therefore absorbs near infrared rays. There is an advantage that there is almost no fading of the functional dye.

Therefore, the decolorizable toner of the present invention is used, for example, for an image support such as a copy sheet, a ticket that can be printed at the time of boarding and erased when getting off and can be used repeatedly, a ticket for boarding a passenger ticket, and various admission tickets. It can be preferably used for printing of the above paper pieces.

Next, the decolorizable toner of the present invention will be described in more detail based on examples, but the present invention is not limited to these examples.

Examples 1 to 10 and Comparative Examples 1 to 4 The raw materials shown in Tables 1 to 3 were blended in the blending ratios shown in Table 4 and mixed to give a uniform composition to obtain a mixture.

[0048]

[Table 1]

[0049]

[Table 2]

[0050]

[Table 3]

Next, 20 parts of the obtained mixture and 80 parts of 1,1,2,2-tetrachloroethane were mixed, and the mixture was sufficiently dissolved and dispersed to obtain a toner solution.

The obtained toner solution was applied on a white copy paper in a layered manner by a brush so that the thickness of the toner layer after drying was about 20 to 30 μm, and the solvent was volatilized and removed to obtain a sample.

The light resistance A of the obtained sample was examined according to the following method. The results are shown in Table 4.

(Light resistance A) The sample was allowed to stand for 10 days at room temperature in the shade of the room where direct sunlight enters through the window glass in fine weather, and the discoloration of the sample was compared with that of the sample before irradiation with natural light. And evaluated based on the following evaluation criteria.

(Evaluation Criteria) A: No discoloration of the sample is observed.

B: Discoloration of the sample is slightly observed.

C: Discoloration of the sample is slightly recognized.

D: Discoloration of the sample is clearly recognized.

When the color erasability of the color erasable toners obtained in Examples 1 to 10 was examined by irradiation with near infrared rays, the color erasable toners obtained in any of the Examples were blended with a heat resistant antioxidant. It was confirmed that there was no inferiority to the non-existent product (Comparative Example 1) and that it had a decoloring property that was practically satisfactory.

[0060]

[Table 4]

From the results shown in Table 4, it can be seen that the toners obtained in Examples 1 to 10 in which the heat resistant anti-aging agent is blended all have excellent light resistance.

Examples 11 to 19 and Comparative Examples 5 to 7 Toner solutions were prepared in the same manner as in Examples 1 to 10 and Comparative Examples 1 to 4 by blending the raw materials shown in Tables 1 to 3 in the blending ratio shown in Table 5. I got it.

Then, Examples 1 to 10 and Comparative Examples 1 to 4
A sample was prepared in the same manner as above, and the light resistance B as a physical property of the obtained sample was examined according to the following method. The results are shown in Table 5.

(Light resistance B) After the sample was left under a fluorescent lamp of 1500 lux for 1 week, the reflection densities of the sample before and after being left were measured by using a Macbeth densitometer, and the formula: ) = (Reflection density after leaving / reflection density before leaving) × 100, the rate of change in reflection density was calculated and evaluated based on the following evaluation criteria.

(Evaluation Criteria) A: Reflection density change rate of 80% or more (excellent light resistance) B: Reflection density change rate of 60% or more and less than 80% (excellent light resistance) C: Reflection density change rate of 40% or more and less than 60% (normal light resistance) D: Reflection density change rate of less than 40% (light resistance is low)

[0066]

[Table 5]

From the results shown in Table 5, it can be seen that the toners obtained in Examples 11 to 19 in which the heat resistant anti-aging agent is blended all have excellent light resistance. When the color erasability of the color erasable toners obtained in Examples 11 to 19 was examined by near infrared rays, those obtained in any of the Examples did not contain a heat resistant antioxidant ( It was confirmed that it has no inferiority to Comparative Examples 5 to 7) and has a practically satisfactory decoloring property.

[0068]

The decolorizable toner of the present invention has excellent light resistance.

Therefore, the decolorizable toner of the present invention and the image formed using the decolorizable toner have excellent storage stability even in an atmosphere exposed to natural light and are easy to handle. is there.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Toshio Kaji 3-15-15 Meiwadori, Hyogo-ku, Kobe City, Hyogo Prefecture Bando Kagaku Co., Ltd. (72) Inventor Kiyotaka Yamaguchi 3-chome, Meiwa-dori, Hyogo-ku, Hyogo Prefecture No. 2-15 Bandou Kagaku Co., Ltd. (72) Inventor Takayuki Yoshida 3-2-15 Meiwadori, Hyogo-ku, Kobe, Hyogo Prefecture Bando Kagaku Co., Ltd. (72) Inventor Yuki Abe Meiwadori, Hyogo-ku, Hyogo Prefecture 3-2-15 Bando Kagaku Co., Ltd.

Claims (2)

[Claims] 1. A binding resin, general formula (I): (In the formula, X is halogen ion, perchlorate ion, PF _{6
^{-, SbF 6 -, OH -}} , sulfonic acid ion or BF
₄ ^- shows a) or general formula (II): ## STR2 ## (In the formula, R ¹ , R ² , R ³ and R ⁴ are each independently a hydrogen atom, a hydrocarbon group or a hydrocarbon group containing a hetero atom; Y is a cation having an absorption property in the near infrared region. ) A near-infrared absorbing dye represented by the general formula (III): (In the formula, R ⁵ , R ⁶ , R ⁷ and R ⁸ are each independently an alkyl group, an aryl group, an allyl group, an aralkyl group,
An alkenyl group, an alkynyl group, a silyl group, a heterocyclic group, a substituted alkyl group, a substituted aryl group, a substituted allyl group, a substituted aralkyl group, a substituted alkenyl group, a substituted alkynyl group or a substituted silyl group, R ⁵ , R ⁶ and R ^At least one of ⁷ and R ⁸ is an alkyl group having 1 to 12 carbon atoms;
R ⁹ , R ¹⁰ , R ¹¹ and R ¹² are each independently a hydrogen atom, alkyl group, aryl group, allyl group, aralkyl group, alkenyl group, alkynyl group, heterocyclic group, substituted alkyl group, substituted aryl group, substituted A toner containing a decoloring agent represented by an allyl group, a substituted aralkyl group, a substituted alkenyl group or a substituted alkynyl group), which is a heat-resistant antioxidant with respect to 100 parts by weight of a binder resin.
A decolorizable toner characterized by being blended with 05 to 30 parts by weight. 2. The decolorizable toner according to claim 1, wherein the heat-resistant antiaging agent is selected from the group consisting of hydroquinone derivative antiaging agents and phenol derivative antiaging agents.