JP2001272816A - Electrostatic charge image developing toner - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an electrostatic charge image developing toner excellent in fixing property, light transmitting property and resistance against toner spent with which a sharp high-quality image can be obtained and which can be used for various kinds of toner and particularly, which gives a significant effect when used for color toner. SOLUTION: A specified cyclic olefin polymer is used as the binder resin for the electrostatic charge image developing toner.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a toner for developing an electrostatic image. More specifically, the present invention relates to a toner using a cyclic olefin polymer.

[0002]

BACKGROUND OF THE INVENTION With regard to electrostatic image developing type copiers and printers, with the spread of office automation, there has been a demand for high-quality, vivid, light-transmitted, offset, and fixed copy images. Increasingly. In such a copying machine and printer, after supplying a toner to the electrostatic image on the latent image carrier to obtain a visible image,
The toner image is transferred to plain paper or an OHP film and fixed. At present, styrene / acrylic resins and polyester resins are often used as binder resins.In the former case, however, it is difficult to obtain high-quality images due to insufficient light transmittance and sharpness of the toner. In the latter, light transparency can be obtained, but the resin has a yellow tint, and therefore has a disadvantage in sharpness.

[0003]

SUMMARY OF THE INVENTION In view of the above problems, it is an object of the present invention to provide a higher quality copy image of an electrostatic image developing type copying machine and a printer, that is, a fixing property, a releasing property and a light transmitting property. Another object of the present invention is to provide a dry two-component system, a dry non-magnetic one-component system, a dry magnetic one-component system, and a toner in a liquid toner developer having excellent clarity.

[0004]

The present invention comprises at least a binder resin and a colorant, wherein the binder resin has the following (A):
At least one selected from (B), (C) and (D)
The present invention provides a toner for developing an electrostatic image, comprising a kind of cyclic olefin polymer. (A) a polymer of a vinyl alicyclic hydrocarbon-based compound or a copolymer with a monomer copolymerizable with the compound, and (B) a polymer of a vinyl aromatic hydrocarbon-based compound having at least an aromatic ring. A polymer obtained by hydrogenating at least 30% of an aromatic ring of a copolymer obtained by hydrogenating 30% or a copolymer of the compound and a monomer copolymerizable with the compound; (C) a monocyclic monoolefin (D) a hydrogenated product of a polymer of a monocyclic conjugated diene-based compound, or a copolymer of a polymer of a monocyclic conjugated diene-based compound, A hydrogenated product of a copolymer with a monomer.

[0005] A preferred embodiment of the present invention is a toner for developing an electrostatic image, wherein the cyclic olefin polymer has at least one functional group selected from a carboxyl group, a hydroxyl group and an amino group.

[0006]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail. The electrostatic image developing toner of the present invention is an electrostatic image developing toner comprising at least a binder resin and a colorant, and contains a specific cyclic olefin polymer as the binder resin. Such polymers include the following (A), (B),
At least one type of cyclic olefin-based polymer selected from (C) and (D) is included. (A) a polymer of a vinyl alicyclic hydrocarbon-based compound or a copolymer with a monomer copolymerizable with the compound, and (B) a polymer of a vinyl aromatic hydrocarbon-based compound having at least an aromatic ring. A polymer obtained by hydrogenating at least 30% of an aromatic ring of a copolymer obtained by hydrogenating 30% or a copolymer of the compound and a monomer copolymerizable with the compound; (C) a monocyclic monoolefin (D) a hydrogenated product of a polymer of a monocyclic conjugated diene-based compound, or a copolymer of a polymer of a monocyclic conjugated diene-based compound, A hydrogenated product of a copolymer with a monomer.

The vinyl alicyclic hydrocarbon-based (co) polymer (A) The vinyl alicyclic hydrocarbon-based compound which is a monomer of the vinyl alicyclic hydrocarbon-based (co) polymer (A) includes: Vinyl group or α
-An alkyl-substituted vinyl group, a monocyclic cycloalkyl group,
Alkyl-substituted cycloalkyl group, cycloalkenyl group,
Or a compound having a structure in which an alkyl-substituted cycloalkenyl group is bonded.

[0008] Such compounds include vinylcyclobutane, vinylcyclopentane, vinylcyclohexane, vinylcycloheptane, vinylcyclooctane, and those compounds in which the α-position of the vinyl group is an alkyl group such as methyl, ethyl or propyl. Examples include substituted compounds. Also, 4-vinylcyclohexene, 4-isopropenylhexene, 1-methyl-4-vinylcyclohexene, 1-methyl-4-isopropenylcyclohexene, 2-methyl-4-vinylcyclohexene, 2-methyl-4-isopropenylhexene And vinylcyclohexene derivatives.

The above compounds can be polymerized alone or in combination of two or more. Further, other monomers copolymerizable with the above compounds can be combined and copolymerized within a range not to impair the purpose of the present invention.

Other monomers copolymerizable with the vinyl alicyclic hydrocarbon compound include α-olefins having 3 or more carbon atoms such as propylene and butene, conjugated dienes such as butadiene and isoprene, and ethylidene. Non-conjugated dienes such as norbornene, acrylonitrile, acrylic acid, methacrylic acid, maleic anhydride, acrylates,
Examples include methacrylic acid ester, maleimide, vinyl acetate, vinyl chloride and the like. Of these, α-olefins are preferably used, and particularly when they are combined with monomers such as propylene and butene, flexibility and impact resistance can be imparted. Other monomers copolymerizable with such a vinyl alicyclic hydrocarbon-based compound are 0 to 9 based on the total amount of the monomers.
It is desirable to use 5 mol%, more preferably 0 to 90 mol%.

The polymerization method for obtaining the vinyl alicyclic hydrocarbon-based (co) polymer (A) is not particularly limited, and includes known radical polymerization, coordination anion polymerization (Ziegler polymerization), cationic polymerization, anionic polymerization and the like. Can be applied.

The vinyl aromatic hydrocarbon (co) polymer (B) The vinyl aromatic hydrocarbon compound as a monomer of the vinyl aromatic hydrocarbon (co) polymer (B) is a vinyl group or a vinyl group. A compound in which an aromatic hydrocarbon substituent is bonded to an α-alkyl-substituted vinyl group.

Such compounds include styrene, α
-Methylstyrene, α-ethylstyrene, α-propylstyrene, α-isopropylstyrene, α-t-butylstyrene, 2-methylstyrene, 3-methylstyrene, 4-methylstyrene, 2,4-diisopropylstyrene, 2, 4-dimethylstyrene, 4-t-butylstyrene, 5-t-butyl-2-methylstyrene, monochlorostyrene, dichlorostyrene,
Monofluorostyrene, 4-phenylstyrene, vinylnaphthalene, vinylanthracene and the like can be exemplified.

The above compounds can be polymerized alone or in combination of two or more. Further, other monomers copolymerizable with the above compounds can be combined and copolymerized within a range not to impair the purpose of the present invention.

Other monomers copolymerizable with the vinyl alicyclic hydrocarbon-based compound include α-olefins having 3 or more carbon atoms, such as propylene and butene, conjugated dienes such as butadiene and isoprene, and ethylidene. Examples include non-conjugated dienes such as norbornene, acrylonitrile, acrylic acid, methacrylic acid, maleic anhydride, acrylate, methacrylate, maleimide, vinyl acetate, vinyl chloride, and the like. Of these, α-olefins are preferably used, and particularly when they are combined with monomers such as propylene and butene, flexibility and impact resistance can be imparted.

The other monomer copolymerizable with the vinyl alicyclic hydrocarbon-based compound is 0 to 0 based on the total amount of the monomer.
It is desirable to use 95 mol%, more preferably 0 to 90 mol%. As the polymerization method, the same method as the polymerization method (A) can be applied.

The desired vinyl aromatic hydrocarbon (co) polymer (B) can be obtained from the thus obtained polymer by hydrogenating the aromatic ring by a known method. A conventionally known method can be applied to the method of hydrogenation, for example,
JP-A-7-247321, U.S. Pat. No. 5,612,4
For example, a method described in JP-A No. 22 can be exemplified.
Hydrogenation rate of aromatic ring in polymer (measured by NMR)
Is at least 30%, preferably at least 60%, more preferably at least 90%.

Monocyclic Cyclic Monoolefin (Co) polymer (C) Monocyclic Cyclic Monoolefin Compound (C) is a monomer of monocyclic cyclic monoolefin (co) polymer (C). The monocyclic monoolefin which may be possessed, for example, cyclobutene, cyclopentene, cyclohexene, cyclooctene and the like.

The above compounds can be polymerized alone or in combination of two or more. Further, other monomers copolymerizable with the above compounds can be combined and copolymerized within a range not to impair the purpose of the present invention.

Other monomers copolymerizable with the monocyclic monoolefinic compound include ethylene, propylene, butene; conjugated dienes such as butadiene and isoprene; non-conjugated dienes such as ethylidene norbornene; acrylonitrile and acrylic. Examples thereof include acids, methacrylic acid, maleic anhydride, acrylic esters, methacrylic esters, maleimides, vinyl acetate, and vinyl chloride. Such other monomer copolymerizable with the monocyclic monoolefin compound is 0 to 95 mol% based on the total amount of the monomer,
More preferably, it is used in a ratio of 0 to 90 mol%.

Monocyclic cyclic monoolefin (co) polymer (C)
The polymerization method for obtaining is not particularly limited, and a known method of addition-polymerizing a monomer containing a cyclic monoolefin-based compound can be employed.

The monocyclic conjugated diene compound as a monomer monocyclic cyclic conjugated diene (co) polymer (D) a monocyclic cyclic conjugated diene (co) polymer (D) is have a substituent Monocyclic conjugated dienes which may be mentioned, for example, cyclopentadiene, cyclohexadiene, cycloheptadiene, cyclooctadiene and the like.

The above compounds can be polymerized alone or in combination of two or more. Further, other monomers copolymerizable with the above compounds can be combined and copolymerized within a range not to impair the purpose of the present invention.

Other monomers copolymerizable with the monocyclic conjugated diene compound include ethylene, propylene, butene; conjugated dienes such as butadiene and isoprene; non-conjugated dienes such as ethylidene norbornene; acrylonitrile and acrylic. Examples thereof include acids, methacrylic acid, maleic anhydride, acrylic esters, methacrylic esters, maleimides, vinyl acetate, and vinyl chloride. Such a monomer copolymerizable with the monocyclic conjugated diene-based compound is used at a ratio of 0 to 95 mol%, more preferably 0 to 90 mol%, based on the total amount of the monomers. It is desirable.

The polymerization method is not particularly limited, and a known method for addition-polymerizing a monomer containing a cyclic conjugated diene compound can be employed.

The polymer thus obtained can be hydrogenated by a known method to obtain a desired monocyclic conjugated diene (co) polymer (D). In particular,
For example, polycyclohexadiene and a hydrogenated product thereof can be obtained by using the method disclosed in JP-A-11-106571. The hydrogenation rate (measured by NMR) of the double bond in the hydrocarbon ring contained in the (co) polymer is desirably 30% or more, preferably 60% or more, and more preferably 90% or more.

The weight average molecular weight (Mw) of the cyclic olefin polymers (A) to (D) measured by gel permeation chromatography (GPC) used in the present invention is from 5,000 to 5,000 in terms of polystyrene molecular weight. One,
00000, preferably 10,000 to 500,00
0, more preferably 15,000 to 300,000, and a molecular weight distribution (Mw / Mn; Mn is a number average molecular weight measured by GPC) of 5.0 or less, preferably 3.0.
Or less, more preferably 2.0 or less. Glass transition temperature (Tg; measured by DSC) is 50 to 200 ° C, preferably 60 to 180 ° C, more preferably 70 to 150 ° C.
In the range.

The intrinsic viscosity [η] of the cyclic olefin polymers (A) to (D) measured in decalin at 135 ° C. used in the present invention is preferably 0.01 to 20 dl / g. , More preferably 0.03 to 10 dl /
g, more preferably 0.05 to 5 dl / g.

The glass transition temperature can be adjusted by adding a plasticizer. As the plasticizer added for the purpose of adjusting the glass transition temperature of the polymer, any compound which can be added to the polymer to lower the glass transition temperature can be used without any limitation. Examples of such compounds include liquid paraffin, spindle oil, process oils such as naphthenic oils, squalane, terpene compounds such as limonene, stearic acid, oleic acid, palmitic acid, myristic acid, higher fatty acids such as erucic acid, The higher fatty acids and monohydric alcohols such as methanol, ethanol, propanol and butanol, dihydric alcohols such as ethylene glycol, propylene glycol, tetramethylene glycol and 2-butene-1.4-diol, trihydric alcohols such as glycerin, and pentaerythritol And esters of polyhydric alcohols such as sorbitol, and amides formed by the higher fatty acids and amines or hydroxyamines.

The cyclic olefin polymers (A) to (D) used in the present invention may optionally contain other resins and additives as long as the objects of the present invention are not impaired. Such resins and additives include rubber components, other resin components, petroleum resins, waxes, heat stabilizers, weather stabilizers, light stabilizers, antistatic agents, slip agents, antiblocking agents, antifogging agents, Examples include nucleating agents, lubricants, dyes and pigments that absorb only light of a specific wavelength, natural oils, synthetic oils, waxes, and translucent fillers.

When the cyclic olefin polymer of the present invention is used as a binder resin, the cyclic olefin polymer selected from the above (A) to (D) may be used alone, but a polymer having a low molecular weight may be used. And a polymer having a high molecular weight. Such a low molecular weight polymer has a weight average molecular weight in the range of 1,000 to 30,000, preferably 4000 to 20,000, and 13
The intrinsic viscosity [η] measured in decalin at 5 ° C. is 0.25 d
The polymer having a high molecular weight of less than 1 / g has a weight average molecular weight of 30,000 or more, preferably 30,000 to 5
In the range of 0.00000 and intrinsic viscosity [η] of 0.25d
1 / g or more.

The high molecular weight polymer imparts viscosity to the toner, thereby improving the effect of preventing offset and the adhesiveness to a substrate to be copied such as paper or film. On the other hand, the low molecular weight polymer improves the melt fluidity of the toner and satisfies the toner characteristics that require instantaneous melting and solidification behavior. However, the amount of the high molecular weight polymer used is 50%
Above this, the uniform kneading property is extremely reduced, which hinders the toner performance. In other words, high quality, that is, high fixing strength,
A clear image with excellent thermal response cannot be obtained.

The cyclic olefin polymer (A)
In (D), since the molecular weight distribution is relatively narrow, heat performance, which is a necessary performance as a toner, is fast, and a toner having a high fixing strength can be manufactured. Also, since it has excellent transparency, it can be used for color toners as well as polyester resins. In addition, the polymer has a very small heat of fusion as measured by the DSC method, and it can be expected that the energy consumption for fixing is greatly reduced.

In the present invention, a toner obtained by mixing a cyclic olefin polymer (A) to (D) satisfying the above-mentioned properties with another resin and using it as a binder resin also has high quality, that is, high fixing strength. Provides excellent, clear images. In this case, the use ratio of the cyclic olefin polymer and the other resin in the binder resin is 1 to 100 parts by weight of the former, preferably 20 to 90 parts by weight, more preferably 50 to 90 parts by weight,
0 to 99 parts by weight, preferably 10 to 80 parts by weight of the latter,
More preferably, the amount is 10 to 50 parts by weight.
When the former is less than 1 part by weight, it becomes difficult to obtain a high-quality image.

Further, by introducing an acid anhydride group such as maleic anhydride or acrylic acid, a carboxyl group and an ester thereof into the cyclic olefin polymer by a melt air oxidation method or a graft modification method, it is possible to form a copolymer with another resin. Compatibility,
The dispersibility of the pigment and the adhesion to paper can be improved. A similar improvement can be realized by introducing a polar functional group such as a hydroxyl group, an amino group, or an epoxy group by a known method. Furthermore, a polymer having a functional group as described above and sodium carbonate, calcium carbonate, a metal salt such as zinc chloride is reacted to introduce an ionic crosslinked structure,
The fixing property can be improved by reacting a crosslinking agent such as divinylbenzene or diallyl phthalate with an organic peroxide to introduce a crosslinked structure.

The toner for developing an electrostatic image of the present invention is prepared by adding a colorant, a charge control agent, a release agent and other additives to the above-mentioned binder resin, and by a conventionally known method such as kneading, pulverizing or classifying. And, if necessary, a fluidizing agent or the like is added.

In this case, examples of the coloring agent include carbon black, diazo yellow, phthalocyanine blue, quinacridone, carmine 6B, monoazo red, perylene and the like.
Conventionally known ones can be used.

Examples of the charge control agent include a nigrosine dye, a fatty acid-modified nigrosine dye, a metal-containing nigrosine dye, a combined metal fatty acid-modified nigrosine dye, and 3,5-di-t.
chromium complex of tert-butylsalicylic acid, quaternary ammonium salt, triphenylmethane dye, azochrome complex, etc.
Conventionally known ones can be used.

The toner of the present invention may have, if necessary,
In order to enhance the anti-offset property in heating roller fixing, a known function-imparting agent, preferably having a melting point of 60 to 17 is used.
A wax at 0 ° C. can be added. Examples of the wax having the above melting point include carnauba wax, montan wax, glycerin monostearate, polyethylene wax, and polypropylene wax.

Further, the toner of the present invention contains a fluidizing agent such as colloidal silica, aluminum oxide and titanium oxide;
A lubricant composed of a metal salt of a fatty acid such as barium stearate, calcium stearate, or barium laurate can also be added.

The toner of the present invention is used as a one-component developer,
Further, it can be used as a toner of a two-component developer. Further, the toner of the present invention can be used as a one-component magnetic toner by mixing magnetic powder or as a full-color toner.

[0042]

The toner for developing an electrostatic image of the present invention contains at least one specific cyclic olefin polymer as a binder resin, and thus has excellent fixability, light transmittance and toner spent resistance. And a clear, high-quality image can be obtained, and its characteristics are exhibited particularly when used for a color toner.

[0043]

The present invention will be described more specifically below with reference to examples. The present invention is not limited by these examples. Reference Example 1 In a stainless steel autoclave having an internal volume of 5 liters, the number average molecular weight (Mn) was 15,200, the weight average molecular weight (Mw) was 18,000, and Mw / Mn was 1.1.
240 g of polystyrene and cyclohexane 1000
g, 36 g of a hydrogenation catalyst (manufactured by Nippon Chemical Industry Co., Ltd., silica supported on 40% nickel, alumina carrier), and the system is purged with nitrogen. Next, a hydrogenation reaction is performed at 230 ° C. and a hydrogen pressure of 45 kg / cm ² for 8 hours while stirring the inside of the system at a speed of 1000 rpm. After the completion of the hydrogenation reaction, the reaction solution was filtered through Celite, and after adding 4000 g of cyclohexane,
The polymer was precipitated in addition to a large excess of methanol. Physical properties of the obtained polymer were as follows: Mn: 4,200, Mw: 7,80.
0, Mw / Mn: 1.85, hydrogenation rate: 100%, T
g: 138 ° C., density: 0.95 g / cm ³ . Next, liquid paraffin% was kneaded into the resin thus obtained, and the glass transition point was adjusted to 80 ° C.

Reference Example 2 A 5 liter stainless steel autoclave having a number average molecular weight (Mn) of 110
Mw / Mn with a weight average molecular weight of 130,000
Is 1.18 polystyrene 240g, cyclohexane 1
000 g and 36 g of a hydrogenation catalyst (manufactured by Nippon Chemical Industry Co., Ltd., 40% nickel-supported silica, alumina carrier) are charged, and the system is purged with nitrogen. Next, while stirring the inside of the system at a speed of 1000 rpm, the system was heated at 230 ° C. and a hydrogen pressure of 45 Kg / cm ² at 8
Perform the hydrogenation reaction for hours. After the completion of the hydrogenation reaction, the reaction solution is filtered through celite, and after adding 4000 g of cyclohexane, the polymer is added to a large excess of methanol to precipitate a polymer.
Physical properties of the obtained polymer were as follows: Mn: 43,000, Mw:
87,000, Mw / Mn: 1.85, hydrogenation rate: 10
0%, Tg: 140 ° C., density: 0.95 g / cm ³ . Next, liquid paraffin was kneaded into the resin thus obtained, and the glass transition point Tg was adjusted to 83 ° C.

<Evaluation> The prepared toner was put into a commercially available electrophotographic copying machine to perform a performance test. (1) Fixing property A sample obtained by copying on a recycled paper a copying speed and a fixing temperature of 10 sheets / min using a toner prepared according to each prescription in a range of 110 to 140 ° C. every 10 ° C. Rubbing was performed 10 times with an eraser using an abrasion tester. The print density of the sample was measured by a Macbeth reflection densitometer. The print density after rubbing was represented by a ratio (%) to the density before rubbing. Judgment was made according to the following criteria using the lowest value of the measured values at each temperature. ：: The minimum value was 75% or more. Δ: The minimum value was 65% or more and less than 75%. X: The lowest value was less than 65%.

(2) Image Clarity Material copied on recycled paper was measured using an image sample manufactured by DataQuest. The fine line resolution and the gray scale of the copied image were used as the judgment items, and the judgment was made according to the following criteria. Fine line resolution: ：: Fine line resolution was 301 dots / inch or more. Δ: Fine line resolution was 201 to 300 dots / inch. X: Fine line resolution was 200 dots / inch or less. Gray scale: ：: The reflection density ratio between the image sample and the copy image measured at each gray scale step was 75% or more. Δ: The reflection density ratio was 65% or more and less than 75%. X: The reflection density ratio was less than 65%.

(3) Light Transmissivity Using magenta toner prepared according to the prescriptions of the examples and comparative examples, sheet-shaped samples each having a thickness of 100 μm were prepared. The light transmittance at 624 nm was measured and determined according to the following criteria. ：: The light transmittance was 11% or more. Δ: The light transmittance was 8% or more and less than 11%. X: The light transmittance was less than 8%.

(4) Toner Spent Resistance A predetermined amount of the toner and the ferrite carrier are put in a developer box, and 5 g of the toner-adhered carrier that has been stirred and friction-treated for one week is weighed. It is put in soapy water, the toner adhering to the surface is removed by static electricity, and only the carrier magnetic powder is taken out with a magnet. The magnetic powder was immersed in acetone to dissolve and remove the surface-fused spent toner, and the change in weight before and after the immersion treatment was measured and judged according to the following criteria. ：: The change in weight was less than 2%. Δ: The change in weight was 0.2 to less than 0.5%. X: The weight change was 0.5% or more.

(5) Storage The toner was evaluated based on the toner aggregation rate. 2 g of the toner is taken in a sample tube, and after tapping 500 times with a tapping denser, the resultant is left at 60 ° C. and 20% RH for 2 hours. This was put into a 48-mesh sieve, sieved with a constant vibration, and the ratio of the amount of toner remaining on the mesh was measured to obtain the toner aggregation rate. The toner aggregation rate was determined based on the following criteria. A: The aggregation rate was less than 15% by weight. Good: Less than 15-45% by weight. C: The aggregation rate was less than 45 to 60% by weight. X: The aggregation rate was 60% by weight or more.

Example 1 5% by weight of a charge controlling agent, polyethylene wax (Mw: 4600, Mn: 1000, T
m: 75 ° C.) 2.5% by weight, 0.5% by weight of hydrophobic silica, 5% by weight of magenta pigment and Reference Example 1 as a binder resin
Is mixed and melt-kneaded at 130 ° C. with two rolls, cooled and solidified, coarsely pulverized and then finely classified by a jet mill, and then adjusted to an average particle size of about 10 μm to form a toner. It was created. The prepared toner was put into a commercially available electrophotographic copying machine to perform a performance test. The results are summarized in Table 1.

Example 2 5% by weight of a charge controlling agent, polyethylene wax (Mw: 4600, Mn: 1000, T
m: 75 ° C.) 2.5% by weight, 0.5% by weight of hydrophobic silica, 5% by weight of magenta pigment and Reference Example 1 as a binder resin
57% by weight of the resin of Reference Example 2 and 30% by weight of the resin of Reference Example 2 were melted and kneaded at 130 ° C. by two rolls, cooled and solidified, coarsely pulverized, then finely classified by a jet mill, and then averaged. The toner was prepared by adjusting the particle diameter to about 10 μm. The prepared toner was put into a commercially available electrophotographic copying machine to perform a performance test. The results are summarized in Table 1.

Example 3 40% by weight of magnetic powder, 5% by weight of charge control agent, polyethylene wax (Mw: 4600,
Mn: 1000, Tm: 75 ° C) 2.5% by weight, hydrophobic silica 0.5% by weight, calcium carbonate 2.0% by weight, and 50% by weight of the resin of Reference Example 1 as a binder resin were mixed, After melt-kneading at 150 ° C. with a two-roll mill, the mixture was cooled and solidified, coarsely pulverized, finely classified by a jet mill, and adjusted to an average particle size of about 10 μm to prepare a toner.
The prepared toner was put into a commercially available electrophotographic copying machine to perform a performance test. The results are summarized in Table 1.

Comparative Example 1 A toner was obtained in the same manner as in Example 1 except that a polyester resin (manufactured by Kao Corporation, Tufton ^™ NE2155) was used as the binder resin. The prepared toner was put into a commercially available electrophotographic copying machine to perform a performance test. The results are summarized in Table 1.

Comparative Example 2 A toner was obtained in the same manner as in Example 1 except that a styrene acrylic resin (NC100, manufactured by Nippon Carbide Industries) was used as the binder resin.
The prepared toner was put into a commercially available electrophotographic copying machine to perform a performance test. The results are summarized in Table 1.

<Comparative Example 3> A random copolymer of ethylene and norbornene (Mw: 6000, M
n: 3200, Tg: 65 ° C.), except that toner was obtained in the same manner as in Example 1. The prepared toner was put into a commercially available electrophotographic copying machine to perform a performance test.
The results are summarized in Table 1.

[0056]

[Table 1]

Claims (2)

[Claims] 1. An electrostatic image developing toner comprising at least a binder resin and a colorant, wherein the binder resin is at least one selected from the following (A), (B), (C) and (D): An electrostatic image developing toner comprising a cyclic olefin polymer. (A) a polymer of a vinyl alicyclic hydrocarbon-based compound or a copolymer with a monomer copolymerizable with the compound, and (B) a polymer of a vinyl aromatic hydrocarbon-based compound having at least an aromatic ring. A polymer obtained by hydrogenating at least 30% of an aromatic ring of a copolymer obtained by hydrogenating 30% or a copolymer of the compound and a monomer copolymerizable with the compound; (C) a monocyclic monoolefin (D) a hydrogenated product of a polymer of a monocyclic conjugated diene-based compound, or a copolymer of a polymer of a monocyclic conjugated diene-based compound, A hydrogenated product of a copolymer with a monomer. 2. The electrostatic image developing apparatus according to claim 1, wherein the cyclic olefin polymer has at least one functional group selected from a carboxyl group, a hydroxyl group, and an amino group. toner.