JPH06110244A - Capsule toner - Google Patents

Abstract

PURPOSE:To provide a capsule toner having fine dispersion of a coloring agent, excellent fixing property and sharp distribution of particle size and good electrification property which forms high-density picture images and does not deteriorate an org. photosensitive body. CONSTITUTION:This capsule toner consists of a core material and a shell material which coveres the core material. The core material contains copolymers consisting of at least monomers expressed by formula (I), monomers expressed by formula (II) and/or monomers expressed by formula (III) as the monomer component. In formulae, R, R' and R'' are hydrogen atoms or methyl groups, (r) and (t) are integers 1 to 6, (p) and (q) are integers 1 to 3. R1 is an alkyl group of 8-18 carbon number, Y is oxygen atom or -NH-, and Z is an atomic group which forms a heteroring with nitrogen atom.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a capsulated toner used in an electrophotographic apparatus, and more particularly to a capsulated toner which is suitable for a fixing type fixing device. More specifically, it relates to a color capsule toner.

[0002]

2. Description of the Related Art Conventionally, various capsule toners composed of a core substance and a shell substance have been proposed, for example, JP-A-51-119231 and JP-A-52-8.
2239, JP-A-55-18630, and JP-A-59-159177 describe capsule toners using a soft solid as a core substance. Also,
JP-A-58-145964 and JP-A-60-83958.
The publication discloses an encapsulated toner containing a core substance containing at least a high boiling point solvent and a polymer. Further, JP-A-63-163373 discloses that a specific chlorinated paraffin is used as a high boiling point solvent in a core material. Furthermore, JP-A-51-132838 discloses a capsule toner using a saturated aliphatic hydrocarbon solvent and a long-chain alkyl ester polymer of acrylic acid or a petroleum resin as a core substance.

[0003]

However, the conventionally proposed capsule toner has not been sufficiently satisfactory. For example, JP-A-51-119231, JP-A-52-82239 and JP-A-55-1.
Soft solids such as lauryl methacrylate polymers, polyolefin polymers, and waxes described in JP-A-8630 and JP-A-59-159177 have long saturated hydrocarbon chains and belong to so-called non-polar substances.
It has been difficult to finely disperse a highly polar colorant such as a pigment in such a non-polar substance. As a result, a large amount of colorant has to be added to the toner in order to obtain a sufficient image density, and as a result, the fixability of the toner is impaired, and it is difficult to firmly fix it on paper by pressure fixing. It was necessary to apply pressure (eg 300-400 kg / cm ² ). Therefore, there is a drawback that the fixing device becomes large and heavy. In addition, JP-A-58-1
In the cases described in JP-A-45964, JP-A-60-83958 and JP-A-63-163373, the fixability is good, but the high boiling point solvent used for the core substance is a so-called plasticizer. However, when an organic photoconductor is used as the photoconductor, there is a drawback that the photoconductor is deteriorated. That is, these high-boiling solvents can finely disperse a highly polar colorant such as a pigment, but have a high dissolving power for the resin, and therefore, the high-boiling solvent exuded from the capsule or volatilized. However, there is a drawback that the photoreceptor is deteriorated.

On the other hand, for example, Japanese Unexamined Patent Publication No. 51-132838.
As described in the publication, when a saturated aliphatic hydrocarbon is used as the solvent and a long-chain alkyl ester polymer of acrylic acid or a petroleum resin is used as the polymer, both the solvent and the polymer are Since it is a non-polar substance, it is difficult to finely disperse the colorant as in the case of using the soft solid described above. Further, as is known in the field of printing inks or paints, it is conceivable to add an additive such as a surfactant in order to enhance dispersion, but an interfacial polymerization method, an in-situ polymerization method, a coacervation method When encapsulating by a method such as in-liquid drying and obtaining a capsule toner, granulation is carried out by emulsification in water, so the surfactant affects the emulsification and deteriorates the particle size distribution of the toner. As a result, there is a problem that the fluidity of the toner deteriorates. Further, there is a problem that the surfactant lowers the chargeability of the toner.

The present invention has been made in view of the above problems in the conventional capsule toner. That is, an object of the present invention is to provide a capsule toner in which a colorant is finely dispersed, the image density is high, the organophotoreceptor is not deteriorated, the fixing property is excellent, the particle size distribution is sharp, and the charging property is good. To provide.

[0006]

As a result of intensive studies, the inventors of the present invention have found that the core substance and / or
Alternatively, the shell substance may contain a colorant, and the core substance may contain a copolymer obtained by copolymerizing two or more monomer components using a specific monomer as a monomer component. As a result, they have found that the above object can be achieved, and completed the present invention.

That is, the capsule toner of the present invention is a capsule toner comprising a core substance and a shell substance coating the core substance, the core substance being a monomer represented by the following general formula (I) and the following: It is characterized by containing a copolymer containing at least a monomer represented by the general formula (II) and / or a monomer represented by the general formula (III) as a monomer component.

[Chemical 2]

[Chemical 3] (In the formula, R, R ′, and R ″ each represent a hydrogen atom or a methyl group, r and t each represent an integer of 1 to 6, and p and q each represent an integer of 1 to 3; (R ₁ represents an alkyl group of 8 to 18, Y represents an oxygen atom or —NH—, and Z represents an atomic group forming a heterocycle with a nitrogen atom.)

The present invention will be described in detail below. In the encapsulated toner of the present invention, as the binder resin contained in the core substance, the monomer represented by the general formula (I) and the monomer represented by the general formula (II) and / or the general formula A copolymer obtained by copolymerizing with the monomer represented by (III) or by copolymerizing these monomers with another monomer as the third component is used. .

Specific examples of the monomer represented by the general formula (I) include octyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, nonyl (meth) acrylate, and (meth) acrylate. Examples include (meth) acrylic acid ester monomers selected from decyl acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, and the like.
Examples of the monomer represented by the general formula (II) include N, N-dimethylaminoethyl (meth) acrylate, N, N-dimethylaminopropyl (meth) acrylate, and N, N- (meth) acrylate. Contains an amino group selected from diethylaminoethyl, (meth) acrylic acid N, N-dimethylaminoethylamide, (meth) acrylic acid N, N-dimethylaminopropylamide, (meth) acrylic acid N, N-diethylaminoethylamide ( Examples of the monomer represented by the general formula (III) include (meth) acrylic acid ester and amino group-containing (meth) acrylic acid amide.
Piperidinemethyl (meth) acrylate, Piperidineethyl (meth) acrylate, Piperidinepropyl (meth) acrylate, Pyrrolidinemethyl (meth) acrylate, Pyrrolidineethyl (meth) acrylate, Piperidineethylamide (meth) acrylate, ( Examples thereof include a nitrogen-containing heterocyclic group-containing (meth) acrylic acid ester or a nitrogen-containing heterocyclic group-containing (meth) acrylamide selected from (meth) acrylic acid pyrrolidineethylamide. In the present invention,
Among these, a copolymer with an amino group-containing monomer having a dimethylamino group and a copolymer with a piperidine ethyl (meth) acrylate monomer are more preferable from the viewpoint of pigment dispersibility. Further, as the monomer added as the third component, for example, (meth) acrylic acid ester such as methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, cyclohexyl (meth) acrylate, etc. Vinyl esters such as vinyl acetate, vinyl benzoate, vinyl t-butyl benzoate, vinyl formate, vinyl pivalate, vinyl propionate; styrene, p-pentylstyrene, p-butylstyrene, 3-chlorostyrene, 2-
Examples thereof include styrene derivatives such as ethylstyrene.

The copolymerization ratio of the amino group- or nitrogen-containing heterocyclic group-containing copolymer is such that the monomer represented by the general formula (I): the monomer represented by the general formula (II) or the general formula (III). 9 in quantity
9 mol%: 1 mol% to 20 mol%: 80 mol%, preferably 95 mol%: 5 mol% to 40 mol%: 60 mol%, more preferably 90 mol%: 10 mol% to 50 mol%
Mol%: 50 mol%. Also, the other monomer added as the third component is 50 mol% with respect to all the monomers used.
It can be contained in the following range. The weight average molecular weight of the copolymer is 5,000 to 500,000.
It is 0, preferably 10,000 to 300,000.

In the present invention, the amino group-containing or nitrogen-containing heterocyclic group-containing copolymer may be used alone as the core substance, and further, the monomer represented by the above general formula (I) may be used. It is also possible to contain a homopolymer composed of the components or a copolymer thereof. In this case, there is an advantage that the fixing performance can be easily adjusted by changing the mixing ratio with the copolymer containing the amino group or the nitrogen-containing heterocyclic group. Examples of the other monomer that can be copolymerized with the monomer represented by the general formula (I) include methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, and (meth). (Meth) acrylic acid esters such as cyclohexyl acrylate; vinyl esters such as vinyl acetate, vinyl benzoate, vinyl t-butyl benzoate, vinyl formate, vinyl pivalate, vinyl propionate;
Examples thereof include styrene derivatives such as styrene, p-pentylstyrene, p-butylstyrene, 3-chlorostyrene and 2-ethylstyrene.

The core substance is composed of a binder resin composed of the above-mentioned polymer, a high-boiling-point solvent which dissolves the binder resin and a colorant, or mainly a soft solid substance or a liquid substance and a colorant. Is preferred. If necessary, magnetic powder may be added in place of the colorant, or silicone oil may be added for the purpose of improving the fixability. It is also possible to add a high boiling point solvent which does not dissolve the binder resin to a high boiling point solvent which dissolves the binder resin. It is desirable to change the kinds or composition ratios of the constituents depending on whether the purpose is pressure fixing or heat fixing.

As a method of incorporating the above-mentioned polymer into the capsule as a component of the core substance, the polymer is preliminarily charged in the state of the polymer together with the other core substance component, the low boiling point solvent, and the shell-forming component, and the shell is prepared. At the same time as the formation, or after the formation of the outer shell, a method of driving the low boiling point solvent out of the system to form the core substance, and charging in the state of a monomer, after forming the outer shell, polymerizing the monomer The method of forming the core material is preferably used. When the core substance is mainly composed of a binder resin, a high-boiling solvent that dissolves the binder resin, and a colorant, the high-boiling solvent that dissolves the binder resin has a boiling point of 140 ° C. or higher, preferably 160 ° C. or higher. Can be used. For example, Modern Plastics Enc
Cyclopedia (1975-1976), Plas
Those described in the section of ticizers can be used. Further, it may be selected from the high boiling point solvents disclosed as the core substance of the pressure fixing capsule toner (for example, JP-A-58-145964 and JP-A-63-163373). Specifically, phthalic acid esters, (eg, diethyl phthalate, dibutyl phthalate); Aliphatic dicarboxylic acid esters (eg, diethyl malonate, dimethyl oxalate); Phosphate esters (eg,
Tricresyl phosphate, trixylyl phosphate); citric acid esters (eg, o-acetyltriethyl citrate); benzoic acid esters (eg, butylbenzoate, hexylbenzoate); fatty acid esters (eg, hexadecylmyristate, Dioctyl adipate); alkylnaphthalenes (eg, methylnaphthalene,
Dimethylnaphthalene, monoisopropylnaphthalene, diisopropylnaphthalene); alkyldiphenyl ethers (eg, o-, m-, p-methyldiphenyl ether); amide compounds of higher fatty acids or aromatic sulfonic acids (eg, N, N-dimethyllauroamide) , N-butylbenzenesulfonamide); trimellitic acid esters (eg, trioctyl trimellitate); diarylalkanes (eg, diarylmethane such as dimethyldiphenylmethane, 1-phenyl-1-methylphenylethane, 1
-Diallylethane such as dimethylphenyl-1-phenylethane and 1-ethylphenyl-1-phenylethane); and chlorinated paraffins. When a polymer having a long-chain alkyl group is used as the binder resin, an aliphatic saturated hydrocarbon or an organic solvent containing an aliphatic saturated hydrocarbon as a main component (for example, Isopar-G and Isopar manufactured by Exxon Chemical Co., Ltd.) is used. -H, Isopar-
L, Isopar-M, etc.) can also be used.

Petroleum resin or rosin resin may be added to the core substance. Examples of the petroleum resin include an aliphatic resin, an aromatic resin, a copolymer resin, an alicyclic hydrogenated petroleum resin, an alkyl / phenol resin, and a coumarone / indene resin. Among them, aromatic petroleum resin
It is particularly preferable in compatibility with the polymer. Examples of the rosin-based resin include rosin, modified rosin, glycerin ester of rosin, pentaerythritol ester of rosin, and the like.

In the encapsulated toner of the present invention, for the purpose of preventing offset, a wax may be contained as a component of the core substance in addition to the above-mentioned polymers and resins. Examples of the wax include paraffin wax, microcrystalline wax, montan wax, carnauba wax, candelilla wax, natural wax such as beeswax, polyethylene wax, modified wax, cetyl alcohol, and synthetic wax such as stearic acid.

On the other hand, the outer shell is composed of a resin component, and any resin component known in encapsulation can be used as the resin component. For example, polyurea resin, polyurethane resin, polyamide resin, polyester resin, epoxy resin or epoxy urea resin, epoxy urethane resin is preferable, and among them, polyurea resin or polyurethane resin alone or a mixture of both, or an epoxy urea resin or The epoxy urethane resin alone or a mixture of both is more preferable from the viewpoint of the hermeticity of the capsule. Further, the surface of the outer shell may be graft-polymerized by, for example, graft-polymerizing with a vinyl monomer such as acrylic acid ester or methacrylic acid ester. It is desirable to change the thickness of the outer shell depending on the purpose of pressure fixing and the purpose of heat fixing, and the kind or composition ratio of the constituent components may be changed.

A known encapsulation method can be used for producing the encapsulated toner in the present invention. Among them, in-s is particularly preferable because of the completeness of coating and the ease of encapsulation.
It is preferable to use the encapsulation method by the in situ polymerization method or interfacial polymerization method. The encapsulation method by the in-situ polymerization method is, for example, as disclosed in JP-B-49-45133 and JP-A-50-22507, the first capsule shell-forming unit amount present in oily droplets. A method in which the body and the second capsule shell forming monomer react with each other inside and / or at the interface of the oily droplet to form a capsule shell.

A method for producing microcapsules by the interfacial polymerization method is described in, for example, Japanese Patent Publication No. 38-19574.
42-446, JP-B-2-31381,
JP-A-58-66948, 59-148066.
As disclosed in JP-A-59-162562, the first capsule shell-forming monomer present in the oily droplets and the second capsule shell-forming monomer present in the solvent are This is a method of forming a capsule shell by reacting at the interface of oily droplets.

The first capsule shell-forming monomer present in the oily droplets includes isocyanate, acid halide,
An epoxy compound can be given. Specifically, metaphenylene diisocyanate, tolylene diisocyanate, diphenylmethane diisocyanate, 3,3′-dimethyl-diphenyl-4,4′-diisocyanate, 3,3 ′
-Dimethyl-diphenylmethane-4,4'-diisocyanate, xylylene diisocyanate, naphthalene diisocyanate, hexamethylene diisocyanate and other diisocyanates, or known as so-called burette type, adduct type, isocyanurate type There are polyisocyanates. Examples of acid halides include dibasic acid halides such as adipoyl dichloride, phthaloyl dichloride, terephthaloyl dichloride, and 1,4-cyclohexanedicarbonyl chloride. Examples of the epoxy compound include epoxy compounds known as bisphenol A type, resorcin type, bisphenol F type, tetraphenylmethane type, novolac type, polyalcohol type, polyglycol type, and glycerin triether type.

The second capsule shell-forming monomer used in the in-situ polymerization method is a compound having two or more hydroxyl groups, specifically, ethylene glycol, 1,4-butanediol, Catechol, resorcinol, hydroquinone, o-dihydroxymethylbenzene, 4,4'-dihydroxydiphenylmethane, 2,2
Examples include polyols such as -bis (4-hydroxyphenyl) -propane.

On the other hand, when encapsulation by interfacial polymerization is used, the second capsule shell forming monomer is ethylene glycol, 1,4-butanediol, catechol, resorcinol, hydroquinone, o-dihydroxymethylbenzene, Polyols such as 4,4′-dihydroxydiphenylmethane, 2,2-bis (4-hydroxyphenyl) -propane or ethylenediamine, tetramethylenediamine, hexamethylenediamine, phenylenediamine, diethylenetriamine, triethylenetetramine, diethylaminopropylamine, tetraethylene Polyamines such as pentamine, or piperazine, 2-
Examples thereof include piperazine compounds such as methylpiperazine and 2,5-dimethylpiperazine. In this case, water can be used instead of the second capsule shell forming monomer.

Examples of the colorant include inorganic pigments such as carbon black, red iron oxide, dark blue and titanium oxide, azo pigments such as fast yellow, disazo yellow, pyrazolone red, chelate red, brilliant carmine and para brown, copper phthalocyanine and metal-free phthalocyanine. And condensed polycyclic pigments such as flavantron yellow, dibromoanthrone orange, perylene red, quinacridone red, and dioxazine violet. Further, disperse dyes, oil-soluble dyes and the like can also be used. Furthermore, when used as a magnetic one-component toner, all or part of the black colorant can be replaced with magnetic powder. As the magnetic powder, magnetite, ferrite, a metal carrier such as cobalt, iron, nickel, or an alloy thereof can be used. Further, the coloring agent or magnetic powder charged as one component of the core substance may be present at the interface between the core and the outer shell or in the outer shell after capsule formation.

An external additive may be added to the capsule toner of the present invention in order to impart fluidity or chargeability. As external additives, long-chain fatty acids such as stearic acid and esters, amides, metal salts that have been conventionally used, and fine particles of molybdenum dioxide, boron nitride, silica, aluminum oxide, titanium dioxide, zinc oxide, etc. Powder,
Examples include fine powders such as fluororesins, polycyclic aromatic compounds, wax-like substances, crosslinked or non-crosslinked fat fine powders, etc., and generally have a low surface energy or a solid surface with a low friction coefficient. Fine particles or fine particles having non-adhesiveness and slight polishing property are preferably used. The external additive may be added to the toner after drying the capsule toner by using a mixer such as a V blender or a Henschel mixer, or the external additive may be water or a water-based liquid such as water / alcohol. After dispersion, a method of adding it to a capsule toner in a slurry state and drying it to attach an external additive to the toner surface can be mentioned.

[0024]

In the present invention, by using the aforementioned amino group- or nitrogen-containing heterocyclic group-containing copolymer as the binder resin component of the core substance, a polymer having a long-chain alkyl group,
Alternatively, even when the polymer and the aliphatic saturated hydrocarbon are used as the core substance, the dispersibility of the pigment is good, and the fluidity and chargeability of the encapsulated toner are good without inhibiting the encapsulation reaction. To be

[0025]

EXAMPLES The present invention will be specifically described below with reference to examples. In the examples, "part" means "part by weight".

Example 1 (Preparation of capsule particles) N, N-dimethylaminoethyl methacrylate-lauryl methacrylate copolymer (copolymerization ratio = 15 mol%: 85 mol%, Mw = 1 × 10 ⁵ ) 40
g and polylauryl methacrylate (Mw = 5 × 10
⁴ ) 50 g was dissolved in 200 g of ethyl acetate. 5 g of a magenta pigment (Carmine 6B: manufactured by Dainichiseika Co., Ltd.) was added to the obtained solution, and a dispersion treatment was performed for 3 hours using a sand mill (tabletop sand mill: manufactured by Campehapio). When a part of the dispersion was taken out and observed with an optical microscope, pigment particles of 1 μm or more were not found, and the pigment was dispersed in submicron. Next, 50 g of this dispersion was mixed with 50 g of polylauryl methacrylate (Mw = 5 × 10 ⁴ ),
40 g of isocyanate (Sumijour L: manufactured by Sumitomo Bayer Urethane Co., Ltd.) and 15 g of ethyl acetate were added and thoroughly mixed (this liquid is referred to as liquid A). On the other hand, 200 ion-exchanged water
10 g of hydroxypropylmethyl cellulose (Metrose 65SH50: manufactured by Shin-Etsu Chemical Co., Ltd.) was dissolved in g, and 5
It was cooled to 0 ° C. (this liquid is referred to as liquid B).

The liquid B was stirred with an emulsifying machine (auto homomixer: manufactured by Tokushu Kika Kogyo Co., Ltd.), and the liquid A was slowly charged into the liquid to emulsify the liquid. Thus, an O / W emulsion in which the average particle size of the oil droplet particles in the emulsion was about 12 μm was obtained. Next, in place of the emulsifier, a stirrer (three-one motor: manufactured by Shinto Kagaku Co., Ltd.) equipped with a propeller-type stirring blade was used.
Stirred at 00 rpm. After 10 minutes, 100 g of a 5% aqueous solution of diethylenetriamine was added dropwise thereto. After the completion of dropping, warm to 60 ° C and degas the ethyl acetate.
A time encapsulation reaction was performed. After completion of the reaction, the mixture was poured into 2 liters of ion-exchanged water, and the capsule particles were separated by centrifugation. This operation was repeated 7 times to wash the capsule particles. The capsule slurry thus obtained was placed in a stainless steel vat and dried in a freeze dryer for 24 hours. Next, 0.5 part of hydrophobic silica (R972: manufactured by Nippon Aerosil Co., Ltd.) was added to 100 parts of the capsule particles and sufficiently mixed to obtain a capsule toner. 3 parts of this capsule toner and 97 parts of iron powder carrier are heated at a temperature of 20 ° C
After mixing in an environment of 50% humidity, a copy sample was obtained using a copying machine (2700 manufactured by Fuji Xerox Co., Ltd. modified for capsule toner). The image density of the solid image was 1.5 when measured with a Macbeth densitometer.

Comparative Example 1 Pigment dispersion was carried out in the same manner as in Example 1 except that only polylauryl methacrylate was used instead of the N, N-dimethylaminoethyl methacrylate-lauryl methacrylate copolymer. When a part of the dispersion liquid was taken out and observed with an optical microscope, pigment particles of 1 μm or less were hardly found, and most of the pigments were not dispersed in submicrons. Then, an encapsulation reaction was performed, followed by washing and drying to obtain capsule particles. To 100 parts of the capsule particles, 0.5 part of hydrophobic silica (R972: manufactured by Nippon Aerosil Co., Ltd.) was added and mixed sufficiently to obtain a comparative capsule toner. A copy sample was obtained in the same manner as in the example. When the image density of the solid image was measured with a Macbeth densitometer, it was 0.4 and the density was very low.

Example 2 (Preparation of capsule particles) Piperidine ethyl methacrylate-lauryl methacrylate-styrene copolymer (copolymerization ratio = 15 mol%: 75 mol%: 10 mol%, Mw = 5 × 1)
90 g of 0 ⁴ ) was dissolved in 200 g of ethyl acetate. 5 g of a magenta pigment (Carmine 6B: manufactured by Dainichiseika Co., Ltd.) was added to the obtained solution, and a dispersion treatment was performed for 3 hours using a sand mill (tabletop sand mill: manufactured by Campehapio). When a part of the dispersion was taken out and observed with an optical microscope, pigment particles of 1 μm or more were not found, and the pigment was dispersed in submicron. Next, 50 g of this dispersion liquid was mixed with 50 g of piperidinoethyl methacrylate-lauryl methacrylate-styrene copolymer (copolymerization ratio = 15 mol%: 75 mol%: 10 mol%, Mw = 5 × 10 ⁴ ). 20 g of epoxy resin (Epicote 801: manufactured by Yuka Shell Epoxy Co., Ltd.), and isocyanate (Takenate D110N:
25 g (manufactured by Takeda Pharmaceutical Co., Ltd.) and 15 g of ethyl acetate were added and mixed thoroughly (this liquid is referred to as liquid A). On the other hand, 10 g of hydroxypropylmethylcellulose (Metrose 65SH50: manufactured by Shin-Etsu Chemical Co., Ltd.) was dissolved in 200 g of ion-exchanged water and cooled to 5 ° C. (this liquid is referred to as liquid B).

The liquid B was stirred with an emulsifying machine (auto homomixer: manufactured by Tokushu Kika Kogyo Co., Ltd.), and the liquid A was slowly charged into the liquid for emulsification. Thus, an O / W emulsion in which the average particle size of the oil droplet particles in the emulsion was about 12 μm was obtained. Next, in place of the emulsifier, a stirrer (three-one motor: manufactured by Shinto Kagaku Co., Ltd.) equipped with a propeller-type stirring blade was used.
Stirred at 00 rpm. After 10 minutes, 100 g of a 5% aqueous solution of diethylenetriamine was added dropwise thereto. After the completion of dropping, warm to 60 ° C and degas the ethyl acetate.
A time encapsulation reaction was performed. After completion of the reaction, the mixture was poured into 2 liters of ion-exchanged water, and the capsule particles were separated by centrifugation. This operation was repeated 7 times to wash the capsule particles. 100 parts of capsules of the capsule slurry thus obtained were treated with surface-treated silica (RA2
00H: manufactured by Nippon Aerosil Co., Ltd.) was added in an amount of 0.5 part, thoroughly mixed, poured into a stainless steel vat and dried in a freeze dryer for 24 hours to obtain a capsule toner. At this time, the geometric standard deviation (GSD) of the toner was 1.3. Next, 3 parts of this capsule toner and iron powder carrier 97
The parts were mixed in an environment of a temperature of 20 ° C. and a humidity of 50%, and a copy sample was obtained with a copying machine (2700 manufactured by Fuji Xerox Co., Ltd. modified for capsule toner). The image density of the solid image was 1.5 when measured with a Macbeth densitometer.

Comparative Example 2 As in Example 2, except that piperidine ethyl methacrylate-lauryl methacrylate-styrene copolymer was replaced by only polylauryl methacrylate, and 0.5% of a surfactant aerosol OT was added. Pigment dispersion was carried out. When a part of the dispersion liquid was taken out and observed with an optical microscope, pigment particles of 1 μm or more were hardly found, and most of the pigments were dispersed in submicrons. Then, an encapsulation reaction was carried out in the same manner as in Example 2, followed by washing and drying to obtain a comparative capsule toner. At this time, the geometric standard deviation (GSD) of the toner was 1.6, and the flow rate distribution was wide and the fluidity was poor. This was mixed with an iron powder carrier in the same manner as in Example 2, and a copy sample was obtained by modifying 2700 manufactured by Fuji Xerox Co. for capsule toner. This copy sample did not produce a satisfactory image because of poor charging.
When this image density was measured with a Macbeth densitometer, it was 0.2.
The concentration was very low.

[0032]

EFFECTS OF THE INVENTION The capsule toner of the present invention is configured such that one component of the core substance in the capsule particles contains the above-mentioned specific amino group-containing or nitrogen-containing heterocyclic group-containing copolymer. Finely dispersed. Further, the organic photoreceptor is not deteriorated, the fixing property is good, and the particle size distribution is narrow, so that the good charging property can be obtained. Therefore, a copy image with high image density can be obtained.

Claims (4)

[Claims] 1. A capsule toner comprising a core substance and a shell substance coating the core substance, wherein the core substance is represented by a monomer represented by the following general formula (I) and a general formula (II) below. A capsule toner containing a copolymer containing at least a monomer and / or a monomer represented by the general formula (III) as a monomer component. [Chemical 1] (In the formula, R, R ′, and R ″ each represent a hydrogen atom or a methyl group, r and t each represent an integer of 1 to 6, and p and q each represent an integer of 1 to 3; (R ₁ represents an alkyl group of 8 to 18, Y represents an oxygen atom or —NH—, and Z represents an atomic group forming a heterocycle with a nitrogen atom.) 2. The encapsulated toner according to claim 1, wherein the shell material is composed of either one or both of a polyurea resin and a polyurethane resin, or one or both of an epoxy urea resin and an epoxy urethane resin. . 3. The core substance is at least the compound represented by the general formula (I).
The encapsulated toner according to claim 1, further comprising a homopolymer or a copolymer containing a monomer represented by the formula (1) as a monomer component. 4. The encapsulated toner according to claim 1, wherein the core substance contains a hydrocarbon solvent.