WO2001059526A1 - Toner pour le developpement d'images electrostatique et son procede de production - Google Patents
Toner pour le developpement d'images electrostatique et son procede de production Download PDFInfo
- Publication number
- WO2001059526A1 WO2001059526A1 PCT/JP2001/000974 JP0100974W WO0159526A1 WO 2001059526 A1 WO2001059526 A1 WO 2001059526A1 JP 0100974 W JP0100974 W JP 0100974W WO 0159526 A1 WO0159526 A1 WO 0159526A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- toner
- charge control
- monomer
- control resin
- glass transition
- Prior art date
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- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/087—Binders for toner particles
- G03G9/08784—Macromolecular material not specially provided for in a single one of groups G03G9/08702 - G03G9/08775
- G03G9/08797—Macromolecular material not specially provided for in a single one of groups G03G9/08702 - G03G9/08775 characterised by their physical properties, e.g. viscosity, solubility, melting temperature, softening temperature, glass transition temperature
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/097—Plasticisers; Charge controlling agents
- G03G9/09733—Organic compounds
- G03G9/09741—Organic compounds cationic
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/097—Plasticisers; Charge controlling agents
- G03G9/09733—Organic compounds
- G03G9/0975—Organic compounds anionic
Definitions
- the present invention relates to an electrostatic image developing toner for developing an electrostatic image formed by an electrophotographic method, an electrostatic recording method, or the like, and a method for producing the same.
- an electrostatic image formed in an image forming apparatus such as an electrophotographic apparatus and an electrostatic recording apparatus is first formed by a toner for developing an electrostatic image (hereinafter sometimes simply referred to as toner).
- the developed and then formed toner image is transferred onto a transfer material such as paper or OHP phenol, and then fixed by various methods such as heating and pressurized solvent vapor.
- the toner for developing an electrostatic image is composed of colored polymer particles (colored resin particles) containing a binder resin and a colorant.
- the method for producing the toner for developing an electrostatic image is roughly classified into a pulverization method and a polymerization method.
- a colorant, a charge control agent, a release agent, and the like are melt-mixed in a thermoplastic resin, uniformly dispersed to form a composition, and then the composition is pulverized and classified.
- Manufactures toner are used in the pulverization method.
- a monomer composition obtained by uniformly dissolving or dispersing a polymerizable monomer, a colorant, a charge controlling agent, a release agent, and the like is converted into water containing a dispersion stabilizer or water as a main component. Then, the mixture is stirred until the particle diameter of the droplets becomes constant, a polymerization initiator is added thereto, and the mixture is dispersed using a mixing device having a high shearing force. After granulating the monomer composition as fine droplets, polymerization, filtration, washing, dehydration, and drying The toner is manufactured by drying. According to the polymerization method, a toner having a desired particle size and a sharp particle size distribution can be obtained without performing pulverization or classification.
- a process that consumes energy is a so-called fixing process in which toner is transferred from a photoconductor onto a transfer material and then fixed.
- a heat roll of 150 ° C or higher is used for fixing, and electricity is used as the energy source. Reducing the temperature of the hot roll is effective from the viewpoint of energy saving.
- the glass transition temperature of the binder resin may be lowered.
- the toner causes blocking in the toner box or in the toner box, forming an aggregate, which is a so-called poorly preserved toner.
- Japanese Patent Application Laid-Open No. 59-62871 proposes a method for producing a positively chargeable polymerized toner using a polymerizable monomer and a Nig Mouth syn dye as a charge control agent. I have. However, although a small amount of Nig Mouth Shin Dye has excellent charge control properties, its black color makes it unsuitable for color toners.
- Japanese Patent Application Laid-Open No. 59-128382 discloses a method of suspension polymerizing a polymerizable monomer and a cationic polymer in an anionic dispersant.
- Japanese Patent Application Laid-Open No. 63-60458 discloses a toner obtained by a pulverization method using a charge control resin comprising a quaternary ammonium salt group-containing copolymer.
- No. 56 and WO 99/47982 disclose a polymerization method in which a colorant and a polymerizable monomer are polymerized in the presence of a quaternary ammonium base-containing copolymer. A method for producing a toner has been proposed.
- the charge control resins (cationic polymers) specifically described in these publications have a high styrene content.
- the toner using a resin having a styrene content of 80% by weight or more as a charge control resin was found to have poor fixing and printing due to high-speed continuous printing. It has been found that deterioration of the steel occurs. Disclosure of the invention An object of the present invention is to provide a toner for developing an electrostatic image, which is excellent in charge stability, has good durability, has low environmental dependency, and has a good dispersion of a colorant, and a method for producing the same.
- Another object of the present invention is to provide a toner for developing an electrostatic image, which is suitable as a color toner, has a low fixing temperature, has a good balance between preservability and fixability, can cope with high-speed printing, and a method for producing the same. To provide.
- a vinyl monomer unit and a (meth) acrylate monomer unit containing a quaternary ammonium base are included.
- the above object can be achieved by using a copolymer having a glass transition temperature (hereinafter sometimes referred to as Tg) of 40 to 75 ° C as a charge control resin. I found that.
- the charge control resin is composed of a vinyl monomer unit and a quaternary ammonium.
- a toner for developing an electrostatic image comprising a copolymer comprising a base-containing (meta) acrylate monomer unit and having a glass transition temperature of 40 to 75 ° C.
- a monomer composition containing at least a polymerizable monomer, a colorant and a charge control resin is suspended in an aqueous dispersion medium containing a dispersion stabilizer.
- a method for producing a toner for developing an electrostatic image wherein the toner is polymerized by using an initiator, wherein the charge control resin contains a vinyl monomer unit and a quaternary ammonium base (meta) acrylate.
- a method for producing a toner for developing an electrostatic image is provided, which is a copolymer composed of monomer units and has a glass transition temperature of 40 to 75 ° C.
- a core particle is obtained by suspending the composition and polymerizing using a polymerization initiator, and then, in the presence of the core particle, a polymer formed by the polymerizable monomer.
- a copolymer consisting of a vinyl monomer unit and a quaternary ammonium base-containing (meth) acrylate monomer unit, and having a glass transition temperature of 40 to 75 ° C.
- the present invention provides a method for producing a toner for developing an electrostatic image, characterized by the following. BEST MODE FOR CARRYING OUT THE INVENTION
- the toner for developing an electrostatic image of the present invention comprises a (meth) acrylate unit containing at least a vinyl monomer unit and a quaternary ammonium base as a binder resin, a colorant and a charge control resin.
- a copolymer consisting of body units Further, it may contain a release agent or a magnetic material, and may contain other additives as necessary.
- the volume average particle diameter of the toner for developing an electrostatic image of the present invention is generally 2 to 10 / m, preferably 2 to 9 ⁇ , more preferably 3 to 8 ⁇ .
- the volume average particle diameter (dv) / number average particle diameter (dp) is usually 1.7 or less, preferably 1.5 or less, and more preferably 1.3 or less.
- the toner for developing an electrostatic image of the present invention is preferably a core-shell toner having two different polymers inside (core waste) and outside (shell layer) of the toner particles.
- a low-temperature fixing temperature is reduced by encapsulating a polymer having a low glass transition temperature that forms the core layer in a shell layer of a polymer having a higher glass transition temperature. It can balance with the prevention of aggregation during storage. Further, an external additive can be added to the electrostatic image developing toner of the present invention.
- a copolymer comprising a butyl monomer unit and a quaternary ammonium base-containing (meta) acrylate monomer unit is used.
- a charge control resin having a glass transition temperature of 40 to 75 ° C is used.
- the amount of the charge control resin used is usually 0.01 to 5 parts by weight of L, preferably 0.5 to 10 parts by weight, based on 100 parts by weight of the binder resin. If the amount of the charge control resin is small, it is difficult to obtain sufficient chargeability. Conversely, if the amount is large, it tends to cause problems such as increased environmental dependence of image quality, occurrence of offset, and contamination of the photoconductor. It becomes bad.
- the vinyl monomer unit constituting the charge control resin used in the present invention is a repeating unit obtained by a polymerization reaction of a vinyl monomer, and is a typical example of a vinyl monomer.
- Examples include vinyl aromatic hydrocarbon monomers and (meth) acrylate monomers.
- the (meth) acrylate monomer examples include methyl acetyl olenoate, ethyl acrylate, propyl acrylate, and isopropyl acrylate.
- ⁇ -acrylic acid — butyl isoptyl atalinoleate, ⁇ -acrylonitrile ⁇ — amyl, iso-amino acrylate, ⁇ -acrylic acid
- Acrylinoleic acid esters such as xyl, acetic olenoic acid 2-ethylhexynole, hydroxypropyl acrylate, and lauric acrylate; Chinole, ethyl methacrylate, propynole methacrylate, isopropinolate methacrylate, ⁇ -butyl methacrylate, isobutyl methacrylate, isopropyl methacrylate
- Metallinoleic acid ⁇ - ⁇ Millimetric acid isoamyl
- the charge control resin according to the present invention desirably has both a structural unit derived from a vinyl aromatic hydrocarbon compound and a structural unit derived from a (meth) acrylate compound. ) Is usually 70: 30 to 90: 10, preferably 75: 25 to 88: 12. Within this range, it is easy and preferable to obtain the desired T g.
- the quaternary ammonium base-containing (meta) acrylate monomer unit constituting the charge control resin used in the present invention is, for example, a repeating unit represented by the formula (A).
- R 1 is a hydrogen atom or a methyl group
- R 2 is an alkylene group having 1 to 3 carbon atoms
- R 3 to R 5 are each independently a carbon atom.
- X is a nitrogen group, an alkyl sulfonic acid group having 1 to 6 carbon atoms, or a benzene sulfonate group.
- the content of the quaternary ammonium base-containing (meta) acrylate monomer unit in the charge control resin is usually 0.05 to 12% by weight, preferably 0.1 to 10% by weight. %. Within this range, it is easy to control the charge amount. In addition, there is little effect on image quality due to environmental changes. If this is too high, the charge amount becomes too high, which may cause fogging, which is not preferable.
- the content of the quaternary ammonium base-containing (meta) acrylate monomer unit can be calculated based on the charged ratio of each monomer in the polymerization reaction. If the conditions during polymerization are not known, it can be measured by instrumental analysis such as 1 H-NMR spectrum and IR spectrum. ⁇
- the glass transition temperature of the charge control resin is from 40 to 75 ° C, preferably from 40 to 70 ° C.
- T g is lower than 40 ° C., it will be easy to feed from the binder resin at the time of melt cooling, and the storage stability and fluidity will decrease. On the other hand, if the T g is too high, the fixability will decrease.
- the difference between the Tg of the binder resin component described later and the Tg of the charge control resin is 0 to 20 ° C, preferably 0 to 15 ° C.
- T g is a value measured by a differential calorimeter (DSC) because the balance between the properties and the fluidity is excellent and stable printing quality is provided.
- DSC differential calorimeter
- polystyrene Monodisperse polystyrene-equivalent weight-average molecular weight (hereinafter, referred to as “polystyrene”) measured by gel permeation chromatography (GPC) using tetrahydrofuran as the charge control resin.
- M w Monodisperse polystyrene-equivalent weight-average molecular weight measured by gel permeation chromatography (GPC) using tetrahydrofuran as the charge control resin.
- M w Monodisperse polystyrene-equivalent weight-average molecular weight
- M w) the lower limit is usually at least 2,000, preferably at least 10,000, more preferably at least 17,000, especially It is preferably 200,000
- the upper limit is usually 40,000 or less, preferably 35,000 or less, more preferably 30,000 or less, especially It is preferably 28,000. If the weight average molecular weight is too large, the handling during the production of the toner particles is poor, and the size of the
- the charge control resin used in the present invention is produced by the following method. 1 bi
- the copolymer obtained in (2) (1) was obtained by copolymerizing a monomeric monomer and a quaternary ammonium base-containing (meta) acrylate monomer. By reacting with p-toluenesulfonic acid or methanesulfonic acid, etc., (3) the copolymer is obtained by copolymerizing a butyl monomer with a dianolekylaminoalkyl (meth) acrylate monomer.
- the obtained copolymer can be introduced by quaternizing with a quaternizing agent such as methyl paratoluenesulfonate or methyl methanesulfonate.
- Examples of the (meth) acrylate monomer containing a quaternary ammonium base used in the method (1) or (2) include N, N, N—trimethyl-N— (2 — Metal chloride, ammonium chloride (DMC: dimethinourea methyl chloride), N—N-N, N— Dimethyl-N- (2-methacryloyloxyethyl) ammonium chloride (DML: dimethinorea methinobenbenzyl chloride methacrylate) and the like.
- the quaternary ammonium salt-containing (meta) acrylate is used to convert an amino group-containing (meta) acrylate into a quaternary compound such as a halogenated organic compound or an acid esterifying agent. It can also be obtained by forming a quaternary ammonia with an agent.
- the dialkylaminoalkyl (meta) acrylate monomers used in the method (3) include dimethylaminoethyl (meta) acrylate, and methylaminoethyl (meta). Atalylate, dipropylmethylaminoethyl (meta) acrylate, dibutylaminoethyl (meta) acrylate, and the like.
- Examples of the quaternizing agent include halogenated organic compounds such as methyl chloride, methyl bromide, ethyl chloride, ethyl bromide, benzyl chloride, and benzyl chloride; methyl sulfone; Alkyl acid esters, ethynoles olenoate olenoate, propinoles oleno olenoate olenoate olenoate, benzens olenole olenoate olenole estenorate, ⁇ ⁇ .
- Anolequinol esters of sulfonates such as lactone olenoquinolenes tenorenol.
- the polymerization method for obtaining the charge control resin used in the present invention may be any method such as emulsion polymerization, dispersion polymerization, suspension polymerization, and solution polymerization. Solution polymerization is particularly preferred because of its availability.
- organic solvent When polymerizing by solution polymerization, an organic solvent is required.
- the organic solvent include common solvents such as hydrocarbon solvents, alcohol solvents, ketone solvents, ester solvents, amide solvents, ether solvents, and carbon chloride solvents. Can be used. One or more of these can be used in combination.
- the polymerization temperature and the polymerization time can be arbitrarily selected depending on the polymerization method and the type of the polymerization initiator used, but are usually about 50 to 200 ° C, and the polymerization time is 0.5 to 200 ° C. It is about 20 hours. Further, in the polymerization, a commonly known additive, for example, a polymerization aid such as amine can be used in combination.After the solution polymerization, the solution may be used as it is to obtain toner particles, or may be used for polymerization. The copolymer may be separated and used after adding the solution to the poor solvent, removing the solvent with steam, or removing the solvent under reduced pressure.
- Resins such as polystyrene, poly-p-chlorostyrene, and poly (vinyl toluene), and polymers of styrene and its substitutes; polystyrene-p-chloro-styrene Copolymer, styrene-propylene copolymer, styrene-vinylinole toluene copolymer, styrene-vinylinolephthalene copolymer, styrene-methyl acrylate copolymer, styrene Ethylene acrylate copolymer, styrene-butyl acrylate copolymer, styrene-octyl acrylate copolymer, styrene-methyl methacrylate Copolymer, styrene-ethyl meth
- any pigments, pigments, or dyes can be used, in addition to carbon black and titanium white. It is preferable to use a black carbon black having a primary particle size of 20 to 40 nm. If the primary particle size is small, dispersion of carbon black cannot be obtained and The use of a carbon black having a large primary particle size leads to an increase in the amount of the polyvalent aromatic hydrocarbon compound, thereby deteriorating environmental safety. Sometimes.
- pigments and dyes such as yellow colorant, magenta colorant and cyan colorant are usually used. By combining these, a full-color image can be obtained.
- yellow colorant compounds such as azo pigments and condensed polycyclic pigments are used. Specifically, C.I.
- magenta colorant compounds such as azo pigments and condensed polycyclic pigments are used.
- cyanine colorant a copper phthalocyanine compound and its derivative anthraquinone compound can be used. Specifically, C.I.igmentation blue 2,3,6,15,15: 1,15: 2,15: 3,15:
- the amount of the colorant to be used is 1 to 10 parts by weight based on 100 parts by weight of the binder resin or the polymerizable monomer.
- a release agent can be contained in the electrostatic image developing toner.
- the release agent include low-molecular-weight polyols such as low-molecular-weight polystyrene, low-molecular-weight polypropylene, and low-molecular-weight polybutylene.
- Refin waxes oxidized low-molecular-weight polypropylene with molecular ends, low-molecular-weight terminal-modified polypropylene with the molecular end substituted by an epoxy group, and these and low-molecular-weight polyethylene Terminals such as block polymers of low molecular weight oxidized low molecular weight polyethylene, low molecular weight polyethylene whose molecular terminals are substituted with epoxy groups, and block polymers of these and low molecular weight polypropylene.
- Denatured polyrefin waxes candelilla, carnauba, plant-based natural waxes such as rice, wood roe, jojoba, etc .; paraffin, microcrystalline , Petrolactam and other petroleum waxes and their modified waxes; minerals such as montane, seresin, ozokerite, etc .; fisher tropsch Wa Synthetic waxes such as grease; Penta Eristrete-Lute Trimiri State, Penta Erythrite Tolette. Multifunctional esters such as penta erythritol, such as noremitate, and dipentaerythritol ester, such as tramiristate And the like. These are used alone or in combination of two or more.
- the endothermic peak temperature at the time of temperature rise is from 30 to 200, preferably from 50 to: 18 0 ° C, 60 to: Pentaethyl ester in the range of 160 ° C, and the endothermic peak temperature is 50 to 80.
- Polyhydric ester compounds such as dipentaerythritol monoester in the range of C are particularly preferable in terms of balance between fixing and peeling as a toner.
- dipentae having a molecular weight of 1000 or more, dissolving at least 5 parts by weight at 100 ° C. of styrene at 25 ° C., and an acid value of 1 O mg ZK ⁇ H or less.
- Lithritol ester reduces fixing temperature Shows significant effect.
- the endothermic peak temperature is a value measured according to ASTMD 314-82.
- the release agent is used in an amount of 0.1 to 20 parts by weight, preferably 1 to 15 parts by weight, based on 100 parts by weight of the binder resin or the polymerizable monomer.
- the colored fine particles may contain a magnetic material.
- Materials used in this case are magnetite, ⁇ -iron oxide such as iron oxide, ferrite, iron-rich ferrite; metals such as iron, cobalt, nickel or these metals Alloys with metals such as aluminum, cobalt, copper, lead, magnesium, tin, zinc, antimony, beryllium, bismuth, cadmium, calcium manganese, selenium, titanium, tungsten, vanadium And mixtures thereof.
- the above-mentioned charge control resin is used as an essential component as a charge control agent, and if necessary, a commonly used charge control agent may be used in combination. it can.
- Examples of such a charge control agent include Bontron 01 (manufactured by Orient Chemical), Nigguchi Shinbase X (manufactured by Orient Chemical), and Bont No. And positive charge control agents such as BONTRON-53 (manufactured by Orient Chemical Co.).
- charge control agents account for 20 weight of the charge control resin. Can be used at a ratio of / 0 or less. If necessary, a charge control agent having negative chargeability may be used in combination to control the chargeability.
- the volume average particle size of the core particles is usually 2 to 10 ⁇ m, preferably 2 to 9 ⁇ , more preferably 3 to 8 / xm.
- the volume average particle diameter (dv) and the Z number average particle diameter (dp) are usually 1.7 or less, preferably 1.5 or less, and more preferably 1.3 or less.
- the weight ratio of the core layer to the shell layer is usually 80/20 to 99.9 / 0.1 (weight ratio).
- weight ratio of the shell layer When the weight ratio of the shell layer is small, the effect of improving the storage stability is small, and when it is large, the effect of improving the reduction of the fixing temperature is small.
- the average thickness of the shell layer is usually 0.001 to 1.0 / xm, preferably 0.003 to 0.5 / im, more preferably 0.05 to 0.5 / im. 2 m.
- the thickness is large, the fixing property is reduced, and when the thickness is small, the storability is reduced. In the present invention, it is not necessary that the entire core layer of the core-shell toner is covered with the shell layer.
- the core particle diameter and shell layer thickness of the core-shell toner can be observed with an electron microscope, the particle size and shell layer thickness selected at random from the observation photograph are directly measured. However, if it is difficult to observe the core and the shell with an electron microscope, the particle size of the core particles and the monomer used to form the shell layer used in the production of the toner may be reduced. It can be calculated from the quantity.
- the external additive has a function of improving the fluidity of the toner particles (fluidity improver).
- the external additive controls the chargeability of the toner, and imparts abrasiveness to the toner to the photoconductor. It plays a multifunctional role such as preventing the occurrence of toner filming.
- Examples of the external additive that can be used in the present invention include inorganic particles and organic resin particles.
- the inorganic particles include silicon dioxide, aluminum oxide, titanium oxide, zinc oxide, tin oxide, barium titanate, and titanic acid. Strontium and the like.
- Examples of the organic resin particles include metal methacrylate polymer particles, methacrylic acid ester polymer particles, styrene-methacrylic acid ester copolymer particles, and styrene copolymers. Examples thereof include ester lylic acid copolymer particles, and core-shell type particles in which the core is a styrene polymer and the shell is a methacrylic acid ester copolymer.
- inorganic oxide particles particularly silicon dioxide particles
- the surface of these particles can be subjected to a hydrophobic treatment, and hydrophobically treated silicon dioxide particles are particularly preferable.
- the amount of the external additive is not particularly limited, but is usually 0.1 to 6 parts by weight based on 100 parts by weight of the toner particles.
- Two or more external additives may be used in combination.
- an external additive is used in combination, a method of combining two types of inorganic oxide particles or organic resin particles having different average particle diameters is preferable.
- the particles usually have an average particle size of 5 to 20 nm, preferably 7 to 18 nm (preferably inorganic oxide particles), and the average particle size of 201 1 111 to 2 m, preferably Is 3 0 ⁇ ⁇ ! It is preferable to attach particles of up to 1 ⁇ (preferably inorganic oxide particles) in combination.
- the average particle size of the particles for the external additive is an average value obtained by observing the particles with a transmission electron microscope, randomly selecting 100 particles, and measuring the particle size.
- the amount of the two kinds of external additives is preferably 0.1 to 3 parts by weight of particles having an average particle diameter of 5 to 20 nm with respect to 100 parts by weight of toner particles.
- Particles having an average particle diameter of 20: 1111 to 2111 are usually 0.1 to 3 parts by weight, preferably 0.2 to 2 parts by weight.
- the weight ratio to particles of 2 ⁇ is usually in the range of 1: 5 to 5: 1, preferably in the range of 3:10 to: 10: 3.
- the attachment of the external additive is usually carried out by stirring the external additive and the toner particles in a mixer such as a hen-shell mixer.
- the electrostatic image developing toner of the present invention may be produced by any of a pulverization method and a polymerization method.
- the pulverization method The toner is prepared by blending a formulation such as a binder resin, a colorant, the charge control resin, and a release agent, and mixing them using a mixer such as a henshell.
- the compound is melted and kneaded using a kneader such as a two-roller, twin-screw extruder or a press kneader heated to 100 to 200 ° C.
- the kneaded mixture is cooled, pulverized and classified to obtain a toner having a target particle size.
- 3 2. Polymerization toner
- the toner can be produced by a suspension polymerization method, an emulsion polymerization method, or a dispersion polymerization method, but it does not use an organic solvent, does not use an emulsifier, and has a spherical toner shape.
- the suspension polymerization method is preferred because of its advantages.
- a monomer composition containing at least a polymerizable monomer, a colorant and a charge control agent is suspended in an aqueous dispersion medium containing a dispersion stabilizer, and a polymerization initiator is added. It can be manufactured by polymerizing using.
- a monomer prepared by uniformly dispersing toner raw materials such as a colorant, a charge control agent, a release agent, and other additives in a polymerizable monomer using a mixing and dispersing machine such as a bead mill.
- a body composition is prepared.
- the monomer composition is put into an aqueous dispersion medium containing a dispersion stabilizer, and the mixture is stirred until the droplets are stabilized.
- an oil-soluble polymerization initiator is added, and a high-speed rotary stirrer is further added.
- An aqueous dispersion was obtained by granulating the droplets until the droplets became the size of the toner, and the obtained aqueous dispersion was heated to a predetermined polymerization temperature in a reactor equipped with stirring blades. Polymerizes.
- a monovinyl monomer is usually used as the polymerizable monomer.
- styrene-based monomers such as styrene, butyrulene, ⁇ -methylstyrene, etc .
- acrylic acid, methacrylic acid methynole acrylate Ethinole atelinoleate, propinole atelinolenate, petitinole atelinoleate, 2-acrylinoleate hexinoleate, cyclohexyl acrylateinoleate, isoboninole atelinoleate, methacrylate Cyclohexyl oleate, isobonyl methacrylate, dimethylaminoethyl acrylate, methinolate methacrylate, ethinole methacrylate, methacrylate Propinole oleate, activistole methacrylate, Methacrylic acid 2-ethylhexyl acryl
- Monovinyl monomers may be used alone or in combination of a plurality of monomers. Of these monovinyl monomers, styrene monomers, or a combination of a styrene monomer with acrylolenic acid or a derivative of methacrylate acid, may be used. It is preferably used.
- the crosslinkable monomer is a monomer having two or more polymerizable carbon-carbon unsaturated double bonds.
- Specific examples of the crosslinkable monomer include aromatic divinyl conjugates such as divinyl benzene, divinyl naphthalene, and derivatives thereof; ethylene glycol dimethacrylate, and diethyl alcohol. Diethylenically unsaturated carboxylic acid esters such as lenglycol dimethacrylate; N, N—divinylaniline, divinyl ether and other divier compounds having two vinylinole groups; pentaerythryl Compounds having three or more vinyl groups, such as tall triaryl ether and trimethylol pronontriacrylate, can be mentioned.
- the crosslinkable polymer is a polymer having two or more vinyl groups in the polymer, and specifically, a polymer having two or more hydroxyl groups in the molecule (a hydroxyl group-containing polymer).
- crosslinkable monomers and crosslinkable polymers can be used alone or in combination of two or more.
- the amount to be used is usually 100 parts by weight or less, preferably 0.1 to 2 parts by weight, per 100 parts by weight of the polymerizable monomer.
- a macromonomer together with the polymerizable monomer in order to improve the balance between toner preservability and fixability.
- which have a vinyl polymerizable functional group at the terminal usually have an average molecular weight of 1,000 to 300,000. Or polymer. If the number average molecular weight is small, the surface portion of the polymer particles becomes soft and the storage stability is reduced. Conversely, if the number average molecular weight is large, the polymer particles become The melt viscosity of the monomer increases, and the fixability decreases.
- the macromolecule used in the present invention preferably has a glass transition temperature higher than the glass transition temperature of a polymer obtained by polymerizing a polymerizable monomer.
- hydrophilic ones in particular, polymers obtained by polymerizing methacrylate esters or atalinoleate esters alone or in combination thereof, are described in the present invention. It is suitable for the invention.
- the amount of the macromonomer used is usually 0.01 to 10 parts by weight, preferably 0.03 to 5 parts by weight, and more preferably 0.01 to 5 parts by weight, based on 100 parts by weight of the polymerizable monomer. It is preferably 0.05 to 1 part by weight. If the amount of the macromonomer is small, the preservability decreases. The greater the amount of mac-mouth monomer, the lower the fixability.
- Such a polymerizable monomer and a cross-linkable compound (a macromolecule) are polymerized to form a binder resin. .
- dispersion stabilizer examples include sulfates such as barium sulfate and calcium sulfate; carbonates such as barium carbonate, calcium carbonate and magnesium carbonate; Phosphates such as calcium acid; metal oxides such as aluminum oxide and titanium oxide; metal compounds such as aluminum hydroxide, aluminum hydroxide, magnesium hydroxide, ferric hydroxide, etc.
- metal compounds especially difficult water Dispersion stabilizers containing soluble metal hydroxide colloids are preferred because they can narrow the particle size distribution of the polymer particles and improve image clarity.
- the dispersion stabilizer containing the colloid of a poorly water-soluble metal hydroxide is not limited by its manufacturing method, but can be obtained by adjusting the pH of an aqueous solution of a water-soluble polyvalent metal compound to 7 or more.
- the reaction ratio between the water-soluble polyvalent metal salt and the metal hydroxide is the chemical equivalent ratio A of the water-soluble polyvalent metal salt to the water-soluble multivalent metal salt, where A ⁇ 0.4 ⁇ A ⁇ 1.0. Range.
- the colloid of the poorly water-soluble metal compound has a number particle size distribution D50 (50% cumulative value of the number particle size distribution) of 0.5 / xm or less and a D90 (number particle size distribution of 90%).
- D50 50% cumulative value of the number particle size distribution
- D90 number particle size distribution of 90%
- the dispersion stabilizer is usually used in an amount of 0.1 to 100 parts by weight of the polymerizable monomer. Used in a proportion of up to 20 parts by weight. If this ratio is too low, it is difficult to obtain sufficient droplet dispersion stability of the polymerizable monomer composition, and an aggregate of polymer particles tends to be formed. Conversely, if this ratio is too high, the viscosity in the aqueous dispersion medium will increase, and the distribution of the polymerized toner particle diameter will be broadened, so that the yield will decrease.
- polymerization initiator used in the production by the polymerization method examples include persulfates such as potassium persulfate and ammonium persulfate; 4,4′-azobis (41-cyanovaleric acid); '—Azobis (2-amidinopropane) dihydrochloride, 2, 2 '-azobis-1-methinolay N-1, 1-bis (hydroxymethyl)-1-2-hydroxicetylpropioamide, 2, 2'-azobis (2, 4-dimethyl) Azo compounds such as tinoreno relonitrile), 2,2'-azobisuisoptironitrile, 1,1'-azobis (1-cyclohexanecarbonitrile); methyl Ethyl peroxide, di-tert-butyl peroxide, acetyl peroxide, dicumyl peroxide, lauroy norepoxide, benzoy oleperoxide, t—petit peroxyl 2—ethynolehexanoe 1-t-
- an oil-soluble polymerization initiator that is soluble in the polymerizable monomer to be used, and if necessary, a water-soluble polymerization initiator is used in combination therewith. You can do that too.
- the polymerization initiator is used in an amount of from 0.3 to 20 parts by weight, preferably from 0.3 to 15 parts by weight, more preferably from 0.3 to 15 parts by weight, based on 100 parts by weight of the polymerizable monomer. Use 5 to 10 parts by weight.
- the polymerization initiator can be added in advance to the polymerizable monomer composition, but in some cases, can be added to the suspension after the completion of the granulation step.
- a molecular weight modifier can be used.
- the molecular weight regulator include t-dodecyl menoleca butane, n-dodecyl Mercaptans such as mercaptan and n-octyl mercaptan; halogenated hydrocarbons such as carbon tetrachloride and carbon tetrabromide; and the like.
- These molecular weight modifiers can be added before the start of the polymerization or during the polymerization.
- the molecular weight modifier is used in an amount of usually from 0.01 to 10 parts by weight, preferably from 0.1 to 5 parts by weight, based on 100 parts by weight of the monomer. '
- the toner for developing an electrostatic image of the present invention is not particularly limited by its manufacturing method, it contains at least a polymerizable monomer, a colorant and a charge control agent in an aqueous dispersion medium containing a dispersion stabilizer.
- the monomer composition is suspended and polymerized using a polymerization initiator to obtain core particles, and then formed by the polymerizable monomer in the presence of the core particles.
- a monomer for a shell that forms a polymer having a glass transition temperature higher than the glass transition temperature of the polymer to be polymerized, and a polymerization initiator are added to form a core-shell type toner for electrostatic image development. It is preferable to manufacture them.
- a method of adding a monomer for shell to the reaction system of the polymerization reaction performed to obtain the core particles and continuously polymerizing, or another reaction system A method in which the core particles obtained in step (1) are charged, a monomer for shell is added thereto, and polymerization is performed stepwise.
- the shell monomer may be added all at once to the reaction system, or may be added continuously or intermittently using a pump such as a plunger pump.
- Examples of the core monomer may be the same as the above-mentioned polymerizable monomers. Among them, those capable of forming a polymer having a glass transition temperature of usually 60 ° C or lower, preferably 40 to 60 ° C, are suitable as the core monomer. It is. If the glass transition temperature is too high, the fixing temperature increases, and if the glass transition temperature is too low, the storage stability decreases. Usually, the core monomer is often used alone or in combination of two or more.
- the glass transition temperature (T g) of the polymer is a calculated value (calculated T g) calculated by the following equation according to the type and the proportion of the monomer used.
- T g Glass transition temperature of copolymer (absolute temperature)
- T l, ⁇ 2, ⁇ 3 Glass transition temperature (absolute temperature) of homopolymer composed of each monomer constituting the copolymer
- the monomer for the shell must be set so that the glass transition temperature of the polymer obtained from the monomer is at least higher than the glass transition temperature of the polymer constituting the core particles. is there.
- the glass transition temperature of the polymer obtained from the shell monomer is usually 50 to 120, preferably 60 to 1, in order to improve the storage stability of the polymerized toner. It is 10 ° C, more preferably 80 to 105 ° C.
- the difference between the glass transition temperature of the polymer composed of the core monomer and the polymer composed of the shell monomer is usually 10 ° C. or more, preferably 20 ° C. or more, more preferably 30 ° C or higher.
- a water-soluble radiator is used as a polymerization initiator. It is preferable to add a calcium initiator because it makes it easier to obtain a core-shell type toner. If a water-soluble radical initiator is added during the addition of the shell monomer, the water-soluble radical initiator enters the vicinity of the outer surface of the core particle to which the shell monomer has migrated, and the water-soluble radical initiator is superposed on the core particle surface. It is thought that coalescence (shell) is likely to be formed.
- water-soluble radical initiator examples include persulfates such as potassium persulfate and ammonium persulfate; 4,4′-azobis (4-cyanovaleric acid), 2,2′-azobis (2_amido) Dinopropane) dihydrochloride, 2, 2'-azobis-1-2-methyl-N_l, 1-bis (hydroxymethyl) 1-2-hydrazoshetyl Pro-azoamide, etc. Agents; and the like.
- the amount of the water-soluble radical initiator is usually 0.001-1% by weight based on the aqueous medium. / 0 .
- the volume average particle size (dV) and the particle size distribution of the polymer particles, that is, the ratio (dv / dp) between the volume average particle size and the average particle size (dp), are determined by the Multisizer One (Beckman Coulter, Inc.). Was measured. The measurement by this multisizer is as follows: aperture diameter: 100 ⁇ m, medium-isoton ⁇ , concentration The measurement was performed under the following conditions: 100%, number of particles measured: 100,000.
- the shell is thick, it can be measured with a multisizer or an electron microscope.However, in the case of this embodiment where the shell is thin, the calculation is performed using the following equation.
- r radius of core particle size before adding shell monomer (volume particle size of multisizer: ⁇ m)
- the density P (g / cm 3 ) of the shell resin was set to 1.0.
- a commercially available non-magnetic one-component developing printer (12-sheet printer) was modified to change the temperature of the fixing roll. Continuous printing is performed from the beginning in each environment (HZH), temperature of 10 ° C and humidity of 20% (LZL), and the print density is 1.3 with a reflection densitometer (Macbeth). Above, and whiteness meter
- ⁇ The number of continuous prints that can maintain the above image quality is 50,000 to 100,000.
- X The number of continuous prints that can maintain the above image quality is less than 50,000.
- ⁇ The number of continuous prints that can maintain the above image quality is 1500 to 2000.
- X The continuous print number that can maintain the above image quality is less than 1500.
- ® a (weight of toner remaining on 150 ⁇ sieve (g)) / 4 g X 100
- ® b (weight of toner remaining on 75 m sieve (g)) / 4 g Xl 00 X 0.6
- Liquidity (%) 100-(a + b + c)
- a fixing test was performed using the modified printer described above.
- the fixing test was performed by changing the temperature of the fixing roll of the modified printer, measuring the fixing rate of the toner at each temperature, and determining the relationship between the constant temperature and the fixing rate.
- the fixing rate was calculated from the ratio of the image density before and after the tape peeling operation in the black solid area of the test paper printed with the modified printer. That is, assuming that the image density before tape removal is before ID and the image density after tape removal is after ID, the fixing rate can be calculated from the following equation.
- Fixing rate (%) (after ID / before ID) X I 0 0
- the tape peeling operation is to apply an adhesive tape (Scout Mending Tape 8100-3-18) manufactured by Sumitomo Sleep Co., Ltd. to the measurement part of the test paper, and press it with a constant pressure to adhere it. Then, a series of operations to peel off the adhesive tape in the direction along the paper at a constant speed.
- the image density was measured using a reflection type image densitometer manufactured by McBeth.
- the fixing roll temperature corresponding to a fixing rate of 80% was defined as the fixing temperature of the toner.
- the polymerizable monomer composition is added to the magnesium hydroxide colloid dispersion obtained above, and the mixture is stirred until the droplets are stabilized. Then, the polymerization initiator t-butyl peroxyl is added thereto. After adding 6 parts of 2-ethylhexanoate, high-shear stirring was performed at 150,000 rpm for 30 minutes using an Ebara Milder (MDN303V type, manufactured by Ebara Corporation) at 30 rpm. Droplets of the monomer mixture were granulated. The aqueous dispersion of the granulated monomer mixture is put into a reactor equipped with a stirring blade, and the polymerization reaction is started at 90 ° C. After the polymerization was continued for 8 hours, the reaction was stopped to obtain an aqueous dispersion of polymer particles having a pH of 9.5.
- 100 parts of the toner particles obtained as described above were treated with hydrophobically treated silica having an average particle diameter of 8 nm (manufactured by WACKERCHEMIE, trade name).
- HV KH2150 Henschel mixer
- a charge control resin B having a Tg of 68 ° C. was produced.
- a positively chargeable toner was obtained in the same manner as in Example 1, except that this charge control resin B was used as the charge control resin.
- the obtained positively chargeable toner was evaluated, it had excellent fixability, preservability, and fluidity, and had good color tone, high image density, and capri under both high temperature and high humidity and low temperature and low humidity. An extremely good image without any was obtained. Table 1 shows the evaluation results. [Example 3]
- magnesium hydroxide colloid a poorly water-soluble metal hydroxide colloid
- the monomer composition for cores described above was added to the magnesium hydroxide colloid dispersion obtained above, and the mixture was added to the dispersion using Ebara Milder (MDN303V type, manufactured by Ebara Corporation). The mixture was subjected to high-shear stirring and mixing at a rotation speed of 5, OOO rpm for 30 minutes, uniformly dispersed, and granulated into droplets of the monomer composition for the core.
- Ebara Milder MDN303V type, manufactured by Ebara Corporation
- the granulated core monomer composition was put into a reactor equipped with a stirring blade, and the polymerization reaction was started at 90 ° C. When the polymerization conversion reached 95%, sampling was performed.
- T g 105 ° C
- the shell thickness calculated from the core particle size immediately before the addition of the shell monomer and the amount of the shell monomer was 0.02 ⁇ m, and the sphericity (r 1 / rs) was 1.1.
- hydrophobized colloidal silica (trade name “RX200” manufactured by Nippon Aerosil Co., Ltd.) was added.
- a positively charged capsule toner was prepared by mixing using a Henschel mixer.
- the fixing temperature of the positively-charged toner obtained above was measured at 120 ° C.
- the storage stability of this toner was as very good as 3%.
- the results are shown in Table 1. In other image evaluations, images with high image densities, no capri and glares, and extremely good resolution were obtained. Was. ⁇
- a charge control resin C of 000 was obtained.
- a toner having a positive charge was prepared and evaluated in the same manner as in Example 3 except that the charge control resin C was used as the charge control resin. Poor quality, lots of capri, and insufficient image in durability evaluation. The evaluation results are shown in Table 1 [Comparative Example 2] '
- This charge control resin E is used as the charge control resin, and the colorant is yellow pigment (trade name "tonery ollow H G", manufactured by Clariant).
- VP 2 1 5 5 Except for changing to 5 parts, a positively chargeable toner was prepared and evaluated in the same manner as in Example 3, and the fixability and the environmental dependency under high temperature and high humidity were evaluated. It was not enough. Table 1 shows the evaluation results.
- the toner for electrostatic charge image development which is excellent in charge stability and durability, and has little environmental dependency, and its manufacturing method are provided.
- a toner for developing an electrostatic image which is suitable as a color toner, has a low fixing temperature, has a good balance between storability and fixability, can cope with high-speed printing, and a method for producing the same.
- the core-shell type toner of the present invention has excellent printing characteristics, can fix at lower tone than usual, has excellent fixing even at high speed printing and high speed copying, and has no color unevenness even at color printing and color copying. It can be suitably used for various printing machines and copiers.
- the polymerization method toner of the present invention has excellent charge stability, good durability, low environmental dependence, and does not cause color unevenness even when printed or copied in color.
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- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Developing Agents For Electrophotography (AREA)
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2001558794A JP4214697B2 (ja) | 2000-02-10 | 2001-02-13 | 静電荷像現像用トナーの製造方法 |
DE60130749T DE60130749T2 (de) | 2000-02-10 | 2001-02-13 | Toner zur elektrostatischen bildentwicklung und prozess zu seiner herstellung |
US10/182,708 US6887637B2 (en) | 2000-02-10 | 2001-02-13 | Toner for electrostatic image development and process for producing the same |
EP01904392A EP1273976B1 (en) | 2000-02-10 | 2001-02-13 | Toner for electrostatic image development and process for producing the same |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2000033450 | 2000-02-10 | ||
JP2000/033450 | 2000-02-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2001059526A1 true WO2001059526A1 (fr) | 2001-08-16 |
Family
ID=18557931
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2001/000974 WO2001059526A1 (fr) | 2000-02-10 | 2001-02-13 | Toner pour le developpement d'images electrostatique et son procede de production |
Country Status (5)
Country | Link |
---|---|
US (1) | US6887637B2 (ja) |
EP (1) | EP1273976B1 (ja) |
JP (1) | JP4214697B2 (ja) |
DE (1) | DE60130749T2 (ja) |
WO (1) | WO2001059526A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006064960A (ja) * | 2004-08-26 | 2006-03-09 | Kyocera Chemical Corp | 静電潜像現像用トナー |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPWO2004083964A1 (ja) * | 2003-03-17 | 2006-06-22 | 日本ゼオン株式会社 | 静電荷像現像用トナー |
US7846632B2 (en) * | 2003-09-03 | 2010-12-07 | Zeon Corporation | Toner |
US20080311502A1 (en) * | 2004-08-04 | 2008-12-18 | Zeon Corporation | Toner For Development of Electrostatic Image |
JP2007121882A (ja) * | 2005-10-31 | 2007-05-17 | Nippon Zeon Co Ltd | 静電荷像現像用非磁性トナー |
WO2007114502A1 (ja) * | 2006-03-30 | 2007-10-11 | Zeon Corporation | 正帯電性静電荷像現像用現像剤及びその製造方法 |
JP4963910B2 (ja) * | 2006-09-19 | 2012-06-27 | 株式会社リコー | 画像形成方法 |
JP2008191189A (ja) * | 2007-01-31 | 2008-08-21 | Nippon Zeon Co Ltd | 静電荷像現像用トナー |
JP2008249989A (ja) * | 2007-03-30 | 2008-10-16 | Nippon Zeon Co Ltd | フルカラー画像形成方法 |
JP5758871B2 (ja) * | 2012-12-27 | 2015-08-05 | 京セラドキュメントソリューションズ株式会社 | 静電荷像現像用トナー |
US9683082B2 (en) | 2013-07-31 | 2017-06-20 | Dow Global Technologies Llc | Process to produce polycarbamate using a gradient feed of urea |
JP5934271B2 (ja) * | 2014-03-13 | 2016-06-15 | 京セラドキュメントソリューションズ株式会社 | 静電荷像現像用トナー |
US9904192B2 (en) | 2015-02-19 | 2018-02-27 | Zeon Corporation | Toner |
JP2021182034A (ja) * | 2020-05-18 | 2021-11-25 | 株式会社リコー | トナー及びその製造方法、トナー収容ユニット、画像形成装置、並びに画像形成方法 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
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JPH03175456A (ja) * | 1989-12-05 | 1991-07-30 | Fujikura Kasei Co Ltd | 静電荷像現像用トナーの製造方法 |
JPH09204073A (ja) * | 1996-01-25 | 1997-08-05 | Mita Ind Co Ltd | 電子写真用トナー |
EP0836122A1 (en) * | 1996-10-14 | 1998-04-15 | Nippon Zeon Co., Ltd. | Polimerized toner and production process thereof |
JPH1115192A (ja) * | 1997-06-24 | 1999-01-22 | Nippon Zeon Co Ltd | 静電荷像現像用トナーの製造方法 |
JPH11288129A (ja) * | 1998-03-31 | 1999-10-19 | Nippon Zeon Co Ltd | コア・シェル構造トナー及びその製造方法 |
US6136490A (en) * | 1996-12-05 | 2000-10-24 | Nippon Zeon Co., Ltd. | Polymerized toner |
Family Cites Families (7)
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JPS5962871A (ja) | 1982-10-04 | 1984-04-10 | Canon Inc | トナ−の製造方法 |
JPS59123852A (ja) | 1982-12-29 | 1984-07-17 | Canon Inc | トナ−の製造方法 |
JP2552133B2 (ja) | 1986-04-17 | 1996-11-06 | 藤倉化成株式会社 | 電子写真用正帯電性トナ− |
JPH0815893A (ja) * | 1994-06-29 | 1996-01-19 | Mita Ind Co Ltd | 接触現像方法 |
JP3956618B2 (ja) * | 1998-03-19 | 2007-08-08 | 日本ゼオン株式会社 | 静電荷像現像用トナー及びその製造方法 |
WO1999052019A1 (fr) * | 1998-03-31 | 1999-10-14 | Nippon Zeon Co., Ltd. | Toner destine au developpement d'une image electrostatique, et procede de production associe |
JP2000347445A (ja) * | 1999-03-26 | 2000-12-15 | Nippon Zeon Co Ltd | 静電荷像現像用トナー |
-
2001
- 2001-02-13 US US10/182,708 patent/US6887637B2/en not_active Expired - Lifetime
- 2001-02-13 EP EP01904392A patent/EP1273976B1/en not_active Expired - Lifetime
- 2001-02-13 JP JP2001558794A patent/JP4214697B2/ja not_active Expired - Fee Related
- 2001-02-13 WO PCT/JP2001/000974 patent/WO2001059526A1/ja active IP Right Grant
- 2001-02-13 DE DE60130749T patent/DE60130749T2/de not_active Expired - Lifetime
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
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JPH03175456A (ja) * | 1989-12-05 | 1991-07-30 | Fujikura Kasei Co Ltd | 静電荷像現像用トナーの製造方法 |
JPH09204073A (ja) * | 1996-01-25 | 1997-08-05 | Mita Ind Co Ltd | 電子写真用トナー |
EP0836122A1 (en) * | 1996-10-14 | 1998-04-15 | Nippon Zeon Co., Ltd. | Polimerized toner and production process thereof |
US6136490A (en) * | 1996-12-05 | 2000-10-24 | Nippon Zeon Co., Ltd. | Polymerized toner |
JPH1115192A (ja) * | 1997-06-24 | 1999-01-22 | Nippon Zeon Co Ltd | 静電荷像現像用トナーの製造方法 |
JPH11288129A (ja) * | 1998-03-31 | 1999-10-19 | Nippon Zeon Co Ltd | コア・シェル構造トナー及びその製造方法 |
Non-Patent Citations (1)
Title |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006064960A (ja) * | 2004-08-26 | 2006-03-09 | Kyocera Chemical Corp | 静電潜像現像用トナー |
Also Published As
Publication number | Publication date |
---|---|
EP1273976A1 (en) | 2003-01-08 |
DE60130749T2 (de) | 2008-07-17 |
JPWO2001059526A1 (ja) | 2004-03-04 |
US20030027070A1 (en) | 2003-02-06 |
US6887637B2 (en) | 2005-05-03 |
DE60130749D1 (de) | 2007-11-15 |
EP1273976B1 (en) | 2007-10-03 |
EP1273976A4 (en) | 2004-12-15 |
JP4214697B2 (ja) | 2009-01-28 |
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