WO2010032686A1 - トナー、現像剤、トナーの製造方法 - Google Patents
トナー、現像剤、トナーの製造方法 Download PDFInfo
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- WO2010032686A1 WO2010032686A1 PCT/JP2009/065913 JP2009065913W WO2010032686A1 WO 2010032686 A1 WO2010032686 A1 WO 2010032686A1 JP 2009065913 W JP2009065913 W JP 2009065913W WO 2010032686 A1 WO2010032686 A1 WO 2010032686A1
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- toner
- image
- particles
- fatty acid
- acid ester
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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
- G03G9/087—Binders for toner particles
- G03G9/08775—Natural macromolecular compounds or derivatives thereof
- G03G9/08782—Waxes
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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
- G03G9/0802—Preparation methods
- G03G9/0804—Preparation methods whereby the components are brought together in a liquid dispersing medium
- G03G9/0806—Preparation methods whereby the components are brought together in a liquid dispersing medium whereby chemical synthesis of at least one of the toner components takes place
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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
- G03G9/093—Encapsulated toner particles
- G03G9/09307—Encapsulated toner particles specified by the shell material
- G03G9/09314—Macromolecular compounds
- G03G9/09321—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
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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
- G03G9/093—Encapsulated toner particles
- G03G9/0935—Encapsulated toner particles specified by the core material
- G03G9/09357—Macromolecular compounds
- G03G9/09364—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
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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
- G03G9/093—Encapsulated toner particles
- G03G9/09392—Preparation thereof
Definitions
- the present invention relates to a toner used for electrophotographic image formation, and more particularly to a so-called low-temperature fixing compatible toner that fixes an image at a lower temperature than conventional ones.
- a printed material is generally manufactured through the following steps. First, exposure light is irradiated onto the photoconductor to form a latent image on the photoconductor, and then toner is supplied onto the photoconductor to develop the latent image to form a toner image. Next, the toner image on the photoconductor is transferred to a transfer material such as paper, and the transferred image is fixed by applying heat, pressure, or the like to produce a printed matter. The toner remaining on the photoconductor after the toner image is transferred is removed by the cleaning device, and the next image can be formed.
- the low-temperature fixing compatible toner produced using a binder resin having a low glass transition temperature and a softening point has a property that it is easily affected by thermal stress and mechanical stress. Specifically, when the toner is stored over time, depending on the environmental conditions, a phenomenon called blocking in which the toners adhere to each other occurs, and stable storage performance may not be obtained. Also, when a large number of prints are made and the printed material just after fixing is placed on the paper discharge tray, or when a large number of printed materials are stored in a stack, the images or A phenomenon called tacking, in which the image and white paper are bonded, occurred.
- the toner for low-temperature fixing is required to have stable storage performance and stability that does not cause tacking even when subjected to thermal or mechanical stress during and after image formation.
- the present invention is a thermal and mechanical apparatus that can fix a toner image at a temperature lower than that of the prior art, does not cause blocking even when unused toner is stored over time, and does not cause tacking of the toner image after fixing.
- An object of the present invention is to provide a low-temperature fixing toner excellent in mechanical stress.
- the present inventor has found that the above-described problem can be solved by any of the configurations described below. That is, The invention described in claim 1 “Toner comprising at least a binder resin, a colorant, and a wax, A toner comprising a fatty acid ester wax having a hydroxyl group and an aliphatic alcohol. ].
- the invention according to claim 3 3.
- the invention described in claim 5 “A method for producing a toner comprising at least a binder resin, a colorant, and a wax, At least a step of polymerizing a polymerizable monomer containing a fatty acid ester wax having a hydroxyl group and an aliphatic alcohol to form the resin particles constituting the binder resin, and agglomerating the resin particles and the colorant particles, And a step of fusing the toner to produce the toner. ].
- the present invention it is possible to fix a toner image at a temperature lower than that of the prior art, and even when unused toner is stored over time, blocking does not occur, and the toner image after fixing does not cause tacking. Low-temperature fixing toner with excellent mechanical stress.
- 2 is an example of a monochrome type image forming apparatus in which the toner according to the present invention can be used.
- 2 is an example of a tandem type color image forming apparatus in which the toner according to the present invention can be used. It is another example of a color image forming apparatus in which the toner according to the present invention can be used.
- the present inventors include a fatty acid ester wax having a hydroxyl group and an aliphatic alcohol in the toner, so that the toner image after fixing does not cause tacking even when stored in a unused state for a long period of time. It has been found that a toner compatible with low-temperature fixing excellent in mechanical and mechanical stress can be obtained. The reason why the effect of the present invention has been realized by the above configuration is probably that the binder resin exhibits fluidity only by heating at the time of fixing due to the action of the fatty acid ester wax and the aliphatic alcohol. This is probably because the fluidity was suppressed.
- the binder resin molecule, the fatty acid ester wax molecule, and the aliphatic alcohol molecule coexist in the toner particles, an interaction due to hydrogen bonding or the like works between these molecules, and the toner particles
- the melting point is considered to increase.
- an environment in which a hydroxyl group is present on the fatty acid ester wax molecule and a strong hydrogen bond is easily formed between the molecules is realized by the presence of the hydroxyl group of the aliphatic alcohol.
- the fluidity of the binder resin is suppressed and the occurrence of blocking and tacking is avoided when the toner is not subjected to large heat, such as unused toner during storage or toner images after fixing. It is thought that.
- the fluidity of the binder resin is instantly expressed and low-temperature fixing is realized, and as soon as the heat source disappears, the toner is easily solidified by the action of strong hydrogen bonds. It is thought that there is.
- the thermal characteristics and fluidity can be appropriately controlled even for a binder resin that easily exhibits fluidity at low temperatures. It is thought that it became.
- the above structure exhibits a low melt viscosity with respect to heating during fixing, and after fixing, the toner itself is given elasticity by the formation of a cross-linked structure such as a relatively gradual hydrogen bond on the surface of the toner image. Can be considered to improve.
- the present inventor has found a toner containing at least a binder resin, a colorant, and a wax and containing an aliphatic ester wax having a hydroxyl group and an aliphatic alcohol. It was found that the effect was expressed.
- the aliphatic ester wax having a hydroxyl group contained in the toner according to the present invention will be described.
- the aliphatic ester wax having a hydroxyl group used in the present invention is a compound obtained by bonding at least one hydroxyl group in its structure, and is obtained by a known synthesis method. Specifically, a representative example is a dehydration condensation reaction between an aliphatic carboxylic acid having a hydroxyl group and an aliphatic alcohol.
- the aliphatic carboxylic acid having a hydroxyl group is generally called an aliphatic hydroxycarboxylic acid, a hydroxycarboxylic acid or a hydroxy acid.
- the aliphatic carboxylic acid having a hydroxyl group for producing the aliphatic ester wax used in the present invention is as follows. There are things. That is, citric acid, malic acid, tartaric acid, catechinic acid, lactic acid, ricinoleic acid, isocitric acid, mevalonic acid, shikimic acid, tartronic acid, hydroxybutyric acid, citramalic acid, leucine acid, pantoic acid and the like. Among these, citric acid, tartaric acid, and malic acid are particularly preferable.
- the aliphatic alcohol forming the aliphatic ester wax used in the present invention is preferably an aliphatic alcohol having 10 to 40 carbon atoms, more preferably an aliphatic alcohol having 12 to 30 carbon atoms.
- the hydrocarbon alcohol portion of the aliphatic alcohol may have a linear structure or a branched structure.
- aliphatic alcohols include the following. Decanol, undecanol, dodecanol, tridecanol, tetradecanol, petadecanol, hexadecanol, heptadecanol, octadecanol, nonadecanol, eicosanol, heneicosanol, docosanol, tricosanol, tetracosanol, hexacosanol, octacosanol And triacontanol.
- aliphatic carboxylic acids using docosanol and octadecanol are particularly preferable.
- a natural wax containing a fatty acid ester wax having a hydroxyl group for example, natural waxes such as carnauba wax and rice wax.
- natural waxes such as carnauba wax and rice wax.
- synthetic waxes such as seryl- ⁇ -hydroxyserotate, seryl- ⁇ -hydroxymelitate, myricyl- ⁇ -hydroxymelitate are used. You can also
- the melting point of the fatty acid ester wax having a hydroxyl group is 40 to 120 ° C., preferably 50 to 110 ° C., more preferably 60 to 90 ° C. When the melting point is within the above range, it is considered that the wax contributes to the development of the heat-resistant storage property and low-temperature fixability of the toner.
- the aliphatic alcohol used in the toner according to the present invention it is preferable to use an aliphatic alcohol having the same structure or a similar structure as the alcohol component of the fatty acid ester wax having a hydroxyl group described above. Specifically, those having 10 to 40 carbon atoms are preferable, and aliphatic alcohols having 12 to 30 carbon atoms are more preferably used.
- the hydrocarbon alcohol portion of the aliphatic alcohol may have a linear structure or a branched structure.
- the aliphatic alcohol used in the toner according to the present invention is preferably an aliphatic alcohol having the same structure or a similar structure as the alcohol component of the fatty acid ester wax having a hydroxyl group described above.
- docosanol and octadecanol are particularly preferably used.
- the amount of the aliphatic alcohol added to the toner is preferably from 3 mol% to 80 mol%, more preferably from 10 mol% to 70 mol%, based on the ester wax having a hydroxyl group.
- the toner according to the present invention contains a fatty acid ester wax having a hydroxyl group and an aliphatic alcohol in the toner particles, and these compounds can be contained in the toner particles by a known method. Specifically, for example, a fatty acid ester wax having a hydroxyl group and an aliphatic alcohol are added to a liquid of a polymerizable monomer that is a raw material for a binder resin, and the compound is contained by polymerizing this. Resin particles are formed. Then, a toner containing these compounds can be produced by agglomerating and fusing the formed resin particles together with the colorant particles.
- a mixture of a fatty acid ester wax having a hydroxyl group and an aliphatic alcohol is heated to a temperature higher than the melting temperature of these compounds, added in the same manner to a heated surfactant aqueous solution, and dispersed by a dispersion method such as ultrasonic wave or high-speed stirring. Make fine particles.
- a toner containing a fatty acid ester wax having a hydroxyl group and an aliphatic alcohol can be produced.
- the content of the fatty acid ester wax having a hydroxyl group and the aliphatic alcohol in the toner according to the present invention is preferably 1% by mass to 30% by mass, and more preferably 5% by mass to 20% by mass.
- the toner according to the present invention can be used in combination with the following known waxes together with a fatty acid ester wax having a hydroxyl group and an aliphatic alcohol.
- a fatty acid ester wax having a hydroxyl group and an aliphatic alcohol for example, the method used when the fatty acid ester wax having a hydroxyl group and an aliphatic alcohol described above are contained.
- a method of dissolving in a polymerizable monomer solution for forming a binder resin there is a method of dissolving in a polymerizable monomer solution for forming a binder resin. Further, the wax is heated to the melting temperature or higher, added to the heated aqueous surfactant solution in the same manner, and finely divided by a dispersion method such as ultrasonic wave or high-speed stirring. There is also a method in which the fine particles are aggregated together with resin particles and colorant particles to fuse the aggregated particles.
- the toner according to the present invention will be further described.
- the toner according to the present invention contains at least a binder resin and a colorant, and contains a fatty acid ester wax having a hydroxyl group and an aliphatic alcohol.
- the above configuration makes it possible to provide a low-temperature fixing-compatible toner excellent in thermal and mechanical stress that does not cause blocking even when stored for a long time in an unused state, and does not cause tacking of a toner image after fixing. ing.
- the toner according to the present invention it is preferable to use a binder resin having a glass transition temperature of 60 ° C. to 70 ° C. in addition to the above-mentioned configuration “containing a fatty acid ester wax having a hydroxyl group and an aliphatic alcohol”.
- the glass transition temperature of the binder resin can be measured using, for example, “DSC-7 differential scanning calorimeter (manufactured by Perkin Elma)” or “TAC7 / DX thermal analysis controller (manufactured by Perkin Elma)”.
- DSC-7 differential scanning calorimeter manufactured by Perkin Elma
- TAC7 / DX thermal analysis controller manufactured by Perkin Elma
- the measurement conditions are a measurement temperature of -30 ° C. to 200 ° C., a temperature increase rate of 10 ° C./min, a temperature decrease rate of 10 ° C./min, and a Heat-Cool-Heat temperature control, and analysis is performed based on the data in the 2nd Heat. .
- glass transition temperature For the glass transition temperature, an extension line of the baseline before the rise of the first endothermic peak and a tangent line showing the maximum inclination between the rising portion of the first endothermic peak and the peak vertex are drawn, and the intersection is shown as the glass transition temperature. .
- the toner according to the present invention preferably has a volume-based median diameter (D50v) of 3 to 20 ⁇ m, more preferably 5 to 12 ⁇ m.
- the volume-based median diameter (D50v diameter) of the toner can be measured and calculated using an apparatus in which a computer system for data processing is connected to “Multisizer 3 (manufactured by Beckman Coulter)”.
- toner As a measurement procedure, 0.02 g of toner is blended with 20 ml of a surfactant solution (for example, a surfactant solution obtained by diluting a neutral detergent containing a surfactant component 10 times with pure water for the purpose of dispersing the toner). After that, ultrasonic dispersion is performed for 1 minute to prepare a toner dispersion. This toner dispersion is injected into a beaker containing ISOTON II (manufactured by Beckman Coulter, Inc.) in a sample stand with a pipette until the measured concentration reaches 5 to 10%, and the measuring machine count is set to 2500. To do. The aperture diameter of “Multisizer 3” is 50 ⁇ m.
- a surfactant solution for example, a surfactant solution obtained by diluting a neutral detergent containing a surfactant component 10 times with pure water for the purpose of dispersing the toner.
- ultrasonic dispersion is performed for 1 minute to prepare a toner dis
- the toner according to the present invention contains at least a binder resin, a colorant, and a wax
- the production method is not particularly limited, and can be produced by a conventional toner production method.
- a toner production method by a so-called pulverization method in which a toner is prepared through kneading, pulverization, and classification steps, or a so-called polymerization method in which a polymerizable monomer is polymerized and particles are formed while controlling the shape and size at the same time. It can be produced by a toner production method.
- a toner production method using a polymerization method is preferable because the produced toner (so-called polymerized toner) is easy to obtain characteristics such as uniform particle size distribution, shape distribution, and sharp charge distribution.
- the present invention is capable of fixing a toner image at a temperature lower than that of the prior art, and can obtain a toner image that does not cause tacking after fixing. It provides a toner excellent in mechanical stress.
- a toner having two functions of low-temperature fixability and heat stability there is a core-shell structure type toner, and a toner production method by a polymerization method is preferable also in producing such a function-separated type toner.
- the toner production method using a polymerization method is a method for producing toner particles through a step of forming a resin particle by performing a polymerization reaction such as suspension polymerization or emulsion polymerization.
- the toner according to the present invention contains a fatty acid ester wax having a hydroxyl group and an aliphatic alcohol.
- the toner according to the present invention is prepared by adding these compounds by a known method during the polymerization step. Can do.
- a toner production method by an emulsion association method in which resin particles are produced by emulsion polymerization and toner particles are produced through a process of aggregating and fusing the resin particles is particularly preferable.
- Toner preparation by an emulsion association method which is an example of a toner preparation method according to the present invention, will be described. Toner preparation by the emulsion association method is performed through the following steps.
- This step is a step of forming resin particles having a size of about 100 nm by introducing a polymerizable monomer that forms resin particles into an aqueous medium and performing polymerization. .
- resin particles containing the fatty acid ester wax having a hydroxyl group and the aliphatic alcohol are produced. Can do.
- aqueous medium refers to a medium composed of 50 to 100% by mass of water and 0 to 50% by mass of a water-soluble organic solvent.
- water-soluble organic solvent include known ones such as methanol, ethanol, isopropanol, butanol, acetone, and methyl ethyl ketone.
- the colorant particle dispersion is prepared by dispersing the colorant in the aqueous medium according to the procedure described above.
- a colorant particle dispersion is prepared using a colorant having a number average primary particle size of 30 nm to 200 nm. Then, by producing a toner using the colorant particle dispersion, the number average particle size of the colorant in the toner particles is 1.1 to 2.5 times the number average primary particle size. is there.
- the particles are aggregated by adding an aggregating agent such as an alkali metal salt or an alkaline earth metal salt represented by magnesium chloride into an aqueous medium in which resin particles, colorant particles and the like are present.
- an aggregating agent such as an alkali metal salt or an alkaline earth metal salt represented by magnesium chloride
- the agglomeration is progressed by fusing the agglomerated resin particles at the same time by heating the aqueous medium above the glass transition temperature of the resin particles and above the melting peak temperature of the mixture.
- a salt such as salt is added to stop the aggregation and form colored particles.
- the core resin particles and the colorant particles are first aggregated and fused to form the core particles, and then the shell resin particles are added to the core particle surface. Aggregate and fuse. In this way, colored particles having a core-shell structure can be produced by performing aggregation and fusion in two stages.
- This step is a step called a so-called shape control step in which the reaction system is heated until the desired average circularity is reached by heating the reaction system subsequent to the aggregation / fusion step. .
- the shape of the colored particles can be controlled by heating to a temperature higher than the glass transition temperature of the binder resin constituting the colored particles formed in the above-described aggregation / fusion step.
- Cooling step This step is a step of cooling (rapid cooling) the dispersion of the colored particles. Cooling is performed at a cooling rate of 1 to 20 ° C./min.
- the cooling treatment method is not particularly limited, and examples thereof include a method of cooling by introducing a refrigerant from the outside of the reaction vessel, and a method of cooling by directly introducing cold water into the reaction system.
- Washing step This step consists of a step of solid-liquid separation of the colored particles from the colored particle dispersion cooled to a predetermined temperature in the above step, and a surface active agent and agglomeration from the surface of the colored particles in the wet state after solid-liquid separation. It consists of a cleaning process to remove deposits such as agents.
- the solid-liquid separated colored particles are usually in the form of a cake-like aggregate called a toner cake, and the cleaning process is performed by crushing the toner cake.
- the filtrate is washed with water until the electrical conductivity of the filtrate reaches, for example, about 10 ⁇ S / cm.
- the solid-liquid separation method include a centrifugal separation method, a vacuum filtration method using Nutsche and the like, a filtration method using a filter press and the like, and are not particularly limited in the present invention.
- Drying step This step is a step of drying the washed colored particles to obtain dried colored particles.
- the dryer used in this step include a spray dryer, a vacuum freeze dryer, and a vacuum dryer, and a stationary shelf dryer, a mobile shelf dryer, a fluidized bed dryer, and a rotary dryer. It is preferable to use a stirring dryer or the like.
- the water content of the dried colored particles is preferably 5% by mass or less, more preferably 2% by mass or less.
- the aggregate may be crushed.
- a mechanical crushing apparatus such as a jet mill, a Henschel mixer, a coffee mill, or a food processor can be used.
- External additive processing step is a step of adding external additives and a lubricant to the dried colored particles to form toner particles that can be used for image formation.
- the colored particles that have undergone the drying step are used as toner particles as they are.
- an external additive by adding an external additive, the chargeability, fluidity, and cleaning properties of the toner can be improved.
- known inorganic fine particles, organic fine particles, and aliphatic metal salts can be used, and the addition amount thereof is 0.1 to 10.0% by mass, preferably 0.5%, based on the whole toner. -4.0 mass%. Further, various external additives can be added in combination.
- a mixing apparatus used when adding an external additive there exist well-known mechanical mixing apparatuses, such as a turbula mixer, a Henschel mixer, a Nauta mixer, a V-type mixer, and a coffee mill, for example.
- a toner according to the present invention comprising a fatty acid ester wax having a hydroxyl group and an aliphatic alcohol can be produced.
- the polymerization initiator, dispersion stabilizer, and surfactant that can be used when the toner according to the present invention is prepared by the above-described emulsion association method will be described later.
- the binder resin used in the toner according to the present invention is not particularly limited, and for example, a known resin such as a vinyl resin can be used.
- Styrene or styrene derivatives Styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, ⁇ -methylstyrene, p-phenylstyrene, p-ethylstyrene, 2,4-dimethylstyrene, p-tert- Butyl styrene, pn-hexyl styrene, pn-octyl styrene, pn-nonyl styrene, pn-decyl styrene, pn-dodecyl styrene, etc.
- the vinyl polymerizable monomers constituting the resin that can be used in the toner according to the present invention include those having an ionic dissociation group such as a carboxyl group, a sulfonic acid group, and a phosphoric acid group shown below. Can be used.
- those having a carboxyl group include acrylic acid, methacrylic acid, maleic acid, itaconic acid, cinnamic acid, fumaric acid, maleic acid monoalkyl ester, itaconic acid monoalkyl ester, and the like.
- examples of those having a sulfonic acid group include styrene sulfonic acid, allyl sulfosuccinic acid, and 2-acrylamido-2-methylpropane sulfonic acid.
- Examples of those having a phosphoric acid group include acid phosphooxyethyl methacrylate. is there.
- Ethylene glycol dimethacrylate ethylene glycol diacrylate, diethylene glycol dimethacrylate, diethylene glycol diacrylate, triethylene glycol dimethacrylate, triethylene glycol diacrylate, neopentyl glycol dimethacrylate, neopentyl glycol diacrylate, and the like.
- colorants can be used for the toner according to the present invention. Specific colorants are shown below.
- black colorant for example, carbon black such as furnace black, channel black, acetylene black, thermal black and lamp black, and magnetic powder such as magnetite and ferrite can be used.
- coloring agent for orange or yellow C.I. I. Pigment orange 31, 43, C.I. I. Pigment Yellow 12, 14, 15, 17, 74, 83, 93, 94, 138, 155, 162, 180, 185, and the like.
- colorants for green or cyan C.I. I. Pigment Blue 2, 3, 15, 15, 15: 2, 15: 3, 15: 4, 16, 17, 17, 60, 62, 66, C.I. I. Pigment Green 7 etc.
- C.I. I. Solvent Red 1 49, 52, 58, 63, 111, 122
- C.I. I. Solvent Yellow 2 6, 14, 15, 16, 19, 21, 21, 33, 44, 56, 61, 77, 79, 80, 81, 82, the same 93, 98, 103, 104, 112, 162, C.I. I. Solvent Blue 25, 36, 60, 70, 93, 95, etc.
- colorants can be used alone or in combination of two or more as required.
- the addition amount of the colorant is in the range of 1 to 30% by mass, preferably 2 to 20% by mass, based on the whole toner, and a mixture thereof can also be used.
- the number average primary particle diameter varies depending on the type, but is preferably about 10 to 200 nm.
- the resin fine particles are added at the stage of agglomeration by the addition of the flocculant to color the polymer.
- the colorant can also be used by treating the surface with a coupling agent or the like.
- external additive By adding the external additive, the fluidity and chargeability of the toner are improved, and the cleaning property is improved.
- the type of external additive is not particularly limited, and examples thereof include inorganic fine particles, organic fine particles, and lubricants exemplified below.
- inorganic fine particles conventionally known fine particles can be used.
- silica, titania, alumina, strontium titanate fine particles and the like are preferable.
- hydrophobized these inorganic fine particles can also be used as needed.
- silica fine particles include, for example, commercial products R-805, R-976, R-974, R-972, R-812, R-809 manufactured by Nippon Aerosil Co., Ltd., HVK-2150 manufactured by Hoechst, H -200, commercial products TS-720, TS-530, TS-610, H-5, MS-5 manufactured by Cabot Corporation.
- titania fine particles examples include commercially available products T-805 and T-604 manufactured by Nippon Aerosil Co., Ltd., commercially available products MT-100S, MT-100B, MT-500BS, MT-600, MT-600SS, JA- 1.
- alumina fine particles examples include commercial products RFY-C and C-604 manufactured by Nippon Aerosil Co., Ltd. and commercial products TTO-55 manufactured by Ishihara Sangyo Co., Ltd.
- organic fine particles spherical organic fine particles having a number average primary particle diameter of about 10 to 2000 nm can be used. Specifically, homopolymers such as styrene and methyl methacrylate and copolymers thereof can be used.
- a lubricant to further improve the cleaning property and transfer property.
- metal salts of the following higher fatty acids That is, salts of zinc stearate, aluminum, copper, magnesium, calcium, etc., zinc oleate, salts of manganese, iron, copper, magnesium, etc., zinc palmitate, salts of copper, magnesium, calcium, etc., linoleic acid
- salts of zinc, calcium and the like, and zinc and calcium of ricinoleic acid are salts of zinc, calcium and the like, and zinc and calcium of ricinoleic acid.
- the addition amount of these external additives and lubricants is preferably 0.1 to 10.0% by mass with respect to the whole toner.
- a known oil-soluble or water-soluble polymerization initiator can be used.
- the oil-soluble polymerization initiator include the following azo or diazo polymerization initiators and peroxide polymerization initiators. That is, (1) Azo or diazo polymerization initiator 2,2'-azobis- (2,4-dimethylvaleronitrile), 2,2'-azobisisobutyronitrile, 1,1'-azobis (cyclohexane-1 -Carbonitrile), 2,2'-azobis-4-methoxy-2,4-dimethylvaleronitrile, azobisisobutyronitrile, etc.
- peroxide-based polymerization initiators benzoyl peroxide, methyl ethyl ketone peroxide, diisopropyl Peroxycarbonate, cumene hydroperoxide, t-butyl hydroperoxide, di-t-butyl peroxide, dicumyl peroxide, 2,4-dichlorobenzoyl peroxide, lauroyl peroxide, 2,2-bis- (4 4-tert-butylperoxycyclohexyl) propane, tris (T-butylperoxy) triazine
- a water-soluble radical polymerization initiators can be used.
- water-soluble polymerization initiator examples include persulfates such as potassium persulfate and ammonium persulfate, azobisaminodipropane acetate, azobiscyanovaleric acid and its salts, hydrogen peroxide and the like.
- a known chain transfer agent can be used to adjust the molecular weight of the resin particles.
- Specific examples include octyl mercaptan, dodecyl mercaptan, tert-dodecyl mercaptan, n-octyl-3-mercaptopropionate, terpinolene, carbon tetrabromide, ⁇ -methylstyrene dimer and the like.
- the polymerizable monomer dispersed in the aqueous medium is polymerized, or the resin particles dispersed in the aqueous medium are aggregated and fused to produce a toner.
- a dispersion stabilizer that is stably dispersed therein.
- the dispersion stabilizer include tricalcium phosphate, magnesium phosphate, zinc phosphate, aluminum phosphate, calcium carbonate, magnesium carbonate, calcium hydroxide, magnesium hydroxide, aluminum hydroxide, calcium metasilicate, calcium sulfate, Examples include barium sulfate, bentonite, silica, and alumina.
- polyvinyl alcohol, gelatin, methylcellulose, sodium dodecylbenzenesulfonate, ethylene oxide adduct, higher alcohol sodium sulfate and the like which are generally used as surfactants can also be used as the dispersion stabilizer.
- usable surfactants are not particularly limited, but for example, the following ionic surfactants can be used as preferable ones.
- the ionic surfactant include a sulfonate, a sulfate ester salt, and a fatty acid salt.
- the sulfonate include sodium dodecylbenzenesulfonate, sodium arylalkylpolyethersulfonate, 3,3-disulfonediphenyl.
- sulfate salts include sodium dodecyl sulfate, sodium tetradecyl sulfate, sodium pentadecyl sulfate, and sodium octyl sulfate.
- Fatty acid salts include sodium oleate, sodium laurate, sodium caprate, sodium caprylate, Examples include sodium caproate, potassium stearate, and calcium oleate.
- Nonionic surfactants can also be used. Specifically, polyethylene oxide, polypropylene oxide, a combination of polypropylene oxide and polyethylene oxide, esters of polyethylene glycol and higher fatty acids, alkylphenol polyethylene oxide, higher fatty acids and Examples include polyethylene glycol esters, higher fatty acid and polypropylene oxide esters, sorbitan esters, and the like.
- the toner according to the present invention can be used as a two-component developer composed of a carrier and a toner, or as a non-magnetic one-component developer composed only of a toner.
- Carriers that are magnetic particles used when used as a two-component developer include conventionally known materials such as metals such as iron, ferrite, and magnetite, and alloys of these metals with metals such as aluminum and lead. It is possible to use. Among these, ferrite particles are preferable.
- the volume-based particle diameter of the carrier is preferably 15 to 100 ⁇ m, more preferably 25 to 80 ⁇ m.
- the saturation magnetization value is preferably 20 to 80 emu / g.
- the volume reference particle size is measured by a laser diffraction particle size analyzer “HELOS (manufactured by Sympatec Co., Ltd.)” equipped with a wet disperser, and the saturation magnetization is “DC magnetization characteristic automatic recording device 3257-35 (horizontal). It is possible to measure by “Kawaden Co., Ltd.”).
- the two-component developer can be obtained by mixing toner and carrier by a known method.
- the mixing amount of the toner with respect to the carrier is preferably 2 to 10% by mass.
- the mixing device is not particularly limited, and for example, a Nauter mixer, a W cone, a V-type mixer, or the like can be used.
- the toner when used as a non-magnetic one-component developer that forms an image without using a carrier, the toner is charged by sliding and pressing against the charging member and the developing roller surface during image formation.
- Image formation by the non-magnetic one-component development method can simplify the structure of the developing device, and thus has an advantage that the entire image forming device can be made compact. Therefore, by using the above-mentioned toner as a non-magnetic one-component developer, it is possible to create full-color prints with a compact color printer, making it possible to create full-color prints with excellent color reproducibility in space-constrained work environments. To do.
- the image forming method using the toner according to the present invention uses at least the following steps using the above-mentioned “toner containing at least a binder resin, a colorant, and a fatty acid ester wax having a hydroxyl group and an aliphatic alcohol”.
- a print is made by forming a toner image on a transfer paper.
- a latent image forming step for forming a latent image on the surface of the electrophotographic photosensitive member (2) A toner obtained by developing the electrostatic latent image formed on the surface of the electrophotographic photosensitive member with a developer carried on a developer carrying member Developing step for forming an image (3) Transfer step for transferring the toner image to the surface of the transfer member (4) Fixing step for thermally fixing the toner image transferred to the surface of the transfer member.
- FIG. 1 is an example of a monochrome type image forming apparatus capable of producing a print with toner according to the present invention.
- the image forming apparatus shown in FIG. 1 is a digital image forming apparatus and includes an image reading unit A, an image processing unit B, an image forming unit C, and a transfer paper transport unit D.
- automatic document feeding means for automatically conveying the document.
- the document is placed on the document placing table 11, and the placed document is separated and conveyed one by one by the conveying roller 12, and the image is read at the reading position 13a.
- the document after reading is discharged onto the document discharge tray 14 by the transport roller 12.
- the original image is read by a plurality of mirror units 15 and 16 including an illumination lamp constituting a scanning optical system and a plurality of mirrors.
- the image read by the image reading unit A is formed on the light receiving surface of the image sensor CCD through the projection lens 17.
- the optical image formed on the image sensor CCD is sequentially converted into an electric signal (luminance signal), A / D converted, and subjected to processing such as density conversion and filter processing in the image processing unit B as image data. Once stored in memory.
- the image forming unit C has a drum-shaped electrophotographic photosensitive member 1 which is an image carrier.
- Precharge lamps 8 are arranged in the order of operation.
- density detecting means 222 for measuring the reflection density of the patch image formed on the photoreceptor 1 is provided downstream of the developing means 4. The photoreceptor 1 is driven to rotate in the clockwise direction shown in the figure.
- the photoreceptor 1 is uniformly charged by the charging unit 2 and then image-exposed by the image exposure unit 3 based on the image signal from the memory of the image processing unit B.
- the image exposure unit 3 performs image exposure on the photoconductor 1 at the position Ao, whereby an electrostatic latent image is formed on the surface of the photoconductor 1.
- the electrostatic latent image formed on the photoconductor 1 is developed by the developing means 4 to form a toner image on the surface of the photoconductor 1.
- the transfer paper transport unit D includes paper feed units 41 (A), 41 (B), and 41 (C) that store transfer papers P of different sizes, and also provides manual paper feed for performing manual paper feed.
- a paper unit 42 is provided on the side, and an appropriate transfer paper P is selected from these paper feeding units.
- the transfer paper P is transported along the transport path 40 by the guide roller 43, and the inclination and bias are corrected by the registration roller 44.
- the transfer paper P corrected by the registration roller 44 is conveyed again along the conveyance path 40 and guided to the pre-transfer roller 43 a, the paper feed path 46, and the entry guide plate 47.
- the toner image on the photoconductor 1 is transferred to the transfer paper P by the transfer pole 24 and the separation pole 25 at the transfer position Bo, and the transfer paper P is separated from the surface of the photoconductor 21 and conveyed from the transfer means 5 to the fixing means 50.
- the fixing unit 50 includes a fixing roller 51 and a pressure roller 52.
- the transfer sheet P is passed between the fixing roller 51 and the pressure roller 52, and heated and pressed to fix the toner image. After the toner image has been fixed, the transfer paper P is discharged onto the paper discharge tray 64.
- the transfer paper P is conveyed in the direction of the broken line arrow by the operation of the paper discharge switching member 170 and the transfer paper guide section 177. Is done. Further, the transfer paper P is transported downward and switched back by the transport mechanism 178, and the double-sided printing paper feeding unit 130 is transported with the rear end portion of the transfer paper P being the leading end. Then, the transfer paper P is transported again through the transport path 40 by the operation of the transport guide 131 and the paper feed roller 132 of the duplex printing paper supply unit 130, and a toner image is also formed on the back surface of the transfer paper P by the above-described procedure. Can do.
- components such as the photosensitive member, the developing unit, and the cleaning unit may be unitized as a process cartridge and may be configured to be freely detachable from the apparatus main body in units.
- the charging unit, the image exposure unit, the developing unit, the transfer or separation unit, and the cleaning unit may be a process cartridge integrated with the photosensitive member, and may be a single unit that can be freely attached to and detached from the apparatus main body.
- the toner according to the present invention can be used in a high-speed image forming apparatus with a printing speed of 400 mm / sec (output performance of 85 sheets / min in terms of A4 paper), for example.
- a high-speed image forming apparatus for example, there is a POD (print on demand) compatible printer capable of producing on-demand several thousand sheets of printed matter at a time.
- FIG. 2 is a schematic view showing an example of an image forming apparatus for forming a color image using the toner according to the present invention.
- 1Y, 1M, 1C and 1Bk are photoreceptors
- 4Y, 4M, 4C and 4Bk are developing devices
- 5Y, 5M, 5C and 5Bk are primary transfer rolls as primary transfer means
- 5A is a secondary transfer.
- Secondary transfer rolls as means, 6Y, 6M, 6C and 6Bk are cleaning devices
- 7 is an intermediate transfer body unit
- 50 is a heat roll type fixing device
- 70 is an intermediate transfer body.
- This image forming apparatus is called a tandem color image forming apparatus, and includes a plurality of sets of image forming units 10Y, 10M, 10C, and 10Bk, an endless belt-shaped intermediate transfer body unit 7 as a transfer unit, and a recording member P.
- a document image reading apparatus A is disposed on the upper part of the image forming apparatus.
- an image forming unit 10Y that forms a yellow image includes a drum-shaped photoconductor 1Y as a first photoconductor, and a periphery of the photoconductor 1Y.
- an image forming unit 10M that forms a magenta image as another different color toner image is disposed around a drum-shaped photoconductor 1M as a first photoconductor.
- an image forming unit 10C that forms a cyan image as one of different toner images of different colors is arranged around a drum-shaped photoconductor 1C as a first photoconductor, and around the photoconductor 1C.
- the charging unit 2C, the exposure unit 3C, the developing unit 4C, the primary transfer roll 5C as the primary transfer unit, and the cleaning unit 6C are provided.
- an image forming unit 10Bk that forms a black image is a drum-shaped photosensitive member 1Bk as a first photosensitive member, and a charging device disposed around the photosensitive member 1Bk.
- the endless belt-shaped intermediate transfer body unit 7 has an endless belt-shaped intermediate transfer body 70 as an intermediate transfer endless belt-shaped second image carrier wound around a plurality of rolls and supported rotatably.
- Each color image formed by the image forming units 10Y, 10M, 10C, and 10Bk is sequentially transferred onto the rotating endless belt-shaped intermediate transfer body 70 by the primary transfer rolls 5Y, 5M, 5C, and 5Bk, and is combined.
- a colored image is formed.
- a recording member P such as a sheet as a transfer material accommodated in the sheet feeding cassette 20 is fed by the sheet feeding / conveying means 21, passes through a plurality of intermediate rolls 22 A, 22 B, 22 C, 22 D, and a registration roll 23, and is secondary A color image is transferred onto the recording member P at a time by being conveyed to a secondary transfer roll 5A as a transfer means.
- the recording member P to which the color image has been transferred is fixed by the heat roll type fixing device 50, is sandwiched by the paper discharge roll 25, and is placed on the paper discharge tray 26 outside the apparatus.
- the residual toner is removed by the cleaning means 6A from the endless belt-shaped intermediate transfer body 70 from which the recording member P is separated by curvature.
- the primary transfer roll 5Bk is always in pressure contact with the photoreceptor 1Bk.
- the other primary transfer rolls 5Y, 5M, and 5C are in pressure contact with the corresponding photoreceptors 1Y, 1M, and 1C, respectively, only during color image formation.
- the secondary transfer roll 5A comes into pressure contact with the endless belt-shaped intermediate transfer body 70 only when the recording member P passes through the secondary transfer roll 5A and secondary transfer is performed.
- toner images are formed on the photoreceptors 1Y, 1M, 1C, and 1Bk by charging, exposure, and development, and the toner images of the respective colors are superimposed on the endless belt-shaped intermediate transfer body 70, and are collectively applied to the recording member P.
- the image is transferred and fixed by the fixing device 50 by pressure and heating.
- the photoreceptors 1Y, 1M, 1C, and 1Bk after transferring the toner image to the recording member P are cleaned with the cleaning device 6A to remove the toner remaining on the photoreceptor, and then the above-described charging, exposure, and development cycle. The next image formation is performed.
- FIG. 3 is a cross-sectional view of the color image forming apparatus as in FIG. 2, but is different from the image forming apparatus in FIG.
- the image forming apparatus shown in FIG. 3 includes a charging unit, an exposure unit, a plurality of developing units, a transfer unit, a cleaning unit, and an intermediate transfer body around the organic photoreceptor.
- the belt-shaped intermediate transfer body 70 uses an elastic body having a medium resistance.
- the photosensitive member 1 is a rotating drum type photoreceptor that is repeatedly used as an image forming body, and is driven to rotate at a predetermined peripheral speed in a counterclockwise direction indicated by an arrow. While rotating, the photosensitive member 1 is uniformly charged to a predetermined polarity / potential by the charging unit 2 and then subjected to image exposure by an image exposure unit 3 (not shown), whereby yellow (Y) of the target color image is obtained. An electrostatic latent image corresponding to the color component image (color information) is formed.
- the electrostatic latent image is developed with yellow toner as the first color by the yellow (Y) developing means 4Y.
- the magenta, cyan, and black developing units 4M, 4C, and 4Bk which are the second to fourth developing units, are not activated and do not act on the photoreceptor 1, and the yellow toner image of the first color is There is no influence from the second to fourth developing means.
- the intermediate transfer member 70 is stretched by rollers 79a, 79b, 79c, 79d, and 79e, and is driven to rotate in the clockwise direction at the same peripheral speed as the photosensitive member 1.
- the first color yellow toner image formed and supported on the photosensitive member 1 is applied to the intermediate transfer member 70 from the primary transfer roller 5a in the process of passing through the nip portion between the photosensitive member 1 and the intermediate transfer member 70.
- the intermediate transfer (primary transfer) is sequentially performed on the outer peripheral surface of the intermediate transfer body 70 by the electric field formed by the primary transfer bias.
- the surface of the photoreceptor 1 after the transfer of the first color yellow toner image corresponding to the intermediate transfer body 70 is cleaned by the cleaning device 6a.
- the second color magenta toner image, the third color cyan toner image, and the fourth color black (black) toner image are sequentially superimposed and transferred onto the intermediate transfer body 70 to correspond to the target color image.
- a superimposed color toner image is formed.
- the secondary transfer roller 5b is supported in parallel with the secondary transfer counter roller 79b so as to be separated from the lower surface portion of the intermediate transfer body 70.
- the primary transfer bias for sequentially superimposing and transferring the first to fourth color toner images from the photosensitive member 1 to the intermediate transfer member 70 has a polarity opposite to that of the toner and is applied from a bias power source.
- the applied voltage is, for example, in the range of +100 V to +2 kV.
- the secondary transfer roller 5b and the intermediate transfer member cleaning means 6b can be separated from the intermediate transfer member 70. is there.
- the secondary transfer roller 5b When the superimposed color toner image transferred onto the belt-shaped intermediate transfer member 70 is transferred to the transfer material P, which is the second image carrier, the secondary transfer roller 5b is brought into contact with the belt of the intermediate transfer member 70. At the same time, the transfer material P is fed from the pair of paper registration rollers 23 through the transfer paper guide to the belt of the intermediate transfer body 70 to the contact nip with the secondary transfer roller 5b at a predetermined timing.
- a secondary transfer bias is applied to the secondary transfer roller 5b from a bias power source. By this secondary transfer bias, the superimposed color toner image is transferred (secondary transfer) from the intermediate transfer body 70 to the transfer material P as the second image carrier.
- the transfer material P that has received the transfer of the toner image is conveyed to the fixing means 50 and heated and fixed.
- Synthesis of “fatty acid ester waxes 1 to 6” (1) Synthesis of “fatty acid ester waxes 1 to 4” In a reaction vessel equipped with a stirrer, a temperature sensor, a cooling pipe, and a nitrogen introduction pipe, 155 parts of citric acid and 790 parts of docosanol Then, methanesulfonic acid was added as an acid catalyst, the temperature was set to 120 ° C. under a nitrogen stream, and the reaction treatment was performed for 3 hours while distilling off the reaction water. Thereafter, an aqueous sodium hydroxide solution and a hydrogen peroxide solution were added, followed by filtration to synthesize “fatty acid ester wax 1”.
- “Fatty acid ester wax 2” was synthesized in the same manner as in “Fatty acid ester wax 1” except that the amount of citric acid added was changed to 180 parts and octadecanol 760 parts were used instead of 790 parts of docosanol. Was made. Further, in the synthesis of the above “fatty acid ester wax 1”, “fatty acid ester wax 3” was prepared in the same procedure except that 175 parts of tartaric acid was used instead of 155 parts of citric acid and the addition amount of docosanol was changed to 762 parts. Was made.
- Table 1 shows compound names of carboxylic acid and alcohol used in the synthesis of the above “fatty acid ester waxes 1 to 6”.
- the “colorant particle C” in the “colorant particle dispersion C” had a volume-based median diameter of 98 nm.
- the volume-based median diameter was measured using “MICROTRAC UPA-150 (manufactured by HONEYWELL)” under the following measurement conditions.
- Sample refractive index 1.59 Sample specific gravity 1.05 (in terms of spherical particles) Solvent refractive index 1.33 Solvent viscosity 0.797 (30 ° C), 1.002 (20 ° C) 0-point adjustment Ion-exchanged water was added to the measurement cell for preparation.
- Resin particle 1 for core part having a multilayer structure was produced through first-stage polymerization, second-stage polymerization and third-stage polymerization shown below.
- an aqueous solution in which 2 parts by mass of magnesium chloride hexahydrate was dissolved in 1000 parts by mass of ion-exchanged water was added at 30 ° C. over 10 minutes with stirring. After standing for 3 minutes, the heating was started, and the system was heated to 65 ° C. over 60 minutes to associate the particles. In this state, the particle size of the associated particles was measured by “Multisizer 3 (manufactured by Beckman Coulter)”, and when the volume-based median diameter of the associated particles reached 5.5 ⁇ m, 40.2 parts by mass of sodium chloride was added to ion-exchanged water. The association was stopped by adding an aqueous solution dissolved in 1000 parts by mass.
- the core temperature 1 was further produced by continuing the fusion by heating and stirring for 1 hour at a liquid temperature of 70 ° C. as an aging treatment.
- the average circularity of “core part 1” was measured by “FPIA2100 (manufactured by Sysmex Corporation)” and found to be 0.92.
- Toner 1 was produced by adding the following external additive to the produced “colored particles 1” and performing external addition treatment with a Henschel mixer (Mitsui Miike Mining Co., Ltd.).
- Silica treated with hexamethylsilazane (average primary particle size 12 nm) 0.6 part by mass n-octylsilane-treated titanium dioxide (average primary particle size 24 nm) 0.8 parts by mass
- the external addition treatment by the Henschel mixer was performed under the conditions of a peripheral speed of the stirring blade of 35 m / second, a treatment temperature of 35 ° C., and a treatment time of 15 minutes.
- Table 2 shows the configurations of “Toners 1 to 23” produced by the above procedure.
- the “alcohol ratio (mol%)” in the table represents the amount of aliphatic alcohol added to the toner as a ratio to the fatty acid ester wax.
- Evaluation 1 Evaluation of heat-resistant storage stability of toner
- the heat resistant storage property of the toner was evaluated by the following procedure. First, 0.5 g of each toner is put into a 10 ml glass bottle having an inner diameter of 21 mm, the lid is closed, and the mixture is shaken 600 times with a tap denser “KYT-2000” (manufactured by Seishin Enterprise Co., Ltd.). And left in an environment with a humidity of 35% RH for 2 hours.
- KYT-2000 manufactured by Seishin Enterprise Co., Ltd.
- the toner was placed on a 48 mesh (aperture 350 ⁇ m) sieve so as not to be crushed, set in a “powder tester (manufactured by Hosokawa Micron)”, and fixed with a pressing bar and a knob nut.
- the above-mentioned “powder tester” was adjusted to a vibration intensity of 1 mm in feed width, and vibration was applied for 10 seconds. Thereafter, the amount of toner remaining on the sieve was measured, and the ratio of the remaining toner was calculated to determine the toner aggregation rate (mass%). This was evaluated as heat resistant storage stability.
- ⁇ Fixing performance evaluation> Using the digital copier remodeling machine, development was performed on the transfer paper under the condition that the toner adhesion amount was 11 mg / cm 2 to form a toner image.
- the transfer paper on which the toner image was formed was subjected to a fixing process by changing the temperature of the fixing heat roller in the range of 120 ° C. to 210 ° C. in increments of 5 ° C. in an environment of temperature 20 ° C. and humidity 50% RH.
- the image portion of the transfer paper after the fixing process is folded using a folding machine, air of 0.35 MPa is blown to the folded portion, and the state of the image of the folded portion is evaluated based on the following evaluation criteria. did.
- the evaluation is based on the following five ranks, and the fixing temperature at rank 3 is defined as the lower limit fixing temperature. Those having a lower limit fixing temperature of 150 ° C. or lower were regarded as acceptable. That is, Rank 5: No folds Rank 4: Some peeling is observed according to some folds, but there is no problem Rank 3: Thin linear peeling is observed according to the folds, but there is no practical problem Rank 2: Folding As a result, thick peeling was observed and there was a problem in practical use. Rank 1: Large peeling occurred on the image.
- Photoconductor 2 Charging means 3 Image exposure means 4 (4Y, 4M, 4C, 4Bk) Developing device (developing means) 5 (5Y, 5M, 5C, 5Bk) Primary transfer means (primary transfer roller) 6 (6Y, 6M, 6C, 6Bk) Cleaning device (cleaning means) 10 (10Y, 10M, 10C, 10Bk), C Image forming section 50 Fixing means 70 (Endless belt-like) Intermediate transfer body A Image reading section B Image processing section D Transfer paper transport section P Transfer material (transfer paper, recording member)
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Abstract
Description
請求項1に記載の発明は、
『少なくとも結着樹脂、着色剤、及び、ワックスを含有してなるトナーであって、
水酸基を有する脂肪酸エステルワックスと脂肪族アルコールを含有するものであることを特徴とするトナー。』というものである。
『前記脂肪族アルコールは、炭素原子数が10以上40以下のものであることを特徴とする請求項1に記載のトナー。』というものである。
『前記脂肪族アルコールが、前記水酸基を有する脂肪酸エステルワックスに対して3モル%以上80モル%以下含有されるものであることを特徴とする請求項1または2に記載のトナー。』というものである。
『請求項1~3の何れか1項に記載のトナーを含有してなることを特徴とする現像剤。』というものである。
『少なくとも結着樹脂、着色剤、及び、ワックスを含有してなるトナーの製造方法であって、
少なくとも、水酸基を有する脂肪酸エステルワックスと脂肪族アルコールを含有した重合性単量体を重合して前記結着樹脂を構成する樹脂粒子を形成する工程と、前記樹脂粒子と着色剤粒子とを凝集、融着させる工程と、を経て前記トナーを作製することを特徴とするトナーの製造方法。』というものである。
『少なくとも結着樹脂、着色剤、及び、ワックスを含有してなるトナーの製造方法であって、
少なくとも、重合性単量体を重合して形成された前記結着樹脂を構成する樹脂粒子と、水酸基を有する脂肪酸エステルワックスと脂肪族アルコールの混合物粒子と、着色剤粒子とを凝集、融着させる工程を経て前記トナーを作製することを特徴とするトナーの製造方法。』というものである。
(1)ポリオレフィン系ワックス
ポリエチレンワックス、ポリプロピレンワックス等
(2)長鎖炭化水素系ワックス
パラフィンワックス、サゾールワックス等
(3)ジアルキルケトン系ワックス
ジステアリルケトン等
(5)アミド系ワックス
エチレンジアミンジベヘニルアミド、トリメリット酸トリステアリルアミド等
これらワックスのトナー中への添加方法としては、たとえば、前述した水酸基を有する脂肪酸エステルワックスと脂肪族アルコールを含有させるときに用いた方法が挙げられる。具体的には、結着樹脂を形成する重合性単量体溶液中に溶解させる方法がある。また、溶融温度以上にワックスを加熱しておき、同様に加熱した界面活性剤水溶液に添加して、超音波や高速撹拌などの分散方法により微粒子化しておく。この微粒子を樹脂粒子や着色剤粒子とともに凝集させて凝集粒子を融着させる方法もある。
(2)着色剤粒子分散液の作製工程
(3)樹脂粒子等の凝集・融着工程
(4)熟成工程
(5)冷却工程
(6)洗浄工程
(7)乾燥工程
(8)外添剤処理工程
以下、各工程について説明する。
この工程は樹脂粒子を形成する重合性単量体を水系媒体中に投入して重合を行うことにより100nm程度の大きさの樹脂粒子を形成する工程である。なお、本発明では水酸基を有する脂肪酸エステルワックスと脂肪族アルコールを存在下で重合性単量体の重合を行うことにより、水酸基を有する脂肪酸エステルワックスと脂肪族アルコールを含有した樹脂粒子を作製することができる。
前述した手順により、水系媒体中に着色剤を分散させて、着色剤粒子分散液を作製する工程である。特に、本発明では、数平均1次粒径が30nm~200nmの着色剤を用いて着色剤粒子分散液を作製するものである。そして、当該着色剤粒子分散液を用いてトナーを作製することにより、トナー粒子中における着色剤の数平均粒径が数平均1次粒径の1.1倍~2.5倍になるものである。
この工程は、水系媒体中で樹脂粒子と着色剤粒子を凝集させて粒子を形成し、凝集により形成した粒子を融着させてトナーの母体粒子、すなわち、外添処理をする前のトナーの母体となる粒子(以下、着色粒子ともいう)を作製する工程である。つまり、この工程は、本発明でいう「樹脂粒子を凝集させる工程」に該当するものである。
この工程は、上記凝集・融着工程に引き続き、反応系を加熱処理することにより着色粒子の形状を所望の平均円形度になるまで熟成するいわゆる形状制御工程とも呼ばれる工程である。熟成工程では、前述の凝集・融着工程で形成された着色粒子を構成する結着樹脂のガラス転移温度以上に加熱することにより、着色粒子の形状制御が行える。
この工程は、前記着色粒子の分散液を冷却処理(急冷処理)する工程である。冷却処理条件としては、1~20℃/分の冷却速度で冷却する。冷却処理方法としては特に限定されるものではなく、反応容器の外部より冷媒を導入して冷却する方法や、冷水を直接反応系に投入して冷却する方法を例示することができる。
この工程は、上記工程で所定温度まで冷却された着色粒子分散液から着色粒子を固液分離する工程と、固液分離されたウェット状態の着色粒子表面より界面活性剤や凝集剤等の付着物を除去する洗浄工程からなる。
この工程は、洗浄処理された着色粒子を乾燥処理し、乾燥された着色粒子を得る工程である。この工程で使用される乾燥機としては、スプレードライヤ、真空凍結乾燥機、減圧乾燥機などを挙げることができ、静置棚乾燥機、移動式棚乾燥機、流動層乾燥機、回転式乾燥機、撹拌式乾燥機等を使用することが好ましい。
この工程は、乾燥処理した着色粒子に外添剤や滑剤を添加して画像形成に供することが可能なトナー粒子にする工程である。なお、前記乾燥工程を経た着色粒子をそのままトナー粒子として使用するケースもあるが、外添剤を添加することによりトナーの帯電性や流動性、クリーニング性を向上させることができる。これら外添剤には、公知の無機微粒子や有機微粒子、脂肪族金属塩を使用することができ、その添加量はトナー全体に対して0.1~10.0質量%、好ましくは0.5~4.0質量%である。また、外添剤は種々のものを組み合わせて添加することができる。なお、外添剤を添加する際に使用する混合装置としては、たとえば、タービュラミキサ、ヘンシェルミキサ、ナウターミキサ、V型混合機、コーヒーミル等の公知の機械式の混合装置がある。
(1)スチレンあるいはスチレン誘導体
スチレン、o-メチルスチレン、m-メチルスチレン、p-メチルスチレン、α-メチルスチレン、p-フェニルスチレン、p-エチルスチレン、2,4-ジメチルスチレン、p-tert-ブチルスチレン、p-n-ヘキシルスチレン、p-n-オクチルスチレン、p-n-ノニルスチレン、p-n-デシルスチレン、p-n-ドデシルスチレン等
(2)メタクリル酸エステル誘導体
メタクリル酸メチル、メタクリル酸エチル、メタクリル酸n-ブチル、メタクリル酸イソプロピル、メタクリル酸イソブチル、メタクリル酸t-ブチル、メタクリル酸n-オクチル、メタクリル酸2-エチルヘキシル、メタクリル酸ステアリル、メタクリル酸ラウリル、メタクリル酸フェニル、メタクリル酸ジエチルアミノエチル、メタクリル酸ジメチルアミノエチル等
(3)アクリル酸エステル誘導体
アクリル酸メチル、アクリル酸エチル、アクリル酸イソプロピル、アクリル酸n-ブチル、アクリル酸t-ブチル、アクリル酸イソブチル、アクリル酸n-オクチル、アクリル酸2-エチルヘキシル、アクリル酸ステアリル、アクリル酸ラウリル、アクリル酸フェニル等
(4)オレフィン類
エチレン、プロピレン、イソブチレン等
(5)ビニルエステル類
プロピオン酸ビニル、酢酸ビニル、ベンゾエ酸ビニル等
(6)ビニルエーテル類
ビニルメチルエーテル、ビニルエチルエーテル等
(7)ビニルケトン類
ビニルメチルケトン、ビニルエチルケトン、ビニルヘキシルケトン等
(8)N-ビニル化合物類
N-ビニルカルバゾール、N-ビニルインドール、N-ビニルピロリドン等
(9)その他
ビニルナフタレン、ビニルピリジン等のビニル化合物類、アクリロニトリル、メタクリロニトリル、アクリルアミド等のアクリル酸あるいはメタクリル酸誘導体等。
(1)アゾ系またはジアゾ系重合開始剤
2,2′-アゾビス-(2,4-ジメチルバレロニトリル)、2,2′-アゾビスイソブチロニトリル、1,1′-アゾビス(シクロヘキサン-1-カルボニトリル)、2,2′-アゾビス-4-メトキシ-2,4-ジメチルバレロニトリル、アゾビスイソブチロニトリル等
(2)過酸化物系重合開始剤
ベンゾイルパーオキサイド、メチルエチルケトンペルオキサイド、ジイソプロピルペルオキシカーボネート、クメンヒドロペルオキサイド、t-ブチルヒドロペルオキサイド、ジ-t-ブチルペルオキサイド、ジクミルペルオキサイド、2,4-ジクロロベンゾイルペルオキサイド、ラウロイルペルオキサイド、2,2-ビス-(4,4-t-ブチルペルオキシシクロヘキシル)プロパン、トリス-(t-ブチルペルオキシ)トリアジン等
また、乳化重合法で樹脂粒子を形成する場合は水溶性ラジカル重合開始剤が使用可能である。水溶性重合開始剤としては、過硫酸カリウム、過硫酸アンモニウム等の過硫酸塩、アゾビスアミノジプロパン酢酸塩、アゾビスシアノ吉草酸及びその塩、過酸化水素等がある。
(1)電子写真感光体表面に潜像を形成する潜像形成工程
(2)電子写真感光体表面に形成された静電潜像を現像剤担持体に担持させた現像剤で現像してトナー画像を形成する現像工程
(3)トナー画像を転写体表面に転写する転写工程
(4)転写体表面に転写させたトナー画像を熱定着する定着工程。
(1)「脂肪酸エステルワックス1~4」の合成
撹拌装置、温度センサ、冷却管、窒素導入管を備えた反応容器に、クエン酸155部、ドコサノール790部、酸触媒としてメタンスルホン酸を投入し、窒素気流下で温度を120℃にして反応水を留去しながら3時間反応処理を行った。その後、水酸化ナトリウム水溶液と過酸化水素水を添加した後、ろ過を行って「脂肪酸エステルワックス1」を合成した。
前記「脂肪酸エステルワックス1」の合成で、クエン酸155部に代えてベヘン酸490部を用い、ドコサノールの添加量を470部に変更した。また、反応温度を220℃、反応時間を15時間にした。他は同様の条件で処理を行うことにより「脂肪酸エステルワックス5」を合成した。また、前記「脂肪酸エステルワックス5」の合成で、ベヘン酸の添加量を851部に変更し、ドコサノール470部に代えてペンタエリスリトール85部を用いた他は同様の手順で「脂肪酸エステルワックス6」を合成した。
2-1.「トナー1」の作製
下記手順により、コアシェル構造を有する「トナー1」の母体粒子となる「着色粒子1」を作製した。
n-ドデシル硫酸ナトリウム11.5質量部をイオン交換水160質量部に投入し、溶解、撹拌して界面活性剤水溶液を調製した。この界面活性剤水溶液中に、C.I.ピグメントブルー15:3を25質量部徐々に添加し、「クリアミックスWモーションCLM-0.8(エムテクニック社製)」を用いて分散処理を行って、「着色剤粒子分散液C」を調製した。
サンプル比重 1.05 (球状粒子換算)
溶媒屈折率 1.33
溶媒粘度 0.797(30℃)、1.002(20℃)
0点調整 測定セルにイオン交換水を投入し調製した。
「脂肪酸エステルワックス1」を21質量部、「ドコサノール」2.5質量部の混合物を調製した後、前記「着色剤粒子分散液C」の調製と同様の手順により「脂肪酸エステルワックス1及びドコサノール混合物粒子分散液D」を調製した。具体的には、前記「C.I.ピグメントブルー15:3」に代えて前記混合物25質量部を前記界面活性剤水溶液中に徐々に添加し、「クリアミックスWモーションCLM-0.8(エムテクニック社製)」を用いて分散処理を行って調製した。前記「脂肪酸エステルワックス1及びドコサノール混合物粒子分散液D」中の「粒子D」は体積基準メディアン径が98nmであった。なお、体積基準メディアン径は上記測定条件下で得られたものである。
下記に示す第1段重合、第2段重合及び第3段重合を経て多層構造を有する「コア部用樹脂粒子1」を作製した。
撹拌装置、温度センサ、冷却管、窒素導入装置を取り付けた反応容器に下記(構造式1)に示すアニオン系界面活性剤4質量部をイオン交換水3040質量部とともに投入し、界面活性剤水溶液を調製した。
上記界面活性剤水溶液中に、過硫酸カリウム(KPS)10質量部をイオン交換水400質量部に溶解させた重合開始剤溶液を添加し、温度を75℃に昇温させた後、下記化合物よりなる単量体混合液を1時間かけて反応容器中に滴下した。
n-ブチルアクリレート 200質量部
メタクリル酸 68質量部
n-オクチルメルカプタン 16.4質量部
上記単量体混合液を滴下後、この系を75℃にて2時間にわたり加熱、撹拌することにより重合(第1段重合)を行って「樹脂粒子分散液A1」を作製した。第1段重合で作製した「樹脂粒子分散液A1」中の「樹脂粒子A1」の重量平均分子量は16,500だった。
撹拌装置を取り付けたフラスコ内に下記化合物からなる単量体混合液を投入した。続いて、前述の「脂肪族エステルワックス1」を84質量部と炭素原子数が22の脂肪族アルコールである「ドコサノール」を9.8質量部添加して84℃に加温して溶解させた。この様にして単量体溶液を調製した。なお、前記「ドコサノール」の添加量は、前記「脂肪酸エステルワックス1」に対して39.9モル%となるものである。
n-ブチルアクリレート 123.7質量部
メタクリル酸 24.5質量部
n-オクチルメルカプタン 3.48質量部
一方、前記アニオン界面活性剤3質量部をイオン交換水1560質量部に溶解させた界面活性剤水溶液を調製して80℃に加熱した。この界面活性剤水溶液中に前記「樹脂粒子A1」を32.8質量部(固形分換算)添加し、さらに、前記「脂肪酸エステルワックス1」と「ドコサノール」を含有する単量体溶液を添加した。その後、循環経路を有する機械式分散機「クレアミックス(エムテクニック社製)」で30分間混合分散処理を行い、分散粒子径が340nmの乳化粒子を含有する乳化粒子分散液を調製した。
上記第2段重合で得られた「樹脂粒子分散液A2」に、過硫酸カリウム3.19質量部をイオン交換水130質量部に溶解させた重合開始剤溶液を添加し、80℃の温度条件下で、下記化合物からなる単量体混合液を1時間かけて滴下した。
n-ブチルアクリレート 83.4質量部
n-オクチルメルカプタン 4.16質量部
滴下終了後、2時間にわたり加熱撹拌を行って重合(第3段重合)を行い、重合終了後、28℃に冷却して「コア部用樹脂粒子分散液1」を作製した。第3段重合で作製した「コア部用樹脂粒子分散液1」中の「コア部用樹脂粒子1」の重量平均分子量は26,800であった。
前記「コア部用樹脂粒子1」の作製における第1段重合で使用された単量体混合液を以下のものに変更した以外は同様にして、重合反応及び反応後の処理を行って「シェル用樹脂粒子1」を作製した。
n-ブチルアクリレート 33質量部
メタクリル酸 8質量部
n-オクチルメルカプタン 4.5質量部
(5)「トナー1」の作製
下記の手順により、トナーの母体粒子である「着色粒子1」を作製した。
撹拌装置、温度センサ、冷却管、窒素導入装置を取り付けた反応容器に、
コア部用樹脂粒子1 420質量部(固形分換算)
イオン交換水 900質量部
着色剤粒子1 200質量部(固形分換算)
を投入、撹拌した。反応容器内の温度を30℃に調整後、5モル/リットルの水酸化ナトリウム水溶液を添加して、pHを10に調整した。
次に、上記液を65℃にして「シェル用樹脂粒子1」を210質量部(固形分換算)添加し、さらに、塩化マグネシウム・6水和物2質量部をイオン交換水1000質量部に溶解した水溶液を10分間かけて添加した後、70℃まで昇温させて1時間にわたり撹拌を行った。この様にして、「コア部1」の表面に「シェル用樹脂粒子1」を融着させた後、75℃で20分間熟成処理を行ってシェルを形成した。
作製した「着色粒子1」に下記外添剤を添加して、ヘンシェルミキサ(三井三池鉱業社製)にて外添処理を行うことにより「トナー1」を作製した。
0.6質量部
n-オクチルシラン処理した二酸化チタン(平均一次粒径24nm)
0.8質量部
なお、ヘンシェルミキサによる外添処理は、撹拌羽根の周速35m/秒、処理温度35℃、処理時間15分の条件の下で行った。
(1)「トナー2~5」の作製
前記「トナー1」の作製で前記「コア部用樹脂粒子1」の作製における第2段重合で使用した「脂肪酸エステルワックス1」及び「ドコサノール」の添加量を表2に示す様に変更した他は同様の手順で「トナー2~5」を作製した。
前記「トナー1」の作製で前記「コア部用樹脂粒子1」の作製における第2段重合で使用した「ドコサノール」9.8質量部に代えて、表2に示す様に、アルコール化合物の種類と添加量を変更した他は同様の手順で「トナー6~12」を作製した。なお、「トナー10」を作製する際に用いたアルコール化合物(※)は下記に示す構造の炭素原子数40の脂肪族アルコールである。また、「トナー12」を作製する際に用いたアルコール化合物(※※)は下記に示す構造の炭素原子数42の脂肪族アルコールである。
前記「トナー1」の作製における第2段重合で使用した「脂肪酸エステルワックス1」84.0質量部に代えて、表2に示す様に、脂肪酸エステル化合物の種類と添加量を変更した他は同様の手順で「トナー13~21」を作製した。また、前記「トナー1」の作製における第2段重合で、「ドコサノール」を添加せず、「脂肪酸エステルワックス1」を90.0質量部に添加するものに変更した他は同様の手順で「トナー22」を作製した。
前記「トナー1」を作製する際の第2段重合で「脂肪族エステルワックス1」と「ドコサノール」を添加しないで樹脂粒子分散液の作製を行った他は同様の手順により、で樹脂粒子分散液を作製し、「コア部用樹脂粒子分散液2」を作製した。
コア部用樹脂粒子2 420質量部(固形分換算)
イオン交換水 900質量部
着色剤粒子C 200質量部(固形分換算)
脂肪酸エステルワックス1及びドコサノール混合物粒子D
200質量部(固形分換算)
を投入、撹拌した他は同様の手順で「トナー23」を作製した。上記手順で作製した「トナー23」では、「脂肪酸エステルワックス1」及び「ドコサノール」の含有量を前記「トナー1」と同量になる様にした。
上記手順で作製した「トナー1~23」について下記評価を行った。ここで、本発明の構成を有する「トナー1~15、23」を「実施例1~16」、本発明の構成を満たしていない「トナー16~22」を「比較例1~7」とした。
トナーの耐熱保管性を以下の手順で評価した。先ず、前記各トナー0.5gをそれぞれ内径21mmの10mlガラス瓶に取り、蓋を閉めてタップデンサー「KYT-2000(セイシン企業社製)」で600回振とうした後、蓋を取り、温度57℃、湿度35%RHの環境下に2時間放置した。次いで、前記トナーを48メッシュ(目開き350μm)の篩上に解砕しない様に載せ、「パウダーテスター(ホソカワミクロン社製)」にセットし、押さえバー、ノブナットで固定した。
トナー凝集率(質量%)
=〔(篩上の残存トナー質量(g))/0.5(g)〕×100
耐熱保管性の評価は以下の基準に基づいて行った。すなわち、
◎:トナー行収率が15質量%未満(耐熱保管性が極めて良好)
○:トナー凝集率が15質量%以上20質量%以下(耐熱保管性が良好)
×:トナー凝集率が20質量%を超える(トナーの耐熱保管性が悪く使用不可)
上記基準のうち、◎と○を合格とした。
(1)「現像剤1~23」の調製
前記「トナー1~23」の各々に、スチレンアクリル樹脂を被覆した体積平均粒径35μmのフェライトキャリアを混合し、トナー濃度が8%の「現像剤1~23」を調製した。
前記「現像剤1~23」を、市販のデジタル複写機「bizhub PRO C500(コニカミノルタビジネステクノロジーズ(株)製)」の定着装置を改造した評価機に搭載して、タッキング性能と定着性能を評価した。
タッキングの評価は、上記「現像剤1~23」を用いて上記デジタル複写機改造機より出力した未定着の画像2枚を、定着温度が150℃の外部定着装置により定着した。定着を行った2枚の画像は、画像部と非画像部及び画像部同士が重なり合う様に向かい合わせに重ね、重ねた部分に対し80g/cm2の荷重が加わる様に錘を載せた。この状態で温度60℃、湿度50%RHの恒温恒湿槽内に3日間放置した。放置後、重ねた2枚の定着画像の重ね合わせた部分について画像不良の発生の有無を以下の基準に基づいて評価した。すなわち、
優良:トナーの移行に起因する画像不良の発生がなく、また、重ねた画像を離す際に軽微な貼り付きも見られず、全く問題なしと評価したもの
良好:重ねた画像を離す際にジッピング音がするが、トナーの移行に起因する画像不良の発生がなく、問題なしと評価したもの
実用可:重ねた画像を離したとき、双方の画像に光沢ムラの発生がみられたが、画像不良の発生がほとんどみられないと評価したもの
不良:重ねた画像を離すと、非画像部に画像転写の発生がみられ、接触画像間でトナーの移行による剥離も認められたもので、実用上使用不可と評価したもの
上記基準のうち、「優良」、「良好」、「実用可」を合格とした。
前記デジタル複写機改造機を用い、転写紙上にトナー付着量が11mg/cm2となる条件で現像を行ってトナー画像を形成した。トナー画像を形成した転写紙を温度20℃、湿度50%RHの環境下で定着ヒートローラの温度を120℃~210℃の範囲で5℃刻みで変化させて定着処理を行った。
ランク5:折れ目が全くなし
ランク4:一部折れ目にしたがって若干の剥離がみられるが問題なし
ランク3:折れ目にしたがって細い線状剥離がみられるが実用上問題なし
ランク2:折れ目にしたがって太い剥離が認められ実用上問題あり
ランク1:画像上に大きな剥離が発生している。
2 帯電手段
3 像露光手段
4(4Y、4M、4C、4Bk) 現像装置(現像手段)
5(5Y、5M、5C、5Bk) 1次転写手段(1次転写ローラ)
6(6Y、6M、6C、6Bk) クリーニング装置(クリーニング手段)
10(10Y、10M、10C、10Bk)、C 画像形成部
50 定着手段
70 (無端ベルト状)中間転写体
A 画像読取部
B 画像処理部
D 転写紙搬送部
P 転写材(転写紙、記録部材)
Claims (6)
- 少なくとも結着樹脂、着色剤及びワックスを含有してなるトナーであって、
水酸基を有する脂肪酸エステルワックスと脂肪族アルコールを含有するものであることを特徴とするトナー。 - 前記脂肪族アルコールは、炭素原子数が10以上40以下のものであることを特徴とする請求項1に記載のトナー。
- 前記脂肪族アルコールが、前記水酸基を有する脂肪酸エステルワックスに対して3モル%以上80モル%以下含有されるものであることを特徴とする請求項1または2に記載のトナー。
- 請求項1~3の何れか1項に記載のトナーを含有してなることを特徴とする現像剤。
- 少なくとも結着樹脂、着色剤、及び、ワックスを含有してなるトナーの製造方法であって、
少なくとも、
水酸基を有する脂肪酸エステルワックスと脂肪族アルコールを含有した重合性単量体を重合して前記結着樹脂を構成する樹脂粒子を形成する工程と、
前記樹脂粒子と着色剤粒子とを凝集、融着させる工程と、を経て前記トナーを作製することを特徴とするトナーの製造方法。 - 少なくとも結着樹脂、着色剤、及び、ワックスを含有してなるトナーの製造方法であって、
少なくとも、重合性単量体を重合して形成された前記結着樹脂を構成する樹脂粒子と、水酸基を有する脂肪酸エステルワックスと脂肪族アルコールの混合物粒子と、着色剤粒子とを凝集、融着させる工程を経て前記トナーを作製することを特徴とするトナーの製造方法。
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US12/810,355 US8557492B2 (en) | 2008-09-19 | 2009-09-11 | Toner, developer, and method of manufacturing toner |
JP2010510005A JP5251975B2 (ja) | 2008-09-19 | 2009-09-11 | トナー、現像剤、トナーの製造方法 |
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JP5251975B2 (ja) | 2013-07-31 |
JPWO2010032686A1 (ja) | 2012-02-09 |
US8557492B2 (en) | 2013-10-15 |
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