WO2011078224A1 - Liant pour toner, et toner contenant celui-ci - Google Patents

Liant pour toner, et toner contenant celui-ci Download PDF

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Publication number
WO2011078224A1
WO2011078224A1 PCT/JP2010/073130 JP2010073130W WO2011078224A1 WO 2011078224 A1 WO2011078224 A1 WO 2011078224A1 JP 2010073130 W JP2010073130 W JP 2010073130W WO 2011078224 A1 WO2011078224 A1 WO 2011078224A1
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Prior art keywords
toner
binder
particles
parts
temperature
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PCT/JP2010/073130
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English (en)
Japanese (ja)
Inventor
武 渡邉
伊藤　俊之
達也 阿部
信弘 松田
石川　理
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Jsr株式会社
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Priority to JP2011547593A priority Critical patent/JPWO2011078224A1/ja
Publication of WO2011078224A1 publication Critical patent/WO2011078224A1/fr

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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
    • 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
    • G03G9/08784—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
    • 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
    • G03G9/09783—Organo-metallic compounds
    • G03G9/09791—Metallic soaps of higher carboxylic acids

Definitions

  • the present invention relates to toner particles that can be used in an electrophotographic apparatus (image forming apparatus) using an electrophotographic process such as a copying machine, a printer, and a facsimile machine, and a toner containing the toner particles.
  • an electrostatic latent image formed in an image forming apparatus such as an electrophotographic apparatus or an electrostatic recording apparatus is first developed with toner, and then the formed toner image is transferred to a transfer material such as paper as necessary. After being transferred to the top, it is fixed by heating, pressing, or the like.
  • electrophotographic copying machines, printers, and the like are required to clearly perform color copying and color printing by electrophotography.
  • a pulverized toner obtained by melting, pulverizing, and classifying a resin containing a colorant or the like has been mainstream, but particle size control is easy, classification and the like.
  • the polymerization method toner which does not go through the complicated manufacturing process has been attracting attention.
  • the particle diameter of this toner is about several ⁇ m.
  • it is attempted to further reduce the particle diameter and increase the sharpness of printing the cleaning performance in the process of scraping off the toner adhering to the developing roll with a doctor blade is improved. Deteriorate.
  • a polymer obtained by polymerizing a monomer composition capable of forming a polymer having a glass transition temperature of 70 ° C. or lower in the presence of a dispersant containing a colloid of a poorly water-soluble metal hydroxide as the toner is disclosed, which contains polymer particles obtained by suspension polymerization of a hydrophilic macromonomer having a glass transition temperature higher than the glass transition temperature of the coalescence and a crosslinkable monomer (for example, Patent Document 1).
  • Patent Document 1 contains polymer particles obtained by suspension polymerization of a hydrophilic macromonomer having a glass transition temperature higher than the glass transition temperature of the coalescence and a crosslinkable monomer.
  • An electrophotographic image-receiving material provided with a heat insulating layer containing at least one hollow particle on a support and a toner receiving layer containing at least one thermoplastic resin and a binder on the heat insulating layer.
  • the softening point of the at least one hollow particle is 20 ° C. to 70 ° C. lower than the surface temperature of the fixing roller at the time of fixing the toner image, and the softening point of the hollow particle is 130 ° C. or higher and 180 ° C. or lower.
  • a method of improving glossiness, density, and image clarity by using an image receiving material is disclosed (for example, Patent Document 2).
  • Patent Document 2 since the softening point of the hollow particle layer of the toner receiving phase is high and it does not fundamentally contribute to the fixing property of the binder resin for toner, it does not lead to improvement of the low temperature fixing property.
  • a toner comprising a binder resin having a high porosity can reduce the amount of toner applied to a substrate in electrophotography (EP).
  • the porous binder resin disclosed here is a particle
  • the use of particles with high porosity reduces the amount of toner, but such a large particle size binder is not suitable for producing toner particles with a small particle size, and can be obtained by the method disclosed in Patent Document 3. Since the particles have fine pores randomly present in the particles, it is difficult to adjust the uniformity of the voids when the toner particles are formed. Such non-uniformity of voids adversely affects image reproducibility when using the obtained toner.
  • the present invention provides a toner binder for use in a toner that is suitable for high-speed printing due to its high print density after toner fixing and excellent low-temperature fixability, and further a toner using the same. It is to provide.
  • the present invention relates to (B) a binder for toner comprising hollow resin particles having a number average particle diameter of 100 to 1500 nm in which at least one void is formed inside the particles.
  • the present invention relates to a toner including the toner binder and a colorant.
  • a toner binder used for a toner that is suitable for high-speed printing due to a high print density after toner fixing and excellent low-temperature fixability, and further, a toner using the same Can be provided.
  • FIG. 1 is a diagram showing an example in which the particle (B) is observed with a transmission electron microscope and the particle diameter of each particle is measured.
  • FIG. 2 is a diagram showing a softening temperature (Ts), an outflow start temperature (Tfb), and an end temperature (Tend) in a general chart obtained from a flow tester.
  • FIG. 3 is a diagram showing “T1 / 2 melting temperature” and “tilt from T1 / 2 to ⁇ 2 mm” in a general chart obtained from a flow tester.
  • the binder for toner of the present invention includes (B) hollow resin particles having a number average particle diameter of 100 to 1500 nm in which at least one void is formed inside the particles (hereinafter, sometimes simply referred to as “(B)”). And a toner binder.
  • (B) hollow resin particles in which at least one void is formed inside the particles will be described.
  • (B) is one in which at least one void is formed inside the particle.
  • (B) is caused by at least one void formed inside the particle, and from the difference in refractive index between the shell polymer of (B) (portion other than the void of the hollow resin particle) and the void portion, (B) Can be scattered.
  • the toner containing (B) improves the concealability of the base (paper, colored paper) when printed out, and improves the color of the pigment. Therefore, (B) is useful as a binder for toner.
  • the concealment property specifically refers to the property that coloring is good even when printed on black paper, and there is little show-back even when printed on white paper. If the concealing property is excellent, there is an advantage that it is difficult to be influenced by the color of the ground due to the above properties.
  • the toner containing (B) has a smaller volume of resin compared to the toner containing no (B) due to the fact that (B) has at least one void formed inside the particles, The amount of heat required for image fixing can be reduced. Therefore, (B) is also useful as a binder for toner in this respect.
  • the glass transition temperature (Tg) of (B) is not particularly specified, but a glass transition temperature of 50 ° C. or higher can be used. 50 ° C to 130 ° C is preferable, and 60 ° C to 120 ° C is more preferable.
  • (B) is used for a toner, it is preferable that it is appropriately deformed by heat in consideration of the above-described action. If it is less than 50 ° C., it may be too crushed during thermal transfer. On the other hand, when it exceeds 130 ° C., it may be hardly crushed during thermal transfer.
  • the method for measuring the glass transition temperature (Tg) is not particularly specified, but can be measured, for example, using a differential scanning calorimeter according to the ASTM method.
  • the average particle size of (B) is a number average particle size of 100 nm to 1500 nm.
  • the thickness is preferably 150 to 1300 nm, more preferably 200 to 1200 nm. If it is less than 100 nm, the production may be difficult. In addition, since the volume of the gap is relatively small, the above effect may be small. On the other hand, when the thickness exceeds 1500 nm, the number of manufacturing steps increases, and productivity may decrease. Moreover, since the particle
  • the method for measuring the average particle size is not particularly specified, but for example, in order to obtain the porosity of (B) described later, it is usually observed with an electron microscope and can be measured as the number average particle size. Moreover, it can also measure as a weight average particle diameter using a light scattering diffraction particle size measuring device (particle size distribution measuring device).
  • the porosity per particle of (B) is not particularly specified, but 10 to 75% by volume can be used. 15 to 70% by volume is preferred. If it is in this range, the above-mentioned action is effectively exhibited. If it is less than 10% by volume, the low-temperature fixability may be inferior or the fixing density may be inferior. On the other hand, if it exceeds 75% by volume, production for maintaining the porosity may be difficult.
  • the porosity means the ratio of voids to the total volume. The porosity is obtained as “(void diameter 3 / longest particle diameter 3 ) ⁇ 100%”.
  • the void diameter refers to the diameter of the largest void within the observation range.
  • the longest particle diameter is the longest particle diameter in the observation range.
  • the void diameter and the longest particle diameter are usually observed with an electron microscope.
  • gap (B) used by this invention is a single inner hole.
  • the inner pore diameter of the void (B) is not particularly specified, but 1.1 ⁇ m or less is used.
  • the inner pore diameter is an average value of inner diameters of voids (inner holes) in a plurality of particles.
  • the inner diameter of the void (inner hole) refers to the longest diameter among the inner diameters of the void (inner hole) in one particle.
  • they are 0.05 micrometer or more and 1.1 micrometers or less, More preferably, they are 0.06 micrometer or more and 1.0 micrometers or less.
  • the thickness exceeds 1.1 ⁇ m, the number of manufacturing processes increases, and productivity may decrease.
  • the amount of heat per unit volume of (B) is not particularly specified, but 0.7 J / cm 3 or less is used. 0.2 to 0.7 J / cm 3 is preferable. If it is in this range, the above-mentioned action is effectively exhibited. In addition, in the case of less than 0.2 J / cm 3 , it seems necessary to make the porosity of (B) 75% or more, and the production is difficult, and in the case of exceeding 0.7 J / cm 3 , Conversely, it is necessary to make the hollow ratio less than 10%. In (B) used in the present invention, since the amount of heat is small, it is possible to add heat during toner fixing, reduce time, or perform high-speed printing.
  • the method for measuring the amount of heat per unit volume is not particularly specified.
  • the amount of heat per unit volume can be obtained from the reciprocal of this value (heat amount).
  • the weight average molecular weight of (B) is not particularly limited, but those having a weight average molecular weight of 5,000 to 1,000,000 can be used. More preferred is 10,000 to 500,000. If it exists in this range, the said effect
  • the method for measuring the weight average molecular weight is not particularly specified, but can be determined by conversion with standard polystyrene using a gel permeation chromatography (GPC) measuring device.
  • GPC gel permeation chromatography
  • the manufacturing method of (B) is demonstrated.
  • the production method (B) is not particularly specified. Usually, it can manufacture by the following (1) to (3).
  • (1) The monomer is polymerized to produce seed particles serving as a core.
  • the obtained core-shell type resin particles (polymer particles) are neutralized with a base (alkali) to swell the polymer particles, whereby particles having voids in the interior [(B) ] Is manufactured.
  • the produced (B) when the produced (B) is produced by emulsion polymerization using an aqueous medium, it can be used as a binder for toner as an aqueous dispersion (emulsified state). Moreover, (B) can be made into a powder state by performing a drying treatment as necessary. Further, the dried product of (B) and an aqueous medium can be mixed and used as an aqueous dispersion (so-called redispersion). From the viewpoint that productivity is further improved, (B) is preferably prepared by emulsion polymerization using an aqueous medium such as water and adjusted as an aqueous dispersion that does not undergo a drying step. Further, the aqueous dispersion can be dried after adding an additive as required.
  • the monomer constituting the seed particles is not particularly limited as long as the seed particles formed thereby are used in the above (2) to (3). Usually, it is obtained by emulsion polymerization of a monomer composition containing an unsaturated carboxylic acid monomer (I), a nonionic unsaturated monomer (II), and a crosslinkable monomer (III) added as necessary.
  • Examples of the unsaturated carboxylic acid monomer (I) include mono- or dicarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, maleic acid, fumaric acid, itaconic acid, acid anhydrides or monoalkyl esters of dicarboxylic acids, monoamides, and the like. Can be mentioned. These can be used alone or in combination of two or more.
  • the blending amount of the unsaturated carboxylic acid monomer (I) is not particularly limited, but it can be used at 5% by mass or more based on the whole monomer composition for constituting the seed particles. 8 to 90% by mass is preferable, and 10 to 60% by mass is more preferable.
  • the amount of the unsaturated carboxylic acid monomer (I) used is less than 5% by mass, the swelling action due to alkali is low and the formation of voids may be insufficient. When used in toner, the concealability is poor. It may become a thing. On the other hand, if the amount of the unsaturated carboxylic acid monomer (I) used exceeds 90% by mass, the water resistance and alkali resistance tend to be insufficient when used in a toner.
  • Nonionic unsaturated monomers (II) include hydrophilic and hydrophobic monomers.
  • Hydrophilic monomers include acrylic acid or methacrylic acid alkyl esters such as methyl acrylate, ethyl acrylate, butyl acrylate, 2-ethylhexyl acrylate, methyl methacrylate, 2-hydroxyethyl acrylate, and 2-hydroxyethyl methacrylate.
  • Vinyl cyanide compounds such as acrylonitrile and methacrylonitrile: Organic acid vinyls such as vinyl acetate, vinyl propionate and vinyl stearate: Vinyl ethers such as vinyl methyl ether, vinyl ethyl ether, vinyl isobutyl ether and vinyl phenyl ether: Acrylamide and methacrylamide , N-methylol methacrylamide, diacetone acrylamide, ethacrylamide, crotonamide, itaconamide, methyl itaconamide, macro Amide monomers such as inic acid monoamide and ethylene diacrylamide: ⁇ -hydroxyethyl acrylate, ⁇ -hydroxyethyl methacrylate, n-hydroxyethyl acrylamide, 1-hydroxypropyl acrylate, 1-hydroxypropyl methacrylate, hydroxyethyl acrylate, hydroxy Examples of the hydroxyl group-containing monomer such as ethyl methacrylate include glycidyl group-containing monomers such as
  • Hydrophobic monomers include aromatic vinyl compounds such as styrene, ⁇ -methylstyrene, vinyltoluene, paramethylstyrene: butadiene, isoprene, 2-chloro-1,3-butadiene, 1-chloro-1,3-butadiene, etc.
  • Aliphatic conjugated diene compounds ⁇ -olefins such as ethylene, propylene, butylene, 4-methylpentene-1, etc .
  • vinyl halides such as vinyl fluoride and vinyl bromide.
  • the amount of the nonionic unsaturated monomer (II) used is not particularly specified, but is determined by the balance between alkali swellability and hydrophilicity required for the seed particles.
  • the nonionic hydrophilic unsaturated monomer (II) is usually preferably 10 to 95% by weight, 20 to 90% by weight, more preferably 40 to 90% by weight, based on the total amount of monomers for forming seed particles. .
  • crosslinked monomer (III) can be used for a seed particle as needed.
  • the crosslinkable monomer (III) include divinyl monomers such as divinylbenzene, ethylene glycol dimethacrylate, 1,3-butylene glycol dimethacrylate, trimethylolpropane trimethacrylate, and allyl methacrylate, or trivinyl monomers.
  • divinylbenzene, ethylene glycol dimethacrylate and trimethylolpropane trimethacrylate are preferred.
  • the amount of the crosslinkable monomer (III) used is preferably 0.1 to 40 parts by weight, more preferably 0.1 to 20 parts by weight with respect to 100 parts by weight of the monomer composition for forming seed particles. is there.
  • the average particle size of the seed particles is not particularly limited, but usually 10 nm to 1000 nm is used. 50 to 700 nm is preferable.
  • the method for measuring the average particle size is not particularly specified, but for example, it can be measured as a weight average particle size using a light scattering diffraction particle size measuring device (particle size distribution measuring device).
  • the method for producing the seed particles is not particularly limited, but can usually be produced by emulsion polymerization or suspension polymerization.
  • the seed particles particles obtained by one-stage polymerization may be used.
  • the second stage polymerization is performed using the seed particles obtained by the first stage polymerization as the core, Those having a larger particle size can be used as seed particles.
  • seed particles that are produced by repeating polymerization of one stage, two stages, or three or more stages as required can be used.
  • the ratio of the seed particles to the polymer particles is not particularly limited, but is usually 0.5 to 90% by mass. 0.7 to 60% by mass is preferable, and 1 to 40% by mass is more preferable.
  • the ratio is less than 0.5% by mass, the formation of the voids in (B) becomes insufficient, and the concealability may be inferior when used in toner.
  • the ratio of seed particles exceeds 90% by mass, the polymerization stability of the system may be lowered. Further, when used in toner, the blending stability, concealability, water resistance and alkali resistance of the coating film may be inferior.
  • the emulsifier used when producing seed particles and polymer particles (including seed particles and shell polymer) using the seed particles by emulsion polymerization is not particularly specified, and is usually used when producing a resin by emulsion polymerization. Anything is fine.
  • the emulsifier include an anionic surfactant, a nonionic surfactant, a cationic surfactant, an amphoteric surfactant, and an organic suspension protective agent, and particularly anionic surfactants. Surfactants and nonionic surfactants can be preferably used. These emulsifiers can be used alone or in combination of two or more.
  • rosinate such as potassium rosinate and sodium rosinate, sodium oleate, potassium laurate, sodium laurate, sodium stearate, sodium stearate, sodium salt of fatty acid
  • potassium salts, sulfate esters of aliphatic alcohols such as sodium lauryl sulfate, and alkylallyl sulfonic acids such as sodium dodecylbenzene sulfonate
  • nonionic surfactants include polyethylene glycol alkyl esters, alkyl ethers, alkylphenyl ethers, and the like.
  • the polymerization initiator used for producing seed particles and polymer particles (including seed particles and shell polymer) using the seed particles by emulsion polymerization is not particularly specified, and usually when producing a resin by emulsion polymerization. Anything can be used.
  • organic hydroperoxides represented by cumene hydroperoxide, diisopropylbenzene hydroperoxide, paramentane hydroperoxide and the like
  • sugar-containing pyrophosphate formulation sulfoxylate formulation
  • persulfates such as potassium persulfate, sodium persulfate, ammonium persulfate, azobisisobutyronitrile
  • benzoyl Peroxide lauroyl peroxide and the like
  • sulfite such as potassium persulfate, sodium persulfate, ammonium sulfite, azobisisobutyronitrile, benzoyl peroxide as necessary.
  • the polymerization temperature is usually preferably 5 to 95 ° C, particularly preferably 40 to 90 ° C.
  • the various monomers described above can be added to the system in a batch, divided, or continuously dropwise.
  • the polymer particles are obtained by polymerizing monomers using seed particles as a core. Usually, it can manufacture by emulsion polymerization. (Regarding monomers constituting polymer particles) When the polymer particles are produced, the monomer used for the shell is not particularly defined as long as it can create voids by alkali swelling.
  • unsaturated aromatics such as styrene, ⁇ -methylstyrene, halogenated styrene, divinylbenzene; unsaturated esters such as vinyl acetate and vinyl propionate; unsaturated nitriles such as acrylonitrile; methyl acrylate, ethyl acrylate, Unsaturated carboxylic acid alkyl esters such as ethyl methacrylate, butyl acrylate, 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, lauryl acrylate, lauryl methacrylate, ethylene glycol diacrylate, ethylene glycol dimethacrylate; in addition, butadiene, isoprene, acrylic acid, Methacrylic acid, acrylamide, methacrylamide, glycidyl acrylate, glycidyl methacrylate, N-methylol acrylamide, N-methyl Lumpur methacryl
  • polystyrene polymers examples include styrene polymers, acrylic polymers, styrene-acrylonitrile copolymers, styrene-acrylonitrile-butadiene copolymers and the like styrene.
  • styrene polymers acrylic polymers, styrene-acrylonitrile copolymers, styrene-acrylonitrile-butadiene copolymers and the like styrene.
  • -Acrylic copolymers polypropylene resins, polyvinyl chloride resins, polyvinylidene chloride resins, vinyl copolymers, urea formalin resins and the like.
  • styrene-acrylic copolymers are preferably used, but are not particularly limited thereto.
  • a crosslinked hollow particle is also preferably used as (B).
  • the crosslinking type means that the resin constituting the shell of (B) is crosslinked by some method.
  • the resin constituting the shell of (B) is crosslinked by some method.
  • hollow particles mainly composed of a styrene-acrylic copolymer those that are crosslinked with divinylbenzene or the like during particle synthesis, or those that are generally crosslinked with divinylbenzene or the like during particle synthesis. Point to.
  • the polymer particles can generally be produced by a method of making a polymer from monomers, except that seed particles are used as the core. Usually, it can be produced by emulsion polymerization or suspension polymerization. The polymerization reaction may be one-stage or multi-stage.
  • a molecular weight adjusting agent can be added to the seed particles and polymer particles (including seed particles and shell polymers) using the seed particles, if necessary.
  • chain transfer agent There is no restriction
  • chain transfer agents examples include mercaptans having an alkyl group having 1 to 30 carbon atoms such as propyl mercaptan, butyl mercaptan, and t-dodecyl mercaptan, octyl thioglycolate, thioglycolic acid, diphenylsulfuric acid.
  • organic sulfur compounds having 1 to 30 carbon atoms such as id, halogenated hydrocarbons having 1 to 20 carbon atoms such as carbon tetrachloride, carbon tetrabromide and bromotrichloromethane, and ⁇ -methylstyrene dimer Hydrocarbons having an unsaturated group are included.
  • chain transfer agents may be used alone or in combination of two or more.
  • Such a chain transfer agent employs a method of mixing with a monomer, a method of batch charging at an initial stage, a method of sequential addition, a method of changing the introduction rate or its composition continuously or stepwise, etc. be able to.
  • the plasticizer is an optional component, and a plasticizer can be added to the binder of the present invention as necessary.
  • the plasticizer include dibutyl phthalate (dibutyl phthalate), diisooctyl phthalate, dioctyl adipate, tricresyl phosphate, triethyl citrate, octyl alcohol, fatty acid amide, and wax.
  • the plasticizer can be added, for example, after the formation of the polymer particles and before and after the alkali swelling described later.
  • the amount added is not particularly specified, but usually (B) 100 parts by mass (when the toner contains (A), the total amount of (B) and (A) is 100 mass. Per part) is 30 parts by mass or less. 1 to 30 parts by mass is preferable, and 2 to 20 parts by mass is more preferable. If it exceeds 30 parts by mass, the particles tend to thicken and become unstable, which may be undesirable.
  • the wax by adding a wax, it is possible to obtain a toner binder that is more excellent in toner fixing property and toner blocking property.
  • the wax those having a melting point of 50 to 140 ° C. are generally used, but those having a melting point of 70 to 140 ° C. are preferred.
  • the wax used is not particularly limited. For example, (1) hydrocarbon synthetic waxes such as Fischer-Tropsch wax (melting point to 120 ° C.), polyethylene wax (melting point 90 ° C.
  • mineral-derived waxes such as (7) montan wax.
  • the fatty acid amide include hydrin K808 (trade name hydrin K808, manufactured by Chukyo Yushi Co., Ltd., methylol fatty acid amide, melting point 110 ° C.).
  • the fatty acid ester wax include Nopcoat 5400 (trade name Nopcoat 5400, manufactured by San Nopco, fatty acid ester, melting point 55 ° C.).
  • paraffin wax include Cellosol 686 (trade name Cellosol 686, manufactured by Chukyo Yushi Co., Ltd., paraffin type, melting point 54 ° C.).
  • fatty acid amides, fatty acid ester waxes, polyethylene waxes, carnauba waxes and the like are preferable.
  • the content of the wax is not particularly specified, but is 20 parts by mass or less per 100 parts by mass of (B) (when the toner contains (A), the total amount of (B) and (A) is 100 parts by mass). is there. 1 to 20 parts by mass is preferable, and 5 to 15 parts by mass is more preferable. If the wax content exceeds 20 parts by mass, the gloss of the surface after toner fixing may be reduced, or the toner may become brittle and may be damaged or destroyed.
  • the binder for toner of the present invention containing wax exhibits a very sharp heat melting property and a decrease in melting temperature in the flow tester measurement. This is because the addition of wax increases the crystallinity and makes it excellent in sharp melt properties. It can be quickly melted by heating during fixing, and the binder resin can be softened more quickly. Can be improved. This greatly improves the toner fixability during high-speed printing, for example.
  • the alkali-swellable polymer particles obtained in this way are core-shell resin particles and have almost no voids (inner pores) before neutralization with a base. It becomes (B) which has a space
  • emulsion powdering methods can be used, for example, spray drying (135 to 155 ° C.), using a hot air dryer.
  • a tray drying method 50 to 70 ° C.
  • a fluidized bed drying method room temperature to 70 ° C.
  • Multistage polymers comprising a core and a shell swell when they are subjected to a base capable of swelling the core, forming (B).
  • Swelling, or expansion, of the core can include partial integration of the outer periphery of the core into pores of the inner periphery of the shell and / or partial expansion or expansion of the entire shell and particles.
  • Suitable swelling agents are bases that penetrate the shell and swell the core in the presence of a multi-stage emulsion polymer (polymer particles).
  • the base include alkaline compounds of sodium hydroxide, potassium hydroxide, lithium hydroxide, strontium hydroxide, and barium hydroxide.
  • a volatile base such as ammonium hydroxide can also be used.
  • the amount of these bases (alkaline compounds) used is usually such that the pH of water as an aqueous medium is 7.0 to 11.5, preferably 8.0 to 11.0.
  • the temperature during the alkali treatment is usually 20 ° C. to 100 ° C., preferably 30 to 90 ° C., and the alkali treatment time is usually 0.5 to 24 hours, preferably 1.0 to 12 hours.
  • Applicable (B) includes, in addition to the above, an acidic group-containing monomer and a monomer copolymerizable therewith, for example, Japanese Patent Publication No. 7-21011 and Japanese Patent No. 3601215. It can be produced with reference to the methods described in JP-A-7-35448, JP-A-3465826, and the like.
  • the medium used in the production of (B) is not particularly defined, but an aqueous medium is preferable from the viewpoint of being obtained as an aqueous dispersion after production and before drying.
  • examples of the aqueous medium include water and alcohol, but water is preferable.
  • the number of polymerization reactions is not particularly limited, and may be one-stage polymerization or multistage polymerization.
  • the reaction temperature and reaction time are not particularly limited, and can be adjusted appropriately. For example, the reaction at 40 to 90 ° C. for 1 to 4 hours can be performed 2 to 3 times. Further, the reaction temperature and reaction time for alkali swelling are not particularly limited, and can be appropriately adjusted. For example, it can be performed at 20 to 100 ° C. for 1 to 24 hours.
  • (A) Resin particles The resin particles are optional components and can be added when the toner containing (B) is produced. Of course, when making the toner, (B) and a plasticizer can be mixed in advance.
  • the resin particles other than the (B) hollow resin particles will be described. Since (A) is a resin particle other than the above (B), it is a resin particle having substantially no void. This is sometimes referred to as a solid particle.
  • (A) is not particularly limited as long as it can be used as a binder, and may be, for example, resin particles produced by emulsion polymerization from monomers, or resin particles obtained by pulverizing a resin to form particles. Further, (A) may be a core / shell type.
  • the glass transition temperature (Tg) of (A) is not particularly specified, but a glass transition temperature of ⁇ 60 ° C. or higher and lower than 90 ° C. can be used. -50 ° C to 80 ° C is preferred.
  • the temperature is lower than ⁇ 60 ° C., when used as a toner, the printed matter may become sticky, or the toner may be blocked, resulting in poor storage stability.
  • the temperature exceeds 90 ° C., the heat fixability may be reduced when used as a toner.
  • the method for measuring the glass transition temperature (Tg) is not particularly specified, but can be measured, for example, using a differential scanning calorimeter according to the ASTM method.
  • the average particle diameter of (A) is not particularly limited, but those having a diameter of 20 nm to 1 ⁇ m can be used. 30 nm to 500 nm is preferable, and 50 nm to 400 nm is more preferable. If it is less than 20 nm, the production may be difficult. On the other hand, when the thickness exceeds 1 ⁇ m, the number of manufacturing steps increases, and productivity may decrease. Moreover, since the particle
  • the method for measuring the average particle size is not particularly specified, but for example, it can be measured as a weight average particle size using a light scattering diffraction particle size measuring device (particle size distribution measuring device).
  • the weight average molecular weight of (A) is not particularly specified, but those having a weight average molecular weight of 5,000 to 300,000 can be used. 7000 to 200,000 is preferable, and 10,000 to 100,000 is more preferable. If it is in this range, the above-mentioned action is effectively exhibited.
  • the weight average molecular weight is less than 5,000, the high temperature offset property may be inferior, whereas when it exceeds 300,000, the low temperature fixability may be inferior.
  • the weight average molecular weight is high, the melting temperature is relatively high, and therefore it tends to be unsuitable for the present invention.
  • the method for measuring the weight average molecular weight is not particularly specified, but can be determined by conversion with standard polystyrene using a gel permeation chromatography (GPC) measuring device.
  • GPC gel permeation chromatography
  • (A) can be produced by emulsion polymerization from a monomer.
  • the aqueous dispersion may be used as it is, or may be used after drying.
  • the following can be used as a monomer which forms (A).
  • a monovinyl monomer can be mentioned as a main component of the polymerizable monomer used in the present invention. This polymerizable monomer is polymerized to become a binder resin constituting the colored polymer particles.
  • monovinyl monomers include styrene monomers such as styrene, 4-methylstyrene and ⁇ -methylstyrene; unsaturated carboxylic acid monomers such as acrylic acid, methacrylic acid and itaconic acid; acrylic acid Methyl, ethyl acrylate, propyl acrylate, butyl acrylate (butyl acrylate), 2-ethylhexyl acrylate, dimethylaminoethyl acrylate, methyl methacrylate (methyl methacrylate), ethyl methacrylate, propyl methacrylate, butyl methacrylate, Unsaturated carboxylic acid ester monomers such as 2-ethylhexyl methacrylate and dimethylaminoethyl methacrylate; derivatives of unsaturated carboxylic acids such as acrylonitrile, methacrylonitrile, acrylamide and methacrylamide; ethylene, propylene
  • (A) may be a styrene / (meth) acrylic ester, a styrene / butadiene binder resin, and a mixture thereof, for example.
  • crosslinkable monomer When any crosslinkable monomer is used as the polymerizable monomer together with these monovinyl monomers, the fixing property, particularly the offset property is improved.
  • the crosslinkable monomer include aromatic divinyl compounds such as divinylbenzene, divinylnaphthalene, and derivatives thereof; polyfunctional ethylenically unsaturated carboxylic acid esters such as ethylene glycol dimethacrylate and diethylene glycol dimethacrylate; N, N-divinyl. Aniline, divinyl ether; a compound having three or more vinyl groups; and the like.
  • These crosslinkable monomers can be used alone or in combination of two or more. In the present invention, it is desirable to use the crosslinkable monomer at a ratio of usually 0.05 to 15 parts by mass, preferably 0.1 to 10 parts by mass with respect to 100 parts by mass of the monovinyl monomer.
  • the same emulsifier, molecular weight regulator, polymerization initiator, and plasticizer as those used in the emulsion polymerization can be used.
  • the medium used in the production of (A) is not particularly defined, but an aqueous medium is preferable from the viewpoint of being obtained as an aqueous dispersion after production and before drying.
  • examples of the aqueous medium include water and alcohol, but water is preferable.
  • the number of polymerization reactions is not particularly limited, and may be one-stage polymerization or multistage polymerization.
  • the reaction temperature and reaction time are not particularly limited, and can be adjusted appropriately. For example, the reaction at 40 to 85 ° C. for 1 to 24 hours can be performed 2 to 3 times.
  • (A) can use the resin particle which grind
  • the production method is not particularly limited.
  • pulverization in which the resin pellets that are the raw material of (A) are uniformly mixed and then melted and kneaded, and the kneaded product is cooled and then pulverized with a jet mill or the like, and a fluidity modifier is externally added. Can be used.
  • the resin particles are optional components and can be added when the toner containing (B) is produced.
  • the ratio of (A) to (B) is not particularly specified.
  • the ratio of (B) to (A) is 3 to 100% by mass for (B) and 97 to 0% by mass for (A), preferably 5 to 100% by mass for (B), ( A) is 95 to 0% by mass.
  • (B) is less than 3% by mass, the amount of heat of the resin particles increases, and the low-temperature fixability deteriorates.
  • (B) and (A) can be mixed in advance.
  • the method for adding (A) to (B) is not particularly specified.
  • the above (B) and (A) can be produced by emulsion polymerization and the aqueous dispersion can be used after drying.
  • (B) and (A) can each be manufactured by emulsion polymerization with an aqueous medium, and used as an aqueous dispersion that does not undergo a drying step.
  • (B) is produced by emulsion polymerization in an aqueous medium and does not undergo a drying step
  • (A) is produced by emulsion polymerization in an aqueous medium and does not undergo a drying step.
  • An aqueous dispersion can be mixed to prepare an intermediate for producing a toner.
  • the dried product of (B) and (A) can be used by mixing, and further the dried product of (B) or (A) can be used as (A) or It may be mixed in the aqueous dispersion (B) (so-called redispersion). From the above preparation method, an aqueous dispersion containing (B) and (A) can be prepared.
  • (B) and (A) are present as an aqueous dispersion in an intermediate for producing a toner. From the viewpoint that productivity is further improved, it is preferable that (B) and (A) are produced by emulsion polymerization in an aqueous medium such as water, and the aqueous dispersions not subjected to a drying step are mixed with each other. Further, the mixed aqueous dispersion can be dried after adding an additive as necessary.
  • hydrophilic media such as water and alcohol, etc. can be mentioned, for example.
  • a medium having a high water content is preferred, and only water is more preferred.
  • the toner of the present invention contains (B) as a binder.
  • additives generally used for toner can be used, but at least a colorant is included.
  • (A) can be added as needed.
  • Colorant generally known dyes and pigments can be used as colorants for toner.
  • black colorants include carbon black and nigrosine-based dyes and pigments; magnetic particles such as cobalt, nickel, iron tetroxide, manganese iron oxide, zinc iron oxide, and nickel iron oxide.
  • carbon black it is preferable to use carbon black having a primary particle size of 20 to 40 nm because good image quality can be obtained and the safety of the toner to the environment is enhanced.
  • Colorants for color toners include yellow colorants, magenta colorants, and cyan colorants.
  • compounds such as azo pigments and condensed polycyclic pigments are used. Specifically, C.I. I.
  • magenta colorant compounds such as azo pigments and condensed polycyclic pigments are used. Specifically, C.I. I. Pigment Red 48, 57, 58, 60, 63, 64, 68, 81, 83, 87, 88, 89, 90, 112, 114, 122, 123, 144, 146, 149, 163, 170, 184, 185, 187, 202, 206, 207, 209, 251 and C.I. I. Pigment violet 19, and the like.
  • cyan colorant copper phthalocyanine compounds and derivatives thereof, anthraquinone compounds, and the like can be used. Specifically, C.I. I. Pigment Blue 2, 3, 6, 15, 15: 1, 15: 2, 15: 3, 15: 4, 16, 17, and 60. These colorants are usually 0.1 to 50 parts by mass with respect to 100 parts by mass of (B) (when the toner contains (A), the total amount of (B) and (A) is 100 parts by mass). The ratio is preferably 1 to 20 parts by mass.
  • charge control agent various positively chargeable or negatively chargeable charge control agents can be used.
  • a metal complex of an organic compound having a carboxyl group or a nitrogen-containing group, a metal-containing dye, nigrosine and the like can be mentioned. More specifically, Spiron Black TRH (made by Hodogaya Chemical Co., Ltd.), T-77 (made by Hodogaya Chemical Co., Ltd.), Bontron S-34 (made by Orient Chemical Co., Ltd.), Bontron E-84 (made by Orient Chemical Co., Ltd.), Bontron N -01 (manufactured by Orient Chemical Co.), copy blue-PR (manufactured by Clariant), etc.
  • a charge control resin can be used.
  • the charge control agent is usually 0.01 to 10 parts by mass with respect to 100 parts by mass of (B) (when the toner contains (A), the total amount of (B) and (A) is 100 parts by mass). In particular, it is preferable to use 0.03 to 8 parts by mass.
  • the method for producing the toner of the present invention is not particularly limited and can be produced by a general method.
  • the toner binder of the present invention, a colorant, and, if necessary, a toner material mixture containing a charge control agent and (A) are kneaded using an open roll type kneader, and then kneaded.
  • the resin kneaded material is melted into fibers to be processed into fibers, and the resin kneaded material processed into fibers in the fiberizing step can be pulverized.
  • the properties of the resin particles were measured by the following method.
  • Weight average particle diameter of seed particles of A and B (excluding B11) The weight average particle diameter is measured by a light scattering diffraction particle size measuring device (particle size distribution measuring device “Coulter Counter Multisizer II”, Beckman-Coulter ). The unit is nm.
  • Weight average particle size of B11 seed particles The particle size was measured using a particle size measuring device “LPA-3100 (trade name)” manufactured by Otsuka Electronics Co., Ltd. The unit is nm.
  • Porosity of B Porosity means the ratio of voids to the total volume. Arbitrarily 10 particles observed with a transmission electron microscope (“H-7650”, manufactured by Hitachi High-Technologies Corporation) are selected, and for these particles, “the ratio of voids to the total volume” is calculated by the following formula. Calculated. The unit is%. Formula: (void diameter 3 / particle longest diameter 3 ) x 100% The void diameter is the diameter of the largest void that is confirmed when observed with the electron microscope. The longest particle diameter is the longest particle diameter among the particle diameters observed with the electron microscope.
  • Glass transition temperature (Tg) A or B was dried at 40 ° C. for 3 days to produce a film.
  • the glass transition temperature (Tg) of the dried film was measured according to the ASTM method using a differential scanning calorimeter (DSC6100: manufactured by Seiko Instruments Inc.). The unit is ° C.
  • Weight average molecular weight The weight average molecular weight is converted by standard polystyrene using a gel permeation chromatography (GPC) measuring device “LC Module 1 plus” (manufactured by Waters).
  • GPC gel permeation chromatography
  • Production Example 1 [Production Method of “A” (A1 to A8)] The composition and properties of “A” are shown in Table 1. In the following production examples, “A” was all obtained as an aqueous dispersion.
  • An aqueous dispersion of the monomer mixture was prepared. 20% of the total mass of the aqueous dispersion of the monomer mixture was charged into the reaction vessel, and the temperature was raised to 75 ° C. while stirring the liquid in the reaction vessel to conduct a polymerization reaction for 1 hour. Thereafter, the remaining aqueous dispersion of the monomer mixture (80% of the total mass) was continuously added to the reaction vessel over 3 hours while maintaining the temperature at 75 ° C. After completion of the continuous addition, the mixture was further reacted at 85 ° C. for 2 hours to obtain an aqueous dispersion of seed particles (i) having a weight average particle diameter of 240 nm. The final polymerization conversion was 99%.
  • 225 parts of water, 8 parts of the seed particles (i), and 0.5 part of sodium persulfate as a polymerization initiator were charged into an autoclave (reaction vessel) equipped with a stirrer and capable of adjusting the temperature.
  • 80 parts of methyl methacrylate and 20 parts of methacrylic acid were mixed and stirred to prepare an aqueous dispersion of the monomer mixture.
  • the monomer mixture was heated to a temperature of 75 ° C. while stirring the liquid in the reaction vessel, and then added to the reaction vessel over 3 hours while maintaining the temperature at 75 ° C. After completion of the continuous addition, the mixture was further reacted at 85 ° C.
  • the final polymerization pass-through rate was 99%.
  • the liquid in the reaction vessel was stirred, and 1.3 parts of 6% ammonium hydroxide was added all at once while maintaining the temperature at 85 ° C. Then, the temperature was raised to 90 ° C. and aged by stirring for 2 hours to obtain B1 having a number average particle diameter of 1050 nm.
  • B3 was obtained in the same manner as B1, except that 0.6 part of 6% ammonium hydroxide was used.
  • B5 was obtained in the same manner as in B4 except that the amount of the emulsifier (sodium dodecylbenzenesulfonate) added to the seed particles (i) was 0.2 part.
  • the amount of the emulsifier sodium dodecylbenzenesulfonate
  • B10 was prepared in the same manner as B1 except that ammonium hydroxide was added at room temperature.
  • Test example Evaluation with toner
  • Tables 3 and 4 show the types and ratios of “B” and “A” in the toner, and the evaluation results.
  • aqueous dispersion “B” produced above and the aqueous dispersion “A” were mixed according to the ratios in Tables 3 and 4 and sufficiently stirred to prepare a binder for toner.
  • the toners to which the respective binders for toner were added by the method described later were designated as Examples 1 to 9, 11 to 17, and Comparative Examples 1 to 3.
  • Toner evaluation method ⁇ Production of toner coated body> The toner solution obtained above was applied to a copy paper with a wire bar so as to be 10 g / m 2 and dried at room temperature for 1 day to obtain a toner coated body.
  • a gloss calender Yuri Roll Co., Ltd.
  • the density of the part (a) peeled off with this mending tape and the density of the solid part (b) other than that were measured with a Macbeth densitometer, and it was judged that the toner was fixed at a / b ⁇ 100 90%.
  • Comparative Example 1 is an example in which “B” is not used.
  • Comparative Example 2 is an example using A8 having a relatively high glass transition temperature.
  • Comparative Example 3 is an example using B10 having a porosity of 0%.
  • B11 (Method for producing B11 (hollow resin particles))
  • the composition and properties of B11 are shown in Table 5.
  • B11 was obtained as an aqueous dispersion.
  • the final polymerization pass-through rate was 99%.
  • A9 ((B) resin particles other than hollow resin particles)
  • Table 5 The composition and properties of A9 are shown in Table 5.
  • A9 was obtained as an aqueous dispersion.
  • An autoclave equipped with a stirrer and adjustable in temperature was charged with 120 parts of water, 0.2 part of sodium dodecylbenzenesulfonate and 0.5 part of sodium persulfate, and the temperature was raised to 65 ° C.
  • T1 / 2 melting temperature and the gradient from T1 / 2 to -2 mm obtained by a flow tester are conventionally used as substitute characteristics (indexes) for estimating the fixing temperature and characteristics of the toner.
  • indexes indexes
  • a chart of test temperature (° C.) [X axis] ⁇ stroke (nm) [Y axis] was obtained.
  • Ts indicates the softening temperature of the resin and is not yet melted.
  • C point (Smin) Tfb is the resin outflow start temperature.
  • E point Tend is an end temperature at which all of the resin charged in the piston inserted into the flow tester flows out.
  • Table 6 shows the results.
  • the toner binder of the present invention can be used as a toner material that is suitable for high-speed printing due to its high print density after toner fixing and excellent low-temperature fixability, and can reduce power consumption.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Developing Agents For Electrophotography (AREA)

Abstract

L'invention concerne : un liant pour toner, utilisé pour un toner présentant une haute densité d'impression après fixation du toner et une excellente fiabilité aux basses températures, ce qui le rend adapté à l'impression à grande vitesse et susceptible de réduire la consommation d'énergie ; ainsi qu'un toner utilisant ledit liant pour toner. Plus précisément, l'invention concerne un liant pour toner, composé de particules creuses en résine présentant un diamètre de particules moyenné en nombre de 100 à 1500 nm, chacune desdites particules étant dotée d'au moins un pore à l'intérieur de celle-ci. L'invention concerne également en particulier un toner, contenant le liant pour toner et un agent colorant.
PCT/JP2010/073130 2009-12-25 2010-12-22 Liant pour toner, et toner contenant celui-ci WO2011078224A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2015045861A (ja) * 2013-07-31 2015-03-12 キヤノン株式会社 トナー
WO2022000126A1 (fr) 2020-06-28 2022-01-06 Dow Global Technologies Llc Dispersion aqueuse de particules polymères à plusieurs étages et son procédé de préparation

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JPH02176756A (ja) * 1988-12-28 1990-07-09 Toshiba Corp 静電荷像現像用トナー
JPH03269541A (ja) * 1990-03-20 1991-12-02 Seiko Epson Corp トナー
JPH04174863A (ja) * 1990-11-08 1992-06-23 Japan Imeejingu Syst:Kk 光導電性トナー
JPH10319626A (ja) * 1997-05-19 1998-12-04 Ricoh Co Ltd 静電荷像現像用トナーおよびそれを用いた画像形成方法
JP2009020518A (ja) * 2007-07-10 2009-01-29 Samsung Electronics Co Ltd 中空トナー及びその製造方法

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JPH041658A (ja) * 1990-04-18 1992-01-07 Minolta Camera Co Ltd 静電荷像現像用トナー
JPH08137130A (ja) * 1994-11-04 1996-05-31 Toshiba Corp 電子写真用現像剤および画像定着方法
JP2002030113A (ja) * 2000-05-09 2002-01-31 Jsr Corp 中空ポリマー粒子の製造方法
JP4650595B2 (ja) * 2000-09-28 2011-03-16 Ｊｓｒ株式会社 中空ポリマー粒子の製造方法
JP2010128335A (ja) * 2008-11-28 2010-06-10 Ricoh Co Ltd 中空粒子、トナー、現像剤、画像形成方法及びプロセスカートリッジ

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Publication number Priority date Publication date Assignee Title
JPH02176756A (ja) * 1988-12-28 1990-07-09 Toshiba Corp 静電荷像現像用トナー
JPH03269541A (ja) * 1990-03-20 1991-12-02 Seiko Epson Corp トナー
JPH04174863A (ja) * 1990-11-08 1992-06-23 Japan Imeejingu Syst:Kk 光導電性トナー
JPH10319626A (ja) * 1997-05-19 1998-12-04 Ricoh Co Ltd 静電荷像現像用トナーおよびそれを用いた画像形成方法
JP2009020518A (ja) * 2007-07-10 2009-01-29 Samsung Electronics Co Ltd 中空トナー及びその製造方法

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2015045861A (ja) * 2013-07-31 2015-03-12 キヤノン株式会社 トナー
WO2022000126A1 (fr) 2020-06-28 2022-01-06 Dow Global Technologies Llc Dispersion aqueuse de particules polymères à plusieurs étages et son procédé de préparation
EP4172281A4 (fr) * 2020-06-28 2024-02-21 Dow Global Technologies LLC Dispersion aqueuse de particules polymères à plusieurs étages et son procédé de préparation

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