WO1993008510A1 - Toner colore de developpement d'image electrostatique - Google Patents

Toner colore de developpement d'image electrostatique Download PDF

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Publication number
WO1993008510A1
WO1993008510A1 PCT/JP1992/001371 JP9201371W WO9308510A1 WO 1993008510 A1 WO1993008510 A1 WO 1993008510A1 JP 9201371 W JP9201371 W JP 9201371W WO 9308510 A1 WO9308510 A1 WO 9308510A1
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WIPO (PCT)
Prior art keywords
toner
particles
color
particle
value
Prior art date
Application number
PCT/JP1992/001371
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English (en)
Japanese (ja)
Inventor
Hiroshi Kamada
Hitoshi Masuda
Yukinobu Hasegawa
Hiroyoshi Shimomura
Hiroshi Serizawa
Kensuke Okuda
Masatoshi Maruyama
Original Assignee
Nippon Carbide Kogyo Kabushiki Kaisha
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from JP3301214A external-priority patent/JP3037799B2/ja
Priority claimed from JP03308237A external-priority patent/JP3114295B2/ja
Application filed by Nippon Carbide Kogyo Kabushiki Kaisha filed Critical Nippon Carbide Kogyo Kabushiki Kaisha
Priority to DE69228314T priority Critical patent/DE69228314T2/de
Priority to CA002121893A priority patent/CA2121893C/fr
Priority to EP92921832A priority patent/EP0609443B1/fr
Publication of WO1993008510A1 publication Critical patent/WO1993008510A1/fr

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Classifications

    • 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
    • G03G9/09—Colouring agents for toner particles
    • G03G9/0906—Organic dyes
    • 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
    • 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
    • G03G9/0821—Developers with toner particles characterised by physical parameters
    • 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
    • G03G9/0825—Developers with toner particles characterised by their structure; characterised by non-homogenuous distribution of components
    • 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
    • G03G9/08791—Macromolecular material not specially provided for in a single one of groups G03G9/08702 - G03G9/08775 characterised by the presence of specified groups or side chains

Definitions

  • the present invention relates to a color toner for forming an electrostatic image in electrophotography, electrostatic recording, electrostatic printing, and the like.
  • a widely used toner is prepared by appropriately blending a coloring agent such as carbon black, a charge controlling agent and / or a magnetic material with a styrene Z acrylate copolymer powder obtained by a suspension polymerization method, It has been manufactured by melt-kneading with an extruder or the like, followed by pulverization and classification. (See Japanese Patent Application Laid-Open No. Sho 51-233354).
  • the toner obtained by the above-mentioned melt-kneading and pulverization method has a limitation in controlling the particle size of the toner, and it is difficult to produce a toner having a small particle size with good yield, and the dispersion is not uniform.
  • the resolution cannot be avoided and the drawbacks such as capri and scattering can not be avoided.
  • the present invention has high image density and resolution, and generates capri and scattering It is another object of the present invention to provide a toner having excellent color developability, color reproducibility, and color transparency when copied on a 0 HP sheet.
  • the present invention provides a polymer particle having an acidic polar group or a basic polar group, and a treating agent containing a surface treating agent having the same ionicity as the polymer particle, so that the absolute value of the f potential at PH 5 is 10 to 1
  • a secondary particle comprising an organic pigment and Z or an organic dye that has been treated to have an O mV and is characterized by having a gelation degree of 2.0% or less.
  • the toner of the present invention preferably has a toner particle shape factor S value of 100.5-16.0.
  • the present invention provides an electrostatic image developer containing the toner for developing an electrostatic image and a carrier.
  • the toner of the present invention comprises a polymer particle having an acidic polar group or a basic polar group (hereinafter sometimes referred to as a primary particle), an organic pigment specifically treated as described below, and Z or an organic pigment.
  • Secondary particles composed of dyes Consists of associated particles.
  • the association means that a plurality of secondary particles aggregate to form particles having a larger particle size.
  • Preferred examples of the polymer having an acidic polar group or a basic polar group include styrenes, alkyl (meth) acrylates, and comonomers having an acidic polar group or a basic polar group (hereinafter, referred to as “comonomer having a polar group”). ) Is a copolymer of
  • the copolymer may optionally contain a comonomer that can be copolymerized to such an extent that the performance of the toner of the present invention is not impaired.
  • styrenes examples include styrene, n-methylstyrene, m-methylstyrene, p-methylstyrene, -methylstyrene, p-ethylstyrene, 2,4-dimethylstyrene, ⁇ -n-butylstyrene, p-tert-butyl Styrene, p-n-hexynolestyrene, p-n-octylstyrene, p-n-nonylstyrene, p-n-decylstyrene, p-n-dodecylstyrene, p-methoxystyrene, p-phenylstyrene, p- Chlorstyrene, 3,4-dichlorostyrene, p-Chlorme And styrene.
  • alkyl (meth) acrylate examples include methyl acrylate, ethyl acrylate, ⁇ -butyl acrylate, isoptyl acrylate, butyl acrylate pill, ⁇ -octyl acrylate, dodecyl acrylate, acrylyl acrylate, 2-Ethylhexyl acrylate, stearyl acrylate, 2-chloroethyl acrylate, methyl methacrylate, methyl methacrylate, methyl methacrylate, ethyl methacrylate, butyl methacrylate, ⁇ -butyl methacrylate, isobutyl methacrylate, methacrylate
  • Examples include ⁇ -octyl acrylate, dodecyl methacrylate, lauryl methacrylate, 2-ethylhexyl methacrylate, stearyl methacrylate and the like.
  • those having 1 to 12 carbon atoms in the ester portion are preferable, those having 3 to 8 carbon atoms are more preferable, and (meth) acrylic acid esters of aliphatic alcohols having 4 carbon atoms are particularly preferably used. .
  • Examples of the comonomer having an acidic polar group include a ⁇ -ethylenically unsaturated compound having a carboxyl group and an a, ⁇ -ethylenically unsaturated compound having a sulfone group.
  • S ethylenically unsaturated compound having a carboxyl group examples include acrylic acid, methacrylic acid, fumaric acid, maleic acid, itaconic acid, gay cinnamate, monobutyl maleate, monooctyl maleate, And metal salts thereof such as sodium and zinc.
  • Examples of the a, yS ethylenically unsaturated compound having a sulfone group include sulfonated ethylene, Na salt thereof, arylsulfosuccinic acid, arylyl And octyl sulfosuccinate, and its Na salt.
  • Examples of the comonomer having a basic polar group include an ester group having an amine group or a quaternary ammonium group having 1 to 12 carbon atoms, preferably 2 to 8 carbon atoms, and particularly preferably (meth) acryl.
  • Acid ester, (meth) acrylic acid amide or (meth) acrylic acid amide optionally mono- or di-substituted with an alkyl group having 1 to 18 carbon atoms on N, and N as a ring member
  • a (meth) acrylate of an aliphatic alcohol having an amine group or a quaternary ammonium group is preferably used as a comonomer having a basic polar group.
  • Examples of the (meth) acrylate of the aliphatic alcohol having an amine group or a quaternary ammonium group include, for example, dimethylaminoethyl acrylate, dimethylaminoethyl methacrylate, acetylaminoethyl acrylate, dimethylaminoethyl methacrylate, and the like. Quaternary ammonium salt, 3-dimethylaminophenyl acrylate, 2-hydroxy-3-methacryloxypropyltrimethylammonium salt and the like.
  • Examples of the above (meth) acrylic acid amide or (meth) acrylic acid amide mono- or di-monosubstituted with an alkyl group having 1 to 18 carbon atoms on N include acrylamide and N-butyl.
  • Acrylamide, N, N-dibutyl acrylamide, piperidyl acrylamide, methacryl amide, N-butyl methacryl amide, N, N-dimethyl acryl amide, N-butadecyl acryl Amides and the like can be mentioned.
  • Examples of the vinyl compound substituted with a heterocyclic group having N as a ring member include vinyl pyridine, vinyl pyrrolidone, vinyl N-methylpyridinium chloride, and vinyl N-ethylpyridinium chloride. And the like.
  • N, N-diarylmonoalkylamine examples include N, N-diarylmethylammonium chloride, N, N-diarylethylammonium chloride and the like.
  • the polymer particles of the present invention can be obtained by polymerizing the above monomer composition by an emulsion polymerization method, a suspension polymerization method, a precipitation polymerization method, or an interfacial polymerization method (including a coacervate method).
  • the resin particles may be mechanically pulverized into particles. If necessary, a method of associating primary particles of a polymer by using a zeta potential is also used.
  • Preferred methods for producing polymer particles are an emulsion polymerization method, a suspension polymerization method, and a method utilizing zeta potential.
  • the above polymer is used in the toner in an amount of 40 to 99.9% by weight.
  • the polymer preferably has a glass transition point of from 190 to 100 ° C, more preferably from 130 to 80 ° C, and still more preferably from 110 to 70 ° C. .
  • the average particle size of the primary particles of the polymer is , Preferably from 0.11 to 10 / rrn, more preferably from 0.01 to 8 m, even more preferably from 0.01 to 5 m, particularly preferably from 0.01 to 3 ⁇ .
  • the zeta potential of the polymer particles is preferably set to an appropriate value when a toner is produced by an association method utilizing the zeta potential described below.
  • Acidic polar group ⁇ Potential P 5 ) at pH 5 of the containing polymer particles is -2 to 60 mV, ⁇ potential ( ⁇ P 9 ) at pH 9 is -20 to 110 OmV, and P 5 is greater than ⁇ P 9 Is preferred.
  • polymer particles ⁇ TP 5 is + 20 ⁇ +10 OmV.
  • ⁇ ⁇ 9 is the + 2 tens 6 OMV, and it Ganmaro 5 is larger than ⁇ P 9 Is desirable.
  • the organic pigments and organic dyes used in the present invention were treated with a surface treating agent having the same ionicity as the polymer particles used, and as a result, the absolute value of the ⁇ potential at pH 5 became 10 to 10 OmV. Things.
  • a surface treating agent having the same ionicity as the polymer particles used, and as a result, the absolute value of the ⁇ potential at pH 5 became 10 to 10 OmV. Things.
  • the surface treatment agent used must have the same ionicity as the polymer particles used, but may contain other types of surface treatment agents.
  • a disperse dye used in a state of being dispersed in a medium is used in order to set the absolute value of the ⁇ electric position at pH 5 to 10 to 10 OmV by the treatment as described above.
  • organic pigments and organic dyes are not particularly limited as long as they exhibit a color other than black, and one or more organic pigments and / or organic dyes may be combined as necessary. good. Further, a metal may be contained in these organic pigments and organic dyes.
  • organic pigments include the following. Wear.
  • Nonzaiello-G Benzijin Yellow, Benzidin Orange, Permanent Red 4R, Pyrazolone Red, Risole Red, Brilliant Toss Powerlet G, Bon Maroon Light, etc.
  • Orange I I, Acid Orange R, Jaoxin, Quinoline Yellow, Tartrazine Yellow, Acid Green, Peacock Blue, Alkali Blue, and other dyes precipitated with a precipitant.
  • Dyes such as rhodamine, magenta, makalite green, methyl violet, and Victoria blue are precipitated with tannic acid, tartar, PTA, PMA, PTMA, etc.
  • Phthalocyanine blue Phthalocyanine blue, sulfonated copper phthalocyanine, etc.
  • organic dye a Nig mouth dye, an aniline dye, or the like is used.
  • Examples of surface treatment agents for treating pigments or dyes as described above include the following.
  • Polyoxyethylene sorbate tetraoleate coconutamine acetate, stearylamine acetate, coconutamine hydrochloride, stearylamine hydrochloride, stearylamine oleate, lauryl methylammonium chloride, stearyltrimethyl Ammonium chloride mouth ride, distearyl dimethyl ammonium chloride, alkyl base N-dimethylammonium chloride, lauryl betaine, stearyl betaine, lauryl dimethyl amine oxide, lauryl carboxymethyl hydroxyshethyl imidazolinium betaine, silicon surfactant, fluorine surfactant, etc.
  • a surfactant of nonionic and anionic and a surfactant of nonionic and cationic can be used in one molecule.
  • the organic pigment and / or organic dye is used in the toner in the range of 60 to 0.1% by weight.
  • the production of the toner of the present invention is performed by aggregating a mixture of the polymer particles primary particles in a water-dispersed state, a surface-treated organic pigment and / or organic dye, and an optional charge control agent, a release agent, and the like. This is accomplished by making particles and further aggregating the secondary particles to form associated particles.
  • the form of the secondary particles constituting the associated particles which is the toner of the present invention, is not limited as long as the present invention is not impaired. However, it is preferable that the primary particles of the polymer and the colorant be used. Secondary particles that are agglomerated with particles due to ionic bonds, hydrogen bonds, metal bonds, weak acid-weak base bonds, etc.
  • the form of aggregation of the associated particles is not particularly limited as long as the polymer particles and the colorant are aggregated.
  • aggregated particles are formed by associating secondary particles.Association methods using potential, coagulation, coagulation, interfacial polymerization, etc. Any of the following methods can be used. Among them, the association method is preferably used.
  • the average particle diameter of the secondary particles is preferably 0.05 to 12 m, more preferably 0.2 to 8 ⁇ , and particularly preferably 0.5 to 5 ⁇ m.
  • the particle size of the bright associated particles is preferably 2.5 to 12 zm, more preferably 2.5 to llm.
  • An example of a preferred method for producing the toner of the present invention is as follows. Pigments and / or dyes and other compounds are added to the polymer dispersion obtained by emulsion polymerization, and the mixture is uniformly dispersed.After stirring for 0.5 to 10 hours, preferably for 1 to 5 hours, polarity is maintained. The primary particles of the polymer having a group and the surface-treated organic pigment and the like aggregate to form secondary particles of 1 to 5 zm. When this dispersion is further stirred for 0.5 to 10 hours, preferably 1 to 5 hours while heating, the secondary particles further aggregate and grow into associated particles of 1 to 20 m.
  • the obtained dispersion of the associated particles is stabilized, and further heated to a temperature higher than the glass transition point of the polymer, preferably at a temperature higher than 20 ° C. for 1 to 12 hours, preferably 1 to 10 hours. Continue stirring for hours. Then, associated particles are formed in which at least a part of the contact portion between the secondary particles in the associated particles is film-formed and fused.
  • the dispersion liquid of the obtained associated particles is dehydrated, washed and dried to obtain a toner as the associated particles. Since such associated particles are formed by film fusion between the secondary particles, they become toners that are hardly disintegrated during storage, transportation, production of magnetic developers, and the like.
  • the above manufacturing method is an example of an association method using the f potential.
  • the ⁇ -potential of the polymer particles and the surface-treated pigment particles is reduced by a rise in temperature, so that the aggregation and association of the secondary particles are promoted.
  • Other methods for lowering the electric potential include controlling the pH, adding a metal salt, and the like.
  • the magnetic toner of the magnetic developer of the present invention is externally and internally added with a performance-imparting agent such as a fluidizing agent, a life stabilizer, and a printing durability improver as long as its performance is not impaired. It does not matter.
  • Such performance-imparting agents include metal oxides such as silica, titanium oxide, aluminum oxide, zinc oxide, cerium oxide, and magnetite, and hydrophobized products thereof, and Cd, Mn, P of stearic acid.
  • metal oxides such as silica, titanium oxide, aluminum oxide, zinc oxide, cerium oxide, and magnetite, and hydrophobized products thereof, and Cd, Mn, P of stearic acid.
  • the toner of the present invention has a low gelation degree of 2% or less. When the gelling degree exceeds 2%, the light transmittance of the toner is lowered, and good color developability cannot be obtained.
  • the gelation degree is preferably 1.80% or less, more preferably 1.00% or less, and particularly preferably 0.50% or less.
  • the shape factor S value representing the shape of the toner of the present invention is preferably 100.5 to; L60, more preferably 102.0 to 155, more preferably 1 5.0 to 155, still more preferably 107.0 to 140, and particularly preferably 107.0 to 140. 1 10.0 to 135.
  • the S value is a shape factor obtained by dividing the square of the perimeter of the toner particles by the area. That is, the planar image of the toner particles is processed by an image processor or the like, the perimeter (PM) and the area (A) are calculated, and are obtained by the following equation.
  • the S value expresses the feeling of planar unevenness of the particles.
  • the S value becomes closer to 100 as the shape of the toner particles approaches a circle (sphere), and increases as the surrounding shape becomes more complicated. Value.
  • the toner particles tend to be spherical, and when used as a developer, the charge amount is low, and image density is insufficient or fogging is likely to occur. Etc., and the life tends to be shortened.
  • the value exceeds the above upper limit the surface condition becomes unstable and the surface becomes stochastically non-uniform, so that when the developer is used, the charge amount is not stable and the charge amount distribution is not uniform.
  • the above-described problems on the image are likely to occur, and the life characteristics tend to be shortened due to the generation of fine powder and the like.
  • the average of the particle diameter of the toner (the average rm of 100 particles) and the average of the minimum value of the radius of curvature of the surface of each particle constituting the toner (the average of 1000 particles) rn Should have the following relationship:
  • the V value is more preferably from 1.01 to 320, more preferably from 1.05 to 3 hours, and particularly preferably from 2.0 to 250.
  • the particle diameter of the toner is the distance between two circumscribed parallel lines.
  • the above toner preferably has a volume average particle size of 2.5 to 12 zm.
  • the meaning of the V value here is that the aforementioned S value expresses a flat feeling of unevenness, and further expresses unevenness three-dimensionally. Such unevenness is caused by the primary particles of the polymer, the colorant particles, the charge controlling agent, and the secondary particles thereof.
  • the unevenness of the particle surface can be quantified as a radius of curvature, and by deriving the relationship with the average particle diameter of each toner, the overall toner particles can be obtained. It is possible to express the concavo-convex feeling (especially as associated particles).
  • the toner particles When the V value is smaller than the above lower limit, the toner particles have a substantially spherical shape with no surface irregularities and are almost spherical. As described above, when such a toner is used as a developer, the charge amount is low, and the image density is insufficient or fogging is likely to occur. Regarding the life characteristics, in the case of an electrophotographic system in which cleaning is performed with a cleaning blade, the frictional force of the toner catching the blade is extremely reduced, causing cleaning failure and the like to occur. Tend to be shorter.
  • the color toner obtained by the present invention is a color toner excellent in color developing property due to very good transparency, excellent in color reproducibility and resolution, less fogging and scattering, and excellent in various physical properties.
  • a developer is produced by mixing the toner of the present invention and a magnetic carrier.
  • a magnetic carrier For example, it is manufactured by stirring, mixing and charging 20 to 95 parts by weight of a magnetic carrier and 5 to 80 parts by weight of a toner with a V-type mixer or a ball mill.
  • magnétique carrier iron or ferrite, which is well known, is used. Further, ferromagnetic fine particles bound with a resin can also be used.
  • the average particle diameter of the magnetic carrier is preferably 10 to 200, more preferably 20 to 180 m, and particularly preferably 30 to 17 Om. If the upper limit value is exceeded, clogging occurs between the doctor blade and the sleeve when restricting the spike of the developer. Therefore, it is preferable to use a particle size of 1Z2 or less, preferably 1 to 5 or less for the doctor gap.
  • test method used in the examples is as follows.
  • W L b Weight of wire mesh and residue in metal steel after drying
  • W m Weight of wire mesh
  • Transmitted light measurement was performed with 800 MK2.
  • Tm is the transmission percentage at the wavelength m
  • the case of 55% or less was evaluated as XX.
  • n 540 nm
  • a solid portion image (paper) of the toner single color was taken out, and the color difference ⁇ (in NBS unit) was measured using a color analyzer TC-1800 MK2 manufactured by Tokyo Denshoku Co., Ltd.
  • the whiteness is measured using a color difference meter (CR-200) manufactured by Minolta Co., Ltd. Calculate color difference L, a, b and whiteness of natural paper before copying ''
  • Fog (%) KZK. xlOO
  • the electrophotographic society test chart N01-R1975 was copied, and the 8.0-point resolution pattern was magnified 100 times with an optical microscope, and visually judged as follows.
  • a resolution of 4 or less is considered good, and a resolution of 3 or less is bad.
  • the obtained toner was subjected to image processing using LUZEX 3 U manufactured by Nikon Corporation to determine the S value. At this time, the number of measured samples was 10,000, and the average value was taken as the S value. An electron micrograph (10000x) of the toner particles was applied to the same processor to determine the V value, and the average value of 1000 measured pieces was taken as the V value. Done c
  • a life test (10000 sheets) was performed on the copy test of the working example and the comparative example, and the distribution of several toners in the initial developer (5% / m or less of the particle number%) and the A comparison value with the toner number distribution was taken.
  • the resulting mixture was polymerized at 80 ° C. for 8 hours with stirring using a persulfuric acid catalyst as a catalyst to obtain an acidic polar group-containing emulsion having a solid content of 50%.
  • Anion-based surface treatment agent 1 Anion-based surface treatment agent 1
  • the above mixture was kept at about 25 ° C. for 2 hours while being dispersed and stirred by a disperser to obtain a mixed wave of the surface-treated organic pigment.
  • the above mixture was kept at about 30 ° C for 2 hours while being dispersed and stirred by a slasher. Thereafter, the mixture was heated to 80 ° C. with further stirring and maintained for 3 hours. Observation with an optical microscope during this time revealed that the particle size of the polymer particles and the secondary particles of the organic pigment was 1.2 ⁇ , and that the associated particles (toner particles) in which the secondary particles were associated had a particle size of about 6,5. It was confirmed to grow to jtt m. Cooled and obtained tona One was separated by a dispersion centrifuge, washed with water, and vacuum dried at 50 ° C for 10 hours. The gel content of the obtained toner was measured and found to be 0.3%. Further, as a result of image processing of this toner, the S value was 119.5 and the V value was 2.35.
  • the average particle diameter of the acidic polar group-containing polymer of the primary particles is a 0.08 ⁇ M, in ⁇ potential ⁇ P 5 gar 21 mV at pH 5, the potential P 9 in pH9 is one 8 OMV and the average particle diameter of the organic pigments wherein the surface treatment is a 0.2 / m, was ⁇ photoelectric position tC 5 gar 23mV at pH 5.
  • Example 2 Instead of the organic pigment of Example 1, CI Pigment Yellow Y-17 is used in Example 2, CI Pigment Blue B-15: 3 is used in Example 3, and the other components are the same as in Example 1. I got When the toners of Examples 2 and 3 were put into the above-described copying machine and tested, an image having excellent color reproducibility was obtained. The results are shown in Tables 1 and 2.
  • the above mixture was kept at about 25 ° C. for 2 hours while being dispersed and stirred by a disperser, and a dispersion liquid of a surface-treated organic pigment was obtained while being dispersed by a Gaulin homogenizer.
  • the above mixture was kept at about 30 ° C for 5 hours while stirring with a slasher. Thereafter, the mixture was heated to 80 ° C. with further stirring and maintained for 3 hours. Observation with an optical microscope during this time confirmed that the associated particles of the polymer particles and the secondary particles of the organic pigment grew to about 5.2 m. After cooling, the obtained toner dispersion was separated by a centrifugal separator, washed with water, and dried in a vacuum at 50 ° C for 10 hours.
  • the gel content of the obtained toner was measured and found to be 0.2%.
  • To 100 parts of the obtained toner 1.2 parts of hydrophobic silica as a fluidizing agent was added and mixed using a pen mixer to obtain a test toner.
  • This toner was combined with a commercially available ferrite carrier to a toner concentration of 5% and used as a test developer.
  • ART AG E5330 manufactured by Ricoh Co., Ltd.
  • an image with high density and high resolution was obtained.
  • the color development was good, and the transparency was excellent when copied on an OHP sheet.
  • Example 5 In the same manner as in Example 4, CI Pigment Yellow Y-17 was used in Example 5 instead of the organic pigment of Example 4, and CI Pigment Blue B-15: 3 was used in Example 6. To obtain a toner.
  • Tables 1 and 2. [Examples 7, 8, 9]
  • the organic pigment in the preparation of the surface-treated organic pigment and dye of Example 1 was used.
  • a toner was obtained in the same manner as in Example 1 except that the organic pigment C.I.
  • this toner was put into the copying machine of Example 1 and tested, an image having good transparency was obtained. The results are shown in Tables 1 and 2.
  • Example 2 the same stirring conditions as in Example 1 except that the stirring conditions in the toner preparation of Example 1 were maintained at about 30 ° C for 5 hours, further heated to 93 ° C, and maintained for 5 hours To obtain a toner.
  • this toner was put into the copying machine of Example 1 and tested, an image having good transparency was obtained.
  • Example 2 Using the same monomer composition as in Example 1, suspension polymerization was carried out using benzoyl peroxide as a catalyst to obtain a resin for toner.
  • the organic pigment used in Example 1 was added to this resin at the same ratio without surface treatment, melt-kneaded, and pulverized with a dip mill to obtain a toner with an average particle size of 9.3 // m. Was.
  • the gel content of this toner was 6.5%.
  • a developer was prepared in the same manner as in Example 1, and a similar copy test was performed. As a result, an image having poor transparency and low resolution was obtained. The results are shown in Tables 1 and 2.
  • Example 2 An emulsion containing an acidic polar group was obtained in the same manner as in Example 1. Using an organic pigment without surface treatment, a toner was prepared in the same manner as in Example 1, and a copying test was performed. The gel content of this toner was 4.2%. The results are shown in Tables 1 and 2.
  • the toner obtained in Comparative Example 1 was subjected to spheroidizing treatment using a high pretizer (manufactured by Nara Machinery Co., Ltd.), and a copy test was performed using this toner in exactly the same manner as in Example 1.
  • the results are shown in Tables 1 and 2.

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

Abstract

Un toner coloré de développement d'image électrostatique a un degré de gélification de 2,0 % ou moins et comprend une association de particules secondaires contenant des particules polymères ayant des groupes polaires acides ou basiques ainsi qu'un pigment organique et/ou un colorant organique soumis à un traitement consistant en un traitement de surface présentant le même caractère ionique que celui des particules polymères, de manière que la valeur absolue du potentiel z est compris entre 10 et 100 mV à une valeur de pH de 5. Un révélateur d'images électrostatiques comprenant ledit toner ainsi qu'un agent véhiculeur sont également décrits.
PCT/JP1992/001371 1991-10-22 1992-10-21 Toner colore de developpement d'image electrostatique WO1993008510A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
DE69228314T DE69228314T2 (de) 1991-10-22 1992-10-21 Farbtoner für die entwicklung elektrostatischer bilder
CA002121893A CA2121893C (fr) 1991-10-22 1992-10-21 Toner colore pour le developpement d'images electrostatiques
EP92921832A EP0609443B1 (fr) 1991-10-22 1992-10-21 Toner colore de developpement d'image electrostatique

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP3301214A JP3037799B2 (ja) 1991-10-22 1991-10-22 静電荷像現像用カラ−トナ−
JP3/301214 1991-10-22
JP3/308237 1991-10-29
JP03308237A JP3114295B2 (ja) 1991-10-29 1991-10-29 静電荷像現像用トナ−

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WO1993008510A1 true WO1993008510A1 (fr) 1993-04-29

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PCT/JP1992/001371 WO1993008510A1 (fr) 1991-10-22 1992-10-21 Toner colore de developpement d'image electrostatique

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EP (1) EP0609443B1 (fr)
CA (1) CA2121893C (fr)
DE (1) DE69228314T2 (fr)
WO (1) WO1993008510A1 (fr)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9708815D0 (en) 1997-05-01 1997-06-25 Zeneca Ltd Process for making particulate compositions
GB9806934D0 (en) 1998-04-01 1998-05-27 Zeneca Ltd Process for making particulate compositions
JP6310827B2 (ja) * 2014-09-16 2018-04-11 株式会社東芝 電子写真用トナーの製造方法

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JPS63121060A (ja) * 1986-11-11 1988-05-25 Toyo Ink Mfg Co Ltd 静電荷現像用トナ−
JPS63186253A (ja) * 1987-01-29 1988-08-01 Nippon Carbide Ind Co Ltd 静電荷像現像用トナ−
JPS63282749A (ja) * 1987-05-15 1988-11-18 Nippon Carbide Ind Co Ltd 静電荷像現像用トナ−

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US3615749A (en) * 1970-06-19 1971-10-26 American Cyanamid Co Printing ink of improved blackness
US4218530A (en) * 1977-05-02 1980-08-19 Xerox Corporation Single component magnetic toner
US4621039A (en) * 1984-12-18 1986-11-04 Xerox Corporation Developer compositions with fast admixing characteristics
WO1988005930A1 (fr) * 1987-01-29 1988-08-11 Nippon Carbide Kogyo Kabushiki Kaisha Toner pour developpement electrostatique d'une image chargee
JPH01186964A (ja) * 1988-01-20 1989-07-26 Minolta Camera Co Ltd 光導電性トナーおよびその製造方法
JPH03267947A (ja) * 1989-07-31 1991-11-28 Ricoh Co Ltd 静電荷像現像用カラートナー
US5118588A (en) * 1990-03-30 1992-06-02 Eastman Kodak Company Toner particles having improved transfer efficiency and which comprise a pigment surface modifier

Patent Citations (3)

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JPS63121060A (ja) * 1986-11-11 1988-05-25 Toyo Ink Mfg Co Ltd 静電荷現像用トナ−
JPS63186253A (ja) * 1987-01-29 1988-08-01 Nippon Carbide Ind Co Ltd 静電荷像現像用トナ−
JPS63282749A (ja) * 1987-05-15 1988-11-18 Nippon Carbide Ind Co Ltd 静電荷像現像用トナ−

Non-Patent Citations (1)

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Title
See also references of EP0609443A4 *

Also Published As

Publication number Publication date
DE69228314T2 (de) 1999-06-10
CA2121893C (fr) 2003-01-21
CA2121893A1 (fr) 1993-04-29
DE69228314D1 (de) 1999-03-11
EP0609443A1 (fr) 1994-08-10
EP0609443A4 (fr) 1995-04-19
EP0609443B1 (fr) 1999-01-27

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