EP0066395B1 - Entwicklerzusammensetzungen - Google Patents

Entwicklerzusammensetzungen Download PDF

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Publication number
EP0066395B1
EP0066395B1 EP19820302468 EP82302468A EP0066395B1 EP 0066395 B1 EP0066395 B1 EP 0066395B1 EP 19820302468 EP19820302468 EP 19820302468 EP 82302468 A EP82302468 A EP 82302468A EP 0066395 B1 EP0066395 B1 EP 0066395B1
Authority
EP
European Patent Office
Prior art keywords
group
toner
developer composition
functional group
polar functional
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
EP19820302468
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English (en)
French (fr)
Other versions
EP0066395A1 (de
Inventor
Ken C/O Fuji Xerox Co. Ltd. Hashimoto
Koichi C/O Fuji Xerox Co. Ltd. Takashima
Izuri C/O Fuji Xerox Co. Ltd. Matsui
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Xerox Ltd
Original Assignee
Rank Xerox Ltd
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Filing date
Publication date
Application filed by Rank Xerox Ltd filed Critical Rank Xerox Ltd
Publication of EP0066395A1 publication Critical patent/EP0066395A1/de
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Expired legal-status Critical Current

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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
    • G03G9/087—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
    • G03G9/087—Binders for toner particles
    • 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

  • This invention relates to a developer composition for a dry system for developing electrostatic latent images in electrophotography, electrostatic recording, etc., and more particularly to a developer composition having a pressure-fixing property.
  • electrostatic latent images are well known.
  • an electrophotographic process after the usual charging of the photoconductive layer, it is exposed to a light image based on an original to reduce or eliminate electrostatic charge in the exposed areas, whereby an electrostatic latent image is formed.
  • the latent image is then developed by a developer called a "toner".
  • the development process can use either a liquid or a dry developer.
  • the latter process may be further classified into a two-component development process, using two kinds of particles, carrier and toner, and a one-component development process, using a toner only.
  • the developed image is transferred onto a material such as paper. Thereafter, the toner is fixed on the paper by fusing the toner with heat or by softening a binding resin of the toner with a solvent, or by deforming the toner with only pressure.
  • a pressure-fixing process has various merits with respect to energy saving, pollution and fire prevention as well as not requiring preheating for the fixing means.
  • Other advantages are also obtained as compared with other fixing processes. However, these advantages have to be offset against other considerations, such as the strength of the fixed toner image, the producibility of the toner, antiblocking property, impact resistance, i.e. as one property is improved others are made worse. Therefore, it is very difficult to improve all these properties simultaneously.
  • Japanese Patent Publication No. 9880/69 proposes a toner containing an aliphatic component having 6-25 carbon atoms
  • Japanese published Patent Application 119231/77 proposes a toner containing a crystalline wax and an ethylene-vinyl acetate copolymer.
  • Known wax-like materials may be excellent with respect to deformability by pressure.
  • the strength of the fixed image is weak and hence the image readily comes off or smears when it is rubbed.
  • the toner is liable to attach to the surface of a photoconductive material, or to the surfaces of carrier particles when such a toner is used for a two-component type developer. This results in deterioration and changes in the characteristics of the carrier.
  • a crystalline resin such as polyethylene is used as a main binding resin for a toner, the producibility of the toner is reduced and a toner having stable characteristics is not obtained since it is difficult to control the degree of crystallization and the crystal form.
  • Japanese published Patent Applications 75033/73 and 78931/73 propose a material designed to meet the above requirements by using a block copolymer composed of hard and soft resins.
  • the amount of the soft component is increased to the extent necessary to impart sufficient pressure deformability to the toner, grinding of the toner becomes difficult when preparing a toner powder by a kneading and grinding method.
  • a toner powder is prepared by a spray drying method, this difficulty does not occur since a grinding step is unnecessary.
  • liquid preparation becomes difficult and it is difficult to impart both a good fixing property and anti-blocking property to the toner obtained.
  • a multi-phase polymer such as a block copolymer or a graft copolymer
  • the morphology of the toner is greatly influenced by a slight change in the production conditions and the properties of raw materials, resulting in great changes in the characteristics of the toner.
  • Japanese published Patent Application 87042/76 discloses an attempt to improve the pressure fixability of a toner by blending a crystalline resin such as polyethylene wax as a main component with a small amount of material such as a vinylic resin.
  • a crystalline resin is used as the main binding resin, there exist the above-mentioned difficulties which are specific to the crystalline resin.
  • the present invention aims at producing a developer composition having an excellent pressure-fixing property.
  • the present invention provides a pressure fixable developer composition as claimed in claims 1 to 8.
  • the binding resinous material (A) in the developer composition of the present invention includes those having a glass transition temperature below 0°C, preferably below -30°C.
  • Material (A) is selected from resinous materials which show plastic deformation or viscoelastic deformation with a pressure of less than about 20 N/mm 2 at room temperature and has a polar functional group.
  • Polar functional groups of material (A) include a hydroxy group, a carbonyl group, a carboxy group, an epoxy group, a glicidyl group, a nitro group, a sulfonic acid group, an amino group, an amido group, a cyano group, an isocyanate group, a diazonium group, an aziridine group, an aldehyde group, an acid anhydride, a methylol group, a thiol group, a mercapto group, a phosphoric acid group, and a halogen-containing group.
  • These functional groups may be substituted by a group such as a methyl group, ethyl group, phenyl group or may have an ether linkage, ester linkage, etc.
  • a hydroxy group, a carboxyl group and a carbonyl group are preferred, because they are very stable, have no deleterious effect on the characteristics of a toner, and have a large interaction with material (B).
  • the resinous material (A) which has a polar functional group and which is capable of being deformed by pressure at normal temperature may be synthetic or natural resinous material.
  • examples of such materials include higher fatty acids (e.g. stearic acid, oleic acid, etc.,) and derivatives thereof (e.g.
  • fatty acid amides fatty acid amides
  • chlorinated paraffin chlorinated polyethylene, chlorinated polypropylene, oxidized polyethylene, polypropylene oxide, ethylene-acrylic acid copolymer, ethylene-vinyl acetate copolymer, ethylene-vinyl alcohol copolymer, organic acid graft polyethylene, rubber-like acrylic acid copolymer, polyvinyl acetate, polyvinyl butyral, silicone and modified resins thereof, polycarbonate, fluorinated rubber, fluorinated wax, nitrile rubber, chloroprene rubber, polyamide, polyester, polyether, polyurethane, and polyalkyd.
  • oxidized polyethylene, ethylene-acrylic acid copolymer and organic acid graft polyethylene which have a hydroxy group, a carboxyl group or a carbonyl group are particularly preferred for material (A).
  • Binding resinous material (B) in the developer composition of the present invention can be selected from natural and synthetic resinous materials having a glass transition temperature above 40°C, more preferably 60-80°C, and having a polar functional group as defined for material (A).
  • a hydroxy group, a carboxyl group and dialkylamino group are particularly preferred as the polar functional group of material (B).
  • styrene-acrylic acid copolymer, epoxy resin, phenol resin, polyester resin, etc. satisfying the aforesaid factors are preferably used since they meet many required parameters for toner.
  • Material (A) is chemically incompatible with material (B) and the polar functional group of material (A) must interact with the polar functional group of material (B).
  • Solubility is a suitable parameter for compatibility.
  • the parameter of the solubility of material (A) is taken as 5A and the parameter of the solubility of material (B) is taken as ⁇ ⁇
  • ⁇ A - ⁇ B is higher than about 0.5 it is defined as being incompatible.
  • the solubility parameters of the resinous materials can be obtained by calculation. However, standard values which can be relied on are disclosed in "Polymer Handbook", 2nd Ed. (John Wiley & Sons).
  • the interaction of the functional groups may involve (1) hydrophobic bonding (2) electrostatic bonding, (3) hydrogen bonding, (4) charge transfer bonding, and (5) covalent bonding interactions.
  • hydrophobic bonding (2) electrostatic bonding, (3) hydrogen bonding, (4) charge transfer bonding, and (5) covalent bonding interactions.
  • the interactions polar functional groups is important in this invention, the interaction of (2) to (5) are of greater importance.
  • preferred materials which meet various electric, mechanical, rheological, thermal, optical and chemical properties required for a toner, include the combination of an olefinic polymer having group -OH, -COOH or as material (A), and a styrenic copolymer or de-natured resin thereof, or a polyester resin each having group -OH, -COOH or-NR l R 2 wherein R, and R 2 , which may be the same or different, each represents an alkyl group (e.g., methyl, ethyl), as material (B).
  • R, and R 2 which may be the same or different, each represents an alkyl group (e.g., methyl, ethyl), as material (B).
  • R, and R 2 which may be the same or different, each represents an alkyl group (e.g., methyl, ethyl), as material (B).
  • R, and R 2 which may be the same or different, each represents an alkyl group (e.g.
  • the acid value is higher than 5 in both materials (A) and (B).
  • Other polar group contents are similar in this regard.
  • considerable care must be taken so that the content of the functional group is not too high. If the content gets too high, the interaction or reaction between the same kinds of molecules or different kinds of molecules as well as the intramolecular interaction or reaction become too strong. This can cause difficulties.
  • a resin having an acid value of from about 10 to about 100 is preferred. The acid value is shown by the number of milligrams of potassium hydroxide necessary for neutralizing the acid contained in one gram of the resin.
  • the present invention involves introducing a polar functional group into each of two resinous materials (A) and (B) which are incompatible with each other and have largely different physical and chemical properties, whereby materials (A) and (B) interact with each other.
  • materials (A) and (B) interact with each other.
  • the effects and merits of the present invention are briefly explained below.
  • the toner must be constructed so that it exhibits these properties independently in each step of the image-forming processes.
  • resin materials having different properties are made to adopt a proper multiphase structure.
  • the mixture obtained cannot exhibit the individual different properties of each resinous material.
  • the mixture will meet certain of the various required parameters.
  • the heterogeneous interface between them frequently reduces the properties of the toner.
  • the interaction in this case may be a secondary bonding type of interaction such as hydrogen bonding, electrostatic bonding or alternatively may be a covalent bonding type of interaction such as grafting or crosslinking. It has also been found that when secondary bonding takes place, the stabilization in multi-phase dispersion structure not only facilitates the control of electric characteristics and mechanical properties, but also strengthens the shearing stress and shearing time reliance of the mechanical properties of the toner, which are advantageous because the resulting fixed toner image is free of smudges or smears even when rubbed.
  • material (B), which is the hard component, having a glass transition temperature above 40°C be contained in the range of 50-95% by weight, based on the total weight of the resinous materials.
  • the toner further contains a resinous material additional to materials (A) and (B)
  • resinous material having good compatibility with material (A)
  • the additional material is a soft component having a glass transition temperature below 0°C
  • material (B) if the additional material is a hard component having a glass transition temperature above 40°C.
  • the proportion of the total soft components containing material (A) be 5-50% by weight of the resinous materials, and the proportion of the total hard components containing material (B) be 50-95% by weight.
  • the toner may contain various kinds of additives such as coloring agents.
  • useful coloring agents used in this invention include carbon black, magenta, yellow, cyan series pigments as well as Nigrosine, Fast Blue and other dyes.
  • various kinds of magnetic powder can be included in the toner.
  • the amount of magnetic powder in the toner depends upon various factors such as the conditions of the development process, but generally in the range of 20-80% by weight based on the total weight of the toner.
  • the magnetic toner is preferably adjusted to have an electric resistance of 10" to 10" ohm. cm in view of its transferring and developing properties.
  • the magnetic powder is preferably added in an amount of 30-60% by weight based on the total weight of the toner.
  • useful magnetic powder include metals such as iron, cobalt, nickel, and alloys and oxides of these metals.
  • Such magnetic powders may be granular form or acicular form depending on the application of the toner, and the size of the powders is generally from 0.01 to 2 pm. Furthermore, these magnetic powders may be treated on their surfaces with a surface active agent or a fatty acid-, silane- or titanate-series coupling agent before being used.
  • the toners may further contain materials such as plasticizers, granular or fibrous organic or inorganic reinforcing fillers, extenders, antioxidants, foaming agents, ionic or nonionic surface active agents.
  • an external additive may be used in combination with the toners.
  • useful external additives include long chain fatty acids (e.g.
  • stearic acid and amides or metal salts thereof, fine powders of molybdenum disulfide, carbon black, graphite, fluorinated graphite, silicon carbide, boron nitride, silica, aluminum oxide, titanium dioxide, zinc oxide, fine powders of fluorine resins, polycyclic aromatic compounds, wax-like materials, and fine powders of crosslinked or non- crosslinked resins.
  • These additives are usually solid fine particles having a low surface energy, below 30 pN/mm in critical surface tension or having a smooth surface which is below 0.1 in friction coefficient.
  • the additives may also be comprised of fine particles having non-tackiness and some abrasive property. However the additives are not restricted to any such materials.
  • these external additives may be fixed on the surface of toner powders by a hot blast method or otherwise.
  • the developer composition of this invention can be produced by any conventional methods for example, a method comprising fusing whole components, kneading and grinding, a method comprising mixing the binding resinous materials in the form of solution followed by fusing whole components, kneading and grinding, or a spray drying method.
  • the molecular weight of the hard components including material (B) is preferably controlled so as to make the composition of the particle surface of the developer composition uniform. By controlling the number average molecular weight to about 1000-30 000, the ground interfaces can selectively become a hard component phase containing component (B).
  • the particle sizes of the toner are generally 1-50 pm, preferably 5-30 pm.
  • the particle sizes may be controlled by classification if necessary.
  • the developer composition of this invention There is no particular restriction regarding the form of the developer composition of this invention.
  • the developer composition When the developer composition is used as a toner for a two-component developer, after controlling the static property of the toner with a static-controlling agent, the toner is used as a mixture thereof with a carrier material such as an iron powder.
  • the developer composition of this invention can also be used as magnetic toner for a one-component developer by mixing the developer composition with a magnetic powder as described above.
  • it is used as a magnetic toner it is possible to develop not only electrostatic latent images but also magnetic latent images.
  • the developer composition of this invention shows excellent fixibility with only the application of pressure.
  • the composition of this invention can be securely fixed by heat and pressure or by heating or by the use of a solvent.
  • a polystyrene resin Polystyrene resin
  • the toner was mixed with 0.8% by weight fine powder of hydrophobic colloidal silica. After further mixing a carrier iron powder having particle size of about 80 ⁇ m was added. The carrier/toner weight ratio was then adjusted to about 100/5. An image test was then performed using a Xerox (registered trademark) 2300 copying machine. In addition, fixing was performed using a pressure fixing apparatus composed of three metallic rolls at a line pressure of 25 N/mm. The initial image quality was relatively good, but when 5,000 copies were made by repeating the operation, the image density was reduced and background fog increased greatly.
  • Fixing was good in appearance but when the images were rubbed, the images came off partially, and fingers and clothes were readily stained.
  • the toner was also found to be inferior in powder fluidity and antiblocking property at high temperature.
  • the toner was mixed with 0.5% by weight carbon black and a copy test was performed using a one-component-type copying machine.
  • a copy test was performed using a one-component-type copying machine.
  • good development and good transferring property were shown under ordinary circumstances, but when 2000 copies were continuously made, a roughness of image was observed.
  • the cause is considered to be that since filming of the toner onto the photoconductive material occurred and the development and transfer were carried out selectively, the particle sizes of the toner changed with time.
  • the properties of the rough particle portion of the toner were compared with those of the fine powder portion, they differed from each other and it is considered that the distribution of the composition and multi-phase dispersion structure of the toner were broad and the toner was unstable.
  • the pressure fixing of the toner at a line pressure of 25N/mm showed the same defects as in Example 1.
  • a toner having a mean particle size of 14 pm was prepared by the same manner as in Example 1 using the following components;
  • a developer was prepared by mixing the toner with 0.8% by weight fine powder of hydrophobic colloidal silica and further mixing with an iron carrier powder having a particle size of about 80 ⁇ m in such manner that the carrier/toner weight ratio became about 100/5 and a copy test was performed as in Example 1.
  • 20,000 copies were made by repeating the operation, images were good. Furthermore, no change with the passage of time was observed.
  • the pressure-fixing property was evaluated at a line pressure of 20, 25 and 30 N/mm and each case showed good fixing property. It is believed that a stable and proper multi-phase dispersion structure was formed by the interaction of the functional group of the styrenic copolymer and that of the modified ethylene resin. Also, it is considered that since the surface composition of the toner particle was mainly composed of the styrenic resin and was uniform, the charge distribution was narrow. This was also confirmed by the analytical result by ESCA, etc.
  • a magnetic toner having a mean particle size of 15 pm was prepared in the same manner as in Example 2 using the following components:
  • the toner was mixed with 0.5% by weight carbon black and when a copy test was performed using a one-component copying machine, all good development and transferring property were shown under all circumstances. Also, when 10,000 copies were continuously made, no change in image quality was observed. When a pressure fixing was applied at a line pressure of 25N/mm, the image was strongly fixed. When the fixed image was subjected to a friction test using an adhesive tape or rubbed by a finger, the image did not come off or stain clothes.
  • a toner having a mean particle size of 17 ⁇ m was prepared in the manner as in the other examples from the following composition;
  • the toner was mixed with 0.4% by weight carbon black and 0.2% by weight silica powder.
  • a copy test was performed as in Example 6, a good pressure fixing level and good image quality was obtained.
  • a styrenic copolymer produced by copolymerizing styrene, methyl methacrylate, butyl methacrylate
  • the toner was mixed with 0.2% by weight zinc stearate and 0.6% by weight fine powder of hydrophobic silica, and a copy test was performed using a one-component copying machine. When 10,000 copies were made by repeating the operation, the development, transferring property and image quality were good and the pressure fixing at a line pressure of 30N/mm was very excellent.
  • the toner of the present invention provides an excellent toner image, free of background fogs, with high resolution even after 5,000 reproductions and is thoroughly fixed by the application of pressure so that, in contrast to a conventional toner for pressure fixing, the fixed toner image does not smudge or adhere to a finger when rubbed. Further the fixed toner image does not transfer to a back surface of a sheet in contact with the image during storage. Furthermore, the toner transfer rate of the toner of the present invention is not so decreased even at an increased humidity.
  • the magnetic toner of the present invention has a markedly stable toner transfer rate as compared to a conventional magnetic toner.

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

Claims (8)

1. Druckfixierbare Entwicklerzusammensetzung, umfassend eine innige Mischung aus einem harzartigen Material (A) mit einer polaren, funktionellen Gruppe, einer Glasübergangstemperatur unterhalb 0°C und das plastische Deformation zeigt; und
einem harzartigen Material (B) mit einer Glasübergangstemperatur oberhalb 40°C und einer polaren, funktionellen Gruppe, die fähig ist, mit der polaren, funktionellen Gruppe des Materials (A) in Wechselwirkung zu treten, wobei die harzartigen Materialien miteinander unverträglich sind, wie definiert durch den Unterschied der Löslichkeitsparameter, der größer als 0,5 ist, wobei die funktionelle Gruppe der Materialien (A) und (B) jeweils eine Hydroxy-, Carbonyl-, Carboxyl-, Epoxy-, Glicidyl-, Nitro-, Sulphonsäure-, Amino-, Dialkylamino-, Amido-, Cyano-, Isocyanat-, Diazonium-, Aziridin-, Aldehyd-, Säureanhydrid-, Methylol-, Thiol-, Mercapto-, Phosphorsäure- oder eine Halogen enthaltende Gruppe ist.
2. Entwicklerzusammensetzung nach Anspruch 1, umfassend weiterhin ein feines, magnetisches Pulver, das in einer Menge von 20 bis 80 Gew.%, bezogen auf das Gesamtgewicht der Entwicklerzusammensetzung, vorliegt.
3. Entwicklerzusammensetzung nach Anspruch 1 oder 2, wobei das Material (A) ein olefinisches Polymer mit einer Hydroxygruppe, Carboxylgruppe oder Carbonylgruppe als polare, funktionelle Gruppe und das Material (B) ein Styrolpolymer mit einer Hydroxygruppe, Carboxylgruppe oder Dialkylaminogruppe als polare, funktionelle Gruppe ist.
4. Entwicklerzusammensetzung nach Anspruch 1 oder 2, wobei das Material (A) ein olefinisches Polymer mit einer Hydroxygruppe, Carboxylgruppe oder Carbonylgruppe als polare, funktionelle Gruppe und das Material (B) ein Polyesterharz mit einer Hydroxygruppe, Carboxylgruppe oder Dialkylaminogruppe als polare, funktionelle Gruppe ist.
5. Entwicklerzusammensetzung nach Anspruch 3 oder 4, wobei das olefinische Polymer oxidiertes Polyethylen, Ethylen-Acrylsäure-Copolymer oder organische Säure-Pfropfpolyethylen ist.
6. Entwicklerzusammensetzung nach Anspruch 1 oder 2, wobei die Kombination aus den Materialien (A) und (B) besteht aus oxidiertes Polyethylen und Styrol-Allylalkohol-Copolymer; organische Säure-Pfropfpolyethylen und Styrol-Allylalkohol-Copolymer; Ethylen-Acrylsäure-Copolymer und Styrol-Allylalkohol-Copolymer; Ethylen-Vinylacetat-Copolymer und Styrol-(Meth)acrylsäure-Copolymer; oxidiertes Polyethylen und Styrol-Dimethylaminoethylmethacrylat-Copolymer; organische Säure-Pfropfpolyethylen und Styrol-Dimethylaminoethylmethacrylat-Copolymer oder organische Säure-Pfropfpolyethylen und Hydroxygruppen enthaltender, aromatischer Polyester.
7. Entwicklerzusammensetzung nach einem der vorangehenden Ansprüche, wobei das Material (B) 50-95 Gew.-% des Gesamtgewichts der harzartigen Materialien ausmacht.
8. Entwicklerzusammensetzung nach Anspruch 2 oder nach Anspruch 2 und irgendeinem darauf rückbezogenen Anspruch, wobei das magnetische Pulver 30 bis 60 Gew.-% des Gesamtgewichts der Entwicklerzusammensetzung ausmacht und wobei die Entwicklerzusammensetzung einen elektrischen Widerstand von 10" bis 10" Ohm/cm besitzt.
EP19820302468 1981-05-15 1982-05-14 Entwicklerzusammensetzungen Expired EP0066395B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP72201/81 1981-05-15
JP56072201A JPS57188045A (en) 1981-05-15 1981-05-15 Developer composition

Publications (2)

Publication Number Publication Date
EP0066395A1 EP0066395A1 (de) 1982-12-08
EP0066395B1 true EP0066395B1 (de) 1986-09-17

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EP (1) EP0066395B1 (de)
JP (1) JPS57188045A (de)
CA (1) CA1183033A (de)
DE (1) DE3273295D1 (de)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4656111A (en) * 1983-04-12 1987-04-07 Canon Kabushiki Kaisha Pressure-fixable toner comprising combination of a compound having hydrocarbon chain and a compound having amino group
JPS60164754A (ja) * 1984-02-06 1985-08-27 Hitachi Chem Co Ltd 静電荷像現像用トナ−
JPS60225168A (ja) * 1984-04-23 1985-11-09 Hitachi Chem Co Ltd 静電荷像現像用トナ−
JPH0740142B2 (ja) * 1985-11-05 1995-05-01 日本カーバイド工業株式会社 静電荷像現像用トナ−
JPH075850B2 (ja) * 1986-04-05 1995-01-25 株式会社リコー 着色剤及びその利用
EP0380813A1 (de) * 1989-01-31 1990-08-08 Agfa-Gevaert N.V. Trockene elektrophotographische Tonerzusammensetzung
US5213740A (en) * 1989-05-30 1993-05-25 Xerox Corporation Processes for the preparation of toner compositions
JPH0588406A (ja) * 1991-04-16 1993-04-09 Minolta Camera Co Ltd 電子写真用トナーおよびその製造法
JPH07181727A (ja) * 1993-12-24 1995-07-21 Kao Corp 電子写真用トナー及びトナー用補強剤
JPH07209905A (ja) * 1994-01-13 1995-08-11 Ricoh Co Ltd 複写部材および電子写真現像剤の再生方法
WO1996007702A1 (en) * 1994-09-09 1996-03-14 Shell Internationale Research Maatschappij B.V. Block copolymer containing binder composition and electrophotographic toner composition derived therefrom
JPH1090947A (ja) * 1996-09-18 1998-04-10 Toshiba Corp 現像剤及び画像形成装置
JP3946518B2 (ja) * 2001-12-28 2007-07-18 株式会社リコー 画像形成用カラートナー、画像形成装置及びトナー容器
KR20080033622A (ko) * 2006-10-12 2008-04-17 삼성전자주식회사 토너용 결합제 수지 조성물, 토너조성물 및 토너조성물제조방법
US8278018B2 (en) 2007-03-14 2012-10-02 Xerox Corporation Process for producing dry ink colorants that will reduce metamerism

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE789988A (fr) * 1971-10-12 1973-04-12 Xerox Corp Composition de revelateur et procede pour son emploi
BE793248A (fr) * 1971-12-30 1973-06-22 Xerox Corp Revelateur electrostatographique
BE793554A (fr) * 1971-12-30 1973-06-29 Xerox Corp Revelateur electrostatographique
JPS5751669B2 (de) * 1974-12-16 1982-11-02
CA1062946A (en) * 1974-12-19 1979-09-25 Xerox Corporation Electrostatographic pressure-fixable toner composition
JPS5289928A (en) * 1976-01-22 1977-07-28 Mita Industrial Co Ltd Pressure fixing developing agent for electrostatography
JPS542741A (en) * 1977-06-08 1979-01-10 Canon Inc Pressure fixing toner
JPS5589855A (en) * 1978-12-28 1980-07-07 Canon Inc Pressure-fixable capsule toner

Also Published As

Publication number Publication date
JPS57188045A (en) 1982-11-18
CA1183033A (en) 1985-02-26
JPH0237585B2 (de) 1990-08-24
DE3273295D1 (en) 1986-10-23
EP0066395A1 (de) 1982-12-08

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