EP0488744B1 - Elektrophotographischer Toner für Negativaufladung - Google Patents

Elektrophotographischer Toner für Negativaufladung Download PDF

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Publication number
EP0488744B1
EP0488744B1 EP19910311035 EP91311035A EP0488744B1 EP 0488744 B1 EP0488744 B1 EP 0488744B1 EP 19910311035 EP19910311035 EP 19910311035 EP 91311035 A EP91311035 A EP 91311035A EP 0488744 B1 EP0488744 B1 EP 0488744B1
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EP
European Patent Office
Prior art keywords
charge
toner
controlling
carbon atoms
acid
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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 - Lifetime
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EP19910311035
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English (en)
French (fr)
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EP0488744A1 (de
Inventor
Noriaki Tsubota
Masahiko Kubo
Kazuo Fuji
Akihiro Watanabe
Yoshihisa Kuramae
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Kyocera Mita Industrial Co Ltd
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Mita Industrial Co Ltd
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00—Developers
    • G03G9/08—Developers with toner particles
    • G03G9/097—Plasticisers; Charge controlling agents
    • G03G9/09733—Organic compounds
    • G03G9/09741—Organic compounds cationic
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00—Developers
    • G03G9/08—Developers with toner particles
    • G03G9/087—Binders for toner particles
    • G03G9/08702—Binders for toner particles comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • G03G9/08726—Polymers of unsaturated acids or derivatives thereof
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00—Developers
    • G03G9/08—Developers with toner particles
    • G03G9/097—Plasticisers; Charge controlling agents
    • G03G9/09733—Organic compounds
    • G03G9/0975—Organic compounds anionic

Definitions

  • the charge-controlling agent (A) and the charge-controlling assistant (B) be present at an (A)/(B) weight ratio of from 1/0.05 to 1/1, especially from 1/0.1 to 1/0.7, and it also is preferred that the charge-controlling agent and charge-controlling assistant be used in a total amount of 0.5 to 5 parts by weight, especially 2 to 4 parts by weight, per 100 parts by weight of the fixing resin.
  • Fig. 6 is a diagram illustrating the distribution (curve A) of the initial charge quantity and the distribution (curve B) of the charge quantity after formation of 5,000 copies, observed with respect to the toner of Comparative Example 3.
  • Fig. 7 is a diagram illustrating the distribution (curve A) of the initial charge quantity and the distribution (curve B) of the charge quantity after formation of 50,000 copies, observed with respect to the toner of Example 3.
  • the content of the acrylamide-type copolymer is preferably 2 to 20 % by weight, the negative charging property tends to be lost. Furthermore, the weight average molecular weight (Mw) of the copolymer is preferably 2,000 and 15,000.
  • a known resin which is not compatible with the charge-controlling assistant but is capable of dispersing the charge-controlling assistant therein is used as the fixing resin. Since the fixing resin negatively charges the toner, it is preferred that the fixing resin should have a tendency to be negatively charged.
  • a styrene resin, an acrylic resin, a styrene-acrylic resin and a polyester resin are generally used.
  • acrylic monomer there can be mentioned monomers represented by the following formula: wherein R 3 represents a hydrogen atom or a lower alkyl group, and R 4 represents a hydrogen atom or a substituted or unsubstituted alkyl group having up to 18 carbon atoms, such as ethyl acrylate, methyl methacrylate, butyl acrylate, butyl methacrylate, 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, acrylic acid and methacrylic acid.
  • acrylic monomer there can be used other ethylenically unsaturated carboxylic acids and anhydrides thereof, such as maleic anhydride, crotonic acid and itaconic acid.
  • diol component examples include polyoxypropylene-2,2-bis(4-hydroxyphentl) propane, polyoxyethylene-2,2-bis(4-hydroxyphentl)propane, and polyoxypropylene-polyoxyethylene-2,2-bis(4-hydroxyphenyl) propane.
  • This polyester resin may be produced by polycondensing the diol component with the polycarboxylic acid component. It the reaction, other diol components such as ethylene glycol and bisphenol A in addition to 10 mole% of may be concurrently used etherified bisphenols A of the above formula.
  • benzidine pigments such as C.I. Pigment Yellow 13 (Benzidine Yellow GR) (Registered Trade Mark in one or more designated states), C.I Pigment Yellow 14 (Vulcan Fast Yellow G) (Registered Trade Mark in one or more designated states), C.I. Pigment Yellow 17 (Registered Trade Mark in one or more designated states), C.I. Pigment Yellow 55 (Registered Trade Mark in one or more designated states), C.I. Pigment Yellow 12 (Registered Trade Mark in one or more designated states) and C.I. Pigment Yellow 83 (Registered Trade Mark in one or more designated states).
  • a yellow colorant such as chrome yellow, titanium yellow or quinoline yellow lake can be used in addition to the benzidine pigment according to need.
  • quinacridone pigments such as C.I. Pigment Red 122 (Quinacridone Magneta) (Registered Trade Mark in one or more designated states), C.I. Pigment Red 192 (Registered Trade Mark in one or more designated states), C.I. Pigment Red 209 (Registered Trade Mark in one or more designated states) and C.I. Pigment Violet 19 (Quinacridone Violet) (Registered Trade Mark in one or more designated states) are preferably used.
  • the mixing ratio of the toner and the magnetic carrier depends on the physical properties of the toner and the magnetic carrier, but it is preferred that the mixing weight ratio be in the range of from 1/99 to 10/90, especially from 2/98 to 5/95.
  • the above-mentioned toner and magnetic carrier are mixed, a magnetic brush having a predetermined length is formed on a developing sleeve having a magnet roll arranged therein, and the magnetic brush is brought into sliding contact with a photosensitive material having the electrostatic image, or the magnetic brush is brought into close proximity to the electrostatic image-holding photosensitive material in a field to which a vibrating electric field is applied.
  • a twin-screw kneader 100 parts by weight of a styrene/acrylic copolymer as the fixing resin, 5 parts by weight of carbon black as the colorant, 1.5 parts by weight of low-molecular-weight polypropylene as the offset-preventing agent, 2 parts by weight of a copolymer of styrene and 2-acrylamide-2-methylpropane sulfonic acid (styrene content; 91%, Mw: 8000) as the charge-controlling agent for negative charging and 0.5 part by weight of a quaternary ammonium salt represented by the following formula: as the charge-controlling assistant incompatible with the styrene/acrylic copolymer were melt-kneaded, and the melt-kneaded mixture was cooled, pulverized and sieved to obtain a toner having an average particle size of 11 um.
  • a toner was prepared in the same manner as described in Example 3 except that 0.5 part by weight of C.I. Solvent Yellow 56 compatible with the fixing resin was used instead of the charge-controlling assistant used in Example 3.
  • the distribution of the charge quantity of the toner was measured in the same manner as described in Example 1. A board distribution similar to that shown in Fig. 3 was observed.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Developing Agents For Electrophotography (AREA)

Claims (17)

  1. Elektrophotographischer Toner für negative Aufladung, dadurch gekennzeichnet, daß er ein Fixierharz, ein Farbmittel, ein Ladungskontrollmittel für negative Aufladung, das ein Copolymer eines Acrylamid-Monomers der Formel (I),

            CH2 = CX1 - CONH - X2 -SO3H     (I)

    worin X1 Wasserstoff oder Methyl ist und X2 eine zweiwertige Kohlenwasserstoffgruppe mit 1 bis 6 Kohlenstoffatomen bedeutet, und eines Vinyl-Monomers ist, und ein Ladungskontroll-Hilfsmittel, das ein eine positive Ladung kontrollierender Stoff ist, der mit dem Fixierharz inkompatibel und darin dispergiert ist, umfaßt, und worin das Ladungskontroll-Hilfsmittel eine Verbindung der Formel (II) ist
    Figure imgb0011
     worin eine oder zwei der Reste R Alkyl oder Alkenyl mit mindestens 8 Kohlenstoffatomen bedeuten, und die anderen Reste R Alkyl mit bis zu 4 Kohlenstoffatomen oder Benzyl sind, und A- ein Anion einer Sauerstoffsäure ist.
  2. Toner nach Anspruch 1, dadurch gekennzeichnet, daß mindestens einer der Reste R Alkyl oder Alkyenyl mit 8 bis 22 Kohlenstoffatomen ist.
  3. Toner nach Anspruch 1 oder 2, dadurch gekennzeichnet, daß das Ladungskontroll-Hilfsmittel ein quaternäres Ammoniumsalz einer Orthophosphorsäure, Molybdänsäure, Wolframsäure, Antimonsäure oder Bismutsäure ist.
  4. Toner nach einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, daß das Ladungskontrollmittel und das Ladungskontroll-Hilfsmittel in einem Gewichtsverhältnis von 1:0.05 bis 1:1 vorhanden sind, und in einer Gesamtmenge von 0.5 bis 5 Gewichtsteile pro 100 Gewichtsteile des Fixierharzes verwendet werden.
  5. Toner nach einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, daß das Ladungskontrollmittel ein Copolymer ist, das 2 bis 20 Gew.-% des Acrylamid-Monomers enthält.
  6. Toner nach einem der Ansprüche 1 bis 5, dadurch gekennzeichnet, daß das Ladungskontrollmittel ein Copolymer eines Acrylamids und Styrol ist.
  7. Toner nach Anspruch 6, dadurch gekennzeichnet, daß das Ladungskontrollmittel ein Copolymer von 2-Acrylamid-2-methylpropansulfonsäure und Styrol ist.
  8. Toner nach Anspruch 7, dadurch gekennzeichnet, daß das Copolymer ein mittleres Molekulargewicht (Mw) von 2000 bis 15000 besitzt.
  9. Gelbtoner nach einem der Ansprüche 1 bis 8, dadurch gekennzeichnet, daß das Farbmittel ein Benzidinpigment ist.
  10. Magentatoner nach einem der Ansprüche 1 bis 8, dadurch gekennzeichnet, daß das Farbmittel ein Chinacridonpigment ist.
  11. Cyantoner nach einem der Ansprüche 1 bis 8, dadurch gekennzeichnet, daß das Farbmittel ein Kupferphthalocyaninpigment ist.
  12. Verwendung eines Toner nach einem der Ansprüche 1 bis 11 in elektrophotographischen Druckverfahren und elektrophotographischen Reproduktionsverfahren von Bildern.
  13. Magnetischer Zweikomponenten-Entwickler, dadurch gekennzeichnet, daß er einen Toner nach einem der Ansprüche 1 bis 11 und einen Magnetträger enthält.
  14. Verfahren zur Herstellung eines elektrophotographischen Toners für negative Aufladung, dadurch gekennzeichnet, daß das Verfahren umfaßt: Schmelzkneten einer Mischung umfassend ein Fixierharz, ein Farbmittel, ein Ladungskontrollmittel für negative Aufladung, das ein Copolymer eines Acrylamid-Monomers der Formel (I)

            CH2 = CX1 - CONH - X2 -SO3H     (I)

    worin X1 Wasserstoff oder Methyl und X2 eine zweiwertige Kohlenwasserstoffgruppe mit 1 bis 6 Kohlenstoffatomen bedeutet, und eines Vinyl-Monomers ist, und ein Ladungskontroll-Hilfsmittel, das ein eine positive Ladung kontrollierender Stoff ist, der mit dem Fixierharz inkompatibel und darin dispergiert ist, und worin das Ladungskontrollmittel eine Verbindung der Formel (II) ist
    Figure imgb0012
     worin eine oder zwei der Reste R Alkyl oder Alkenyl mit mindestens 8 Kohlenstoffatomen bedeuten und die anderen Reste R Alkyl mit bis zu 4 Kohlenstoffatomen oder Benzyl sind, und A- ein Anion einer Sauerstoffsäure ist.
  15. Verfahren nach Anspruch 14 zur Herstellung eines Toners gemäß einem der Ansprüche 2 bis 11.
  16. Verfahren zur Herstellung eines magnetischen Zweikomponenten-Entwicklers, dadurch gekennzeichnet, daß das Verfahren umfaßt: Mischen eines Magnetträgers mit einem elektrophotographischen Toner für negative Aufladung, der ein Fixierharz, ein Farbmittel, ein Ladungskontrollmittel für negative Aufladung, das ein Copolymer eines Acryl-Monomers der Formel (I)

            CH2 = CX1 - CONH - X2 -SO3H     (I)

    worin X1 Wasserstoff oder Methyl ist und X2 eine zweiwertige Kohlenwasserstoffgruppe mit 1 bis 6 Kohlenstoffatomen bedeutet, und einem Vinyl-Monomer ist, und ein Ladungskontroll-Hilfsmittel, das ein eine positive Ladung kontrollierender Stoff ist, der mit dem Fixierharz inkompatibel und darin dispergiert ist, umfaßt, und worin das Ladungskontroll-Hilfsmittel eine Verbindung der Formel (II) ist
    Figure imgb0013
     worin eine oder zwei der Reste R Alkyl oder Alkenyl mit mindestens 8 Kohlenstoffatomen bedeuten und die anderen Reste R Alkyl mit bis zu 4 Kohlenstoffatomen oder Benzyl sind, und A- ein Anion einer Sauerstoffsäure ist.
  17. Verfahren nach Anspruch 16, dadurch gekennzeichnet, daß der Toner ein solcher gemäß einem der Ansprüche 2 bis 11 ist.
EP19910311035 1990-11-28 1991-11-28 Elektrophotographischer Toner für Negativaufladung Expired - Lifetime EP0488744B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2328363A JP2609358B2 (ja) 1990-11-28 1990-11-28 負帯電用電子写真トナー
JP328363/90 1990-11-28

Publications (2)

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EP0488744A1 EP0488744A1 (de) 1992-06-03
EP0488744B1 true EP0488744B1 (de) 1996-07-17

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JP (1) JP2609358B2 (de)
DE (1) DE69120908T2 (de)
ES (1) ES2091884T3 (de)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6342328B1 (en) 1998-03-31 2002-01-29 Nippon Zeon Co., Ltd. Toner for development of electrostatic charge image and method for producing the same
JP2000347445A (ja) 1999-03-26 2000-12-15 Nippon Zeon Co Ltd 静電荷像現像用トナー

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4777104A (en) * 1985-05-30 1988-10-11 Mita Industrial Co., Ltd. Electrophotographic toner made by polymerizing monomers in solution in presence of colorant
JPH0812467B2 (ja) * 1987-01-28 1996-02-07 藤倉化成株式会社 電子写真用負帯電トナ−
DE3874176T2 (de) * 1987-03-25 1993-04-08 Hodogaya Chemical Co Ltd Quaternaeres ammoniumsalz und elektrophotographischer toner.
JP2567018B2 (ja) * 1988-02-26 1996-12-25 三田工業株式会社 静電荷像現像用トナーの製造方法
JP2623684B2 (ja) * 1988-05-12 1997-06-25 ミノルタ株式会社 トナー
JP2710342B2 (ja) * 1988-07-11 1998-02-10 株式会社リコー 静電荷像現像用トナー
JPH03171147A (ja) * 1989-11-30 1991-07-24 Mita Ind Co Ltd 静電荷像現像用トナー

Also Published As

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ES2091884T3 (es) 1996-11-16
DE69120908T2 (de) 1996-11-28
JP2609358B2 (ja) 1997-05-14
DE69120908D1 (de) 1996-08-22
JPH04195166A (ja) 1992-07-15
EP0488744A1 (de) 1992-06-03

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