EP0242420B1 - Toner pour le développement d'images latentes électrostatiques ainsi que son utilisation - Google Patents

Toner pour le développement d'images latentes électrostatiques ainsi que son utilisation Download PDF

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Publication number
EP0242420B1
EP0242420B1 EP86105723A EP86105723A EP0242420B1 EP 0242420 B1 EP0242420 B1 EP 0242420B1 EP 86105723 A EP86105723 A EP 86105723A EP 86105723 A EP86105723 A EP 86105723A EP 0242420 B1 EP0242420 B1 EP 0242420B1
Authority
EP
European Patent Office
Prior art keywords
toner
parts
hydroxyl
alkyl
developer
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
EP86105723A
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German (de)
English (en)
Other versions
EP0242420A1 (fr
Inventor
Yoji Kawagishi
Shinichi Narita
Takashi Kiriu
Schunichiro Yamanaka
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Orient Chemical Industries Ltd
Original Assignee
Orient Chemical Industries Ltd
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Filing date
Publication date
Priority to JP60235998A priority Critical patent/JPS6294856A/ja
Application filed by Orient Chemical Industries Ltd filed Critical Orient Chemical Industries Ltd
Priority to AT86105723T priority patent/ATE58973T1/de
Priority to DE8686105723T priority patent/DE3676086D1/de
Priority to EP86105723A priority patent/EP0242420B1/fr
Publication of EP0242420A1 publication Critical patent/EP0242420A1/fr
Application granted granted Critical
Publication of EP0242420B1 publication Critical patent/EP0242420B1/fr
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
    • G03G9/097—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
    • G03G9/097—Plasticisers; Charge controlling agents
    • G03G9/09733—Organic compounds
    • G03G9/0975—Organic compounds anionic
    • 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

Definitions

  • the present invention relates to a novel dry positively chargeable toner for developing electrostatic latent images for use in electrophotography, electrostatic recording, electrostatic printing, etc. as claimed in Claim 1.
  • Electrostatic latent images can be developed into visible images by depositing a toner on the latent image by electrostatic attraction.
  • Powder developers as well as liquid developers are widely used for developing electrostatic latent images.
  • Powder developers can be divided generally into two-component developers and single-component developers.
  • the two-component developer comprises a particulate toner having a mean particle size of 15 ⁇ m and prepared by dispersing a coloring agent, charge control agent, fluidizing agent and the like in a natural or synthetic resin, and a carrier of finely divided iron, ferrite or the like admixed with the toner and having a particle size of 100 to 200 ⁇ m.
  • the latter single-component developer comprises only a particulate toner having a mean particle size of 15 1 1m and prepared by dispersing a coloring agent, charge control agent, fluidizing agent and the like in a natural or synthetic resin.
  • the toner With the two-component developer, the toner is triboelectrically charged by the carrier and deposited on electrostatic latent images for development.
  • the toners heretofore known and serving as single-component developers include those which are triboelectrically chargeable by a brushlike or platelike friction member having the same function as the carrier and serving as a substitute therefor. Further provided in recent years are toners which are triboelectrically chargeable by a dispersed finely divided magnetic material. These developing toners are charged positively or negatively in accordance with the polarity of the electrostatic latent image to be developed.
  • the toner To enable the toner to retain the charge, it is also proposed to utilize the triboelectric chargeability of the resin used as the main component of the toner, but the toner so adapted is low in chargeability and has a great solid surface resistance value. Consequently the toner image obtained is prone to fogging and obscure.
  • a toner is known in which a certain functional group is introduced into the resin to enable the toner to retain positive charges, the toner releases a disagreeable odor during thermal fixing, owing to the functional group, and is subject to variations of the amount of charges retainable.
  • the charge control agents presently used in the art for giving positive chargeability include the nigrosine dyes disclosed in Examined Japanese Patent Publication SHO 41-2427, etc., the quaternary ammonium salts disclosed in U.S. Patent No. 3,565,654, etc. and polyamide resins disclosed in Examined Japanese Patent Publication SHO 53-13284.
  • charge control agents heretofore used are colored and are therefore not suited to color toner compositions although useful for black toner compositions.
  • the above- mentioned quaternary ammonium salts provided as colorless charge control agents are soluble in water, difficult to disperse uniformly in the toner and prone to uneven charging.
  • the toner incorporating the agent has high chargeability immediately after preparation, the chargeability decreases 'exponential functionally depending on the conditions under which the toner is stored, and this tendency becomes more pronounced when the toner is exposed to a high temperature and high humidity.
  • this compound is colorless or pale colored to such an extent that it can be regarded as substantially colorless, thermally stable, highly amenable to pulverization, highly compatible with resins and useful as a charge control agent in preparing a toner which is uniformly chargeable and has outstanding durability against changes of environmental conditions.
  • the present invention has been accomplished.
  • Charge control agents of similar structure are disclosed in FR-A 2 317 688 and EP- A 0 053 888.
  • the charge control compound of the present invention represented by the formula (I) can be prepared from a quaternary ammonium salt represented by the formula wherein R 1 is C 1 - C 8 alkyl or benzyl, R 2 and R 3 are each C 1 - C 18 alkyl, R 4 is C 1 - C 18 alkyl or benzyl, and A is an anion, and a naphthalenesulfonic acid having substituents and represented by the formula wherein X is hydroxyl or amino, and Y is hydroxyl or hydrogen and is not hydrogen when X is hydroxyl, by a known salt forming method.
  • Examples of useful quaternary ammonium salts represented by the formula (II) are tetramethylammonium chloride, benzyltrimethylammonium chloride, stearyltrimethylammonium chloride, benzyltriethylammonium chloride, benzyltributylammonium chloride, tetrabutylammonium bromide, dibenzyldimethylammonium chloride, benzyloctyldimethylammonium chloride and the like.
  • naphthalenesulfonic acids having substituents and represented by the formula (III) are 1,5-dihydroxynaphthalene-4-sulfonic acid, 1,7-dihydroxynaphthalene-3-sulfonic acid, 1,8-dihydroxynaphthalene-4-sulfonic acid, 2,3-dihydroxynaphthalene-6-sulfonic acid, 4-amino-1-naphthol-2-sulfonic acid, 5-amino-1-naphthol-3-sulfonic acid, 6-amino-1-naphthol-3-sulfonic acid, 8-amino-1-naphthol-5-sulfonic acid, 1-amino-2-naphthol-4-sulfonic acid, 1-amino-2-naphthol-6-sulfonic acid, 5-amino-2-naphthol-7-sulfonic acid, 8-amino-1-naphthalene
  • a 54 g quantity of 50% aqueous solution of benzyltripropylammonium chloride was diluted with 80 ml of water.
  • a solution of 26.2 g of sodium 1,7-dihydroxynaphthalene-3-sulfonate in 500 ml of water was added dropwise to the dilution at room temperature with stirring.
  • the mixture was then heated to about 80 ° C and reacted for one hour.
  • the reaction mixture was cooled to about 30 ° C with stirring, filtered, washed with water and dried, giving 42 g of a light yellow powder, m.p. 228 to 232 ° C.
  • a 62 g quantity of 50% aqueous solution of benzyltributylammonium chloride was diluted with 80 ml of water.
  • a solution of 24.5 g of sodium 4-amino naphthalene-1-sulfonate in 500 ml of water was added dropwise to the dilution at room temperature with stirring. The mixture was then heated to about 80° C and reacted for one hour. The reaction mixture was cooled to about 30 ° C with stirring, filtered, washed with water and dried, affording 44 g of a white powder, m.p. 128 to 133° C.
  • the toner of the present invention comprises the salt forming compound of the formula (I) and at least one resin which is selected from among known resins for toners in view of adhesion, preservability, flowability, pulverizability, etc.
  • resins are styrene resin, styrene-acrylic resin, styrene-butadiene resin, epoxy resin, polyester resin, paraffin wax and the like. Such resins can be used in admixture.
  • coloring agents examples include carbon black, lamp black, iron black, nigrosine dyes, Aniline Black, Benzidine Yellow, Hansa Yellow, chrome yellow, Rhodamine 6G Lake, quinacridone, Rose Bengale, Phthalocyanine dyes and pigments, ulramarine, triarylmethane dyes and pigments, anthraquinone dyes, monoazo and disazo dyes and pigments and the like. These coloring agents are used singly or in admixture.
  • the toner of the present invention may further incorporate additives other than the above toner resin and coloring agent.
  • additives such as Teflon (registered trademark) and zinc stearate
  • flowability imparting agents such as colloidal silica, titanium oxide and aluminum oxide
  • caking preventing agent such as carbon black and tin oxide
  • conductivity imparting agents such as carbon black and tin oxide
  • auxiliary fixing agents such as low-molecular-weight polyethylene, etc.
  • the salt forming compound of the formula (I) is incorporated into the toner of the present invention in an amount of 0.1 to 10 parts by weight, preferably 0.5 to 5 parts by weight, per 100 parts by weight of the resin.
  • the toner of the present invention provides a two-component developer when admixed with a carrier, it is also of course usable as a single-component developer.
  • the present toner is usable also as a magnetic toner when incorporating a magnetic material.
  • the toner of the present invention for developing electrostatic latent images can be prepared by thoroughly mixing the salt forming compound, represented by the formula (I) and serving as a charge control agent, with a vinyl or non-vinyl thermoplastic resin, a pigment or dye serving as a coloring agent, and when required, a magnetic material and other additives by a ball mill or like mixer, further kneading the mixture in a molten state by a hot roll, kneader, extruder or like kneader-mixer to disperse the pigment or dye in the resulting molten mixture, solidifying the mixture by cooling and pulverizing the solid mixture, followed by classification to obtain a toner fraction having a mean particle size of 5 to 20 (lm.
  • a method wherein materials are dispersed in a resin solution, and the dispersion is spraydried and a method wherein specified materials are admixed with the monomers to be made into a resin to obtain an emulsified suspension, which is then polymerized to obtain a toner.
  • the toner of the present invention thus prepared is uable by known means for developing electrostatic latent images in electrophotography, electrostatic recording, electrostatic printing and various other applications.
  • the above ingredients were uniformly mixed together by a ball mill to prepare a premix, which was then kneaded by heat rolls in a molten state, cooled, then roughly ground by a vibrating mill and further pulverized by a LABO JET get mill, product of Nippon Pneumatic Co., Ltd.).
  • the fine particles obtained were classified to obtain a black toner 5 to 15 11m in particle size.
  • the amount of initial blowoff charges of the developer was +20.3 (iC/g .
  • the developer was used for making 10,000 copies using a copying machine having a toner recycling device incorporated therein and was thereafter checked for the amount of blowoff charges, which was found to be +19.3 ⁇ C/g , hence high stability.
  • a toner was prepared and then two-component developer was prepared in the same manner as in Example 1 except that Compound (1) used in Example 1 was replaced by 3 parts of BONTRON N-01 (nigrosine-type charge control agent, product of Orient Chemical Industries Ltd.).
  • the developer was +20.6 pC/g in the amount of initial blowoff charges.
  • the developer was used for the copying machine incorporating a toner recycling device for making 10,000 copies and then checked for the amount of blowoff charges, which was found to be a considerably increased value of +25.1 I1C/g . Further when used for the commercial copying machine, the developer initially produced copies of good image density (at least 1.40), but when it was used for making 10,000 copies, a reduced toner image density resulted along with fogging and filming.
  • the above composition was made into a blue toner in the same manner as in Example 1. Three parts of the toner obtained and 97 parts of finely divided iron carrier were mixed together to prepare a developer. The amount of initial blowoff charges of the developer was +23.6 I1 C/g . When used for copying in the same manner as in Example 1, the developer produced sharp sky blue copy images free from fog. Even when used repeatedly for a prolonged period of time (10,000 copies), the developer afforded copy images free from changes.
  • a blue toner was prepared in the same manner as in Example 2 except that 3 parts of Compound (11) was used in place of Compound (2) used in Example 2.
  • the amount of initial blowoff charges of the developer was +18.3 ⁇ C/g .
  • the developer produced fog-free sharp sky blue copy images. Even after the toner was used for making 10,000 copies continually, no degradation was found in the copies obtained.
  • Example 2 The above composition was treated in the same manner as in Example 1 to obtain a green toner. Three parts of the toner obtained was admixed with 97 parts of finely divided iron carrier to prepare a developer.
  • the amount of initial blowoff charges of the developer was +24.1 ⁇ C/g .
  • the developer produced sharp green copy images. Even when the developer was used repeatedly for a prolonged period of time (10,000 copies), the copy images obtained were free from changes.
  • a green toner was prepared in the same manner as in Example 4 except that 3 parts of Compound (12) was used in place of Compound (3) used in Example 4.
  • the above ingredients were uniformly mixed together by a ball mill to prepare a premix, which was then kneaded by heat rolls in a molten state, cooled, then roughly ground by a continuous vibrating mill and further pulverized by a LABO JET (product of Nippon Pneumatic Co., Ltd.).
  • the fine particles obtained were classified to prepare a single-component developer (black toner) 5 to 35 1 1m in particle size.
  • the amount of blowoff charges of the toner was +7.1 p.C/g .
  • the toner produced satisfactory copy images having a high density (at least 1.40) with reduced fog.
  • the toner transfer ratio achieved was 90%.
  • the amount of blowoff charges of the toner was +10.6 ⁇ C/g .
  • the toner produced copy images of high density (at least 1.40) with reduced fog.
  • the toner transfer ratio achieved was 90%.
  • Simulated toners were prepared in the same manner as in Example 1 and checked for environmental charging characteristics with lapse of time, each of the simulated toner comprising 100 parts of styrene- n-butyl methacrylate resin (65/35) and 5 parts of a compound of the invention.
  • a toner was prepared in the same manner as in Example 8 except that 5 parts of stearyldimethylbenzylammonium-p-toluenesulfonate was used in place of 5 parts of the compound of the invention used in Example 8. The toner was similarly checked for charging characteristics. Table 1 shows the results.
  • a toner was prepared in the same manner as in Example 8 with the exception of using 5 parts of stearyldimethylbenzylammonium chloride in place of 5 parts of the present compound used in Example 8. The toner was similarly checked for charging characteristics with the results given in Table 1.
  • a toner was prepared in the same manner as in Example 8 with the exception of using 5 parts of BONTRON N-01 (nigrosine-type charge control agent, product of Orient Chemical Industries Ltd.) in place of 5 parts of the present compound.
  • the toner was similarly checked for charging characteristics with the results given in Table 1.
  • Table 1 reveals that the toners of the present invention are greatly diminished in the amount of attenuation of charges at a high temperature unlike the conventional ones, thus exhibiting outstanding charging characteristics.
  • the toner of the present invention containing the salt forming compound of the formula (I) as a charge control agent is uniform in the amount of triboelectric charges from particle to particle and is easily controllable in the amount of charges thereon.
  • the toner has very high stability without undergoing variations or reduction in the amount of triboelectric charges thereon due to degradation during use, exhibits outstanding durability under various environmental conditions unlike the conventional toners and is preservable for a prolonged period of time.
  • the toner image obtained is excellent in abrasion resistance, fixing properties and adhesion.

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

Claims (4)

1. Procédé de préparation d'un toner pour le développement d'images latentes électrostatiques, par mélange intime d'un composé de stabilisation de charge, représenté par la formule
Figure imgb0018
dans laqauelle R1 représente un groupe alkyle en C1-8 ou un groupe benzyle, R2 et R3 représentent chacun un groupe alkyle en Ci-la, R4 représente un groupe alkyle en C1-18 ou un groupe benzyle, X représente un groupe hydroxyle ou amino, et Y représente un groupe hydroxyle ou un atome d'hydrogène, mais ne représente pas un atome d'hydrogène quand X représente un groupe hydroxyle, avec une résine thermoplastique et un pigment ou un colorant servant d'agent de coloration.
2. Procédé conforme à la revendication 1, dans lequel le composé de stabilisation de charge est incorporé dans le toner à raison de 0,5 à 5 parties en poids pour 100 parties en poids de la résine.
3. Procédé conforme à la revendication 1 ou 2, dans lequel un matériau magnétique est incorporé dans le toner.
4. Utilisation d'un toner préparé selon le procédé de l'une quelconque des revendications 1 à 3, pour l'électrophotographie en couleurs.
EP86105723A 1985-10-21 1986-04-25 Toner pour le développement d'images latentes électrostatiques ainsi que son utilisation Expired EP0242420B1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP60235998A JPS6294856A (ja) 1985-10-21 1985-10-21 静電荷像現像用トナ−
AT86105723T ATE58973T1 (de) 1985-10-21 1986-04-25 Toner zur entwicklung eines elektrostatischen latenten bildes und seine verwendung.
DE8686105723T DE3676086D1 (de) 1985-10-21 1986-04-25 Toner zur entwicklung eines elektrostatischen latenten bildes und seine verwendung.
EP86105723A EP0242420B1 (fr) 1985-10-21 1986-04-25 Toner pour le développement d'images latentes électrostatiques ainsi que son utilisation

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP60235998A JPS6294856A (ja) 1985-10-21 1985-10-21 静電荷像現像用トナ−
EP86105723A EP0242420B1 (fr) 1985-10-21 1986-04-25 Toner pour le développement d'images latentes électrostatiques ainsi que son utilisation

Publications (2)

Publication Number Publication Date
EP0242420A1 EP0242420A1 (fr) 1987-10-28
EP0242420B1 true EP0242420B1 (fr) 1990-12-05

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EP86105723A Expired EP0242420B1 (fr) 1985-10-21 1986-04-25 Toner pour le développement d'images latentes électrostatiques ainsi que son utilisation

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EP (1) EP0242420B1 (fr)
JP (1) JPS6294856A (fr)
AT (1) ATE58973T1 (fr)
DE (1) DE3676086D1 (fr)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4937157A (en) * 1989-08-21 1990-06-26 Xerox Corporation Toner and developer compositions with charge enhancing additives
EP0475263B1 (fr) * 1990-09-12 1997-05-02 Mitsubishi Chemical Corporation Toner pour développer une image électrostatique
JP3100776B2 (ja) * 1992-07-15 2000-10-23 オリヱント化学工業株式会社 荷電制御剤及び静電荷像現像用正帯電性トナー
DE4317059A1 (de) * 1993-05-21 1994-11-24 Basf Ag Elektrostatische Toner, enthaltend Polyamine als Ladungsstabilisatoren
EP2003127B1 (fr) 2006-03-29 2012-08-01 Hodogaya Chemical Co., Ltd. Melange de sulfures de phenols cycliques et agent de regulation de charge ou toner l'utilisant
JP5343560B2 (ja) 2006-04-13 2013-11-13 保土谷化学工業株式会社 酸化型混合環状フェノール硫化物、それを用いた電荷制御剤及びトナー
WO2011105334A1 (fr) 2010-02-26 2011-09-01 保土谷化学工業株式会社 Agent de contrôle de charge et toner l'utilisant
EP2618218A1 (fr) 2010-09-13 2013-07-24 Hodogaya Chemical Co., Ltd. Agent de contrôle de charge et toner l'utilisant
CN103238117A (zh) 2010-09-14 2013-08-07 保土谷化学工业株式会社 电荷控制剂和使用其的调色剂
WO2012036171A1 (fr) 2010-09-15 2012-03-22 保土谷化学工業株式会社 Agent de contrôle de charge et toner utilisant ledit agent
EP2669741A4 (fr) 2011-01-27 2016-05-11 Hodogaya Chemical Co Ltd Agent de contrôle de charge et toner utilisant cet agent
JP2012177827A (ja) 2011-02-28 2012-09-13 Ricoh Co Ltd トナー、このトナーを用いたフルカラー画像形成方法及びフルカラー画像形成装置
JPWO2015046214A1 (ja) * 2013-09-24 2017-03-09 保土谷化学工業株式会社 電荷制御剤及びそれを用いたトナー
WO2017047482A1 (fr) 2015-09-17 2017-03-23 保土谷化学工業株式会社 Agent de régulation de charge et d'encre en poudre utilisant un dérivé de pyrazolone ou un sel de dérivé

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1060696A (fr) * 1975-07-09 1979-08-21 Eastman Kodak Company Compose revelateur et toner electrographique
US4338390A (en) * 1980-12-04 1982-07-06 Xerox Corporation Quarternary ammonium sulfate or sulfonate charge control agents for electrophotographic developers compatible with viton fuser

Also Published As

Publication number Publication date
EP0242420A1 (fr) 1987-10-28
ATE58973T1 (de) 1990-12-15
JPH0445822B2 (fr) 1992-07-28
DE3676086D1 (de) 1991-01-17
JPS6294856A (ja) 1987-05-01

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