JPH01306861A - Electrophotographic toner - Google Patents

Electrophotographic toner

Info

Publication number
JPH01306861A
JPH01306861A JP63135413A JP13541388A JPH01306861A JP H01306861 A JPH01306861 A JP H01306861A JP 63135413 A JP63135413 A JP 63135413A JP 13541388 A JP13541388 A JP 13541388A JP H01306861 A JPH01306861 A JP H01306861A
Authority
JP
Japan
Prior art keywords
toner
formula
ion
colorless
compd
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.)
Pending
Application number
JP63135413A
Other languages
Japanese (ja)
Inventor
Nobuo Aoki
青木 延夫
Jun Kurita
栗田 純
Makoto Ebisawa
海老沢 誠
Isao Isa
伊佐 功
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.)
Japan Carlit Co Ltd
Original Assignee
Japan Carlit Co Ltd
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
Application filed by Japan Carlit Co Ltd filed Critical Japan Carlit Co Ltd
Priority to JP63135413A priority Critical patent/JPH01306861A/en
Publication of JPH01306861A publication Critical patent/JPH01306861A/en
Pending legal-status Critical Current

Links

Classifications

    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00Developers
    • G03G9/08Developers with toner particles
    • G03G9/097Plasticisers; Charge controlling agents
    • G03G9/09783Organo-metallic compounds
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00Developers
    • G03G9/08Developers with toner particles
    • G03G9/097Plasticisers; Charge controlling agents
    • G03G9/09733Organic compounds
    • G03G9/0975Organic compounds anionic

Abstract

PURPOSE:To obtain a colorless electrophotographic toner having high heat stability and being chargeable negatively as well as having superior dispersibility into a resin component by incorporating a specified compd. as charge controller. CONSTITUTION:A compd. expressed by the formula I is incorported as charge controller. In hte formula I, R is an H atom, alkyl group, etc.; each m and n is 1-4; X' is an H ion, alkali metal ion, aliphatic ammonium ion, etc. The compd. expressed by the formula I is incorporated into a toner component in a proportion of generally 0.1-10, more pref. 0.5-5 pts.wt. per 100 pts.wt. of a resin. Thus, a colorless elecetrophotographic toner capable of providing distinct picture images and durable against continuous use is obtd. because a colorless charge controller having high stability against mechanical friction, mechanical shock, temp., and moisture is used therein.

Description

【発明の詳細な説明】 (産業上の利用分野) 本発明は電子写真において静電潜像を現像するためのト
ナーに関する。
DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a toner for developing electrostatic latent images in electrophotography.

(従来の技術) 電子写真は光導電性物質などにより構成された    
′光導電体上に潜像を構成し、これを粉末現像剤で現像
して顕像化、さらに熱あるいは溶剤、場合によっては圧
力によって紙上に定着する方法が一般的である。このよ
うな電子写真の現(!剤としては天然樹脂または合成樹
脂に着色剤、電荷調整剤、流動化剤等を分散させたトナ
ーと鉄粉またはフェライト粉のキャリアとの混合物より
成る2成分系現像剤と、天然υl脂または合成樹脂に着
色剤、電荷調整剤、流動化剤、磁性体より成る1成分系
現像剤とに大別することができる。
(Conventional technology) Electrophotography consists of photoconductive materials, etc.
'The general method is to form a latent image on a photoconductor, develop it with a powder developer to make it visible, and then fix it on paper using heat, a solvent, or in some cases pressure. In this type of electrophotography, the agent is a two-component system consisting of a mixture of a toner in which a coloring agent, a charge control agent, a fluidizing agent, etc. are dispersed in a natural or synthetic resin, and a carrier of iron powder or ferrite powder. Developers can be broadly classified into one-component developers, which are composed of natural υl fats or synthetic resins, colorants, charge control agents, fluidizing agents, and magnetic materials.

2成分系現像剤は、キャリアとの摩擦によl)荷電せし
めたトナーを静電潜像に付着せしめることによ])現像
を達成するものであり、1成分系現像削としては、従来
より、キャリアの代わ1)にこれと同様の機能を有する
ブラシ状、板状の)¥擦部材との摩擦によって荷電され
るトナーが知られており、また最近に至って、磁性体微
粉末を分散状態に保ち、該磁性体微粉末との相互摩擦に
よって荷電されるトナーが知られるようになった。光導
電体層は正または負に荷電することができるので、オリ
ジナルの下で露光により正または負の静電潜像が得られ
る。この静電潜像の極性に応じて、現像用トナーは正ま
たは負に保たれる。
A two-component developer achieves development by causing charged toner to adhere to an electrostatic latent image through friction with a carrier. Toners that are charged by friction with brush-like or plate-like friction members that have the same function as carriers (1) are known as substitutes for carriers. A toner that is charged by mutual friction with the fine magnetic powder has become known. The photoconductor layer can be positively or negatively charged so that exposure under the original produces a positive or negative electrostatic latent image. Depending on the polarity of this electrostatic latent image, the developing toner remains positive or negative.

トナーに荷電を保つためには、トナーの主成分である(
チ(脂の摩擦帯電性を利用することも提案されているが
、この方法ではトナーの荷電が小さく、かつ、固体表面
抵抗値が大きいため、得られた画像はカブリ易く、不鮮
明なものとなる。そこで所望の摩擦帯電性をトナー1こ
付与するために、荷電を付与する染料、顔料さらには電
荷調整剤なるものを添加することが行なわれており、今
日当該技術分野で実用化されている。
In order to keep the toner charged, the main component of the toner (
(It has also been proposed to utilize the triboelectricity of fat, but in this method, the toner has a small charge and a high solid surface resistance value, so the resulting image is prone to fogging and becomes unclear.) Therefore, in order to impart the desired triboelectric charging properties to the toner, it has been attempted to add charge-imparting dyes, pigments, and even charge control agents, and this technique is currently being put into practical use in this technical field. .

(発明が解決しようとする問題点) しかしながら、これらの電荷調整剤としての染料、顔料
は、構造が複雑で安定性に乏しく、例えば、機械的摩擦
および衝撃、温度、湿度条件の変化、電気的衝撃および
光照射等により分解または変質して、電荷8!l整能が
失われ易い。また、1つの本質的欠陥は、有色物質であ
るため1こ、特定の色相を有するトナー用1こは無色ま
たは実質的lこ無色と見なしうる電荷調整剤か必要であ
るという必要条件に違背する点にある。
(Problems to be Solved by the Invention) However, these dyes and pigments used as charge control agents have complex structures and lack stability, such as mechanical friction and impact, changes in temperature and humidity conditions, and electrical resistance. Decomposes or changes in quality due to impact or light irradiation, resulting in a charge of 8! L adjustment is likely to be lost. One essential flaw is that since it is a colored material, it violates the requirement that toners with a specific hue require a charge control agent that can be considered colorless or substantially colorless. At the point.

(問題点を解決するための手段) 本発明者等は、樹脂成分との分散性が良好で、また、溶
融混練が充分できる温度まで熱安定性を有し、しかも無
色の物質であってトナーに負荷電を付与することがでg
る化合物を見い出し、優れたトナーを発明するに至った
(Means for Solving the Problems) The present inventors have developed a toner material that has good dispersibility with the resin component, has thermal stability up to a temperature that allows sufficient melt-kneading, and is colorless. By giving a negative charge to g
They discovered a compound that could achieve this and invented an excellent toner.

すなわち、本発明は一般式(1) (式中、Rは水素原子、アルキル基、アルコキシ基、ハ
ロゲン原子を表わし、n およびn は1、Φ 2.3または4であり、× は水素イオン、アルカリ金
属イオン、脂肪族アンモニウムイオン(置換脂肪族アン
モニワムイオンを含む)、脂環族アンモニウムイオンま
たはへテロ環状アンモニウムイオンを表わす。)で表わ
される化合物を電荷調整剤として含有することをvf徴
とする電子写真用トナーである。
That is, the present invention is based on the general formula (1) (wherein R represents a hydrogen atom, an alkyl group, an alkoxy group, or a halogen atom, n and n are 1, Φ 2.3 or 4, and x is a hydrogen ion, Containing a compound represented by an alkali metal ion, an aliphatic ammonium ion (including substituted aliphatic ammonium ions), an alicyclic ammonium ion, or a heterocyclic ammonium ion as a charge control agent is considered to be a vf characteristic. This is a toner for electrophotography.

一般式(1)で示される化合物のアニオンの具体例を下
記に示す。
Specific examples of the anion of the compound represented by general formula (1) are shown below.

アニオンNo、      構 造 式アニオンNo、
      構 造 式また、−取代([)で表わされ
る化合物のカチオンとしてのアルカリ金属イオンは、L
+  、Na 、K などがあげられる。脂肪族および
脂環族アンモニウムイオンとしては、式(n)で示した
アンモニウムイオンがあげられ、R1、R2、R1およ
びR,の具体例を第1表に示す。
Anion No., Structural formula anion No.,
In addition, the alkali metal ion as a cation of the compound represented by the structural formula ([) is L
+, Na, K, etc. Examples of aliphatic and alicyclic ammonium ions include ammonium ions represented by formula (n), and specific examples of R1, R2, R1 and R are shown in Table 1.

R2−N−R,(H) ヘテロ環状アンモニウムイオンの具体例を下記に示す。R2-N-R, (H) Specific examples of heterocyclic ammonium ions are shown below.

アンモニウム イオンNo、      構 造 式 %式% 本発明の電荷調整剤として使用する化合物(1)の製造
法は、米国特許第3539614号明細書などに述べら
れている。例乏ば、ホウ酸とアミンの水溶液にサリチル
酸を加え反応させることによりボロジサリチル酸アンモ
ニウムが得られる。
Ammonium ion No. Structural formula % Formula % The method for producing the compound (1) used as the charge control agent of the present invention is described in US Pat. No. 3,539,614 and the like. For example, ammonium borodisalicylate can be obtained by adding salicylic acid to an aqueous solution of boric acid and an amine and allowing the reaction to occur.

ちなみに、トナー成分中に添加される一般式(I)で表
わされる化合物の量は、樹脂100重量部に対し、一般
に0.1〜10重量部、好ましくは0.5〜5重量部の
割合で含有せしめる。
Incidentally, the amount of the compound represented by general formula (I) added to the toner component is generally 0.1 to 10 parts by weight, preferably 0.5 to 5 parts by weight, based on 100 parts by weight of the resin. Make it contain.

本発明のトナーは、上記−取代(1)の化合物の池に、
接着性、保存性、流動性、粉砕性等を考慮して、スチレ
ン(5(脂、スチレン−アクリル系樹脂、スチレン−ブ
タジェン樹脂、エポキシ樹脂、ポリエステル+111R
、パラフィンワックス等の公知のトナー用樹脂の1種ま
たは数種を混合して用いられる。また着色剤としては、
公知の多数の染料、顔料を用いることができるが、カラ
ーコピー用トナーとして特に優れているものとして、ベ
ンジ゛ジンエロー、キナクドリン、銅フタロシアニンブ
ルー、銅7タロシアニングリーン等が挙げられる。
The toner of the present invention includes a pond of the compound of the above-mentioned removal allowance (1),
Considering adhesiveness, storage stability, fluidity, crushability, etc., styrene (5 (fat), styrene-acrylic resin, styrene-butadiene resin, epoxy resin, polyester + 111R
, paraffin wax, and other known resins for toners, or a mixture of several types thereof may be used. In addition, as a coloring agent,
Although many known dyes and pigments can be used, some that are particularly excellent as toners for color copying include benzidine yellow, quinacridine, copper phthalocyanine blue, and copper 7 thalocyanine green.

本発明のトナーは、普通は、キャリアと混合して2成分
系現像剤を提供するが、もちろん、1成分系現像剤とし
ても使用できる。
The toner of the present invention is usually mixed with a carrier to provide a two-component developer, but can of course also be used as a one-component developer.

(実施例) 以下、実施例により本発明の詳細な説明する。(Example) Hereinafter, the present invention will be explained in detail with reference to Examples.

なお実施例中の部とは、重量部を表わす。Note that parts in the examples represent parts by weight.

(実施例1) スチレン樹脂100部、カーボンブラック6部、ボロン
サリチル酸ジメチルアンモニウム2部の配合物をボール
ミルで均一に予備混合し、プレミックスを調製する。次
いで加熱溶融混練し、冷却後、振動ミルで粗粉砕し、更
にシェツトミルを用いて微粉砕i、て、黒色トナーを得
た。この黒色トナーの粒径は8〜15μIffであった
(Example 1) A mixture of 100 parts of styrene resin, 6 parts of carbon black, and 2 parts of dimethylammonium boron salicylate is uniformly premixed in a ball mill to prepare a premix. Next, the mixture was heated and melted and kneaded, and after cooling, it was coarsely pulverized using a vibrating mill, and further finely pulverized using a shedding mill to obtain a black toner. The particle size of this black toner was 8 to 15 μIff.

得られたトナー5部に対して鉄粉キャリア95部を混合
して現像剤を調整した。本現像剤の初期ブローオフ帯電
量は−25,9μC/gであった。
A developer was prepared by mixing 95 parts of iron powder carrier with 5 parts of the obtained toner. The initial blow-off charge amount of this developer was -25.9 μC/g.

本現像剤を市販のセレンドラムに磁気ブラシ現像法にて
トナー画像を形成したところ、カブリのない鮮明な画像
が得られた。本トナーは、連続複写1oooo枚後にお
いても複写品質の低下はみられなかった。
When a toner image was formed using this developer on a commercially available selenium drum using a magnetic brush development method, a clear image without fogging was obtained. With this toner, no deterioration in copy quality was observed even after continuous copying of 100 sheets.

(実施例2) スチレン−アクリル共重合樹脂100部、黄色染料(C
,1,ディスバーズイエロー33)6部、ボ     
′ロビ又(3,5−ノーtert−ブチルサリチル酸)
ジメチルアンモニウム2部の配合物を実施例1と同様に
処理して黄色トナーを得た。得られた黄色トナーよ1)
実施例1と同様にして調整した現像剤の初期ブローオフ
帯電量は−23,6μC/8であった。
(Example 2) 100 parts of styrene-acrylic copolymer resin, yellow dye (C
, 1, Disbirds Yellow 33) 6 copies, bottle
'Robimata (3,5-not-tert-butylsalicylic acid)
A formulation of 2 parts dimethylammonium was processed as in Example 1 to obtain a yellow toner. The obtained yellow toner 1)
The initial blow-off charge amount of the developer prepared in the same manner as in Example 1 was -23.6 μC/8.

本現像剤を実施例1と同様に複写したところ、カブリの
ない鮮明な黄色の画像が得られた。本トナーは、連続複
写10000枚後においても複写品質の低下はみられな
かった。
When copies were made using this developer in the same manner as in Example 1, clear yellow images without fog were obtained. With this toner, no deterioration in copy quality was observed even after 10,000 continuous copies were made.

(実施例3) スチレン−n−ブチルメタクリレート共重合体樹脂10
0部、赤色染料(C,I、ピグメントレッド]2)8部
、ボロジサリチル酸トリ輸−ブチル)アンモニウム2部
の配合物を実施例1と同様に処埋して赤色トナーを得た
。得られた赤色トナーより実施例1と同様にして調整し
た現像剤の初期ブローオフ帯電量は−23,7μC/g
であった。
(Example 3) Styrene-n-butyl methacrylate copolymer resin 10
A mixture of 0 parts of red dye (C, I, pigment red), 8 parts of red dye (C, I, pigment red), and 2 parts of tri-butyl)ammonium borodisalicylate was processed in the same manner as in Example 1 to obtain a red toner. The initial blow-off charge amount of the developer prepared from the obtained red toner in the same manner as in Example 1 was -23.7 μC/g.
Met.

本現像剤を実施例1と同様に複写したところ、カブリの
ない鮮明な赤色の画像が得られた。本トナーは、連続複
写10000枚後においても複写品質の低下はみられな
かった。
When copies were made using this developer in the same manner as in Example 1, clear red images without fog were obtained. With this toner, no deterioration in copy quality was observed even after 10,000 continuous copies were made.

(実施例4) ポリエステル樹脂1. O0部、青色染料(C,I。(Example 4) Polyester resin 1. O0 parts, blue dye (C, I.

ピグメントブルーl5)616、ボロジサリチル酸ジエ
チルアンモニウム2部の配合物を実施例1と同様に処理
して青色トナーを得た。得られた青色トナーより実施例
1と同様にして調整した現像剤の初期ブローオフ帯電量
は−29,1μC/ g であった。
Pigment Blue 15) 616 and 2 parts of diethylammonium borodisalicylate were treated in the same manner as in Example 1 to obtain a blue toner. The developer prepared from the obtained blue toner in the same manner as in Example 1 had an initial blow-off charge amount of -29.1 μC/g.

本現像剤を実施例1と同様に複写したところ、カブリの
ない鮮明な青色の画像が得られた。本トナーは、連続複
写10000枚後においても複写品質の低下はみられな
かった。
When copies were made using this developer in the same manner as in Example 1, clear blue images without fog were obtained. With this toner, no deterioration in copy quality was observed even after 10,000 continuous copies were made.

(発明の効果) 本発明に使用する電荷調整剤は、機械的摩擦および衝撃
安定性、温度および湿度安定性等に優れ、かつ無色であ
るので、画像が鮮明で連続使用可能な電子写真用トナー
が得られた。
(Effects of the Invention) The charge control agent used in the present invention has excellent mechanical friction and impact stability, temperature and humidity stability, and is colorless, so it is an electrophotographic toner that provides clear images and can be used continuously. was gotten.

特許出願人 日本カーリット株式会社Patent applicant Nippon Carlit Co., Ltd.

Claims (1)

【特許請求の範囲】  下記一般式( I ) ▲数式、化学式、表等があります▼ (式中、Rは水素原子、アルキル基、アルコキシ基、ハ
ロゲン原子を表わし、mおよびnは1、2、3または4
であり、X^■水素イオン、アルカリ金属イオン、脂肪
族アンモニウムイオン(置換脂肪族アンモニウムイオン
を含む)、脂環族アンモニウムイオンまたはヘテロ環状
アンモニウムイオンを表わす。)で表わされる化合物を
電荷調整剤として含有することを特徴とする電子写真用
トナー。
[Claims] The following general formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, R represents a hydrogen atom, an alkyl group, an alkoxy group, or a halogen atom, and m and n are 1, 2, 3 or 4
and represents a hydrogen ion, an alkali metal ion, an aliphatic ammonium ion (including substituted aliphatic ammonium ions), an alicyclic ammonium ion, or a heterocyclic ammonium ion. ) A toner for electrophotography, characterized in that it contains a compound represented by the following formula as a charge control agent.
JP63135413A 1988-06-03 1988-06-03 Electrophotographic toner Pending JPH01306861A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP63135413A JPH01306861A (en) 1988-06-03 1988-06-03 Electrophotographic toner

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP63135413A JPH01306861A (en) 1988-06-03 1988-06-03 Electrophotographic toner

Publications (1)

Publication Number Publication Date
JPH01306861A true JPH01306861A (en) 1989-12-11

Family

ID=15151148

Family Applications (1)

Application Number Title Priority Date Filing Date
JP63135413A Pending JPH01306861A (en) 1988-06-03 1988-06-03 Electrophotographic toner

Country Status (1)

Country Link
JP (1) JPH01306861A (en)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5256515A (en) * 1992-11-19 1993-10-26 Xerox Corporation Toner compositions with halogenated metal salicyclic acid complex charge enhancing additives
US5863692A (en) * 1996-09-10 1999-01-26 Minolta Co., Ltd. Toner for elastrostatic latent image developing and method of manufacturing same
US5905011A (en) * 1997-03-12 1999-05-18 Minolta Co., Ltd. Nonmagnetic monocomponent negatively chargeable color developer
US6977129B2 (en) 2001-12-10 2005-12-20 Ricoh Company, Ltd. Charge control agent, toner using same developer containing the toner and developing device containing the developer
WO2007111346A1 (en) 2006-03-29 2007-10-04 Hodogaya Chemical Co., Ltd. Cyclic phenol sulfide mixture, and charge controlling agent or toner using the same
WO2007119797A1 (en) 2006-04-13 2007-10-25 Hodogaya Chemical Co., Ltd. Oxidized cyclic phenol sulfide mixture, and charge controlling agent or toner using the same
WO2011105334A1 (en) 2010-02-26 2011-09-01 保土谷化学工業株式会社 Charge controlling agent and toner using same
WO2012035996A1 (en) 2010-09-14 2012-03-22 保土谷化学工業株式会社 Charge control agent and toner using same
WO2012102137A1 (en) 2011-01-27 2012-08-02 保土谷化学工業株式会社 Charge control agent and toner using same
US8790855B2 (en) 2010-09-13 2014-07-29 Hodogaya Chemical Co., Ltd Charge control agent and toner using same
JP2016504221A (en) * 2012-12-19 2016-02-12 イノヴィア フィルムズ リミテッド the film
JPWO2015046214A1 (en) * 2013-09-24 2017-03-09 保土谷化学工業株式会社 Charge control agent and toner using the same
US10474050B2 (en) 2015-09-17 2019-11-12 Hodogaya Chemical Co., Ltd. Toner and charge control agent using pyrazolone derivative or salt of derivative

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6263941A (en) * 1985-09-17 1987-03-20 Fuji Xerox Co Ltd Electric charge exchange controlling agent and developer composition
JPS63226662A (en) * 1987-03-17 1988-09-21 Fuji Xerox Co Ltd Developer for electrostatic charge image

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6263941A (en) * 1985-09-17 1987-03-20 Fuji Xerox Co Ltd Electric charge exchange controlling agent and developer composition
JPS63226662A (en) * 1987-03-17 1988-09-21 Fuji Xerox Co Ltd Developer for electrostatic charge image

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5256515A (en) * 1992-11-19 1993-10-26 Xerox Corporation Toner compositions with halogenated metal salicyclic acid complex charge enhancing additives
US5863692A (en) * 1996-09-10 1999-01-26 Minolta Co., Ltd. Toner for elastrostatic latent image developing and method of manufacturing same
US5905011A (en) * 1997-03-12 1999-05-18 Minolta Co., Ltd. Nonmagnetic monocomponent negatively chargeable color developer
US6977129B2 (en) 2001-12-10 2005-12-20 Ricoh Company, Ltd. Charge control agent, toner using same developer containing the toner and developing device containing the developer
US7901858B2 (en) 2006-03-29 2011-03-08 Hodogaya Chemical Co., Ltd. Mixed cyclic phenol sulfides, and charge control agents and toners using the same
WO2007111346A1 (en) 2006-03-29 2007-10-04 Hodogaya Chemical Co., Ltd. Cyclic phenol sulfide mixture, and charge controlling agent or toner using the same
US7709172B2 (en) 2006-04-13 2010-05-04 Hodogaya Chemical Co., Ltd. Oxidized mixed cyclic phenol sulfides, and charge control agents and toners using the same
US7820832B2 (en) 2006-04-13 2010-10-26 Hodogaya Chemical Co., Ltd. Oxidized mixed cyclic phenol sulfides, and charge control agents and toners using the same
WO2007119797A1 (en) 2006-04-13 2007-10-25 Hodogaya Chemical Co., Ltd. Oxidized cyclic phenol sulfide mixture, and charge controlling agent or toner using the same
WO2011105334A1 (en) 2010-02-26 2011-09-01 保土谷化学工業株式会社 Charge controlling agent and toner using same
US8790855B2 (en) 2010-09-13 2014-07-29 Hodogaya Chemical Co., Ltd Charge control agent and toner using same
US8900785B2 (en) 2010-09-14 2014-12-02 Hodogaya Chemical Co., Ltd. Charge control agent and toner using the same
WO2012035996A1 (en) 2010-09-14 2012-03-22 保土谷化学工業株式会社 Charge control agent and toner using same
KR20140005986A (en) 2011-01-27 2014-01-15 호도가야 가가쿠 고교 가부시키가이샤 Charge control agent and toner using same
WO2012102137A1 (en) 2011-01-27 2012-08-02 保土谷化学工業株式会社 Charge control agent and toner using same
JP2016504221A (en) * 2012-12-19 2016-02-12 イノヴィア フィルムズ リミテッド the film
JPWO2015046214A1 (en) * 2013-09-24 2017-03-09 保土谷化学工業株式会社 Charge control agent and toner using the same
US9835965B2 (en) 2013-09-24 2017-12-05 Hodogaya Chemical Co., Ltd. Charge control agent and toner using same
US10474050B2 (en) 2015-09-17 2019-11-12 Hodogaya Chemical Co., Ltd. Toner and charge control agent using pyrazolone derivative or salt of derivative

Similar Documents

Publication Publication Date Title
JPS63208865A (en) Toner for developing electrostatic charge image
JPH01306861A (en) Electrophotographic toner
JPH02221967A (en) Electrophotographic toner
EP0242420B1 (en) A toner for developing electrostatic latent images and a use thereof
JPS60169857A (en) Electrostatic charge image developing toner
JPH0363664A (en) Electrophotographic toner
JPH0248674A (en) Toner for electrophotography
JPH0248673A (en) Toner for electrophotography
JPH03134672A (en) Toner for electrophotography
JPH0248677A (en) Toner for electrophotography
JP2986967B2 (en) Electrophotographic toner
JP2660739B2 (en) Electrophotographic toner
JP2795899B2 (en) Electrophotographic toner
KR100419765B1 (en) Electrostatic toner
JPH0218568A (en) Toner for electrophotography
JPH0248672A (en) Toner for electrophotography
JPH0236945B2 (en)
JPH0484141A (en) Electrophotographic toner
JPH0154696B2 (en)
JPH0239163A (en) Toner for electrophotography
JPH0496072A (en) Electrophotographic toner
JPH02208662A (en) Yellow toner
JPH02210360A (en) Yellow toner
JP2626995B2 (en) Electrophotographic toner
JPH06313994A (en) Electrophotographic toner