JPS58136048A - Negatively chargeable toner for developing static charge - Google Patents

Negatively chargeable toner for developing static charge

Info

Publication number
JPS58136048A
JPS58136048A JP57018402A JP1840282A JPS58136048A JP S58136048 A JPS58136048 A JP S58136048A JP 57018402 A JP57018402 A JP 57018402A JP 1840282 A JP1840282 A JP 1840282A JP S58136048 A JPS58136048 A JP S58136048A
Authority
JP
Japan
Prior art keywords
toner
styrene
toners
copolymer
resin
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
JP57018402A
Other languages
Japanese (ja)
Inventor
Eiichi Imai
今井 栄一
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.)
Canon Inc
Original Assignee
Canon Inc
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 Canon Inc filed Critical Canon Inc
Priority to JP57018402A priority Critical patent/JPS58136048A/en
Publication of JPS58136048A publication Critical patent/JPS58136048A/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
    • G03G9/09Colouring agents for toner particles
    • G03G9/0906Organic dyes
    • G03G9/0908Anthracene dyes

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

Abstract

PURPOSE:To obtain a toner with superior triboelectric characteristics by adding a specified anthraquinone compound to a toner. CONSTITUTION:To a binding resin is added a compound represented by the general formula (where R1 is alkoxy or phenoxy, and R2 is H, alkoxy or phenoxy) preferably by 0.1-10pts.wt. of the amount of the resin.

Description

【発明の詳細な説明】 本発明はトナー、特に静電荷現像用負荷電性トナーに関
する。
DETAILED DESCRIPTION OF THE INVENTION The present invention relates to toners, particularly negatively charged toners for electrostatic development.

電気的潜像をトナーにより現像して可視画像全形底する
方法として従来、静電印刷法或いは電子写真法等が著名
である。例えば、電子写真法としては、米国特許第2,
297,691号明細書、特公昭42−23910号公
報、特公昭43−24748号公報等に記載された棟々
の方式が周知である。
Conventionally, electrostatic printing, electrophotography, and the like are well-known methods for developing an electrical latent image with toner to form a visible image in its entirety. For example, as an electrophotographic method, U.S. Patent No.
297,691, Japanese Patent Publication No. 42-23910, Japanese Patent Publication No. 43-24748, etc., are well known.

一般には、光導′成性物質を利用し種々の手段により光
導電性を示す感光体上に電気的潜像を形成し、次いで該
潜像金トナーで現像して可視像を得るか、又は必要に応
じて紙等に粉像r転写した後加熱、加圧或いは溶剤蒸気
等により定着して可視像を得るものでおる。父、カラ・
−の多色像を得る為には原稿を色分解フィルターを用い
て露光し上記の工程をイエロー、マゼンタ、シアン等の
カラートナー全相いて複数同繰返し、トナー像を重ね合
せカラー画像とするものである0 電気的潜像を現像する為のトナーとしては、従来、ポリ
スチレン等の結着樹脂中に着色剤(カーボンブラック等
の染顔料等)を分散させたものを1〜30μ程度に微粉
砕した粒子が用いられている。掘るトナーは通常ガラス
ピーズ、鉄粉、又はファー等のキャリヤー物質と混合さ
れ、′1気的宿像の現像に用いられている。
Generally, an electrical latent image is formed on a photoreceptor that exhibits photoconductivity by various means using a photoconductive material, and then the latent image is developed with gold toner to obtain a visible image; If necessary, the powder image is transferred onto paper or the like and then fixed by heating, pressure, solvent vapor, etc. to obtain a visible image. Father, Kara
- To obtain a multicolor image, the original is exposed using a color separation filter, and the above process is repeated multiple times using all color toners such as yellow, magenta, cyan, etc., and the toner images are superimposed to form a color image. 0 Toner for developing electrical latent images has conventionally been produced by dispersing colorants (dyes and pigments such as carbon black) in a binder resin such as polystyrene, which is then finely pulverized to about 1 to 30 microns. particles are used. The digging toner is usually mixed with a carrier material such as glass peas, iron powder, or fur and is used for the development of '1' images.

これらのトナーは種々の物理的及び化学的特性を要求さ
れる。しかし乍ら、既知のトナーの多くは下記に示す様
な幾つかの欠陥を有している。即ち多くのトナーは環境
の湿度変化によって、その摩擦電気特性が悪影響を受け
る。又、多くのトナーでは連続使用による繰返しの現像
によるトナー粒子と担体粒子の衝突、及びそれらの粒子
と感光板表面との接触によるトナー、担体粒子及び感光
板の相互劣化によって、得られる画像の濃度が変化し、
或いは背景濃度が増大し、複写物の品質を低下させる。
These toners require different physical and chemical properties. However, many of the known toners have several deficiencies as described below. That is, the triboelectric properties of many toners are adversely affected by changes in environmental humidity. In addition, with many toners, the density of the resulting image decreases due to mutual deterioration of the toner, carrier particles, and photosensitive plate due to collisions between toner particles and carrier particles due to repeated development due to continuous use, and contact between these particles and the surface of the photosensitive plate. changes,
Alternatively, the background density increases, reducing the quality of the copy.

更に多くのトナーでは渣像を有する感光板表面へのトナ
ーの付着量を増して、複写画像の濃度を増大させ様とす
ると、通常背景′a度が増し、所謂カブリ現象を生じる
Furthermore, with many types of toner, if an attempt is made to increase the density of a copied image by increasing the amount of toner adhering to the surface of the photosensitive plate having a residue, the background density will usually increase, resulting in the so-called fog phenomenon.

既知のトナーの多くが、以上の如き欠陥を一つ又はそれ
以上Mしている為、トナーの改良に対する要望が絶えな
い現状である。
Since many of the known toners have one or more of the above-mentioned defects, there is a constant demand for improved toners.

又、特にカラー電子写真用トナーは上記の欠陥を克服し
た優れた物理的及び化学的特性を要する事は勿論である
が、更に多色重ね合わせによるカラー′畦子写真用トナ
ーとしては次の様な条件をも満足しなければならない。
In addition, it goes without saying that toners for color electrophotography in particular must have excellent physical and chemical properties that overcome the above-mentioned defects. must also satisfy the following conditions.

(1)  多色重ね合せをする為に、トナーは透明性大
である事。
(1) The toner must be highly transparent in order to layer multiple colors.

(2)  各トナーは、熔融混和性に優れている事。(2) Each toner must have excellent melt miscibility.

(3)  原稿を忠実に再現する為に、分光反射特性が
良好である事。
(3) Spectral reflection characteristics must be good in order to faithfully reproduce the original.

加えて、カラートナーに於てはトリボ電位の極性を決定
する因子に左右される半なく、自由にトナーの持つべき
色を、1IAI整できる事が必要である。例えば、公知
の員性荷′区制御剤と開われるもの〔特公昭41−12
915号公報、特公昭43−27596号公報等に記載
されたモノアゾ染料の金属錯塩、特開昭5(1−133
838号公報に記載されたニトロフミン酸(塩)〕は、
殆ど黒色である為、その使用範囲に制約がある。従って
、所望の色(例えはマゼンタ等)を有する荷電制御剤の
出現も望まれている。
In addition, for color toners, it is necessary to be able to freely adjust the color that the toner should have, regardless of the factors that determine the polarity of the triboelectric potential. For example, those that are compatible with known chemical load control agents [Special Publication No. 41-12
Metal complex salts of monoazo dyes described in Japanese Patent Publication No. 915, Japanese Patent Publication No. 43-27596, etc.;
The nitrofumic acid (salt) described in Publication No. 838 is
Since it is mostly black, its range of use is limited. Therefore, the development of a charge control agent having a desired color (for example, magenta, etc.) is also desired.

ITDして、本発明は上述のトナーに関する現況に顕み
なされた。
ITD, the present invention was realized in the current situation regarding toners mentioned above.

本発明の主たる目的は摩擦電気特性の優れた静成荷現像
用負夕f電性トナーを提供する事にある0 本発明の更なる目的は繰返し現像による連続複写で得ら
れる画像濃度が安定しており、複写品質の低下を起させ
ない静電荷現像用負荷電性トナーを提供する事にある。
The main object of the present invention is to provide an electrostatic charge developing toner having excellent triboelectric properties.A further object of the present invention is to provide a statically charged toner with excellent triboelectric properties. The object of the present invention is to provide a negatively charged toner for electrostatic charge development that does not cause deterioration in copy quality.

本発明の別の目的は雄擦電気特性の優れた負荷電性マゼ
ンタトナーを提供することにある。
Another object of the present invention is to provide a negatively charged magenta toner having excellent triboelectric properties.

上記目的は結着樹脂中に下記一般式で表わされる化合物
を、好ましくは、樹脂に対して0.1〜lON量部含有
することを特徴とした負荷電性トナーを提供することに
よって達成することができる。
The above object is achieved by providing a negatively charged toner characterized by containing a compound represented by the following general formula in a binder resin, preferably in an amount of 0.1 to 1 on part based on the resin. I can do it.

またはフェノキシ基。or phenoxy group.

以下本発明のトナーの構成成分につき詳しく説明する。The constituent components of the toner of the present invention will be explained in detail below.

本発明トナーの構成成分として特に重要なものけ、前記
した一般式で表わされるアントラキノン系の化合物であ
る。これらの化合物は結着但(血中に含有されてトナー
に優れた負荷電性を与える。きらにこれらの化合物は大
部分が明るい貢味の赤色を呈し、マゼンタトナーの着色
剤成分として単独であるいは他の着色剤と併用して使用
でき、もちろんその場合も優れた負荷電性を与える。
Particularly important constituents of the toner of the present invention are anthraquinone compounds represented by the above-mentioned general formula. These compounds are present in the blood and give the toner excellent negative charge properties.These compounds mostly exhibit a bright red color and are not used alone as colorant components in magenta toners. Alternatively, it can be used in combination with other colorants, and of course provides excellent negative chargeability in that case as well.

これらの化合物は例えばC,1,Disperse V
iolet26 、 C,1,Disperse Vi
olet 31. C,1,I)isperseRed
 11. C,1,5olvent Violet 2
6等に分類されており、−例を上げれば のようなものがあるが本発明はもちろん上記2棟の化合
物例に限定されるものではない。
These compounds are, for example, C,1,Disperse V
iolet26, C,1,Disperse Vi
olet 31. C, 1, I) isperseRed
11. C,1,5olvent Violet 2
Although the present invention is of course not limited to the above two examples, the present invention is not limited to the above two examples.

こtらの化合物の添加せは、結着樹脂の荷電性、あるい
は補助的に添加される着色剤、あるいけに限定されるも
のではないが総じて言えば結着樹脂に対して略々0.1
〜10(重量)%の範囲で使用することが好−!、1〜
い。0.1(重量)%未満では荷電制御効果が少なく1
0(重量)%を上回っても荷電制御効果が低下して好筐
しくない0 本発明トナーに適用する結着樹脂としては公知のものが
すべて使用可能であるが、例えばポリスチレン、ポリP
−クロルスチレン、ポリビニルトルエンなどのスチレン
及びその置換体の単重合体;スナレンーP−クロルスチ
レン共重合体、スチレン−プロピレン共重合体、スチレ
ン−ビニルトルエン共重合体、スチレン−ビニルナフタ
リン共1合体、スチレン−アクリル酸メチル共重合体、
スチレン−アクリル酸エチル共亜合体、スナレンーアク
リル酸ブチル共重合体、スチレ/−アクリル酸オクチル
共重合体、スチレン−メタクリル酸メチル共重合体、ス
チレン−メタクリル酸エチル共重合体、スチレン−メタ
クリル酸ブチル共1合体、スチレン−αクロルメタクリ
ル酸メチル共重合体、スチレン−アクリロニトリル共重
合体、スチレン−ビニルメチルエーテル共重合体、スチ
レン−ビニルエチルエーテル共重合体、ステレンービニ
ルメナルケトン共那合体、スチレン−ブタジェン共N 
合体、スチレン−イソプレン共1合体、スチレン−アク
リロニトリル−インデン共重合体、スナレンーマレイン
酸共■合体、スチレン−マレイン酸エステル共重合体な
どのスチレン系共重合体;ポリメチルメタクリレ−1・
、ポリブチルメタクリレート、ポリ塩化ビニル、ポリ酢
酸ビニル、ポリエテレン、ポリプロピレン、ポリエステ
ル、ポリウレタン、ポリアミド、エボギシ樹脂、ポリビ
ニルブチラール、ポリアマイドポリアクリル# 111
脂、ロジン、変性ロジン、テルペン樹脂、フェノール樹
脂、脂肪族又は脂環族炭化水素樹脂、芳香族系石油樹脂
、塩素化ノ(ランイン、パラフィンワックスなどが単独
或いは混合して使用できる。
The addition of these compounds is not limited to the chargeability of the binder resin or the coloring agent added as an auxiliary agent, but generally speaking, the addition of these compounds is about 0.0% to the binder resin. 1
It is preferable to use it in the range of ~10% (by weight)! , 1~
stomach. If it is less than 0.1% (by weight), the charge control effect will be small.
Even if it exceeds 0 (weight)%, the charge control effect will deteriorate and the case will not be favorable. All known binder resins can be used as the binder resin for the toner of the present invention, such as polystyrene, polyP, etc.
- Homopolymers of styrene and its substituted products such as chlorostyrene and polyvinyltoluene; Sunalene-P-chlorostyrene copolymers, styrene-propylene copolymers, styrene-vinyltoluene copolymers, styrene-vinylnaphthalene copolymers, Styrene-methyl acrylate copolymer,
Styrene-ethyl acrylate copolymer, Sunalene-butyl acrylate copolymer, Styrene/-octyl acrylate copolymer, Styrene-methyl methacrylate copolymer, Styrene-ethyl methacrylate copolymer, Styrene-methacrylic acid Butyl copolymer, styrene-alpha chloromethyl methacrylate copolymer, styrene-acrylonitrile copolymer, styrene-vinyl methyl ether copolymer, styrene-vinyl ethyl ether copolymer, sterene-vinyl menal ketone copolymer , styrene-butadiene co-N
Styrenic copolymers such as styrene-isoprene copolymer, styrene-acrylonitrile-indene copolymer, sunalene-maleic acid copolymer, and styrene-maleic acid ester copolymer; polymethyl methacrylate-1.
, polybutyl methacrylate, polyvinyl chloride, polyvinyl acetate, polyethylene, polypropylene, polyester, polyurethane, polyamide, evogishi resin, polyvinyl butyral, polyamide polyacrylic #111
Fat, rosin, modified rosin, terpene resin, phenol resin, aliphatic or alicyclic hydrocarbon resin, aromatic petroleum resin, chlorinated resin, paraffin wax, etc. can be used alone or in combination.

また現像剤に使用されるキャリヤーは従来から公知のも
のが使える。例えば鉄、コバルト、ニッケルなどの磁性
物質及びそれらの合金や混合物あるいはこれらの表面に
コーティングを施したものである。
Further, as the carrier used in the developer, conventionally known carriers can be used. For example, magnetic substances such as iron, cobalt, and nickel, alloys and mixtures thereof, or coatings on the surfaces thereof are used.

芒らに本発明トナーが使用される現像剤に対してはコロ
イダルシリカなどの流動性改質剤をトナーに対して(1
,01重Jilt%〜5重蓋%(好ましくは0.1l1
%〜2重量%)程度添加してもよい。
For the developer in which the toner of the present invention is used, a fluidity modifier such as colloidal silica is added to the toner (1
, 01-fold Jilt% to 5-fold Lid% (preferably 0.1l1
% to 2% by weight).

以下実施例により本発明を更に詳細に説明する。部数は
rjL量都Cある。
The present invention will be explained in more detail with reference to Examples below. The number of copies is rjL and C.

〔実施例−1ノ ポリスチレン樹脂100部、カーボンブラック6部、C
,1,Disperae Violet 31に分類さ
れている化合物2部をボールミルで混合粉砕後、ロール
ミルで熔融混練し、冷却後)・ンマーミルを用いて粗粉
砕し、次いでエアージェット方式による微粉砕機で微粉
砕する。得られた微粉末を分級して5〜20μを選択し
トナーとする3、このトナー10部に対しキャリヤー鉄
粉(部品名EF’V 250/400 、 E1本鉄粉
社製)90部tm合し現像剤とした。
[Example-1 100 parts of nopolystyrene resin, 6 parts of carbon black, C
, 1, 2 parts of a compound classified as Disperae Violet 31 were mixed and ground in a ball mill, then melted and kneaded in a roll mill, and after cooling), coarsely ground using a hummer mill, and then finely ground using an air jet type pulverizer. do. The obtained fine powder is classified to select 5 to 20μ and used as a toner. 3. For 10 parts of this toner, 90 parts tm of carrier iron powder (part name EF'V 250/400, manufactured by E1 Iron Powder Co., Ltd.) are added. It was used as a developer.

この現像剤中のトリボ′載荷全測定すると、−4,9μ
c/gでめった。尚トリボ嘔荷蓋の測定は、所謂ブロー
オフ法によった。(#細には、′電子写真学会刊行の賛
稿集(1975,5)に記載されている。)又、以下の
実施例、比較例に於ても、この方法によりトリボ電荷i
t′全測定した。
When the total tribo' load in this developer is measured, it is -4.9μ
It was rare at c/g. Note that the measurement of the tribopod operculum was carried out by the so-called blow-off method. (Details are described in the Collected Papers published by the Society of Electrophotography (1975, 5).) Also, in the following Examples and Comparative Examples, the tribocharge i
t' was completely measured.

この現像剤を用い乾式普通紙電子写真複写機(部品名、
NP 5000 iキャノンに、に、製)で複写を行な
ったところ、カブリのない鮮明な黒色画像が得られた。
Using this developer, a dry plain paper electrophotographic copying machine (parts name,
When copying was performed using an NP 5000 i Canon (manufactured by Nippon, Japan), a clear black image with no fog was obtained.

又、1万枚の連続複写を行なったが、複写画像の品位の
低下は見られなかった。
Furthermore, even though 10,000 copies were made continuously, no deterioration in the quality of the copied images was observed.

このトナーは常温、常湿下で半年間の保存後も緒特性の
劣化は認められなかった。
No deterioration in the properties of this toner was observed even after storage for half a year at room temperature and humidity.

〔実施例−2〕 トナー組成を 5部 に代える半身外は実施例−1と同様にして実施したとこ
ろ、カブリの無い鮮明なマゼンタ色画像が得られた。因
みにトナーのトリボ電荷量は−6,1μc/gであった
6、 〔比較例−1〕 トナー組成を とする以外は実施例−1とほぼ同様に実施したところ、
かぶりがひどく、鮮明な画像は得られなかった。因みに
トナーのトリボ電荷量は、−〇、5μc/gであった。
[Example 2] The same procedure as in Example 1 was performed except for changing the toner composition to 5 parts, and a clear magenta image without fogging was obtained. Incidentally, the tribocharge amount of the toner was -6.1 μc/g6. [Comparative Example-1] The same procedure as in Example-1 was carried out except that the toner composition was changed.
The fogging was so severe that clear images could not be obtained. Incidentally, the triboelectric charge amount of the toner was -0.5 μc/g.

以上、実施例−1〜2及i比較例−1よシ本発明のトナ
ーが優れた特性をもつ負荷電性トナーであることがわか
る。
As described above, it can be seen that the toner of the present invention is a negatively charged toner having excellent characteristics as shown in Examples 1 and 2 and Comparative Example 1.

〔比較例−2〕 トナー組成を以下のようにすること以外は実施例−1と
ほぼ同様に実施したところ、やはりかぶりがひどく鮮明
な画像は得られなかった。因みにトナーのトリボ電荷量
は−1,1μ4でめった。
[Comparative Example-2] When the same procedure as in Example-1 was carried out except that the toner composition was changed as shown below, fogging was still severe and a clear image could not be obtained. Incidentally, the tribocharge amount of the toner was -1.1 μ4.

0.08部 〔比較例−3〕 トナー組成を以下のようにすること以外は実施例−1と
ほぼ同様に実施したところ、画像濃度は十分であるが、
文字部のシャープネスに欠け、不鮮明なマゼンタ色画像
しか得られなかった。
0.08 part [Comparative Example-3] The same procedure as in Example-1 was carried out except that the toner composition was changed as shown below, and the image density was sufficient, but
Characters lacked sharpness, and only vague magenta images were obtained.

25部 〔実施例−3〜6〕 トナー組成を以下のようにする以外は実施例−1とほぼ
同様に実施したところ、カブリのない鮮明なマゼンタ画
像が得られた。
25 parts [Examples 3 to 6] The same procedure as in Example 1 was carried out except that the toner composition was changed as follows, and a clear magenta image without fogging was obtained.

Claims (1)

【特許請求の範囲】 結N衝脂中に下記一般式で表わされる化合物を含有する
ことを特徴とする静電荷現像用負荷電↑ヨヨ ト す 
−。 基、フェノキシ基。
[Claims] Negative charge ↑ Yoyotosu for electrostatic charge development, characterized by containing a compound represented by the following general formula in the N binding resin.
−. group, phenoxy group.
JP57018402A 1982-02-08 1982-02-08 Negatively chargeable toner for developing static charge Pending JPS58136048A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP57018402A JPS58136048A (en) 1982-02-08 1982-02-08 Negatively chargeable toner for developing static charge

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP57018402A JPS58136048A (en) 1982-02-08 1982-02-08 Negatively chargeable toner for developing static charge

Publications (1)

Publication Number Publication Date
JPS58136048A true JPS58136048A (en) 1983-08-12

Family

ID=11970679

Family Applications (1)

Application Number Title Priority Date Filing Date
JP57018402A Pending JPS58136048A (en) 1982-02-08 1982-02-08 Negatively chargeable toner for developing static charge

Country Status (1)

Country Link
JP (1) JPS58136048A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63141073A (en) * 1986-12-03 1988-06-13 Mitsubishi Kasei Corp Electrostatic charge image developing toner
EP0330487A2 (en) * 1988-02-26 1989-08-30 MITSUI TOATSU CHEMICALS, Inc. Color toner composition
US5102764A (en) * 1989-12-15 1992-04-07 Eastman Kodak Company Styrene butylacrylate toner with magenta dye
WO2018021250A1 (en) * 2016-07-29 2018-02-01 日本ゼオン株式会社 Magenta toner

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63141073A (en) * 1986-12-03 1988-06-13 Mitsubishi Kasei Corp Electrostatic charge image developing toner
EP0330487A2 (en) * 1988-02-26 1989-08-30 MITSUI TOATSU CHEMICALS, Inc. Color toner composition
US5102764A (en) * 1989-12-15 1992-04-07 Eastman Kodak Company Styrene butylacrylate toner with magenta dye
WO2018021250A1 (en) * 2016-07-29 2018-02-01 日本ゼオン株式会社 Magenta toner
JP6402845B2 (en) * 2016-07-29 2018-10-10 日本ゼオン株式会社 Magenta toner
JPWO2018021250A1 (en) * 2016-07-29 2018-11-08 日本ゼオン株式会社 Magenta toner

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