JPS6169073A - Toner for developing electrostatic charge image - Google Patents
Toner for developing electrostatic charge imageInfo
- Publication number
- JPS6169073A JPS6169073A JP59191117A JP19111784A JPS6169073A JP S6169073 A JPS6169073 A JP S6169073A JP 59191117 A JP59191117 A JP 59191117A JP 19111784 A JP19111784 A JP 19111784A JP S6169073 A JPS6169073 A JP S6169073A
- Authority
- JP
- Japan
- Prior art keywords
- toner
- parts
- resin
- oxycarboxylic acid
- zinc complex
- 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.)
- Granted
Links
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
- G03G9/09783—Organo-metallic compounds
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Developing Agents For Electrophotography (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は、成子写真、静電記録及び静電印刷等に怠ける
静電潜像を現像するための、新規な乾式負荷電トナーに
関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a new dry negatively charged toner for developing electrostatic latent images that are used in photography, electrostatic recording, electrostatic printing, and the like.
元来、静電潜像は、その静電引力によりトナーを付着せ
しめることにより、現像して可視化することができるが
、この場合における静電潜像の現像剤として、液体現像
剤の他に粉末現像剤が広く用いられている。Originally, an electrostatic latent image can be developed and visualized by adhering toner due to its electrostatic attraction, but in this case, in addition to liquid developer, powder Developers are widely used.
この粉末現像剤は、天然樹脂または合成樹脂□に着色剤
、荷電制御剤、流動化剤等を分散させた平均粒径１５μ
ｍのトナーと、１００〜２００μ諺の鉄粉またはフェラ
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
、天然樹脂または合成樹脂に着色剤、荷重制御剤、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。This powder developer is made by dispersing a coloring agent, a charge control agent, a fluidizing agent, etc. in a natural or synthetic resin with an average particle size of 15 μm.
A two-component developer consisting of a mixture of a toner of m and a carrier of iron powder or ferrite powder of 100 to 200 microns, and a natural or synthetic resin, a colorant, a load control agent, a fluidizing agent, and a magnetic material. It can be broadly classified into one-component type developer.
２成分系現像剤は、キャリアとの摩擦により荷電せしめ
たトナーを静電潜像に付着せしめることにより現像を達
成するものであり、１成分系現像剤としては、従来より
、キャリアの代りにこれと同様の機能を有するブラシ状
、板状の摩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、又最近に至って、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
れるトナーがしられるようになった。而して、これらの
現像用トナーは、現像される静電潜像の極性に応じて、
正または負の荷重が保たれる。A two-component developer achieves development by attaching charged toner to an electrostatic latent image through friction with a carrier. Conventionally, a one-component developer uses this instead of a carrier. Toner is known that is charged by friction with a brush-like or plate-like friction member that has a similar function, and recently, toner that is charged by friction with a brush-like or plate-like friction member is known. It has become known that toner is charged by mutual friction. Therefore, these developing toners have different characteristics depending on the polarity of the electrostatic latent image to be developed.
Positive or negative loads are maintained.
トナーに荷電を保つためには、トナーの主成分である樹
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に付与す
るために、荷電を付与する染料、顔料更には荷電制御剤
なるものを添加することが行われており、今日、当該技
術分野で実用されているものとしては、トナーに正荷電
を付与するものには特公昭４１−２４２７号公報等に示
されているニグロシン系の油溶性・染料等があり、負荷
電を付与するものには特公昭４５−２６４７８号公報等
に示されている如き含金属錯塩染料等がある。In order to keep the toner charged, it has been proposed to utilize the triboelectricity of the resin, which is the main component of the toner, but this method has a small charge on the toner and a large 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, dyes and pigments that impart a charge, as well as charge control agents, are added to the toner. There are oil-soluble dyes such as nigrosine, which are shown in Japanese Patent Publication No. 41-2427, etc., which give a positive charge to the toner, and Japanese Patent Publication No. 45-26478, which gives a negative charge. There are metal-containing complex dyes as shown in publications and the like.
しかしながら、これらの荷電制御剤としてのｊ・ １
゛１゛・Ｗ′！′″＜ａｍ″′″′ｆｆ１ａ°′″！Ｉ
−４・例えば、機械的摩擦および衝撃、温・湿度条件の
変化、電気的衝撃怠よび光照射等により分解または変質
して、荷電制御性が失なわれ易い。However, these charge control agents j・1
゛1゛・W′! ′″<am″′″′ff1a°′″! I
-4 - For example, the charge controllability is likely to be lost due to decomposition or alteration due to mechanical friction and impact, changes in temperature/humidity conditions, electrical shock, light irradiation, etc.
また、一つの本質的欠陥は、有色物質であるために、特
定の色相を有するトナー用には無色又は実質的に無色と
見なし得る荷電制御剤が必要であるという必要条件に違
背する点にある。One essential flaw is that since it is a colored material, it violates the requirement that a charge control agent that can be considered colorless or substantially colorless is required for toners with a specific hue. .
最近に至って、この必要条件を満たすものとして、特開
昭５３−１２７７２８号、特開昭５７−１０４９４０号
、特開昭５７−１１１５４１号、特開昭５７−１２４３
５７号公報等に種々の錯化合物が開示されているが、該
錯化合物は、なお若干の着色を免かれ得ないものである
。Recently, JP-A-53-127728, JP-A-57-104940, JP-A-57-111541, and JP-A-57-1243 have been developed to meet this requirement.
Although various complex compounds are disclosed in Publication No. 57 and the like, these complex compounds are still subject to some coloring.
本発明者らは、樹脂成分との分散性が良好で、また、溶
融練肉が充分出来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出
来る化合物について鋭意研究した結果、置換基があって
もよい芳香族オキシカルボン酸の亜鉛錯化合物が特に優
れていることを見出し、本発明を完成したものである。The present inventors discovered that the substance has good dispersibility with the resin component, is thermally stable up to a temperature at which melt kneading is sufficient, is colorless, and is capable of imparting a negative charge to the toner. As a result of intensive research on the compounds that can be produced, it was discovered that zinc complex compounds of aromatic oxycarboxylic acids which may have substituents are particularly excellent, and the present invention was completed.
本発明は、置換基があってもよい芳香族オキシカルボン
酸の亜鉛錯化合物を荷電制御剤として含有することを特
徴とする、静電荷像現像用トナーである。The present invention is a toner for developing electrostatic images characterized by containing a zinc complex compound of an aromatic oxycarboxylic acid which may have a substituent as a charge control agent.
本発明に係る亜鉛錯化合物を形成し得る、置換基があっ
てもよい芳香族オキシカルボン酸を例示すると、アルキ
ル（０４〜０９）サリチル酸。Examples of aromatic oxycarboxylic acids which may have substituents and which can form the zinc complex compound according to the present invention are alkyl (04-09) salicylic acids.
３．５−ジアルキル（ａ、〜０９）サリチル酸、２−ヒ
ドロキシ−３−ナフトエ酸、アルキル（０４〜０９）−
２−ヒドロキシ−３−ナフトエ酸。3.5-dialkyl(a,~09) salicylic acid, 2-hydroxy-3-naphthoic acid, alkyl(04~09)-
2-Hydroxy-3-naphthoic acid.
５．６．７．８−テトラハロゲン−２−ヒドロキシ−３
−ナフトエ酸等があげられる。5.6.7.8-Tetrahalogen-2-hydroxy-3
-Naphthoic acid etc.
本発明に係る亜鉛錯化合物は、次の方法によって合成す
ることが出、来る。The zinc complex compound according to the present invention can be synthesized by the following method.
オキシカルボン酸に充分なアルカリを加えて水に溶解し
、亜鉛金属付与剤をモル比で１＝２になるように加えて
加熱し、ｐＨを調整し、反応を行ない沈澱物をろ取し、
充分水洗し、乾燥する。Add sufficient alkali to the oxycarboxylic acid and dissolve it in water, add a zinc metallizing agent at a molar ratio of 1=2, heat, adjust the pH, perform the reaction, and collect the precipitate by filtration.
Wash thoroughly and dry.
この生成物は、次の一般式
（式中、ＡおよびムＩは、置換基があってもよい芳香族
オキシカルボン酸の残基を示し、Ｎは、対イオンを示す
。）
で表されるものと推定される。This product is represented by the following general formula (where A and I represent the residue of an aromatic oxycarboxylic acid that may have a substituent, and N represents a counter ion). It is estimated that
この場合にセける対イオンは、生成物の後処理の条件に
よって変更することが出来る。例えば、ろ過前のｐＥＬ
を３以下となし、ろ過後、ｐＥＩが６〜７位になるまで
洗浄すれば、対イオンは水素イオンであり、アルカリで
ｐＨを中性〜アルカリ性にすればアルカリ金属イオン等
となり、更に各種アミンの塩酸塩で処理するならば、各
種のアンモニウム塩が得られる。The counter ions that can be used in this case can be changed depending on the post-treatment conditions of the product. For example, pEL before filtration
If the pH is set to 3 or less, and after filtration, the counter ion is washed until the pEI reaches 6 to 7, the counter ion will be a hydrogen ion, and if the pH is made neutral to alkaline with an alkali, it will become an alkali metal ion, etc., and various amines. When treated with the hydrochloride of , various ammonium salts can be obtained.
ちなみに、トナー成分中に添加される一般式（１）で表
わされる錯化合物の量は、樹脂ｌｏｏ重置部に対し、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 complex compound represented by the general formula (1) added to the toner component is generally 0.1 to 10 parts by weight, preferably 0.5 to 5 parts by weight, based on the overlapping part of the resin loo. Contain in proportion.
本発明トナーは、上記一般式σ）の錯化合物の他に、接
着性、保存性、流動性、粉砕性等を考慮して、スチレン
樹脂、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、ポリエステル樹脂、パラフィン
ワックス等の公知のトナー用樹脂の１櫨又は数種を混合
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出来るが、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
、キナクリドン、銅フタロシアニンブルー、銅フタロシ
アニングリーン等が挙げられる。In addition to the complex compound of the general formula σ), the toner of the present invention is made of styrene resin, styrene-acrylic resin, styrene-butadiene resin, epoxy resin, etc. One or a mixture of known toner resins such as polyester resin, paraffin wax, etc., may be used. As the coloring agent, many known dyes and pigments can be used, but those that are particularly excellent as toners for color copying include benzidine yellow, quinacridone, copper phthalocyanine blue, and copper phthalocyanine green.
本発明トナーは、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、 ｆｔ、５＋
＄ｍＲＭＩ＆Ｉ、ｒＡｓ４１ＭｔＭ’Ｊ、；ｂ・以下に
製造例を示す。The toner of the present invention is typically mixed with a carrier to provide a two-component developer, but of course, 1, ft, 5+
$mRMI&I, rAs41MtM'J,;b・Production examples are shown below.
Ｍａ例 １ （２−ヒドロキシ−３−ナフトエ酸の亜
鉛錯化合物の合成）
２−ヒドロキシ−３−ナフトエ酸４２．２ ｇ ｒ（０
，２２モル）を２．７％苛性ソーダ水溶液５０Ｑｇｒに
完溶させて、約７０℃に昇温する。Ma Example 1 (Synthesis of zinc complex compound of 2-hydroxy-3-naphthoic acid) 2-hydroxy-3-naphthoic acid 42.2 g r(0
, 22 mol) in 50 Qgr of a 2.7% aqueous sodium hydroxide solution, and the temperature was raised to about 70°C.
次いで、硫酸亜鉛３５．５ ｇｒ （０，１３モル）□
を水１００ｇｒに溶かし、３０分間で部下する。Then 35.5 gr (0.13 mol) of zinc sulfate □
Dissolve in 100g of water and boil for 30 minutes.
７０〜８０℃で２時間保ち、ｐＨを７．０±０．５に調
整し、反応を終了する。燕時ろ過、水洗。The temperature is maintained at 70-80°C for 2 hours, the pH is adjusted to 7.0±0.5, and the reaction is completed. Filtered at swallow time and washed with water.
乾燥して、淡黄色の微粉の錯化合＠４７．５ｇｒを得た
（対イオンｊＪａ、以下本楼錯化合吻を化合物（１）と
する。）。After drying, a light yellow fine powder complex compound @47.5gr was obtained (counter ion jJa, hereinafter referred to as Honro complex compound (compound (1)).
製造例 ２ （３，５−ジターシャリブチルサリチル
酸の亜鉛錯化合物の合成）
３．５−ジターシャリブチルサリチル酸４４．４ ｇ
ｒ （０，１８モル）を２哄苛性ソーダ水溶液４００３
ｒ ＆ｃ完溶させて、約７０℃に昇温する。Production Example 2 (Synthesis of zinc complex compound of 3,5-ditertiarybutylsalicylic acid) 44.4 g of 3,5-ditertiarybutylsalicylic acid
r (0.18 mol) 2 liters of caustic soda aqueous solution 4003
R&C is completely dissolved and the temperature is raised to about 70°C.
次いで、硫酸亜鉛２５．５ｇｒ（０，０９モル）を水ｉ
ｏｏｇｒに溶かし、３０分間で滴下する。 □７０
〜８０℃で２時間保ち、ｐｌｉを７．０±０．５に調整
し、反応を終了する。熱時ろ過、水洗。Next, 25.5 gr (0.09 mol) of zinc sulfate was added to water i.
Dissolve in oogr and drip over 30 minutes. □70
It is kept at ~80°C for 2 hours, pli is adjusted to 7.0±0.5, and the reaction is terminated. Filtration when hot, washing with water.
乾燥して、白色の微粉の錯化合物４３５ｒを得た（対イ
オンＮａ、以下本錯化合物を化合物（２）とする。）。After drying, a white fine powder complex compound 435r was obtained (counter ion Na, hereinafter, this complex compound will be referred to as compound (2)).
製造例 ３ （ターシャリブチル−２−ヒドロ牛シー３
−す７トエ酸の亜鉛錯化合物の合成）ターシャリブチル
−２−ヒドロキシ−３−ナフトエ酸１２．２８ ｒ （
０，０５モル）を２％苛性ソーダ水溶液２ｏｏｇｒに完
溶させて、約７０℃に昇温する。次いで、塩化亜鉛３．
４ ｇ ｒ （０゜０２５モル）を水１ｏｏ３ｒに溶か
し、３０分間で滴下する。７０〜８０℃で２時間保ち、
ＰＫを７．０士０．５に調整し、反応を終了する。燕時
ろ過、水洗、乾燥しで、淡黄色の微粉の錯化合物１３．
１８ ｒを得た（対イオンＮａ、以下本錯化合物を化合
物（３）とする。）。Production example 3 (tert-butyl-2-hydrobeef sea 3
- Synthesis of zinc complex compound of tert-butyl-2-hydroxy-3-naphthoic acid 12.28 r (
0.05 mol) was completely dissolved in 20gr of a 2% aqueous sodium hydroxide solution, and the temperature was raised to about 70°C. Next, zinc chloride3.
4 g r (0°025 mol) is dissolved in 103 r of water and added dropwise over 30 minutes. Keep at 70-80℃ for 2 hours,
Adjust PK to 7.0 to 0.5 and terminate the reaction. After swallowing, filtering, washing with water, and drying, a pale yellow fine powder complex compound 13.
18r was obtained (counter ion Na, hereinafter this complex compound will be referred to as compound (3)).
次に実施例を示す。なお実施例中において、「重量部」
を「部」と略して記載する。Next, examples will be shown. In the examples, "parts by weight"
is abbreviated as "part".
実施例１
ポリエステル樹脂 ・・・・・ １００部（花王石
鹸社製、ａｒＲ−２ｏｘｏ）
肯色染訓 ・・・・・２部（オリエ
ント化学工業社９ 、 ｌｉ’ａｌｉｆａｇｔ Ｂｌｕ
ｅ青色顔料 ・・・・・４部（銅フ
タロシアニン）
化合物は） ・・−・・１部上紀配
合物をボールミルで均一に予＠混合し、プレミックスを
調製する。次いで熱ロールで溶融混錬し、冷却便、振動
ミルで粗粉砕し、更にエアージェットミルを用いて’ｉ
ｓ砕した。辱られた微粉末を分級して粒径１０ア２０μ
ｍを有する青色トナーを得た。Example 1 Polyester resin: 100 parts (manufactured by Kao Soap Co., Ltd., arR-2oxo) Affection dyeing: 2 parts (Orient Chemical Industry Co., Ltd. 9, li'alifagt Blu
eBlue pigment... 4 parts (copper phthalocyanine) Compound is)... 1 part The Joki mixture is uniformly mixed in a ball mill to prepare a premix. Next, it is melted and kneaded using hot rolls, cooled, coarsely ground using a vibration mill, and further processed using an air jet mill.
I crushed it. Classify the crushed fine powder to a particle size of 10A and 20μ.
A blue toner having m was obtained.
得られたトナー３部に対して鉄粉キャリア９７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荷電
量は−２８，３μＯ７ｇ ｒであった。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青色の１厳が得られ
た。本トナーは、連続複写５０．０００枚後においても
複写品質の低下はみられなかった。A developer was prepared by mixing 97 parts of iron powder carrier with 3 parts of the obtained toner. The initial blow-off charge amount of this developer was -28.3 μO7gr. When a toner image was formed using this developer on a commercially available selenium drum using a magnetic brush development method, a clear blue color with no fog was obtained. With this toner, no deterioration in copy quality was observed even after 50,000 sheets were continuously copied.
実施例２
エポキシ樹脂 ・・・・・１００部（シェル
化学社製、エピコート１００４）カーボンブラック
・・・・＠６６部化物（２）
・・・・・２部上記配合物を実施例１と同様に処
理して黒色トナーを調製した。Example 2 Epoxy resin...100 parts (manufactured by Shell Chemical Co., Ltd., Epicoat 1004) Carbon black
...@66-part compound (2)
...2 parts The above formulation was treated in the same manner as in Example 1 to prepare a black toner.
得られたトナー３部に対して鉄粉キャリア９７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荷電
量は−２４，１μＯ／ｇｒであった。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黒色の
画像が得られた。本トナーは、連続複写５０．ＯＯ，０
枚後においても複写品質の低下はみられなかった。A developer was prepared by mixing 97 parts of iron powder carrier with 3 parts of the obtained toner. The initial blow-off charge amount of this developer was -24.1 μO/gr. When copies were made using this developer in the same manner as in Example 1, clear black images without fog were obtained. This toner is suitable for continuous copying 50. OO,0
No deterioration in copy quality was observed even after printing.
実施例３
スチレン−ｎ−ブチルメタクリレート共重合樹脂（６５
／３５ ） ・・・・・１００部０、工、５ｏｌ
ｖｓｎｔ Ｙ＠ｌｌ０Ｗ ７７ ｅｌｌ＠＠＠
５部（化合物（１） ・・・・・
２部上記配合物を実施例１と同様に処理して黄色トナー
を調製した。Example 3 Styrene-n-butyl methacrylate copolymer resin (65
/35) ...100 copies 0, engineering, 5ol
vsnt Y@ll0W 77 ell@@@
5 parts (compound (1)...
Two parts of the above formulation were processed as in Example 1 to prepare a yellow toner.
得られたトナー３部に対して鉄粉キャリア９７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荷電
量は−２５，２μＯ／ ｇ ｒであった。本現像剤を実
施例１と同様に複写したところ、カブリのない細線再現
性の優れた画像が得られた。本トナーは、連続複写５０
．０００枚後においても複写品質の低下はみられなかっ
た。A developer was prepared by mixing 97 parts of iron powder carrier with 3 parts of the obtained toner. The initial blow-off charge amount of this developer was -25.2 μO/gr. When copies were made using this developer in the same manner as in Example 1, images with no fog and excellent fine line reproducibility were obtained. This toner supports 50 consecutive copies.
．． No deterioration in copy quality was observed even after 0,000 copies were made.
実施例４
スチレン−ｎ−ブチルメタクリレート共重合樹脂（６５
／３５ ） ・・・・４１００部赤色染料
・・・・６８部（オリエント化学工業社
製、 Ｖａｌｉｆａｇｔ Ｐｉｎｋ化合物（２）
・・・・・２部上記配合物を実施例
１と同様に処理して赤色トナーを調製した。Example 4 Styrene-n-butyl methacrylate copolymer resin (65
/35) ...4100 parts red dye
...68 parts (manufactured by Orient Chemical Industry Co., Ltd., Valifagt Pink compound (2)
... 2 parts The above formulation was treated in the same manner as in Example 1 to prepare a red toner.
得られたトナー３部に対して鉄粉キャリア９７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荷電
量は−２２，９μＯ／ｇｒであった。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ｓ ｏ、ｏ ｏ
ｏ枚後においても複写品質め低下はみられなかった。A developer was prepared by mixing 97 parts of iron powder carrier with 3 parts of the obtained toner. The initial blow-off charge amount of this developer was -22.9 μO/gr. When copies were made using this developer in the same manner as in Example 1, clear red images without fog were obtained. This toner is suitable for continuous copying so, o o
No deterioration in copy quality was observed even after o copies were made.
実施例５
スチレン−ｎ−ブチルメタクリレート共重合樹脂（６５
／３５ ） ・・・・・１００部Ｃ＋１．５ｏｌ
ｖｅｎｔ ｙｅｌｌｏｗ ７７ １１６１１＋１６
６部化合物（３） ・・・会・２
部上記配合物を実施例１と同様に処理して黄色トナーを
１製した。Example 5 Styrene-n-butyl methacrylate copolymer resin (65
/35) ...100 copies C+1.5ol
vent yellow 77 11611+16
6-part compound (3) ... Society 2
The above formulation was treated in the same manner as in Example 1 to prepare one yellow toner.
得られたトナー３部に対して鉄粉キャリア９７部を混合
して現像剤番調整した。本現像剤の初期ブローオフ荷１
を菫は−２１，８μＯ／ ｇ ｒであった。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。The developer number was adjusted by mixing 97 parts of iron powder carrier with 3 parts of the obtained toner. Initial blow-off load 1 of this developer
Violet was -21.8 μO/gr. When copies were made using this developer in the same manner as in Example 1, clear yellow images without fog were obtained.
本トナーは、連続複写５０．０００枚後に詔いても複写
品質の低下はみられなかった。With this toner, no deterioration in copy quality was observed even after continuous copying of 50,000 sheets.
Claims (1)
鉛錯化合物を荷電制御剤として含有することを特徴とす
る、静電荷像現像用トナー。 ２、亜鉛錯化合物が、樹脂１００重量部に対して０．５
〜５重量部である、特許請求の範囲第１項記載の静電荷
像現像用トナー。[Scope of Claims] 1. A toner for developing electrostatic images, which contains a zinc complex compound of an aromatic oxycarboxylic acid which may have a substituent as a charge control agent. 2. The zinc complex compound is 0.5 parts by weight per 100 parts by weight of the resin.
5 parts by weight of the toner for developing an electrostatic image according to claim 1.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59191117A JPS6169073A (en) | 1984-09-12 | 1984-09-12 | Toner for developing electrostatic charge image |
| US06/775,485 US4656112A (en) | 1984-09-12 | 1985-09-12 | Toner for developing electrostatic latent images |
| EP19860100043 EP0227874B1 (en) | 1984-09-12 | 1986-01-03 | Toner for developing electrostatic latent images |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59191117A JPS6169073A (en) | 1984-09-12 | 1984-09-12 | Toner for developing electrostatic charge image |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6169073A true JPS6169073A (en) | 1986-04-09 |
| JPH0260183B2 JPH0260183B2 (en) | 1990-12-14 |
Family
ID=16269146
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59191117A Granted JPS6169073A (en) | 1984-09-12 | 1984-09-12 | Toner for developing electrostatic charge image |
Country Status (2)
| Country | Link |
|---|---|
| EP (1) | EP0227874B1 (en) |
| JP (1) | JPS6169073A (en) |
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63118756A (en) * | 1986-11-07 | 1988-05-23 | Mitsubishi Kasei Corp | Electrostatic charge image developing toner |
| JPH03185457A (en) * | 1989-12-15 | 1991-08-13 | Konica Corp | Color toner |
| US5153090A (en) * | 1990-06-28 | 1992-10-06 | Commtech International Management Corporation | Charge directors for use in electrophotographic compositions and processes |
| US6218065B1 (en) | 1997-12-05 | 2001-04-17 | Canon Kabushiki Kaisha | Toner having negative triboelectric chargeability and developing method |
| US6232027B1 (en) | 1998-05-26 | 2001-05-15 | Canon Kabushiki Kaisha | Toner having negative triboelectric chargeability and image forming method |
| US6514654B1 (en) | 1998-04-10 | 2003-02-04 | Canon Kabushiki Kaisha | Two-component developer and image forming method |
| US6964835B2 (en) | 2002-07-19 | 2005-11-15 | Ricoh Company, Ltd. | Toner and image forming method using the toner |
| 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 |
| US8088540B2 (en) | 2006-01-23 | 2012-01-03 | Hodogaya Chemical Co., Ltd. | Photoreceptor for electrophotography |
| JPWO2010035561A1 (en) * | 2008-09-29 | 2012-02-23 | 日本碍子株式会社 | Gas adsorption material, precursor thereof, and method for producing gas adsorption material |
| 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 |
| WO2012036171A1 (en) | 2010-09-15 | 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 |
| US9152069B2 (en) | 2011-02-28 | 2015-10-06 | Ricoh Company, Ltd. | Toner, and full-color image forming method and full-color image forming apparatus using the toner |
| 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 |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4762763A (en) * | 1985-12-19 | 1988-08-09 | Ricoh Co., Ltd. | Toner for developing electrostatic latent image |
| US4985328A (en) * | 1988-09-22 | 1991-01-15 | Hitachi Chemical Co., Ltd. | Dry toner, dry developer and process for forming electrophotographic images |
| JP2609356B2 (en) * | 1990-11-28 | 1997-05-14 | 三田工業株式会社 | Negatively chargeable electrophotographic toner |
| JP2609359B2 (en) * | 1990-11-28 | 1997-05-14 | 三田工業株式会社 | Electrophotographic toner for negative charging |
| JP2609357B2 (en) * | 1990-11-28 | 1997-05-14 | 三田工業株式会社 | Electrophotographic toner for negative charging |
| AU8897391A (en) * | 1990-12-12 | 1992-06-18 | Mitsubishi Kasei Corporation | Electrostatic image-developing toner |
| GB9306456D0 (en) * | 1993-03-29 | 1993-05-19 | Zeneca Ltd | Composition and use |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5779964A (en) * | 1980-11-06 | 1982-05-19 | Canon Inc | Developing method |
| JPS5979256A (en) * | 1982-10-29 | 1984-05-08 | Ricoh Co Ltd | Toner for developing electrostatic latent image |
| JPS5988745A (en) * | 1982-11-15 | 1984-05-22 | Hodogaya Chem Co Ltd | Toner for electrophotography |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53127726A (en) * | 1977-04-13 | 1978-11-08 | Canon Inc | Electrostatic image developing toner |
| JPS5841508B2 (en) * | 1980-12-22 | 1983-09-12 | オリヱント化学工業株式会社 | Toner for developing electrostatic images |
| JPS5929255A (en) * | 1982-08-12 | 1984-02-16 | Canon Inc | Electrostatic charge developing toner |
-
1984
- 1984-09-12 JP JP59191117A patent/JPS6169073A/en active Granted
-
1986
- 1986-01-03 EP EP19860100043 patent/EP0227874B1/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5779964A (en) * | 1980-11-06 | 1982-05-19 | Canon Inc | Developing method |
| JPS5979256A (en) * | 1982-10-29 | 1984-05-08 | Ricoh Co Ltd | Toner for developing electrostatic latent image |
| JPS5988745A (en) * | 1982-11-15 | 1984-05-22 | Hodogaya Chem Co Ltd | Toner for electrophotography |
Cited By (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63118756A (en) * | 1986-11-07 | 1988-05-23 | Mitsubishi Kasei Corp | Electrostatic charge image developing toner |
| JPH03185457A (en) * | 1989-12-15 | 1991-08-13 | Konica Corp | Color toner |
| US5153090A (en) * | 1990-06-28 | 1992-10-06 | Commtech International Management Corporation | Charge directors for use in electrophotographic compositions and processes |
| US6218065B1 (en) | 1997-12-05 | 2001-04-17 | Canon Kabushiki Kaisha | Toner having negative triboelectric chargeability and developing method |
| US6514654B1 (en) | 1998-04-10 | 2003-02-04 | Canon Kabushiki Kaisha | Two-component developer and image forming method |
| US6232027B1 (en) | 1998-05-26 | 2001-05-15 | Canon Kabushiki Kaisha | Toner having negative triboelectric chargeability and image forming method |
| US6964835B2 (en) | 2002-07-19 | 2005-11-15 | Ricoh Company, Ltd. | Toner and image forming method using the toner |
| US8088540B2 (en) | 2006-01-23 | 2012-01-03 | Hodogaya Chemical Co., Ltd. | Photoreceptor for electrophotography |
| 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 |
| JPWO2010035561A1 (en) * | 2008-09-29 | 2012-02-23 | 日本碍子株式会社 | Gas adsorption material, precursor thereof, and method for producing gas adsorption material |
| JP5759175B2 (en) * | 2008-09-29 | 2015-08-05 | 日本碍子株式会社 | Gas adsorption material, precursor thereof, and method for producing gas adsorption material |
| 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 |
| WO2012036171A1 (en) | 2010-09-15 | 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 |
| US9152069B2 (en) | 2011-02-28 | 2015-10-06 | Ricoh Company, Ltd. | Toner, and full-color image forming method and full-color image forming apparatus using the toner |
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0227874B1 (en) | 1990-09-26 |
| EP0227874A1 (en) | 1987-07-08 |
| JPH0260183B2 (en) | 1990-12-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |