JPH0713765B2 - Electrophotographic toner - Google Patents
Electrophotographic tonerInfo
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- JPH0713765B2 JPH0713765B2 JP1041491A JP4149189A JPH0713765B2 JP H0713765 B2 JPH0713765 B2 JP H0713765B2 JP 1041491 A JP1041491 A JP 1041491A JP 4149189 A JP4149189 A JP 4149189A JP H0713765 B2 JPH0713765 B2 JP H0713765B2
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- toner
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- same manner
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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。Description: FIELD OF THE INVENTION The present invention relates to toners 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
写真の現像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、天然樹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。(Prior Art) In electrophotography, a latent image is formed on a photoconductor made of a photoconductive substance, and the latent image is developed with a powder developer to be visualized. Further, heat or solvent, or pressure in some cases is applied. The method of fixing on paper is common. As such an electrophotographic developer, a two-component developer comprising a mixture of a toner in which a colorant, a charge control agent, a fluidizing agent, etc. are dispersed in a natural resin or a synthetic resin, and a carrier of iron powder or ferrite powder. And a one-component developer composed of a natural resin or a synthetic resin, a colorant, a charge control agent, a fluidizing agent, and a magnetic material.
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、キャリアの代わ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、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。The two-component type developer achieves development by attaching the charged toner to the electrostatic latent image by friction with the carrier. As a one-component type developer, conventionally, this is used instead of the carrier. There is known a toner which is charged by friction with a brush-shaped or plate-shaped friction member having the same function as that of, and recently, the magnetic fine powder is kept in a dispersed state and Toners that are charged by mutual friction have become known. The photoconductor layer can be positively or negatively charged, so that exposure under the original gives a positive or negative electrostatic latent image. The developing toner is kept positive or negative depending on the polarity of the electrostatic latent image.
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, it has been proposed to utilize the triboelectric chargeability of the resin, which is the main component of the toner, but in this method the toner charge is small and the solid surface resistance value is large, The obtained image is easily fogged and becomes unclear. Therefore, in order to impart desired triboelectric charging properties to the toner, dyes and pigments that impart an electric charge, and a charge control agent have been added, and these are practically used in the technical field today.
（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、電荷調整能が失わ
れ易い。また、１つの本質的欠陥は、有色物質であるた
めに、特定の色相を有するトナー用には無色または実質
的に無色と見なしうる電荷調整剤が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, dyes and pigments as these charge control agents have a complicated structure and poor stability, and for example, mechanical friction and impact, changes in temperature and humidity conditions, and electrical changes. It is easily decomposed or deteriorated by impact or light irradiation, and the charge adjusting ability is easily lost. Also, one essential deficiency is that it is a colored material, which violates the requirement that charge control agents, which can be regarded as colorless or substantially colorless, are needed for toners having a particular hue. .
（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き
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 Problems) The present inventors have found that the toner has good dispersibility with resin components, has thermal stability up to a temperature at which melt kneading can be sufficiently performed, and is a colorless substance. They have found a compound capable of imparting a negative charge to, and invented an excellent toner.
すなわち、本発明は一般式（Ｉ） （式中、R1およびR4は水素原子、アルキル基、置換また
は非置換の芳香環（縮合環も含む）を示し、R2およびR3
は置換または非置換の芳香環（縮合環も含む）を示し、
Ｍは３価の金属を示し、Ｘ はカチオンを示す。）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である。That is, the invention has the general formula (I)(In the formula, R1And RFourIs a hydrogen atom, alkyl group, substituted or
Represents an unsubstituted aromatic ring (including condensed ring), R2And R3
Represents a substituted or unsubstituted aromatic ring (including a condensed ring),
M represents a trivalent metal, X Represents a cation. )
Characterized by containing a compound as a charge control agent
Is a toner for electrophotography.
一般式（Ｉ）で示される化合物について詳細に説明す
る。アニオンのR1およびR4のアルキル基には、メチル
基、エチル基、ｎ−ブチル基、iso−アミル基、ｎ−ド
デシル基、ｎ−オクタデシル基、シクロヘキシル基等が
あげられ、R1、R2、R3、R4の芳香環には、ベンゼン環、
ナフタリン環等があげられ、置換基にはアルキル基、ア
ルコキシ基、ハロゲン原子、アリール基、アラルキル
基、ニトロ基、シアン基等があげられる。また、Ｍには
３価の金属であるCr、Al、Fe、Co、Ti、Ｂ等があげられ
る。カチオンには種々の無機カチオン、有機カチオンを
用いることができる。無機カチオンには、水素イオン、
金属イオンがあげられ、１価および２価の金属イオンと
して、Li+、Na+、K+、Mg２＋、Ca２＋、Zn２＋等があげ
られる。The compound represented by formula (I) will be described in detail. Alkyl groups for R 1 and R 4 anion, a methyl group, an ethyl group, n- butyl group, iso- amyl, n- dodecyl group, n- octadecyl group, a cyclohexyl group and the like, R 1, R 2 , the aromatic ring of R 3 , R 4 , a benzene ring,
Examples thereof include naphthalene ring, and examples of the substituent include alkyl group, alkoxy group, halogen atom, aryl group, aralkyl group, nitro group, cyan group and the like. In addition, M includes trivalent metals such as Cr, Al, Fe, Co, Ti and B. As the cation, various inorganic cations and organic cations can be used. Inorganic cations include hydrogen ions,
Examples of the metal ion include Li + , Na + , K + , Mg 2+ , Ca 2+ , and Zn 2+ as the monovalent and divalent metal ions.
また有機カチオンとしては、アンモニウムイオン、イミ
ニウムイオンまたはホスホニウムイオンなどがあげられ
る。Examples of the organic cation include ammonium ion, iminium ion, phosphonium ion and the like.
上記有機カチオン中で好ましいものは、下記の一般式
（II）、（III）、（IV）もしくは（Ｖ）で表わされる
ものである。Preferred among the above organic cations are those represented by the following general formula (II), (III), (IV) or (V).
式中、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14
およびR15は、それぞれ水素原子、置換もしくは無置換
のアルキル基、または置換もしくは非置換のアリール基
を表わし、Z1およびZ2は各式中の窒素原子と結合して５
員または６員環を形成する非金属原子群を表わす。ここ
でアルキル基としては、例えばメチル基、エチル基、ｎ
−ブチル基、iso−アミル基、ｎ−ドデシル基、ｎ−オ
クタデシル基、シクロヘキシル基などをあげることがで
きる。アリール基としては、例えばフェニル基、α−ナ
フチル基などをあげることができる。これらのアルキル
基またはアリール基にはアルキル基、アラルキル基、ハ
ロゲン、アルコキシ基、水酸基、シアノ基、アリール基
など各種の置換基で置換されていてもよい。またZ1およ
びZ2は、例えばピリジン環、イソキノリン環、ピロール
環、イミダゾール環、ピペリジン環、ピロリジン環など
各種の複素環を形成するのに必要な非金属原子群をあげ
ることができる。 In the formula, R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14
And R 15 each represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, and Z 1 and Z 2 are bonded to the nitrogen atom in each formula to form 5
Represents a non-metallic atomic group forming a six-membered or six-membered ring. Here, examples of the alkyl group include a methyl group, an ethyl group, and n.
-Butyl group, iso-amyl group, n-dodecyl group, n-octadecyl group, cyclohexyl group and the like can be mentioned. Examples of the aryl group include a phenyl group and an α-naphthyl group. These alkyl groups or aryl groups may be substituted with various substituents such as alkyl groups, aralkyl groups, halogens, alkoxy groups, hydroxyl groups, cyano groups and aryl groups. Examples of Z 1 and Z 2 include a non-metal atom group necessary for forming various heterocycles such as a pyridine ring, an isoquinoline ring, a pyrrole ring, an imidazole ring, a piperidine ring and a pyrrolidine ring.
一般式（Ｉ）で示される化合物の具体例を下記に示す。
なお、化合物No.は、実施例中でも共通に用いる。Specific examples of the compound represented by formula (I) are shown below.
The compound No. is commonly used in the examples.
本発明の電荷調整剤として使用する一般式（Ｉ）で表わ
される化合物は、例えば、ホウ酸とアミンの水溶液に下
記一般式（VI） （式中、R1、R2は化合物（Ｉ）に同じ）の化合物を加え
反応させることにより容易に得られる。 The compound represented by the general formula (I) used as the charge control agent of the present invention can be prepared, for example, by adding the following general formula (VI) to an aqueous solution of boric acid and amine. (In the formula, R 1 and R 2 are the same as the compound (I)) and easily obtained by reacting.
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。By the way, the amount of the compound represented by the general formula (I) added to the toner component is generally 100 parts by weight of the resin.
The content is 0.1 to 10 parts by weight, preferably 0.5 to 5 parts by weight.
本発明のトナーは、上記一般式（Ｉ）の化合物の他に、
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
エン樹脂、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、ベンジジンイ
エロー、キナクドリン、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。The toner of the present invention comprises, in addition to the compound of the general formula (I),
One of known resins for toner such as styrene resin, styrene-acrylic resin, styrene-butadiene resin, epoxy resin, polyester resin, paraffin wax, etc. in consideration of adhesiveness, storability, fluidity, crushability, or the like. It is used as a mixture of several kinds. Although many known dyes and pigments can be used as the colorant, benzidine yellow, quinacdrine, copper phthalocyanine blue, copper phthalocyanine green and the like are particularly excellent as color copying toners.
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 be used as a one-component developer.
（実施例） 以下、実施例により本発明を詳細に説明する。なお実施
例中の部とは、重量部を表わす。(Examples) Hereinafter, the present invention will be described in detail with reference to Examples. In addition, the part in an Example represents a weight part.
実施例１ スチレン樹脂100部、カーボンブラック６部、化合物No.
1で示される化合物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、更にジェットミ
ルを用いて微粉砕して、黒色トナーを得た。この黒色ト
ナーの粒径は８〜15μｍであった。Example 1 100 parts of styrene resin, 6 parts of carbon black, compound No.
A premix is prepared by uniformly premixing a blend of 2 parts of the compound represented by 1 in a ball mill. Next, the mixture was heated, melted and kneaded, cooled, coarsely pulverized by a vibration mill, and further finely pulverized by a jet mill to obtain a black toner. The particle size of this black toner was 8 to 15 μm.
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−22.3μC/g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。A developer was prepared by mixing 95 parts of an iron powder carrier with 5 parts of the obtained toner. The initial blow-off charge amount of this developer was −22.3 μC / g. When a toner image was formed on the commercially available selenium drum of this developer by a magnetic brush development method, a clear image without fog was obtained. This toner is
Even after 10,000 sheets of continuous copying, the copy quality did not deteriorate.
実施例２ スチレン−アクリル共重合樹脂100部、黄色染料（C.I.
ディスパーズイエロー33）６部、化合物No.2で示される
化合物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−24.2μ
C/gであった。Example 2 100 parts of styrene-acrylic copolymer resin, yellow dye (CI
A mixture of 6 parts of Disperse Yellow 33) and 2 parts of the compound represented by Compound No. 2 was treated in the same manner as in Example 1 to obtain a yellow toner. The developer prepared in the same manner as in Example 1 from the obtained yellow toner has an initial blow-off charge amount of −24.2 μm.
It was C / 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 this developer was copied in the same manner as in Example 1, a clear yellow image without fog was obtained. With this toner, the copy quality was not deteriorated even after 10,000 continuous copies.
実施例３ スチレン−ｎ−ブチルメタクレート共重合体樹脂100
部、赤色染料（C.I.ピグメントレッド12）８部、化合物
No.3で示される化合物２部の配合物を実施例１と同様に
処理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−30.2μC/gであった。Example 3 Styrene-n-butylmethacrylate copolymer resin 100
Part, red dye (CI Pigment Red 12) 8 parts, compound
A formulation of 2 parts of the compound of No. 3 was treated in the same manner as in Example 1 to obtain a red toner. The developer prepared in the same manner as in Example 1 from the obtained red toner had an initial blow-off charge amount of −30.2 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 this developer was copied in the same manner as in Example 1, a clear red image without fog was obtained. With this toner, the copy quality was not deteriorated even after 10,000 continuous copies.
実施例４ ポリエステル樹脂100部、青色染料（C.I.ピグメントブ
ルー15）６部、化合物No.4で示される化合物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−32.5μC/gであった。Example 4 A mixture of 100 parts of polyester resin, 6 parts of blue dye (CI Pigment Blue 15) and 2 parts of the compound represented by Compound No. 4 was treated in the same manner as in Example 1 to obtain a blue toner. The initial blow-off charge amount of the developer prepared from the obtained blue toner in the same manner as in Example 1 was −32.5 μC / g.
本現像剤を実施例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 this developer was copied in the same manner as in the example, a clear blue image without fog was obtained. This toner is a continuous copy
Even after 10,000 sheets, the copy quality was not deteriorated.
実施例５ 化合物No.1で示される化合物の代わりに、化合物No.5で
示される化合物を使用した以外は実施例１と同様にして
黒色トナーを得た。得られた黒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−
27.3μC/gであった。Example 5 A black toner was obtained in the same manner as in Example 1 except that the compound represented by the compound No. 5 was used in place of the compound represented by the compound No. 1. The initial blow-off charge amount of the developer prepared from the obtained black toner in the same manner as in Example 1 is −
It was 27.3 μC / g.
実施例６ 化合物No.2で示される化合物の代わりに、化合物No.6で
示される化合物を使用した以外は実施例２と同様にして
黄色トナーを得た。得られた黄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−
25.1μC/gであった。Example 6 A yellow toner was obtained in the same manner as in Example 2 except that the compound represented by the compound No. 6 was used in place of the compound represented by the compound No. 2. The developer prepared in the same manner as in Example 1 from the obtained yellow toner has an initial blow-off charge amount of −.
It was 25.1 μC / g.
実施例７ 化合物No.3で示される化合物の代わりに、化合物No.7で
示される化合物を使用した以外は実施例３と同様にして
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−
35.3μC/gであった。Example 7 A red toner was obtained in the same manner as in Example 3 except that the compound represented by the compound No. 7 was used in place of the compound represented by the compound No. 3. The initial blow-off charge amount of the developer prepared in the same manner as in Example 1 from the obtained red toner is −
It was 35.3 μC / g.
実施例８ 化合物No.4で示される化合物の代わりに、化合物No.8で
示される化合物を使用した以外は実施例４と同様にして
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−
22.0μC/gであった。Example 8 A blue toner was obtained in the same manner as in Example 4 except that the compound represented by the compound No. 8 was used in place of the compound represented by the compound No. 4. The initial blow-off charge amount of the developer prepared in the same manner as in Example 1 from the obtained blue toner is −
It was 22.0 μC / g.
（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 is excellent in mechanical friction and impact stability, temperature and humidity stability, and the like, and is colorless, so that an electrophotographic toner having a clear image and continuously usable. was gotten.
───────────────────────────────────────────────────── フロントページの続き (56)参考文献 特開 昭63−226664（ＪＰ，Ａ) 特開 昭61−69073（ＪＰ，Ａ) ─────────────────────────────────────────────────── --Continued from the front page (56) References JP-A-63-226664 (JP, A) JP-A-61-69073 (JP, A)
Claims (1)
は非置換の芳香環（縮合環も含む）を示し、R2およびR3
は置換または非置換の芳香環（縮合環も含む）を示し、
Ｍは３価の金属を示し、Ｘ はカチオンを示す。）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。1. The following general formula (I):(In the formula, R1And RFourIs a hydrogen atom, alkyl group, substituted or
Represents an unsubstituted aromatic ring (including condensed ring), R2And R3
Represents a substituted or unsubstituted aromatic ring (including a condensed ring),
M represents a trivalent metal, X Represents a cation. )
Characterized by containing a compound as a charge control agent
Toner for electrophotography.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1041491A JPH0713765B2 (en) | 1989-02-23 | 1989-02-23 | Electrophotographic toner |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1041491A JPH0713765B2 (en) | 1989-02-23 | 1989-02-23 | Electrophotographic toner |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02221967A JPH02221967A (en) | 1990-09-04 |
| JPH0713765B2 true JPH0713765B2 (en) | 1995-02-15 |
Family
ID=12609822
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1041491A Expired - Lifetime JPH0713765B2 (en) | 1989-02-23 | 1989-02-23 | Electrophotographic toner |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0713765B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000347462A (en) * | 1999-06-07 | 2000-12-15 | Canon Inc | Dry toner, its manufacture, and image forming method |
| JP2001175031A (en) * | 1999-12-21 | 2001-06-29 | Konica Corp | Electrostatic charge image developing toner, image forming method and image forming device |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07244422A (en) * | 1994-03-02 | 1995-09-19 | Fujitsu Ltd | Image forming device and photoreceptor |
| US6096468A (en) * | 1998-06-05 | 2000-08-01 | Canon Kabushiki Kaisha | Toner, toner production process, and image forming method |
| DE60033338T2 (en) | 1999-06-07 | 2007-11-29 | Canon Kabushiki Kaisha | Toner and image recording method |
| JP3942520B2 (en) | 2002-09-30 | 2007-07-11 | 株式会社巴川製紙所 | Toner for electrophotography and image forming method using the same |
| JP2005215013A (en) | 2004-01-27 | 2005-08-11 | Ricoh Printing Systems Ltd | Electrophotographic toner and image forming apparatus |
| JP4354963B2 (en) | 2006-03-27 | 2009-10-28 | シャープ株式会社 | Toner production method |
| JP5169304B2 (en) | 2007-03-19 | 2013-03-27 | 株式会社リコー | Toner for electrostatic image development |
| JP4443589B2 (en) | 2007-07-04 | 2010-03-31 | シャープ株式会社 | Developing device and image forming apparatus having the same |
| JP4465371B2 (en) | 2007-07-13 | 2010-05-19 | シャープ株式会社 | Toner and two-component developer |
| JP5555979B2 (en) | 2008-03-14 | 2014-07-23 | コニカミノルタ株式会社 | Pyrazolotriazole compounds |
| JP5109739B2 (en) | 2008-03-14 | 2012-12-26 | コニカミノルタビジネステクノロジーズ株式会社 | Toner for electrophotography |
| JP2009221125A (en) | 2008-03-14 | 2009-10-01 | Konica Minolta Business Technologies Inc | Copper complex compound and electrophotographic toner |
| JPWO2011010509A1 (en) | 2009-07-22 | 2012-12-27 | コニカミノルタビジネステクノロジーズ株式会社 | Electrophotographic toner and metal-containing compound |
| US20130157191A1 (en) | 2010-09-14 | 2013-06-20 | Konica Minolat Business Technologies, Inc. | Toner for electrophotography and image-forming method |
-
1989
- 1989-02-23 JP JP1041491A patent/JPH0713765B2/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000347462A (en) * | 1999-06-07 | 2000-12-15 | Canon Inc | Dry toner, its manufacture, and image forming method |
| JP2001175031A (en) * | 1999-12-21 | 2001-06-29 | Konica Corp | Electrostatic charge image developing toner, image forming method and image forming device |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02221967A (en) | 1990-09-04 |
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