JPH032302B2 - - Google Patents
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- Publication number
- JPH032302B2 JPH032302B2 JP58215083A JP21508383A JPH032302B2 JP H032302 B2 JPH032302 B2 JP H032302B2 JP 58215083 A JP58215083 A JP 58215083A JP 21508383 A JP21508383 A JP 21508383A JP H032302 B2 JPH032302 B2 JP H032302B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- atom
- hydrogen atom
- halogen atom
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- -1 metal complex salt compound Chemical class 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 239000003086 colorant Substances 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical group [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical group [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 239000000843 powder Substances 0.000 description 17
- 239000000203 mixture Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 239000000975 dye Substances 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 229920003002 synthetic resin Polymers 0.000 description 3
- 239000000057 synthetic resin Substances 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- SOGAXMICEFXMKE-UHFFFAOYSA-N alpha-Methyl-n-butyl acrylate Natural products CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 1
- 239000000981 basic dye Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229920003146 methacrylic ester copolymer Polymers 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920002102 polyvinyl toluene Polymers 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229920001909 styrene-acrylic polymer Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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
- G03G9/09—Colouring agents for toner particles
- G03G9/0906—Organic dyes
- G03G9/091—Azo dyes
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Developing Agents For Electrophotography (AREA)
- Pyridine Compounds (AREA)
Description
本発明は電子写真用現像粉に関するものであ
る。電子写真は、光導電性物質などにより構成さ
れた光導電体上に静電潜像を構成し、これを粉末
現像剤で現像し顕像化、さらに熱あるいは溶剤で
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トナーと呼
ばれる樹脂と着色剤とからなる微粒子粉末と、キ
ヤリヤーと呼ばれる微小なガラス玉または鉄粉と
混合物が使用される。
本発明はこのトナーと呼ばれる現像粉に関する
ものである。
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。そこで負の静電潜像上に
正に帯電した現像粉で現像するとオリジナルと一
致したポジーポジ像が生ずる。しかし正の静電潜
像上に負に帯電した現像粉で現像を行うと黒白の
トーンが逆になつてオリジナルの陰画すなわちポ
ジーネガ像が得られる。このように電子写真用の
現像粉としては正に帯電した現像粉と負に帯電し
た現像粉の二種類がある。
本発明はこのうち正に帯電する現像粉に関する
ものである。
一般に現像粉は合成樹脂に染料、顔料などの着
色剤を混合した微粒子粉末である。
現像粉を正に帯電するため、それに混合する染
料は着色とともに荷電制御剤としての静電特性が
重要な役割を果している。
正の荷電制御剤としては、ニグロシン等の塩基
性染料が使用されてきたが、従来用いられてきた
ニグロシン等の染料は、製造ロツト間の帯電特性
にバラツキが大きいこと、およびトナー化した場
合、トナーの繰返しの連続複写に対する耐久性が
良好でないことなどの欠点を有している。
本発明者等は、以上の問題点を解決すべく研究
を重ねた結果、正の荷電制御性を有し、樹脂との
相容性も良好な荷電制御剤を見出し、優れたトナ
ーを発明するに至つた。
すなわち、本発明は下記一般式(1)
（式中、R1は水素原子、炭素数１〜４のアル
キル基、炭素数１〜４のアルコキシ基、炭素数２
〜５のアルコキシカルボニル基、アシルアミノ
基、アミノカルボニル基、アミノスルホニル基、
炭素数２〜５のアルキルアミノカルボニル基、炭
素数１〜３のアルキルスルホニル基、ニトロ基、
シアノ基、ハロゲン原子を表わし、ｍは、１，
２，３または４であり、ｍが２以上の場合、R1
は互いに相違した置換基であることもでき、R2
は、水素原子、ハロゲン原子、シアノ基、ニトロ
基、メチル基、エチル基、プロピル基を表わし、
R3は、水素原子、炭素数１〜10のアルキル基、
置換されていてもよいフエニル基を表わし、R4
は、水素原子、炭素数１〜４のアルキル基、ハロ
ゲン原子を表わし、Ｍは、クロム原子、或いはコ
バルト原子を表わし、Xは、アニオンを表わ
す。）で表わされる２：１型金属錯塩化合物を荷
電制御剤および着色剤として含有する電子写真用
トナーである。
本発明のトナーに使用される一般式(1)の２：１
型金属錯塩化合物は、一般式(2)
（式中、R1、ｍは前に定義した通りである。）
で表わされるジアゾ成分を常法によりジアゾ化
し、このジアゾ化合物を下記一般式(3)
（式中、R2、R3、R4、は前に定義した通りで
ある。）で表わされるカツプリング成分と常法に
従いカツプリングすることにより、下記一般式(4)
（式中、R1、R2、R3、R4、ｍは前に定義した
通りであり、Yは、アニオンを表わす。）で表
わされるモノアゾ化合物を合成し、次にこのモノ
アゾ化合物を水、或いは有機溶媒中、常法によ
り、クロム化付与剤、或いはコバルト化付与剤で
処理して得ることができる。
この様にして得られる本発明に係る錯塩化合物
は、正の帯電性を有し、樹脂、（例えば、ポリス
チレン、ポリビニルトルエンなどのスチレン及び
その置換体の単量体、スチレン−置換スチレン共
重合体、スチレン−アクリル酸エステル系の共重
合体、スチレン−メタアクリル酸エステル系の共
重合体、スチレン−アクリロニトリル共重合体、
ポリ塩化ビニル系、ポリエチレン、シリコーン樹
脂、ポリエステル、ポリウレタン、ポリアミド、
エポキシ樹脂、変性ロジン、フエノール樹脂な
ど。）に混練りにより分散させ、さらに微粉砕し
た粉体も正の帯電性を示す。さらに本染料は、先
に挙げた樹脂との相容性も良好で、樹脂中に均一
に微分散化することができる。一方、この錯塩化
合物は、水への溶解度が極めて小さく、その為環
境の湿度の影響を受けることがなく、安定した正
荷電性を保持することができた。
本発明の現像粉は、式(1)の錯塩化合物を合成樹
脂に対し重量比で１〜50％の範囲で溶融調合し、
固化した後ボールミルその他の粉砕機で粉砕する
か、または合成樹脂モノマーに重合開始剤を加
え、これにこの錯塩化合物をモノマーに対して重
量比で１〜50％の範囲で加え、混合物を水中に懸
濁しながら重合することにより製造することがで
きる。この際錯塩化合物以外に他の着色剤あるい
はカーボンブラツクなどを加えても差支えない。
このようにして製造された現像粉は、キヤリヤー
との摩擦により静電像の現像に適した帯電量を与
え、現像の繰返しにおいても帯電量は一定に保持
されており、帯電分布も均一でしかも一定に保持
される。従つてこの現像粉を用いて現像された画
像は、均一で一定の濃度を有しており、従来の正
の現像粉に比較して非常に鮮明なものである。
以下、実施例により本発明を詳細に説明する。
実施例中、部は重量部を表わす。
実施例 １
で表わされる金属錯塩化合物２部にスチレン−ｎ
−ブチルメタアクリレート共重合物100部とカー
ボンブラツク10部とを加えよく混合後、加熱融解
しながら混練りして、冷却後ミキサーで粗粉砕、
次いで高速遠心式粉砕機で微粉砕し、正に帯電す
る微細なトナーを得た。酸化亜鉛感光体を使用し
た市販の複写機に上記のトナーを重量比５：100
で直径100〜150μmの鉄粉と混合して用いたとこ
ろ、かぶりのない鮮明な画像が得られた。なおト
ナーの帯電量は、ブローオフ法で測定したところ
平均して17.6μC／ｇであり、また帯電分布も17.3
〜18.0μC／ｇでほぼ均一であつた。
実施例 ２〜19
実施例１に準じ、金属錯塩化合物を含有させた
トナーを次表に示す組成で得た。これらのトナー
の帯電特性についてもあわせて表中にまとめた。
The present invention relates to a developing powder for electrophotography. Electrophotography generally involves forming an electrostatic latent image on a photoconductor made of a photoconductive substance, developing this image with a powder developer to make it visible, and then fixing it with heat or a solvent. be. As a developer for such electrophotography, a mixture of a fine particle powder called a toner, which is made of a resin and a colorant, and microscopic glass beads or iron powder, called a carrier, is used. The present invention relates to this developing powder called toner. The photoconductor layer can be positively or negatively charged so that exposure under the original produces a positive or negative electrostatic latent image. Therefore, if the negative electrostatic latent image is developed with positively charged developer powder, a positive image matching the original is generated. However, when a positively electrostatic latent image is developed with negatively charged developer powder, the black and white tones are reversed and a negative image of the original, that is, a positive negative image is obtained. As described above, there are two types of developer powder for electrophotography: positively charged developer powder and negatively charged developer powder. Among these, the present invention relates to positively charged developer powder. Generally, developer powder is a fine powder made by mixing synthetic resin with coloring agents such as dyes and pigments. In order to positively charge the developer powder, the dye mixed therein plays an important role not only in coloring but also in its electrostatic properties as a charge control agent. Basic dyes such as nigrosine have been used as positive charge control agents, but the conventionally used dyes such as nigrosine have large variations in charging characteristics between production lots, and when made into toner, It has drawbacks such as poor durability against repeated continuous copying of toner. As a result of repeated research to solve the above problems, the present inventors have discovered a charge control agent that has positive charge control properties and good compatibility with resins, and have invented an excellent toner. It came to this. That is, the present invention is based on the following general formula (1) (In the formula, R 1 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or 2 carbon atoms.
-5 alkoxycarbonyl group, acylamino group, aminocarbonyl group, aminosulfonyl group,
Alkylaminocarbonyl group having 2 to 5 carbon atoms, alkylsulfonyl group having 1 to 3 carbon atoms, nitro group,
Represents a cyano group or a halogen atom, m is 1,
2, 3 or 4, and when m is 2 or more, R 1
can also be different substituents, R 2
represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a methyl group, an ethyl group, a propyl group,
R 3 is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms,
Represents an optionally substituted phenyl group, R 4
represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a halogen atom, M represents a chromium atom or a cobalt atom, and X represents an anion. This is an electrophotographic toner containing a 2:1 type metal complex salt compound represented by ) as a charge control agent and a colorant. 2:1 of general formula (1) used in the toner of the present invention
The type metal complex salt compound has the general formula (2) (where R 1 and m are as defined previously.)
The diazo component represented by is diazotized by a conventional method, and this diazo compound is expressed by the following general formula (3). (In the formula, R 2 , R 3 , R 4 are as defined above.) By coupling according to a conventional method with the coupling component represented by the formula (4), the following general formula (4) is obtained. (wherein R 1 , R 2 , R 3 , R 4 , and m are as defined above, and Y represents an anion), and then this monoazo compound is Alternatively, it can be obtained by treatment with a chromation-imparting agent or a cobalt-imparting agent in an organic solvent by a conventional method. The complex salt compound according to the present invention obtained in this way has a positive chargeability, and contains resins (for example, monomers of styrene and its substituted products such as polystyrene and polyvinyltoluene, and styrene-substituted styrene copolymers). , styrene-acrylic ester copolymer, styrene-methacrylic ester copolymer, styrene-acrylonitrile copolymer,
Polyvinyl chloride, polyethylene, silicone resin, polyester, polyurethane, polyamide,
Epoxy resin, modified rosin, phenolic resin, etc. ), which is dispersed by kneading and further finely pulverized, also exhibits positive chargeability. Furthermore, this dye has good compatibility with the resins mentioned above and can be uniformly and finely dispersed in the resin. On the other hand, this complex salt compound had extremely low solubility in water, and therefore was not affected by environmental humidity and was able to maintain stable positive chargeability. The developing powder of the present invention is prepared by melting and blending the complex salt compound of formula (1) in a weight ratio of 1 to 50% based on the synthetic resin,
After solidification, the mixture is crushed with a ball mill or other crusher, or a polymerization initiator is added to the synthetic resin monomer, and the complex salt compound is added thereto in a weight ratio of 1 to 50% based on the monomer, and the mixture is immersed in water. It can be produced by polymerizing in suspension. At this time, other coloring agents or carbon black may be added in addition to the complex salt compound.
The developer powder produced in this way provides an amount of charge suitable for developing an electrostatic image through friction with the carrier, and the amount of charge remains constant even after repeated development, and the charge distribution is uniform. held constant. Therefore, images developed using this developing powder have uniform and constant density, and are much clearer than conventional positive developing powders. Hereinafter, the present invention will be explained in detail with reference to Examples.
In the examples, parts represent parts by weight. Example 1 Styrene-n is added to two parts of the metal complex compound represented by
- Add 100 parts of butyl methacrylate copolymer and 10 parts of carbon black, mix well, knead while heating and melting, and after cooling, coarsely crush with a mixer,
Then, it was pulverized using a high-speed centrifugal pulverizer to obtain a fine, positively charged toner. Add the above toner to a commercially available copier using a zinc oxide photoreceptor at a weight ratio of 5:100.
When mixed with iron powder with a diameter of 100 to 150 μm, clear images with no fog were obtained. The charge amount of the toner was measured using the blow-off method and was 17.6μC/g on average, and the charge distribution was 17.3μC/g.
It was almost uniform at ~18.0 μC/g. Examples 2 to 19 According to Example 1, toners containing a metal complex compound were obtained with the compositions shown in the following table. The charging characteristics of these toners are also summarized in the table.
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
Claims (1)
キル基、炭素数１〜４のアルコキシ基、炭素数２
〜５のアルコキシカルボニル基、アシルアミノ
基、アミノカルボニル基、アミノスルホニル基、
炭素数２〜５のアルキルアミノカルボニル基、炭
素数１〜３のアルキルスルホニル基、ニトロ基、
シアノ基、ハロゲン原子を表わしｍは、１，２，
３または４であり、ｍが２以上の場合、R1は互
いに相違した置換基であることもでき、R2は、
水素原子、ハロゲン原子、シアノ基、ニトロ基、
メチル基、エチル基、プロピル基を表わし、R2
は、水素原子、炭素数１〜10のアルキル基、置換
されていてもよいフエニル基を表わし、R4は、
水素原子、炭素数１〜４のアルキル基、ハロゲン
原子を表わし、Ｍはクロム原子、或いはコバルト
原子を表わし、Xは、アニオンを表わす。）で
表わされる２：１型金属錯塩化合物を荷電制御剤
および着色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] 1 The following general formula (1) (In the formula, R 1 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or 2 carbon atoms.
-5 alkoxycarbonyl group, acylamino group, aminocarbonyl group, aminosulfonyl group,
Alkylaminocarbonyl group having 2 to 5 carbon atoms, alkylsulfonyl group having 1 to 3 carbon atoms, nitro group,
Cyano group, represents a halogen atom, m is 1, 2,
3 or 4, and when m is 2 or more, R 1 can be different substituents, and R 2 is
Hydrogen atom, halogen atom, cyano group, nitro group,
Represents a methyl group, ethyl group, or propyl group, R 2
represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an optionally substituted phenyl group, and R 4 is
It represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a halogen atom, M represents a chromium atom or a cobalt atom, and X represents an anion. ) A toner for electrophotography, characterized in that it contains a 2:1 type metal complex salt compound represented by the following formula as a charge control agent and a colorant.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58215083A JPS60107655A (en) | 1983-11-17 | 1983-11-17 | Electrophotographic toner |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58215083A JPS60107655A (en) | 1983-11-17 | 1983-11-17 | Electrophotographic toner |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60107655A JPS60107655A (en) | 1985-06-13 |
| JPH032302B2 true JPH032302B2 (en) | 1991-01-14 |
Family
ID=16666464
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58215083A Granted JPS60107655A (en) | 1983-11-17 | 1983-11-17 | Electrophotographic toner |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60107655A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9723855D0 (en) * | 1997-11-12 | 1998-01-07 | Zeneca Ltd | Compound, composition and use |
| GB2372750B (en) * | 2001-01-18 | 2004-09-08 | Avecia Ltd | Hexa co-ordinated metal complexes of monoazo dyes for use in inks suitable for ink jet printing |
| JP3986488B2 (en) * | 2003-03-31 | 2007-10-03 | 保土谷化学工業株式会社 | Monoazo iron complex compound, charge control agent and toner using the same |
-
1983
- 1983-11-17 JP JP58215083A patent/JPS60107655A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60107655A (en) | 1985-06-13 |
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