JPS6247056A - Coloring composition for image recording - Google Patents

Coloring composition for image recording

Info

Publication number
JPS6247056A
JPS6247056A JP60185765A JP18576585A JPS6247056A JP S6247056 A JPS6247056 A JP S6247056A JP 60185765 A JP60185765 A JP 60185765A JP 18576585 A JP18576585 A JP 18576585A JP S6247056 A JPS6247056 A JP S6247056A
Authority
JP
Japan
Prior art keywords
dye
coloring composition
image recording
developer
pigments
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
Application number
JP60185765A
Other languages
Japanese (ja)
Other versions
JPH0352859B2 (en
Inventor
Hisanori Takami
尚徳 高見
Keiichiro Fukuda
啓一郎 福田
Akio Hara
原 明男
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.)
Dainichiseika Color and Chemicals Mfg Co Ltd
Original Assignee
Dainichiseika Color and Chemicals Mfg 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 Dainichiseika Color and Chemicals Mfg Co Ltd filed Critical Dainichiseika Color and Chemicals Mfg Co Ltd
Priority to JP60185765A priority Critical patent/JPS6247056A/en
Publication of JPS6247056A publication Critical patent/JPS6247056A/en
Publication of JPH0352859B2 publication Critical patent/JPH0352859B2/ja
Granted 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
    • G03G9/091Azo dyes

Landscapes

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

Abstract

PURPOSE:To reduce the variance of electrostatic chargeability among particles, to maintain potential at the interfaces constant, and to enable stable development for a long period by specifying a dye in an image recording coloring composition. CONSTITUTION:The image recording coloring composition is composed of the dye represented by the formula shown on the right and a resin dispersion medium for dispersing the dye, and when the composition is used as the developer, the medium acts as the fixing agent of the dye, and all the media having conventionally been used can been used. The dye is contained in the coloring composition containing said resin dispersion medium and other additives, preferably, in an amount of 60-30wt% of the solid, paste, and liquid composition containing a high concentration of dye, and in the case of using as the colorant of the electrophotographic developer, it is used, preferably, in an amount of 10-3wt%.

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、静電印刷および静電記録等の画像
記録における静電的潜像の現像剤あるいはその製造に使
用する着色組成物および該画像記録用現像剤として使用
する着色組成物に関する。
Detailed Description of the Invention (Field of Industrial Application) The present invention relates to a developer for electrostatic latent images in image recording such as electrophotography, electrostatic printing, and electrostatic recording, or a coloring composition used for the production thereof. and a coloring composition used as the image recording developer.

更に詳しくは、顔料あるいは染料等の色素を含有する静
電的潜像の現像剤において、該色素がもたらす電荷およ
び電荷量に起因する諸欠点を、該色素として特定の構造
の色素を選択することによって改良したものである。
More specifically, in an electrostatic latent image developer containing a dye such as a pigment or dye, various defects caused by the charge and amount of charge brought about by the dye can be avoided by selecting a dye with a specific structure as the dye. It was improved by.

(従来の技術) 一般に有機顔料あるいは染料等の色素は、電子写真現像
剤に使用するキャリアとの摩擦に際して、その構造によ
って、種々の帯電性が変化する。例えば、銅フタロシア
ニンブルー顔料、キナクリドン顔料等は、キャリアとの
摩擦に際して正帯電性を示し、一方、銅フタロシアニン
グリーン顔料等は負帯電性を示す。
(Prior Art) In general, when pigments such as organic pigments or dyes are rubbed against a carrier used in an electrophotographic developer, various charging properties change depending on their structure. For example, copper phthalocyanine blue pigments, quinacridone pigments, and the like exhibit positive chargeability upon friction with a carrier, while copper phthalocyanine green pigments and the like exhibit negative chargeability.

(発明が解決すべき問題点) 色素を電子写真複写機の乾式現像剤に使用する場合、該
色素を必要に応じ他の添加剤と共に樹脂分散媒中に分散
した後、微粉砕したものであり、破砕した粒子の表面は
使用した色素の影響が避けられない、特に顔料を使用し
た場合には、顔料と樹脂の界面で破砕が起こり、顔料の
面が粒子表面に露出することも起きる。
(Problems to be Solved by the Invention) When a dye is used in a dry developer for an electrophotographic copying machine, the dye is dispersed in a resin dispersion medium along with other additives as necessary, and then finely ground. The surface of crushed particles is unavoidably affected by the pigment used. Particularly when pigments are used, crushing occurs at the interface between the pigment and the resin, and the pigment surface may be exposed on the particle surface.

また、電子写真複写機の現像剤においては、要求する複
写画像の色相、色調によって現像剤に使用する色素も限
定される。
Furthermore, in a developer for an electrophotographic copying machine, the dye used in the developer is also limited depending on the hue and tone of the required copy image.

従って、負帯電性の現像剤を必要とするものであって、
且つ要求する複写画像の色相から選定した色素が、キャ
リアとの摩擦に際して正帯電性のものである場合には、
その現像剤粒子の表面の微小部分の帯電性および各粒子
間の帯電性において均一性に欠けてしまうという欠陥を
有している。
Therefore, it requires a negatively charged developer,
In addition, if the dye selected based on the hue of the required copy image is positively charged when it rubs with the carrier,
The defect is that the chargeability of minute portions on the surface of the developer particles and the chargeability between each particle lacks uniformity.

本発明者らは上記の如き静電的潜像の現像剤の欠陥に鑑
み、上記の条件を満たすへく1色素の構造について種々
研究した結果、特定の構造式で表わされる色素を現像剤
の着色剤として使用することにより、前記した条件にお
いてもすぐれた効果を発揮しうろことを知見し本発明を
完成した。
In view of the above-mentioned defects in electrostatic latent image developers, the present inventors conducted various studies on the structure of dyes that satisfy the above conditions. The present invention was completed based on the finding that when used as a coloring agent, excellent effects can be exhibited even under the conditions described above.

(問題点を解決するための手段) すなわち、本発明は1色素および樹脂分散媒からなる画
像記録用着色組成物において、色素が下記構造式で表わ
される色素であることを特徴とする画像記録用着色組成
物である。
(Means for Solving the Problems) That is, the present invention provides a coloring composition for image recording comprising one dye and a resin dispersion medium, wherein the dye is a dye represented by the following structural formula. It is a colored composition.

本発明の詳細な説明すると、本発明で使用し、主として
本発明を特徴づける上記の構造式で表わされる色素は、
例えば下記の如くして得られるものである。(文中の%
および部は重量基準である)。
To explain the present invention in detail, the dye represented by the above structural formula used in the present invention and which mainly characterizes the present invention is:
For example, it can be obtained as follows. (% in sentence
and parts are by weight).

スカーレットLGベース18部を、常法に従って35%
塩酸20部、NaNO24,6部、液量300部、0℃
の条件でジアゾ化する。
18 parts of Scarlet LG base, 35% according to the usual method
20 parts of hydrochloric acid, 24.6 parts of NaNO, 300 parts of liquid, 0°C
Diazotize under the following conditions.

次にナフトールAs 17 、8部を水90部および苛
性ソーダ6.8部中に入れて加熱溶解する・液量を70
0部、温度を10℃とし、ロート油1.5部を注入する
。これに上記ジアゾ液を約90分間で注入しカップリン
グを行い、60分間撹拌する。これを酢酸にてpH3,
5〜4.0に調整後、肩部して90℃とする。5分間撹
拌してプレスおよび水洗を行い顔料ケーキを得る。これ
を100℃で乾燥し、粉砕して赤色顔料粉末を得る。
Next, put 8 parts of naphthol As 17 into 90 parts of water and 6.8 parts of caustic soda and dissolve by heating.The liquid volume is 70 parts.
0 parts, the temperature was set to 10°C, and 1.5 parts of funnel oil was injected. The above-mentioned diazo solution was injected into the solution over a period of about 90 minutes to perform coupling, and the mixture was stirred for 60 minutes. This was adjusted to pH 3 with acetic acid.
After adjusting the temperature to 5 to 4.0, the temperature at the shoulder is set at 90°C. Stir for 5 minutes, press and wash to obtain a pigment cake. This is dried at 100°C and pulverized to obtain a red pigment powder.

本発明において使用する樹脂分散媒は、上記色素の分散
媒体であり、また現像剤として使用する際には、色素の
固着剤として作用するものである。
The resin dispersion medium used in the present invention is a dispersion medium for the above-mentioned dye, and also acts as a fixing agent for the dye when used as a developer.

このような樹脂分散媒としては従来使用されてきたもの
はすべて使用できるものであり、例えば、ポリスチレン
、スチレン−(メタ)アクリル酸エステル共重合体、ス
チレン−マレイン酸エステル共重合体、(メタ)アクリ
ル酸エステル重合体および共重合体、スチレン−ジエン
系共重合体、ポリエチレン、ポリプロピレン、エチレン
−酢酸ビニル共重合体、エチレン−アクリル酸エステル
共重合体等の付加重合系樹脂、ポリエステル系樹脂、エ
ポキシ系樹脂、フェノール系樹脂等のm 合糸mh、ロ
ジンエステル、マレイン化ロジンエステル等の変性樹脂
、石油樹脂、高級脂肪酸ワックス、高級アルコール、高
級脂肪酸、パラフィンワックス、カルナバワックス、シ
ェラツク等の低分子固体等が単独あるいは組合せて使用
できる。
All conventionally used resin dispersion media can be used, such as polystyrene, styrene-(meth)acrylic acid ester copolymer, styrene-maleic acid ester copolymer, and (meth)acrylic acid ester copolymer. Addition polymer resins such as acrylic ester polymers and copolymers, styrene-diene copolymers, polyethylene, polypropylene, ethylene-vinyl acetate copolymers, ethylene-acrylic ester copolymers, polyester resins, epoxy m-based resins, phenolic resins, etc., modified resins such as rosin esters, maleated rosin esters, petroleum resins, higher fatty acid waxes, higher alcohols, higher fatty acids, low molecular solids such as paraffin wax, carnauba wax, shellac, etc. etc. can be used alone or in combination.

本発明において、前記構造式で表わされる色素の樹脂分
散媒やその他の添加剤を含む着色組成物中の含有量は、
その使用する目的によって異なるものであって、該色素
を高濃度に含有する固体状、ペースト状あるいは液状の
組成物においては、約80重量%〜10重量%、好まし
くは60重量%〜30重量%であり、電子写真現像剤の
着色剤として使用する場合には、約15重量%〜2重量
%、好ましくは10重量%〜3重量%位であり、その他
目的に応じて最も好ましい含有量で使用する。
In the present invention, the content of the pigment represented by the above structural formula in the coloring composition containing the resin dispersion medium and other additives is as follows:
It varies depending on the purpose of use, and in a solid, pasty or liquid composition containing the pigment at a high concentration, about 80% to 10% by weight, preferably 60% to 30% by weight. When used as a coloring agent in an electrophotographic developer, the content is approximately 15% to 2% by weight, preferably 10% to 3% by weight, and the most preferred content is used depending on the purpose. do.

本発明の画像記録用着色組成物は、その目的によって種
々の使い方がなされる。
The coloring composition for image recording of the present invention can be used in various ways depending on the purpose.

その1例は色素を高濃度に含み、あらかじめ充分練肉し
て分散させたり、調色等を行なうことによって、後の工
程を容易にするためのものがあり、粗粒、粗粉、微粉、
シート状、小塊状等の固体状、あるいはペースト状また
は液状等のいずれの形状にても使用できる。
One example is one that contains pigment at a high concentration and is used to facilitate the subsequent process by thoroughly kneading it in advance to disperse it or toning it.
It can be used in any solid form such as a sheet or small lump, or in a paste or liquid form.

また、別の例としては最終的な画像記録用現像剤として
使用する組成のものも挙げられ、いわゆる乾式現像剤、
湿式現像剤、静電現像剤等であり、乾式現像剤も二成分
系現像剤および一成分系現像剤に区分される。
Another example is a composition used as a final image recording developer, so-called dry developer,
These include wet developers, electrostatic developers, etc., and dry developers are also classified into two-component developers and one-component developers.

主として一成分系乾式現像剤には、強磁性材料を併用す
る。これらの強磁性材料も本発明の着色組成物中に必要
に応じて添加するものであって、従来公知の磁性現像剤
用として使用されている強磁性微粒状物がいずれも使用
できる。
A ferromagnetic material is mainly used in one-component dry developers. These ferromagnetic materials are also added to the coloring composition of the present invention if necessary, and any of the ferromagnetic fine particles conventionally used for magnetic developers can be used.

例えば、四三酸化鉄粉、三二酸化鉄粉等の酸化物、鉄、
ニッケル、コバルトなどの金属粉等であり、形状として
は立方体状、針状等、形状にこだわるものではない。
For example, oxides such as triiron tetroxide powder and sesquioxide powder, iron,
It is a metal powder such as nickel or cobalt, and the shape is not limited to a cubic shape, a needle shape, etc.

また、必要に応じて添加する可塑化材料は、例えば圧力
定着型現像剤に使用するものであって、可塑剤、油脂、
低融点ワックス、石油樹脂、液状オリゴマー樹脂等あげ
られる。
In addition, the plasticizing materials added as necessary are those used in pressure fixing type developers, such as plasticizers, oils and fats, etc.
Examples include low melting point wax, petroleum resin, liquid oligomer resin, etc.

溶剤としては、色素を高濃度に含有するペーストまたは
液状組成物に使用するものの場合には、その製造工程あ
るいは使用方法により、脂肪族系、脂環族系、芳香族系
炭化水素、ハロゲン化炭化水素、エステル系、ケトン系
、グリコールエーテル系、アルコール系、水系等が使用
され、特に限定されない。
If the solvent is used in a paste or liquid composition containing a high concentration of pigment, depending on the manufacturing process or method of use, aliphatic, alicyclic, aromatic hydrocarbons, halogenated hydrocarbons, etc. Hydrogen, ester-based, ketone-based, glycol ether-based, alcohol-based, water-based, etc. are used, and are not particularly limited.

また、湿式の液状現像剤の媒体として使用する場合には
、従来公知の高絶縁性の石油系溶剤、例えば、アイソパ
ーH、アイソパーG(エッソスタンダード株式会社)シ
ェルゾール71(シェル石油株式会社)およびケロシン
等を使用する。
When used as a wet liquid developer medium, conventionally known highly insulating petroleum solvents such as Isopar H, Isopar G (Esso Standard Co., Ltd.), Shellsol 71 (Shell Oil Co., Ltd.) and Use kerosene etc.

また、色素を更に必要とする場合には、従来公知の顔料
または染料から適切に選択して本発明で使用する色素と
共に使用する0例えば、有機顔料または染料としては、
フタロシアニン系、アゾ系、アンスラキノン系、ペリノ
ン拳ペリレン系、インジゴ・チオインジゴ系、ジオキサ
ジン系、キナクリドン系、インインドリン系、アニリン
ブラ・ンク系、カーボンブラック系顔料が挙げられ。
In addition, if additional pigments are required, they can be appropriately selected from conventionally known pigments or dyes and used together with the pigments used in the present invention.For example, as organic pigments or dyes,
Phthalocyanine pigments, azo pigments, anthraquinone pigments, perylene pigments, indigo/thioindigo pigments, dioxazine pigments, quinacridone pigments, indoline pigments, aniline pigments, and carbon black pigments.

無機顔料としては、酸化チタン系、酸化鉄系、焼成顔料
系、紺青、金属粉顔料、体質顔料等が挙げられる。
Examples of inorganic pigments include titanium oxide based pigments, iron oxide based pigments, fired pigment based pigments, navy blue pigments, metal powder pigments, extender pigments, and the like.

他に電子写真用現像剤として使用する場合においては、
従来公知の電荷制御剤、クリーニング剤、現像剤の流動
性の向上剤等を添加することができる。
When used as an electrophotographic developer,
Conventionally known charge control agents, cleaning agents, developer fluidity improvers, and the like can be added.

(作用・効果) 本発明の画像記録用着色組成物は、その色素成へしI□
−、ヤ〜骨コ番瞼生−+4鴫主A−Jeふ17ノI、4
工士、xI七コ11−ので、最終的に画像記録用着色組
成物として使用するに際して、粒子間の帯電性のばらつ
きを少なくすることができる。液体現像剤として使用す
るに際しても、界面電位が一定し、長時間安定して現象
することができる。
(Action/Effect) The coloring composition for image recording of the present invention has a pigment formation property I□
-, ya~bones eyelids student-+4 Shizukuji A-Jefu 17 no I, 4
Therefore, when the composition is finally used as a coloring composition for image recording, variations in chargeability between particles can be reduced. Even when used as a liquid developer, the interfacial potential is constant and the phenomenon can be stable for a long time.

次に実施例をあげて、本発明を具体的に説明する。尚、
文中、部または%とあるのは特に断りのない限り重量基
準である。
Next, the present invention will be specifically explained with reference to Examples. still,
In the text, parts or percentages are by weight unless otherwise specified.

実施例1 前記構造式で表わされる色素30部をスチレン−メタク
リル系共重合体(軟化点的110℃、ガラス転移点的5
6℃、GPC法重全重量平均分子量約9万0部とともに
三本ロールにて充分混練し、色素を分散させた。冷却後
粗砕して色素を30%の濃度で含有する本発明の高濃度
着色組成物の粗粉を得た。
Example 1 30 parts of the dye represented by the above structural formula was mixed with a styrene-methacrylic copolymer (softening point: 110°C, glass transition point: 5°C).
The mixture was thoroughly kneaded at 6° C. with a three-roll machine with a GPC-based total weight average molecular weight of about 90,000 parts to disperse the dye. After cooling, the mixture was crushed to obtain a coarse powder of the highly concentrated coloring composition of the present invention containing a pigment at a concentration of 30%.

次いで、上記で得た色素を含む高濃度着色組成物20部
を上記で使用したスチレン−メタクリル系共重合体80
部と常法に従って混練し、冷却後粉砕し、更にジェット
ミルで微粉砕し、分級して5〜30ミクロンの本発明の
着色組成物の微粉末を得た。この着色組成物の摩擦帯電
量を測定したところ−8,2÷イクロクーロン/グラム
であった。
Next, 20 parts of the highly concentrated coloring composition containing the dye obtained above was mixed with 80 parts of the styrene-methacrylic copolymer used above.
After cooling, the mixture was kneaded according to a conventional method, pulverized after cooling, further pulverized with a jet mill, and classified to obtain a fine powder of the colored composition of the present invention having a size of 5 to 30 microns. The amount of triboelectrification of this colored composition was measured and found to be -8.2 ÷ microcoulombs/gram.

上記の赤色樹脂微粉末に流動化剤としてコロイダルシリ
カを添加し、常法に従い充分混合し、電子写真乾式現像
剤とし、キャリアの磁性鉄分と混合し、負電荷現像剤用
電子写真複写機にて複写したところ、鮮明で安定した複
写画像が得られた。
Colloidal silica is added as a fluidizing agent to the above red resin fine powder, mixed thoroughly according to a conventional method to form an electrophotographic dry developer, mixed with the magnetic iron of the carrier, and used in an electrophotographic copying machine for negative charge developers. Upon copying, a clear and stable copy image was obtained.

実施例2 実施例1の前記構造式で表わされる色素を30部濃度で
含む高濃度着色組成物20.8部を、脂肪族炭化水素系
溶媒に可溶のアクリルエステル系樹脂15部と共にアイ
ソパーG100部に加え、更にガラスピーズを加えてペ
イントシェイヵーにて20時間振とうし、分散せしめて
本発明の濃厚着色液を調製した。この濃厚着色液5部を
アイソパーGlリットル中に加え分散させて本発明の電
子写真湿式現像剤を得た。これを湿式電子写真複写機に
て複写したところ、鮮明で落着いた色調の複写画像が安
定して得られた。
Example 2 20.8 parts of a highly concentrated coloring composition containing the dye represented by the structural formula of Example 1 at a concentration of 30 parts was mixed with Isopar G100 along with 15 parts of an acrylic ester resin soluble in an aliphatic hydrocarbon solvent. In addition, glass peas were further added to the mixture, and the mixture was shaken in a paint shaker for 20 hours to disperse the mixture to prepare a concentrated colored liquid of the present invention. Five parts of this concentrated colored liquid was added to 1 liter of Isopar G and dispersed to obtain an electrophotographic wet developer of the present invention. When this was copied using a wet-type electrophotographic copying machine, a clear copy image with a subdued color tone was stably obtained.

特許出願人 大日精化工業株式会社 。Patent applicant: Dainichiseika Industrial Co., Ltd.

代理人  弁理士 小 山 輝 晃1、ニー□\゛ご+
、+ン
Agent Patent Attorney Akira Koyama 1, Ni□\゛go+
,+n

Claims (4)

【特許請求の範囲】[Claims] (1)色素および樹脂分散媒からなる画像記録用着色組
成物において、色素が下記構造式で表わされる色素であ
ることを特徴とする画像記録用着色組成物。 ▲数式、化学式、表等があります▼
(1) A coloring composition for image recording comprising a dye and a resin dispersion medium, characterized in that the dye is a dye represented by the following structural formula. ▲Contains mathematical formulas, chemical formulas, tables, etc.▼
(2)色素を高濃度に含有する固体状、ペースト状ある
いは液状の組成物である特許請求の範囲第(1)項に記
載の画像記録用着色組成物。
(2) The coloring composition for image recording according to claim (1), which is a solid, paste or liquid composition containing a dye at a high concentration.
(3)固体微細粉状現像剤である特許請求の範囲第(1
)項に記載の画像記録用着色組成物。
(3) Claim No. 1 which is a solid fine powder developer
) The coloring composition for image recording according to item 1.
(4)液状現像剤である特許請求の範囲第(1)項に記
載の画像記録用着色組成物。
(4) The coloring composition for image recording according to claim (1), which is a liquid developer.
JP60185765A 1985-08-26 1985-08-26 Coloring composition for image recording Granted JPS6247056A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP60185765A JPS6247056A (en) 1985-08-26 1985-08-26 Coloring composition for image recording

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP60185765A JPS6247056A (en) 1985-08-26 1985-08-26 Coloring composition for image recording

Publications (2)

Publication Number Publication Date
JPS6247056A true JPS6247056A (en) 1987-02-28
JPH0352859B2 JPH0352859B2 (en) 1991-08-13

Family

ID=16176483

Family Applications (1)

Application Number Title Priority Date Filing Date
JP60185765A Granted JPS6247056A (en) 1985-08-26 1985-08-26 Coloring composition for image recording

Country Status (1)

Country Link
JP (1) JPS6247056A (en)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS59165069A (en) * 1983-03-11 1984-09-18 Ricoh Co Ltd Color electrophotographic magenta toner
JPS60108863A (en) * 1983-11-18 1985-06-14 Ricoh Co Ltd Negative charge developer for electrophotography

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS59165069A (en) * 1983-03-11 1984-09-18 Ricoh Co Ltd Color electrophotographic magenta toner
JPS60108863A (en) * 1983-11-18 1985-06-14 Ricoh Co Ltd Negative charge developer for electrophotography

Also Published As

Publication number Publication date
JPH0352859B2 (en) 1991-08-13

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