JPH0218568A - Toner for electrophotography - Google Patents

Toner for electrophotography

Info

Publication number
JPH0218568A
JPH0218568A JP63167709A JP16770988A JPH0218568A JP H0218568 A JPH0218568 A JP H0218568A JP 63167709 A JP63167709 A JP 63167709A JP 16770988 A JP16770988 A JP 16770988A JP H0218568 A JPH0218568 A JP H0218568A
Authority
JP
Japan
Prior art keywords
toner
compd
formula
parts
image
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
JP63167709A
Other languages
Japanese (ja)
Inventor
Nobuo Aoki
青木 延夫
Jun Kurita
栗田 純
Makoto Ebisawa
海老沢 誠
Isao Isa
伊佐 功
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.)
Japan Carlit Co Ltd
Original Assignee
Japan Carlit 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 Japan Carlit Co Ltd filed Critical Japan Carlit Co Ltd
Priority to JP63167709A priority Critical patent/JPH0218568A/en
Publication of JPH0218568A publication Critical patent/JPH0218568A/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
    • G03G9/097Plasticisers; Charge controlling agents
    • G03G9/09733Organic compounds
    • G03G9/09741Organic compounds cationic

Landscapes

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

Abstract

PURPOSE:To eliminate the fogging of an image and to sharpen the image by incorporating a specific compd. as a charge control agent into the toner. CONSTITUTION:The compd. expressed by the formula is incorporated as the charge control agent into the title toner. In the formula, R denotes 1-12C alkyl group; X denotes anion. Octamethylene bis-triphenylphosphynium, etc., are usable as the compd. expressed by the formula. This compd. has excellent dispersibility to a resin component and thermal stability, is colorless and imparts a positive charge to the toner; therefore, the toner which forms the sharp image and allows continuous use is obtd.

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。
DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a toner 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 this is developed with a powder developer to make it visible. A two-component developer consisting of a mixture of a toner with a fluidizing agent dispersed therein and a carrier of iron powder or ferrite powder, a natural or synthetic resin, a coloring agent, a charge control agent, etc. They can be broadly classified into fluidizers and one-component developers made of magnetic materials.

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、従来上り
、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1こ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かできるので、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。
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 the same function as that of the toner. It has become known that toner is charged by mutual friction with the toner. The photoconductor layer can be positively or negatively charged so that exposure under the original produces a positive or negative electrostatic latent image. Depending on the polarity of this electrostatic latent image, the developing toner remains positive or negative.

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 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 desired triboelectric charging properties to the toner, it has been attempted to add charge-imparting dyes, pigments, and even charge control agents, and these techniques are now in practical use in this technical field.

(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, these dyes and pigments used as charge control agents have complex structures and lack stability, such as mechanical friction and impact, changes in temperature and humidity conditions, and electrical resistance. It is easily decomposed or altered by impact, light irradiation, etc., and the charge adjustment ability is easily lost. One essential flaw is that, being a colored material, it violates the requirement that toners with a specific hue require a charge control agent that can be considered colorless or substantially colorless. .

(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正荷電を付与することかでと
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 the Problems) The present inventors have developed a toner material that has good dispersibility with the resin component, has thermal stability up to a temperature that allows sufficient melt-kneading, and is colorless. They discovered a compound that can be removed by imparting a positive charge to the toner and invented an excellent toner.

すなわち、本発明は一般式(1) (式中、Rは1〜12のアルキル基を表わし、X はア
ニオンを表わす。)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 present invention provides an electrophotographic method comprising a compound represented by the general formula (1) (wherein R represents an alkyl group of 1 to 12 and X represents an anion) as a charge control agent. It is a toner for use.

一般式(1)で示される化合物のアルキル基は、炭素数
1〜12の直鎖状もしくは分枝鎖状アルキ=3 ル基であり、好ましくは炭素数3〜10のアルキル基で
ある。またアニオンとしては、任意の適当なイオンであ
るが、好ましい例としては、CI、Br−1■−1ci
o″4、B F; 、CH3−@−8o:等を挙げるこ
とができる。
The alkyl group of the compound represented by the general formula (1) is a linear or branched alkyl group having 1 to 12 carbon atoms, preferably an alkyl group having 3 to 10 carbon atoms. The anion may be any suitable ion, but preferable examples include CI, Br-1-1ci
o″4, B F; , CH3-@-8o: and the like.

次に、一般式(1)で示される化合物の合成法について
説明する。トリフェニルホスフィンとジハロゲン化アル
カンをアセトニトリルなどの極性溶媒中で反応させるこ
と(こよって、一般式(1)の化合物が得られる。また
アニオンがハロゲン以外の化合物は通常のアニオンの交
換反応で容易に得られる。
Next, a method for synthesizing the compound represented by general formula (1) will be explained. Reacting triphenylphosphine and a dihalogenated alkane in a polar solvent such as acetonitrile (thus, the compound of general formula (1) is obtained. Compounds whose anions are other than halogen can be easily reacted by an ordinary anion exchange reaction. can get.

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。
Incidentally, the amount of the compound represented by 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 100 parts by weight of the resin. Make it contain.

本発明のトナーは、上記一般式(1)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
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、顔料を用いることか゛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、銅フタロシアニンプル、銅
フタロシアニングリーン等が挙げられる。
In addition to the compound of general formula (1), the toner of the present invention includes:
In consideration of adhesion, preservability, fluidity, crushability, etc., one or more of the known toner resins such as styrene resin, styrene-acrylic resin, styrene-butadiene resin, epoxy resin, polyester resin, paraffin wax, etc. A mixture of several types is 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, quinacridine, copper phthalocyanine purple, and copper phthalocyanine green. .

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 also be used as a one-component developer.

(実施例) 以下、実施例により本発明の詳細な説明する。(Example) Hereinafter, the present invention will be explained in detail with reference to Examples.

なお実施例中の部とは、重量部を表わす。Note that parts in the examples represent parts by weight.

実施例に 臭化オクタメチレンピスト+) 7 xニルホスフィニ
ウムの合成 1.8−ジブロモオクタン 24.5g、トリフェニル
ホスフィン 41.2g、およびアセトニトリル 50
+nlを還流冷却器および攪はん器の付いたフラスコに
入れ、還流下で1時間反応させた。冷却後、沈澱をろ取
し、アセトンで洗浄し、乾燥して目的物の白色粉末52
gを得た。このものの融点および元素分析の結果を下記
に示す。
Examples include octamethylene bromide pist +) 7 x Synthesis of nylphosphinium 1,8-dibromooctane 24.5g, triphenylphosphine 41.2g, and acetonitrile 50g
+nl was placed in a flask equipped with a reflux condenser and a stirrer, and reacted under reflux for 1 hour. After cooling, the precipitate is collected by filtration, washed with acetone, and dried to obtain the desired white powder 52.
I got g. The melting point and elemental analysis results of this product are shown below.

融    点   255°C 元素分析値  C,、H,、P2Br2計算値: C6
6,34% 85.82%実測値:C66、t)6% 
85.79%実施例2〜4 実施例1と同様にして、第1表に示した化合物を合成し
た。第1表に、これらの融点を示す。
Melting point 255°C Elemental analysis value C,, H,, P2Br2 calculated value: C6
6.34% 85.82% Actual value: C66, t) 6%
85.79% Examples 2 to 4 In the same manner as in Example 1, the compounds shown in Table 1 were synthesized. Table 1 shows their melting points.

第  1  表 実施例5 スチレン樹脂100部、カーボンブランク6部、実施例
1で得られた化合物2部の配合物をボールミルで均一に
予備混合し、プレミックスを調整する。次いで゛加熱溶
融混練し、冷却後、振動ミルで粗粉砕し、更にツエン)
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8〜15μ「0であった。
Table 1 Example 5 A blend of 100 parts of styrene resin, 6 parts of carbon blank, and 2 parts of the compound obtained in Example 1 is uniformly premixed in a ball mill to prepare a premix. Next, it is heated, melted and kneaded, cooled, coarsely ground in a vibrating mill, and further crushed.
It was pulverized using a mill to obtain a black toner. The particle size of this black toner was 8 to 15 microns.

得られた黒色Fカー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16.5μC/gであった。
A developer was prepared by mixing 95 parts of iron powder carrier with 5 parts of the obtained black F car. The initial blow-off charge amount of this developer was 16.5 μC/g.

本現像剤を酸化亜鉛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]、 OOO0枚後にお
いても複写品質の低下はみられなかった。
When a toner image was formed using this developer on a zinc oxide drum by magnetic brush development, a clear image without fogging was obtained. With this toner, no deterioration in copy quality was observed even after continuous copying] and after 00 sheets.

実施例6 スチレン−アクリル共重合樹脂100部、黄色染料(C
6I 、ディスバーズイエロー33)6部、実施例2で
得られ化合物2部の配合物を実施例5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I)実施例5
と同様1こして調整した現像剤の初期ブローオフ帯電量
は17.4μC/ gであった。
Example 6 100 parts of styrene-acrylic copolymer resin, yellow dye (C
A mixture of 6 parts of Diverse Yellow 33) and 2 parts of the compound obtained in Example 2 was treated in the same manner as in Example 5 to obtain a yellow toner. The obtained yellow toner I) Example 5
The initial blow-off charge amount of the developer prepared by straining it in the same manner as above was 17.4 μC/g.

本現像剤を実施例5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 copies were made using this developer in the same manner as in Example 5, clear yellow images without fog were obtained. With this toner, no deterioration in copy quality was observed even after 10,000 continuous copies were made.

実施例7 スチレン−n−ブチルメタクリレ−Y共重合体樹脂10
0部、赤色染料(C,I、ピグメントレッド12)8部
、実施例3で得られた化合物2部の配合物を実施例5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5と同様に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] 000 (’)枚
後においても複写品質の低下はみられなかった。
Example 7 Styrene-n-butyl methacrylate-Y copolymer resin 10
A blend of 0 parts of red dye (C, I, Pigment Red 12), 8 parts of the compound obtained in Example 3 was treated in the same manner as in Example 5 to obtain a red toner. As in Example 5, a clear red image without fogging was obtained from the obtained red toner. With this toner, no deterioration in copy quality was observed even after continuous copying of 000 (') sheets.

実施例8 ポリエステル樹脂100部、青色染料(C,I。Example 8 100 parts of polyester resin, blue dye (C, I.

ピグメントブルー15)6部、実施例4で得られた化合
物2部の配合物を実施例5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5と同様にしで
調整した現像剤の初期ブローオフ帯電量は17.3μC
/g であった。
A blend of 6 parts of Pigment Blue 15) and 2 parts of the compound obtained in Example 4 was treated in the same manner as in Example 5 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 5 was 17.3 μC.
/g.

本現像剤を実施例5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 copies were made using this developer in the same manner as in Example 5, clear blue images without fog were obtained. With this toner, no deterioration in copy quality was observed even after 10,000 continuous copies were made.

(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、温度および湿度安一定性等に優れ、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 has excellent mechanical friction and impact stability, temperature and humidity stability, and is colorless, so it can be used for electrophotography with clear images and continuous use. Toner was obtained.

特許出願人 日本カーリット株式会社Patent applicant Nippon Carlit Co., Ltd.

Claims (1)

【特許請求の範囲】 下記一般式( I ) ▲数式、化学式、表等があります▼( I ) (式中、Rは炭素数1〜12のアルキル基を表わし、X
^■はアニオンを表わす。)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。
[Claims] The following general formula (I) ▲There are numerical formulas, chemical formulas, tables, etc.▼(I) (In the formula, R represents an alkyl group having 1 to 12 carbon atoms, and
^■ represents an anion. ) A toner for electrophotography, characterized in that it contains a compound represented by the following formula as a charge control agent.
JP63167709A 1988-07-07 1988-07-07 Toner for electrophotography Pending JPH0218568A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP63167709A JPH0218568A (en) 1988-07-07 1988-07-07 Toner for electrophotography

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP63167709A JPH0218568A (en) 1988-07-07 1988-07-07 Toner for electrophotography

Publications (1)

Publication Number Publication Date
JPH0218568A true JPH0218568A (en) 1990-01-22

Family

ID=15854757

Family Applications (1)

Application Number Title Priority Date Filing Date
JP63167709A Pending JPH0218568A (en) 1988-07-07 1988-07-07 Toner for electrophotography

Country Status (1)

Country Link
JP (1) JPH0218568A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5389486A (en) * 1991-03-05 1995-02-14 Nippon Kayaku Kabushiki Kaisha Electrophotographic toner
US7317423B2 (en) 2004-03-17 2008-01-08 The Yokohama Rubber Co., Ltd. Antenna device

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5389486A (en) * 1991-03-05 1995-02-14 Nippon Kayaku Kabushiki Kaisha Electrophotographic toner
US7317423B2 (en) 2004-03-17 2008-01-08 The Yokohama Rubber Co., Ltd. Antenna device

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