JPS60213959A - Toner for electrostatic charge development - Google Patents

Toner for electrostatic charge development

Info

Publication number
JPS60213959A
JPS60213959A JP59069181A JP6918184A JPS60213959A JP S60213959 A JPS60213959 A JP S60213959A JP 59069181 A JP59069181 A JP 59069181A JP 6918184 A JP6918184 A JP 6918184A JP S60213959 A JPS60213959 A JP S60213959A
Authority
JP
Japan
Prior art keywords
toner
compd
electrifiability
binder resin
group
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
JP59069181A
Other languages
Japanese (ja)
Other versions
JPH0210420B2 (en
Inventor
Takayoshi Aoki
孝義 青木
Koichi Tanaka
田中 公一
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.)
Fujifilm Business Innovation Corp
Original Assignee
Fuji Xerox 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 Fuji Xerox Co Ltd filed Critical Fuji Xerox Co Ltd
Priority to JP59069181A priority Critical patent/JPS60213959A/en
Publication of JPS60213959A publication Critical patent/JPS60213959A/en
Publication of JPH0210420B2 publication Critical patent/JPH0210420B2/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
    • G03G9/097Plasticisers; Charge controlling agents
    • G03G9/09783Organo-metallic compounds

Abstract

PURPOSE:To obtain good frictional electrifiability and negative electrifiability and to enable application to color copying by incorporating a specific compd. into a binder resin. CONSTITUTION:The compd. expressed by the formula (RO)nZr(X)4-n (n is 0-3, R is a hydrocarbon group, etc. X is carboxylic residue having a perfluoroalkyl group in the molecule) is incorporated into a binder resin. Lower alkyl or 1-5C is used for such Zr compd. and the perfluoroalkyl group of >=3C is preferable for X as said group has the large power to decrease surface tension. Such Zr compd. is mixed with a binder such as, for example, styrene or the like, coliring agent, etc. and is made into a toner by melting, kneading and pulverizing. The toner made in such a way is used as a one-component developer or two-component developer together with a carrier. The toner contg. the Zr comp. has negative electrifiability, fast electrifying speed and substantial electrifying quantity, decreases change of the electrifying quantity even at the under a high temp. and high humidity and is stable and has a long life.

Description

【発明の詳細な説明】 産業上の利用分野 本発明は電子写真法、静電記録法において静電荷像を現
像する為の現像剤、特にトナーに関し、更に詳細には負
帯′亀性のトナーに関する。
DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention relates to a developer, particularly a toner, for developing an electrostatic image in electrophotography or electrostatic recording, and more particularly to a toner with a negative band. Regarding.

従来技術 電子写真法あるいは静電記録法は感光体もしくは静電記
録体に形成した静電潜像を磁気ブラシ現像法、カスケー
ド現像法等により現像してトナー像を得、転写紙等に転
写して画像を形成するものである。
Conventional technology In electrophotography or electrostatic recording, an electrostatic latent image formed on a photoconductor or electrostatic recording medium is developed by a magnetic brush development method, cascade development method, etc. to obtain a toner image, which is then transferred to a transfer paper or the like. An image is formed using the images.

現像は静電潜像とトナーとの静電力により行なわれ、ト
ナーは静1潜像と逆極性になる様帯電される。トナーに
所定の電荷を付与する為、トナーとキャリヤあるいはト
ナーと帯電部材との摩擦帯電を利用するのが最も一般的
である。
Development is performed by electrostatic force between the electrostatic latent image and the toner, and the toner is charged to have a polarity opposite to that of the electrostatic latent image. In order to impart a predetermined charge to the toner, it is most common to use frictional charging between the toner and a carrier or between the toner and a charging member.

例えば、Se感感体体形成された正の静電潜像を現像す
る場合、トナーが負に帯電可能となる様にトナーの結着
樹脂としてポリスチレンやポリエステル等の負帯電性の
樹脂を用いる方法あるいはトナー中に帯電制御剤を添加
する方法等が知られている。前者の方法は結着樹脂のみ
では帯電速度あるいは帯電量といった帯電性を十分満足
するトナーが得に<<、又後者の方法は帯電制御剤を均
一にトナー中に分散しにくく帯電のバラツキが生じ又多
くの帯電制御剤は着色されており、カラー複写に適した
トナーを得ることが困難であった。
For example, when developing a positive electrostatic latent image formed on a Se susceptor, a method using a negatively charging resin such as polystyrene or polyester is used as a binder resin for the toner so that the toner can be negatively charged. Alternatively, a method of adding a charge control agent to the toner is known. The former method is effective in producing a toner that satisfies charging properties such as charging speed and amount with only the binder resin, and the latter method makes it difficult to uniformly disperse the charge control agent in the toner, resulting in variations in charging. Furthermore, many charge control agents are colored, making it difficult to obtain toners suitable for color copying.

発明の目的 本発明はこの様な事情に鑑みなされたものであって、摩
擦帯電性が良好でかつ安定した負帯電性を示すトナーを
提供することを目的とし、更にカラー複写に適した負帯
電性トナーを提供することを目的とする。
Purpose of the Invention The present invention was made in view of the above circumstances, and it is an object of the present invention to provide a toner that exhibits good triboelectric chargeability and stable negative chargeability, and further has a negative chargeability that is suitable for color copying. The purpose is to provide sexual toner.

発明の構成 本発明の目的は結着樹脂中に一般式 %式%) 〔式中、nは0〜3の整数、Rは炭化水素基又は置換炭
化水素基、Xは分子中にパーフロロアルキル基を有する
カルボン酸残基を示す。〕で示される化合物を含有する
トナーにより達成することができる。
Structure of the Invention The object of the present invention is to prepare a binder resin with the general formula % (%) [where n is an integer of 0 to 3, R is a hydrocarbon group or a substituted hydrocarbon group, and X is a perfluoroalkyl group in the molecule. Indicates a carboxylic acid residue having a group. ] This can be achieved using a toner containing a compound represented by the following.

前述の一般式で示されるジルコニウム化合物としでは、
例えばRはメチル、エチル、五−プロピル、。−プロピ
ル、n−ブチル、i−ブチル、n−アミル、i−アミル
、t−アミル等の低級アルキルから選ばれ、Xは分子中
にパーフロロアルキル基を含む1価又は多価カルボン1
駿であり、パーフロロアルキル基がカルボキシル基に直
結した化合物及びパーフロロアルキル基が他の基を介し
てカルボキシル基と結合した化合物であり、Xの例とし
てはCF3COOH%C,F。
As for the zirconium compound represented by the above general formula,
For example, R is methyl, ethyl, 5-propyl. - selected from lower alkyl such as propyl, n-butyl, i-butyl, n-amyl, i-amyl, t-amyl, etc., and X is monovalent or polyvalent carbon 1 containing a perfluoroalkyl group in the molecule
It is a compound in which a perfluoroalkyl group is directly bonded to a carboxyl group, and a compound in which a perfluoroalkyl group is bonded to a carboxyl group through another group, and an example of X is CF3COOH%C,F.

C0OH,IC8F7COOH,C,F、CoOH%C
,F、、C0OH。
C0OH, IC8F7COOH, C, F, CoOH%C
,F,,C0OH.

C6F、、 C0OH,C7F、1lCOOH1IC,
F、7COOH,C,F、、C0OH。
C6F,, C0OH, C7F, 1lCOOH1IC,
F,7COOH,C,F,,C0OH.

c、op、、coon、 c、、p、、cooH,Cs
5FsyCOOH,CF、 QCs H4C0OH,3
,5−(CFli、 0)t C,HjCOOH,3,
4,5−(CP、 0 )s C5Ht C0OH,C
o F110C8H4C0OH。
c,op,,coon,c,,p,,cooH,Cs
5FsyCOOH,CF, QCs H4C0OH,3
,5-(CFli, 0)t C,HjCOOH,3,
4,5-(CP, 0)s C5Ht C0OH,C
o F110C8H4C0OH.

C,F、、QC,H,C0OH,C,F、、QC,塩C
0OH等が挙げられ、中でもパーフロロアルキル基のア
ルキル部分が炭素数3以上のものが表面張力の低下能力
が大きく好ましく用いられる。
C, F,, QC, H, C0OH, C, F,, QC, salt C
Among them, those in which the alkyl moiety of the perfluoroalkyl group has 3 or more carbon atoms are preferably used because of their ability to reduce surface tension.

このジルコニウム化合物は、トナーの結着樹脂に対し、
0.05〜10重量%、好ましくは0.5〜5重量%添
加して用いる。
This zirconium compound has a strong resistance to the binder resin of the toner.
It is used in an amount of 0.05 to 10% by weight, preferably 0.5 to 5% by weight.

トナーの結着樹脂としては種々挙げることができ、スチ
レン、クロルスチレン、ビニルスチレン等のスチレン類
;エチレン、プロピレン、ブチレン、インブチレン等の
モノオレフィン;酢酸ビニル、プロピオン酸ビニル、安
息香酸ビニル、酪酸ビニル等のビニルエステル;アクリ
ル酸メチル、アクリル酸エチル、アクリル酸ブチル、ア
クリル酸ドデシル、アクリル酸オクチル、アクリル酸フ
ェニル、メタクリル酸メチル、メタクリル酸エチル、メ
タクリル酸ブチル、メタクリル酸ドデシル等のα−メチ
レン脂肪族モノカルボン酸のエステル−;ビニルメチル
エーテル、ビニルエチルエーテル、ビニルブチルエーテ
ル等のビニルエーテル;ビニルメチルケトン、ビニルヘ
キシルケトン ケトン等のビニルケトン等の単独重合体あるいは共重合
体を例示することができ、特に代表的な結着樹脂として
は、ポリスチレン、スチレン−アクリル酸アルギル共重
合体、スチレン−メタクリル酸アルキル共重合体、スチ
レン−アクリロニトリル共重合体、スチレン−ブタジェ
ン共重合体、スチレン−無水マレイン酸共重合体、ポリ
エチレン、ポリプロピレンを挙げることができる。
Various binder resins can be used for toner, including styrenes such as styrene, chlorostyrene, and vinylstyrene; monoolefins such as ethylene, propylene, butylene, and imbutylene; vinyl acetate, vinyl propionate, vinyl benzoate, and butyric acid. Vinyl esters such as vinyl; α-methylene such as methyl acrylate, ethyl acrylate, butyl acrylate, dodecyl acrylate, octyl acrylate, phenyl acrylate, methyl methacrylate, ethyl methacrylate, butyl methacrylate, dodecyl methacrylate, etc. Esters of aliphatic monocarboxylic acids; vinyl ethers such as vinyl methyl ether, vinyl ethyl ether, and vinyl butyl ether; homopolymers or copolymers of vinyl ketones such as vinyl methyl ketone and vinyl hexyl ketone ketone; Particularly typical binder resins include polystyrene, styrene-argyl acrylate copolymer, styrene-alkyl methacrylate copolymer, styrene-acrylonitrile copolymer, styrene-butadiene copolymer, and styrene-maleic anhydride copolymer. Mention may be made of polymers, polyethylene and polypropylene.

更にポリエステル、ポリウレタン、エポキシ樹脂、シリ
コン樹脂、ポリアミド、変性ロジン、パラフィン、ワッ
クス類を挙げることができる。
Further examples include polyester, polyurethane, epoxy resin, silicone resin, polyamide, modified rosin, paraffin, and waxes.

父、トナーの着色剤としてはカーボンブラック、ニグロ
シン染料、アニリンブルー、カルコイルブルー、クロム
イエロー、タルト2マリンブルー、デーポンオイルレッ
ド、キノリンイエロー、メチレンブルークロリド、フタ
ロシアニンブルー、マラカイトグリーンオキプレート、
ランプブラック、ローズベンガル等を代表的なものとし
て例示することができる。
My father, the toner coloring agents are carbon black, nigrosine dye, aniline blue, calcoyl blue, chrome yellow, Tarte 2 Marine Blue, Dapon Oil Red, quinoline yellow, methylene blue chloride, phthalocyanine blue, malachite green oxiplate,
Representative examples include lamp black and rose bengal.

結着樹脂、着色剤は上述の例示したものに限定されるも
のでない。
The binder resin and colorant are not limited to those exemplified above.

又、磁性材料を内包した磁性トナーをも用いることがで
きる。
Furthermore, a magnetic toner containing a magnetic material can also be used.

このトナーは、約30μmより小さい、好ましくは3〜
20μmの平均粒径を有するものを用いることができる
The toner is smaller than about 30 μm, preferably between 3 and 3 μm.
Those having an average particle size of 20 μm can be used.

このトナーは、結着樹脂、ジルコニウム化合物、必要に
応じ着色剤のトナー成分を混合し、溶融、混線、粉砕に
より、あるいは溶液にした後噴霧乾燥する等種々の方法
により得ることができる。又結着樹脂と着色剤とをよ有
する1晟粉末の表面にこのジルコニウム化合物を付着さ
せて用いても良い。
This toner can be obtained by various methods such as mixing toner components such as a binder resin, a zirconium compound, and a colorant if necessary, and melting, mixing, pulverizing, or forming into a solution and then spray-drying. Alternatively, the zirconium compound may be used by adhering it to the surface of a powder containing a binder resin and a colorant.

本発明のトナーは、キャリヤと共にいわゆる二成分現像
剤として用いても、又キャリヤを用いないいわゆる一成
分現像剤として用いても良い〇 二成分現像剤の場合、キャリヤとの摩擦帯電により、又
−成分現像剤の用台ブレードあるいはロール等の摩擦帯
′上部材によりそれぞれ帯電を得る。
The toner of the present invention may be used as a so-called two-component developer together with a carrier, or as a so-called one-component developer without a carrier. In the case of a two-component developer, due to frictional charging with the carrier, or - Electrification is obtained by means of a member on the friction zone, such as a table blade or a roll for the component developer.

キャリヤを混合して用いる場合、キャリヤとしてはトナ
ーの平均粒径とほぼ同じかないしは500μmまでの粒
子であり、例えば四三酸化鉄、三二酸化物、MnZnフ
ェライト、NiZnフェライト、Baフェライト、二酸
化クロム、鉄、ニッケル、コバルト、ガラスピーズ等の
粒子を例示でき、更にこれら粒子の表面をアクリル系樹
脂、スチレン系樹脂等の被覆剤で被覆しても良い。
When a carrier is used in combination, the carrier is particles with an average particle size of approximately the same as the toner particle size or up to 500 μm, such as triiron tetroxide, sesquioxide, MnZn ferrite, NiZn ferrite, Ba ferrite, chromium dioxide. Examples include particles of iron, nickel, cobalt, and glass beads, and the surfaces of these particles may be coated with a coating agent such as acrylic resin or styrene resin.

又結着樹脂中に磁性粉を分散したいわゆる分散型キャリ
ヤであっても良い。
It may also be a so-called dispersed carrier in which magnetic powder is dispersed in a binder resin.

本発明のトナーは感光体あるいは静電記録体の正極性の
静電潜像を現像する為、あるいは負極性の静電婢像の場
合は反転現像する為用いることができ、更にカラートナ
ーとしても好ましく用いることができる。
The toner of the present invention can be used for developing a positive electrostatic latent image on a photoreceptor or an electrostatic recording medium, or for reversal development in the case of a negative electrostatic latent image, and can also be used as a color toner. It can be preferably used.

発明の効果 特定のジルコニウム化合物を含有した本発明のトナーは
優れた負帯畦性を示す。即ち、本発明のトナーは帯電速
度が速く又帯電量も十分であり、厳しく攪拌を行なって
も又高温高湿下に於いても帯シ性の変化を少なくするこ
とができ、安定な寿命の長いトナーを得ることができる
Effects of the Invention The toner of the present invention containing a specific zirconium compound exhibits excellent negative banding properties. In other words, the toner of the present invention has a fast charging speed and a sufficient amount of charging, and can reduce changes in charging properties even under severe stirring or under high temperature and high humidity, and has a stable lifespan. You can get long toner.

更にこのジルコニウム化合物は実質上無色であり、カラ
ートナーとする際、任意の着色を可能とする。
Furthermore, this zirconium compound is substantially colorless, and can be colored as desired when used as a color toner.

実施例 以下本発明を実施例によって更に具体的に説明する。Example The present invention will be explained in more detail below using Examples.

スチレン−n−ブチルアクリレート樹脂(分子量5万、
スチレンとn−ブチルアクリレートは重量比で8:2)
 90重計部 カーボンブラック 8電縫部 パーフロローn−オクタン酸シルコニウムトリブトギゾ
ド 2重−17i部 上記配合を加圧ニーダ−で黙溶融混練し、冷却固化後ジ
ュツトミルで粉砕した。その後風力分級機を用いて分級
し平均粒子径12μmのトナーを得た。
Styrene-n-butyl acrylate resin (molecular weight 50,000,
Styrene and n-butyl acrylate (weight ratio: 8:2)
90 weight parts carbon black 8 electric resistance stitch parts Perfluoro silconium n-octoate tributogizod 2 weight parts - 17 parts The above formulation was silently melt-kneaded in a pressure kneader, cooled and solidified, and then pulverized in a jutsu mill. Thereafter, the toner was classified using an air classifier to obtain a toner having an average particle size of 12 μm.

比較例 実施例のジルコニウム化合物をJまない点以外は全て実
施例と同様にして平均粒径12μmのトナーを得た。
Comparative Example A toner having an average particle size of 12 μm was obtained in the same manner as in the example except that the zirconium compound of the example was not used.

実hm例及び比較例で得られたトナーを、それぞれ平均
粒子l1oOμmの表面Uチルメタアクリレート樹脂で
コートされた酸化鉄粉キャリヤと混合(トナー3に対し
、キャリヤ100重量%ンして二種項の現像剤を調整し
た。
The toners obtained in the practical example and the comparative example were mixed with an iron oxide powder carrier whose surface was coated with a U-chill methacrylate resin having an average particle size of 100 μm (toner 3 was mixed with 100% by weight of the carrier to obtain two types of carrier). The developer was prepared.

これら二種の現像剤を用いて富士ゼロ、ジス4600複
写機で連続複写試験をおこなった。
Continuous copying tests were conducted using these two types of developers using Fuji Zero and Jisu 4600 copying machines.

その結果比較例のトナーを用いた現像剤は3万枚連続複
写において背景白地部のカブリが許容限度を越え、現像
剤帯電量も著しく低下したのに対し、実施例のトナーを
用いた現像剤はカブリも少く、現像剤帯電量の変化も少
かった。
As a result, when the developer using the toner of the comparative example was used to continuously copy 30,000 sheets, the fog in the white background area exceeded the allowable limit and the amount of developer charge was significantly reduced, whereas the developer using the toner of the example There was little fog and little change in the amount of developer charge.

Claims (1)

【特許請求の範囲】 結着樹脂中に下記一般式 %式%) 〔式中、nは0〜3の整数、Rは炭化水素基又は置換炭
化水素基、Xは分子中にパーフロロアルキル基を有する
′カルボン酸残基を示す。〕で示される化合物を含有し
てなることを特徴とする静電荷現像用トナー。
[Claims] In the binder resin, the following general formula %) [In the formula, n is an integer of 0 to 3, R is a hydrocarbon group or a substituted hydrocarbon group, and X is a perfluoroalkyl group in the molecule. ' indicates a carboxylic acid residue with . ] A toner for electrostatic charge development characterized by containing a compound represented by the following.
JP59069181A 1984-04-09 1984-04-09 Toner for electrostatic charge development Granted JPS60213959A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP59069181A JPS60213959A (en) 1984-04-09 1984-04-09 Toner for electrostatic charge development

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP59069181A JPS60213959A (en) 1984-04-09 1984-04-09 Toner for electrostatic charge development

Publications (2)

Publication Number Publication Date
JPS60213959A true JPS60213959A (en) 1985-10-26
JPH0210420B2 JPH0210420B2 (en) 1990-03-08

Family

ID=13395292

Family Applications (1)

Application Number Title Priority Date Filing Date
JP59069181A Granted JPS60213959A (en) 1984-04-09 1984-04-09 Toner for electrostatic charge development

Country Status (1)

Country Link
JP (1) JPS60213959A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999028792A1 (en) * 1997-12-01 1999-06-10 Hodogaya Chemical Co., Ltd. Electrophotographic toner
US6410198B1 (en) * 1997-09-05 2002-06-25 Hodogaya Chemical Co., Ltd. Zirconium compound and electrophotographic toner employing it

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0535822U (en) * 1991-10-03 1993-05-14 寿美子 鈴木 Lower body outerwear

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6410198B1 (en) * 1997-09-05 2002-06-25 Hodogaya Chemical Co., Ltd. Zirconium compound and electrophotographic toner employing it
US6552211B2 (en) 1997-09-05 2003-04-22 Hodogaya Chemical Co., Ltd. Zirconium compound and electrophotographic toner employing it
WO1999028792A1 (en) * 1997-12-01 1999-06-10 Hodogaya Chemical Co., Ltd. Electrophotographic toner

Also Published As

Publication number Publication date
JPH0210420B2 (en) 1990-03-08

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