JP3158713B2 - Electrophotographic toner - Google Patents
Electrophotographic tonerInfo
- Publication number
- JP3158713B2 JP3158713B2 JP24758992A JP24758992A JP3158713B2 JP 3158713 B2 JP3158713 B2 JP 3158713B2 JP 24758992 A JP24758992 A JP 24758992A JP 24758992 A JP24758992 A JP 24758992A JP 3158713 B2 JP3158713 B2 JP 3158713B2
- Authority
- JP
- Japan
- Prior art keywords
- image
- complex
- salt
- weight
- humidity
- 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 - Fee Related
Links
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
- G03G9/097—Plasticisers; Charge controlling agents
- G03G9/09733—Organic compounds
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Developing Agents For Electrophotography (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明はレーザプリンタ，複写機
等の電子写真用トナーに関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an electrophotographic toner for a laser printer, a copying machine and the like.
【０００２】[0002]
【従来の技術】レーザプリンタ，複写機等の静電現象を
利用した画像形成方法は、米国特許第2297691 号や特公
昭42−23910 号公報等に種々の方法が記載されている。
例えば、現像剤であるトナーを感光体中に形成された静
電潜像に吸着し、次に転写物に転写させた後定着すると
いうプロセスをとる。この際、かぶり等のない鮮明な現
像画像を得るにはトナーに適切な帯電性を持たせること
が重要である。そこで今までトナーに種々の帯電制御剤
を添加することでその帯電性の適正化を図ってきた。帯
電制御剤はこれまでモノクロ画像用ではトリフェニルメ
タン誘導体，ニグロシン，モノアゾ染料の金属塩といっ
た有色の化合物が、またカラー画像用ではサリチル酸等
のオキシカルボン酸の金属塩，種々の四級アンモニウム
塩，イミダゾ−ル誘導体等無色或いは淡色の化合物が用
いられてきた。2. Description of the Related Art Various methods for forming an image utilizing an electrostatic phenomenon in a laser printer, a copying machine, and the like are described in U.S. Pat. No. 2,976,691 and Japanese Patent Publication No. 42-23910.
For example, a process is employed in which a toner as a developer is adsorbed on an electrostatic latent image formed in a photoconductor, and then transferred to a transfer material and then fixed. At this time, in order to obtain a clear developed image without fogging or the like, it is important that the toner has an appropriate chargeability. Therefore, the chargeability of the toner has been optimized by adding various charge control agents to the toner. The charge control agents have been colored compounds such as triphenylmethane derivatives, nigrosine and metal salts of monoazo dyes for monochrome images, and metal salts of oxycarboxylic acids such as salicylic acid, various quaternary ammonium salts for color images. Colorless or pale-colored compounds such as imidazole derivatives have been used.
【０００３】[0003]
【発明が解決しようとする課題】しかし、これら帯電制
御剤の幾つかは樹脂への分散性が悪いためトナーが均一
に帯電せず画像濃度が低かったり、かぶりを生ずるもの
がある。また現像回数が増えたり、温度や湿度の変化に
よって吸水したり変性することで帯電量が変化し鮮明な
現像画像を得ることができなくなるものもある。However, some of these charge control agents have poor dispersibility in resin, so that the toner is not uniformly charged, resulting in low image density or fogging. In some cases, the number of developments increases, or water is absorbed or denatured due to a change in temperature or humidity, so that the charge amount changes and a clear developed image cannot be obtained.
【０００４】更に今後のカラー化に対応するためには可
視領域において極力無色のものが要求される。Further, in order to cope with future colorization, a colorless one is required as much as possible in the visible region.
【０００５】今までこれらの問題を全てクリアするよう
な帯電制御剤の登場が切に期待されてきた。Until now, the appearance of a charge controlling agent which can solve all of these problems has been expected.
【０００６】[0006]
【課題を解決するための手段】本発明者らは、前記目的
を達成するため、鋭意検討した結果、化２で示されるシ
クロデキストリン誘導体を帯電制御剤として用いること
で上記問題が解決することを見出し、本発明に至ったも
のである。Means for Solving the Problems The present inventors have conducted intensive studies in order to achieve the above object, and as a result, have found that the above problem can be solved by using a cyclodextrin derivative represented by the formula (2) as a charge controlling agent. Heading, which has led to the present invention.
【０００７】[0007]
【化２】 Embedded image
【０００８】〔ただし、置換基Ｒの２５％以上はＣＨ3
Ｃ6Ｈ4ＳＯ3基、或いはＣ10Ｈ7ＳＯ3基、ｎは６から
８〕 本発明は帯電制御剤、或いは帯電制御剤の一部としてシ
クロデキストリン誘導体を含有するトナーに関する。多
くの帯電制御剤は塩の構造である。これはトナーに大き
な帯電性を付与するには有利な構造であるが吸湿性等の
上記問題を有している。シクロデキストリン誘導体は一
級水酸基をβナフタレンスルホニル基に置換すると金属
イオンとコンプレックスを形成することが知られている
（ケミストリー レターズ，１９８７年，５８１から５
８４頁）。我々は水酸基全体の２５％以上をβ−ナフタ
レンスルホニル基に置換すれば金属イオンとコンプレッ
クスを形成することを発見した。そして置換基がトルエ
ンスルホニル基或いはα−ナフタレンスルホニル基であ
っても同様のコンプレックスを形成し、更に、これらが
金属イオンばかりでなくアンモニウム塩、或いはアミン
塩ともコンプレックスを形成することも発見した。また
無修飾のシクロデキストリンは親水性であり他の有機化
合物との相溶性も低いが、種々の残基を導入することに
より疎水性でかつ相溶性の高い誘導体に変換することも
可能である。（例えば、アセチル基，プロピオニル基
等）そのため吸湿性が高かったり樹脂への分散性・相溶
性の低い塩であっても、これと錯体を形成することによ
って上記問題を解決することが可能となった。金属イオ
ンと錯体を形成し帯電を制御しようとする例は、着色剤
粒子表面にオキシエチレンユニットを導入し帯電制御剤
の金属イオンとコンプレックスを形成させる例（特開平
4−73664号公報）がある。本発明は帯電制御剤の基本構
造に環状の修飾グルコースユニットを用いており前記発
明とは帯電制御方法が本質的に異なっている。[However, 25% or more of the substituent R is CH 3
C 6 H 4 SO 3 group or C 10 H 7 SO 3 group, n is 6 to 8] The present invention relates to a toner containing a charge control agent or a cyclodextrin derivative as a part of the charge control agent. Many charge control agents have a salt structure. This is an advantageous structure for imparting great chargeability to the toner, but has the above-mentioned problems such as hygroscopicity. It is known that a cyclodextrin derivative forms a complex with a metal ion when a primary hydroxyl group is replaced with a β-naphthalenesulfonyl group (Chemistry Letters, 1987, 581-5).
84). We have found that if more than 25% of the total hydroxyl groups are replaced with β-naphthalenesulfonyl groups, a complex will be formed with metal ions. It was also found that the same complex was formed even when the substituent was a toluenesulfonyl group or an α-naphthalenesulfonyl group, and that they formed a complex not only with a metal ion but also with an ammonium salt or an amine salt. Unmodified cyclodextrin is hydrophilic and has low compatibility with other organic compounds, but can be converted to a hydrophobic and highly compatible derivative by introducing various residues. (For example, acetyl group, propionyl group, etc.) Therefore, even if the salt has high hygroscopicity or low dispersibility and compatibility with resin, it is possible to solve the above problem by forming a complex with the salt. Was. An example of controlling the charge by forming a complex with a metal ion is an example in which an oxyethylene unit is introduced to the surface of the colorant particle to form a complex with the metal ion of the charge control agent (JP-A-Hei.
No. 4-73664). In the present invention, a cyclic modified glucose unit is used for the basic structure of the charge control agent, and the charge control method is essentially different from the above invention.
【０００９】本発明の帯電制御剤は通常シクロデキスト
リン誘導体と有機酸か無機酸の金属塩、アンモニウム
塩、或いはアミン塩等とのコンプレックスの形で用いら
れる。コンプレックスを形成する塩のうち酸ユニットと
しては次のようなものがあげられるが、ここに示すもの
に限定するということではない。The charge controlling agent of the present invention is usually used in the form of a complex of a cyclodextrin derivative and a metal salt, ammonium salt or amine salt of an organic or inorganic acid. Among the salts forming the complex, examples of the acid unit include the following, but are not limited to those shown here.
【００１０】Ｆ-，Ｃｌ-，Ｂｒ-，Ｉ-，ＮＯ3 -，ＳＯ4
2-，ＰＯ4 3-，Ｒ−ＣＯ2 -，（但しＲはアルキル基、或
いは芳香環で置換基の有無は限定しない）、Ｒ（Ｃ
Ｏ2 -）2(但しＲはアルキル基、或いは芳香環で置換基の
有無は限定しない)，Ｒ−ＳＯ3 -（但しＲは芳香環で置
換基の有無は限定しない），Ｒ（ＳＯ3 -)2（但しＲは芳
香環で置換基の有無は限定しない)，Ｒ−Ｏ-（但しＲは
アルキル基、或いは芳香環で置換基の有無は限定しな
い），（Ｃ6Ｈ5）4Ｂ-，（ＦＣ6Ｈ4）4Ｂ-，（（Ｃ
Ｆ3）2（ＣＨ3Ｏ）ＣＣ6Ｈ3）4Ｂ-等。[0010] F -, Cl -, Br - , I -, NO 3 -, SO 4
2-, PO 4 3-, R- CO 2 -, ( where R is the presence of substituents in the alkyl group, or an aromatic ring is not limited), R (C
O 2 − ) 2 (where R is an alkyl group or an aromatic ring and the presence or absence of a substituent is not limited), R—SO 3 − (however, R is an aromatic ring and the presence or absence of a substituent is not limited), R (SO 3 -) 2 (where R is not limited to the presence of substituents in the aromatic ring), R-O - (wherein R is the presence of substituents in the alkyl group, or an aromatic ring are not limited to), (C 6 H 5) 4 B -, (FC 6 H 4 ) 4 B -, ((C
F 3) 2 (CH 3 O ) CC 6 H 3) 4 B - , and the like.
【００１１】この中では無機の酸ユニットに比べて有機
の酸ユニットの方が樹脂との相溶性が高い。更にその中
でもＲが炭素数６以上のアルキル基の酸ユニットを用い
た塩は樹脂との相溶性が極めて高くなるので望ましい。Among these, organic acid units have higher compatibility with resins than inorganic acid units. Further, among them, a salt using an acid unit of an alkyl group having a carbon number of 6 or more is preferable because compatibility with a resin becomes extremely high.
【００１２】また、シクロデキストリン誘導体とコンプ
レックスを形成する塩のうち、塩基ユニットとしては次
のようなものがあげられるが、ここに示すものに限定す
るということではない。Among the salts that form complexes with the cyclodextrin derivative, examples of the base unit include the following, but are not limited to those shown here.
【００１３】[0013]
【化３】 Embedded image
【００１４】塩基ユニットの場合も無機のものに比べて
有機のものの方が樹脂との相溶性が高い。更にその中で
もＲが炭素数６以上のアルキル基の酸ユニットを用いた
塩は樹脂との相溶性が極めて高くなるので望ましい。In the case of base units, organic units have higher compatibility with resins than inorganic units. Further, among them, a salt using an acid unit of an alkyl group having a carbon number of 6 or more is preferable because compatibility with a resin becomes extremely high.
【００１５】更に酸、塩基両ユニットともＲが芳香環の
場合はアルキル基の場合に比べてシクロデキストリン誘
導体とコンプレックスを形成した際の融点が約３０〜１
５０℃上昇するという特徴があるので、対イオンユニッ
トの種類、及び、シクロデキストリン誘導体との組合せ
によって適切な融点を設定することが可能になると考え
られる。Further, when R is an aromatic ring in both the acid and base units, the melting point when forming a complex with the cyclodextrin derivative is about 30 to 1 compared to the case where R is an alkyl group.
Since it has a characteristic of increasing by 50 ° C., it is considered that an appropriate melting point can be set depending on the type of the counter ion unit and the combination with the cyclodextrin derivative.
【００１６】添加量は用いる装置によって要求される帯
電量が異なるため一概には決められない。しかし相溶性
が高いのでほとんどの樹脂の場合、その樹脂１００重量
部に対し１から２０重量部程度は十分添加可能と考えら
れる。The amount of addition cannot be determined unconditionally because the required amount of charge varies depending on the equipment used. However, it is considered that about 1 to 20 parts by weight can be sufficiently added to 100 parts by weight of most resins because of high compatibility.
【００１７】本発明に使用される樹脂は、通常のトナー
用樹脂が用いられる。例えばポリスチレン，ポリメタク
リル酸アルキルエステル，スチレン−メタクリル酸アル
キルエステルの共重合物，スチレン−アクリル酸アルキ
ルエステルの共重合物，スチレン−アクリロニトリルの
共重合物，スチレン−ブタジエンの共重合物，メタクリ
ル酸アルキルエステル−メタクリル酸アルキルエステル
の共重合物，ポリエステル，エポキシ樹脂等があげられ
る。As the resin used in the present invention, an ordinary resin for toner is used. For example, polystyrene, polyalkyl methacrylate, styrene-alkyl methacrylate copolymer, styrene-alkyl acrylate copolymer, styrene-acrylonitrile copolymer, styrene-butadiene copolymer, alkyl methacrylate Examples include ester-alkyl methacrylate copolymers, polyesters, and epoxy resins.
【００１８】本発明に使用される着色剤は通常のトナー
用着色剤が用いられる。例えばカ−ボンブラック，トリ
アリルメタン誘導体，フタリド誘導体，ベンゾイルロイ
コメチレンブルー誘導体等があげられる。As the colorant used in the present invention, an ordinary colorant for toner is used. For example, carbon black, triallylmethane derivative, phthalide derivative, benzoylleucomethylene blue derivative and the like can be mentioned.
【００１９】本発明のトナーはキャリアを用いた二成分
方式だけでなく一成分方式にも用いることができる。そ
の場合は帯電量が不足する恐れがあるので添加する帯電
制御剤の種類を帯電効果の大きいものに代えたり、添加
量を増やす等の方法により解決できる。樹脂，着色剤，
帯電制御剤以外に保存安定性や色調安定性等を向上させ
るための添加剤を加えることは特に制限を受けない。ト
ナーの粒子径は小粒径の方がドットを小さくできる。し
かし分布が大きいと帯電性の差が大きくなるため、なる
べく均一な粒子径が望ましい。The toner of the present invention can be used not only in a two-component system using a carrier but also in a one-component system. In such a case, the charge amount may be insufficient. Therefore, the problem can be solved by changing the kind of the charge control agent to be added to a charge control agent having a large charge effect or increasing the added amount. Resin, colorant,
The addition of an additive other than the charge control agent for improving storage stability, color tone stability, and the like is not particularly limited. The smaller the particle size of the toner, the smaller the dots. However, if the distribution is large, the difference in chargeability becomes large, so that a uniform particle diameter is desirable.
【００２０】[0020]
【作用】従来の塩構造の帯電制御剤の多くはその構造中
に陽イオンユニットと陰イオンユニットしかないため吸
湿しやすいという問題があった。またイオンユニットに
疎水性の残基を導入した場合その帯電制御能力が低下す
る傾向もあった。それらに比べ本発明の帯電制御剤はそ
れらの塩とシクロデキストリン誘導体がコンプレックス
を形成することにより帯電制御能力をほとんど落さず吸
湿性を下げることが可能になったと考えられる。Many conventional charge control agents having a salt structure have only a cation unit and an anion unit in their structure, and thus have a problem that they are easily absorbed by moisture. In addition, when a hydrophobic residue is introduced into the ion unit, the charge control ability tends to decrease. Compared to these, the charge control agent of the present invention is considered to be able to lower the hygroscopicity with almost no decrease in charge control ability by forming a complex between the salt and the cyclodextrin derivative.
【００２１】[0021]
【実施例】本発明を実施例により詳細に説明する。EXAMPLES The present invention will be described in detail with reference to examples.
【００２２】〈実施例１〉β−シクロデキストリン１重
量部とパラトルエンスルホン酸クロライド１重量部をピ
リジン１０重量部に溶解し常温で１２時間撹拌する。こ
の反応液を水100重量部に滴下し、生じる固体をロ取し
水でよく洗い乾燥することにより化１の化合物群のうち
ｎが７でＲの約３０％をパラトルエンスルホニル基とす
るシクロデキストリン誘導体を合成した。このシクロデ
キストリン誘導体１重量部をジクロルメタン１００重量
部に溶かし、これと安息香酸リチウム１重量部を水１０
０重量部に溶かした液を分液ロートに入れ撹拌後水層を
除き、ジクロルメタン層を揮発させることによりシクロ
デキストリン誘導体と安息香酸リチウムのコンプレック
スを得た。Example 1 1 part by weight of β-cyclodextrin and 1 part by weight of paratoluenesulfonic acid chloride are dissolved in 10 parts by weight of pyridine and stirred at room temperature for 12 hours. This reaction solution was added dropwise to 100 parts by weight of water, and the resulting solid was filtered off, washed well with water, and dried to obtain a cyclohexane compound having n = 7 and about 30% of R in the compound group of formula 1 having a paratoluenesulfonyl group. A dextrin derivative was synthesized. One part by weight of this cyclodextrin derivative is dissolved in 100 parts by weight of dichloromethane, and 1 part by weight of lithium benzoate is dissolved in 10 parts of water.
The solution dissolved in 0 parts by weight was put into a separating funnel, and after stirring, the aqueous layer was removed and the dichloromethane layer was volatilized to obtain a complex of a cyclodextrin derivative and lithium benzoate.
【００２３】次にこのコンプレックス５重量部とスチレ
ン−ｎ−ブチルメタクリレート樹脂１００重量部、及び
カーボンブラック５重量部をボールミルで混合し１５０
℃で加熱混練する。カッターミル及びジェットミルで粉
砕後風力分級し平均粒径１０μｍの微粉末を得た。この
微粉末１重量部と平均粒径６０μｍのキャリア粒子１５
重量部を混ぜ、二成分現像剤を得た。Next, 5 parts by weight of this complex, 100 parts by weight of styrene-n-butyl methacrylate resin, and 5 parts by weight of carbon black were mixed in a ball mill and mixed.
Heat kneading at ℃. After pulverization with a cutter mill and a jet mill, air classification was performed to obtain a fine powder having an average particle size of 10 μm. 1 part by weight of this fine powder and carrier particles 15 having an average particle size of 60 μm
The two parts by weight were mixed to obtain a two-component developer.
【００２４】上述の二成分現像剤を入れたホルダを二つ
作成後、一つを気温２０℃・湿度６０％の条件下に、も
う一つを気温３５℃・湿度８５％の条件下に２４時間放
置後リコー製複写機イマジオ４２０にセットし、画像の
鮮明さを目視で評価しながら繰り返し現像試験を行っ
た。現像開始後一万枚目の画像を目視で評価したとこ
ろ、気温２０℃・湿度６０％の条件下においたものも気
温３５℃・湿度８５％の条件下においたものも画像濃度
がほとんど変化せず鮮明で、かぶりもほとんどなかっ
た。After preparing two holders containing the above-described two-component developer, one was prepared under the condition of 20 ° C. and 60% humidity, and the other was prepared under the condition of 35 ° C. and 85% humidity. After leaving for a period of time, it was set in a Ricoh copier Imagio 420, and a development test was repeatedly performed while visually evaluating the sharpness of the image. When the 10,000th image was visually evaluated after the start of development, the image density of the image under the condition of the temperature of 20 ° C. and the humidity of 60% and the image under the condition of the temperature of 35 ° C. and the humidity of 85% almost changed. It was clear and had little fog.
【００２５】〈比較例１〉実施例１のシクロデキストリ
ン誘導体と安息香酸リチウムのコンプレックスの代わり
に四級アンモニウム塩Ｐ−５１（オリエント化学製）５
重量部を用い、以下実施例１と同様にして二成分現像剤
を調製し、異なる環境下に放置後繰り返し現像試験を行
った。現像開始後一千枚目の画像を目視で評価したとこ
ろ、気温２０℃・湿度６０％の条件下においたものは画
像濃度がほとんど変化せず鮮明であった。しかし、気温
３５℃・湿度８５％の条件下においたものは画像がかす
れて不鮮明で、かぶりもひどくこの試験は途中で中断し
た。Comparative Example 1 A quaternary ammonium salt P-51 (manufactured by Orient Chemical) instead of the complex of the cyclodextrin derivative and lithium benzoate of Example 1 was used.
Using two parts by weight, a two-component developer was prepared in the same manner as in Example 1, and the developing test was repeated after being left in different environments. The image of the 1,000th sheet after the start of development was visually evaluated. The image under the conditions of a temperature of 20 ° C. and a humidity of 60% was clear with little change in image density. However, under the conditions of a temperature of 35 ° C. and a humidity of 85%, the image was blurred and unclear, and the fogging was so severe that the test was interrupted halfway.
【００２６】〈実施例２〉実施例１のβ−シクロデキス
トリンの代わりにｎが６のα−シクロデキストリン１重
量部を用い実施例１と同様の方法でｎが６でＲの約３０
％をパラトルエンスルホニル基とするシクロデキストリ
ン誘導体を合成した。次にやはり実施例１と同様にして
安息香酸リチウムとコンプレックスを形成した。更にや
はり実施例１と同様の方法で二成分現像剤を調製し異な
る環境下に放置後繰り返し現像試験を行った。その結果
実施例１と同様に、現像開始後一万枚目の画像は気温２
０℃・湿度６０％の条件下においたものも気温３５℃・
湿度８５％の条件下においたものも画像濃度がほとんど
変化せず鮮明で、かぶりもほとんどなかった。Example 2 In the same manner as in Example 1 except that 1 part by weight of α-cyclodextrin having n of 6 was used instead of β-cyclodextrin of Example 1, n was 6 and R was about 30.
% Was prepared as a paratoluenesulfonyl group. Next, a complex was formed with lithium benzoate in the same manner as in Example 1. Further, a two-component developer was prepared in the same manner as in Example 1, and after standing in different environments, a development test was repeated. As a result, the image on the 10,000th sheet after the start of development was
Temperatures of 35 ° C and those of 0 ° C and 60% humidity
Also under the condition of a humidity of 85%, the image density was clear with little change in image density, and there was almost no fog.
【００２７】〈実施例３〉実施例１の安息香酸リチウム
の代わりに安息香酸ナトリウムを用い以下実施例１と同
様の方法で二成分現像剤を調製し異なる環境下に放置後
繰り返し現像試験を行った。その結果実施例１と同様
に、現像開始後一万枚目の画像は気温２０℃・湿度６０
％の条件下においたものも気温３５℃・湿度８５％の条
件下においたものも画像濃度がほとんど変化せず鮮明
で、かぶりもほとんどなかった。Example 3 A two-component developer was prepared in the same manner as in Example 1 except that sodium benzoate was used in place of lithium benzoate of Example 1, and a development test was repeatedly performed after being left in a different environment. Was. As a result, as in Example 1, the image on the 10,000th sheet after the start of the development has a temperature of 20 ° C. and a humidity of 60.
%, And under a condition of 35 ° C. in temperature and 85% in humidity, the image density hardly changed, the image density was clear, and there was almost no fog.
【００２８】〈実施例４〉実施例１のパラトルエンスル
ホン酸クロライドの代わりにβ−ナフタレンスルホン酸
クロライド２重量部を用い実施例１と同様の方法でｎが
６でＲの約３０％をβ−ナフタレンスルホニル基とする
シクロデキストリン誘導体を合成した。次にやはり実施
例１と同様にして安息香酸リチウムとコンプレックスを
形成した。更に、やはり実施例１と同様の方法で二成分
現像剤を調製し異なる環境下に放置後繰り返し現像試験
を行った。その結果実施例１と同様に、現像開始後一万
枚目の画像は気温２０℃・湿度６０％の条件下においた
ものも気温３５℃・湿度８５％の条件下においたものも
画像濃度がほとんど変化せず鮮明で、かぶりもほとんど
なかった。<Example 4> In the same manner as in Example 1 except that para-toluenesulfonic acid chloride of Example 1 was replaced with 2 parts by weight of β-naphthalenesulfonic acid chloride, n was 6 and about 30% of R was β. A cyclodextrin derivative having a naphthalenesulfonyl group was synthesized. Next, a complex was formed with lithium benzoate in the same manner as in Example 1. Further, a two-component developer was prepared in the same manner as in Example 1, and after being allowed to stand in different environments, a development test was repeated. As a result, as in Example 1, the image of the 10,000th sheet after the start of development has an image density of 20 ° C. and a humidity of 60% and an image of 35 ° C. and a humidity of 85%. It was clear with little change and almost no fogging.
【００２９】〈実施例５〉実施例１の安息香酸リチウム
の代わりにβ−ナフタレンスルホン酸ナトリウムを用い
以下実施例１と同様の方法で二成分現像剤を調製し異な
る環境下に放置後繰り返し現像試験を行った。その結果
実施例１と同様に、現像開始後一万枚目の画像は気温２
０℃・湿度６０％の条件下においたものも気温３５℃・
湿度８５％の条件下においたものも画像濃度がほとんど
変化せず鮮明で、かぶりもほとんどなかった。Example 5 A two-component developer was prepared in the same manner as in Example 1 except that sodium β-naphthalenesulfonate was used in place of lithium benzoate in Example 1, and the composition was repeatedly developed after being left in a different environment. The test was performed. As a result, the image on the 10,000th sheet after the start of development was
Temperatures of 35 ° C and those of 0 ° C and 60% humidity
Also under the condition of a humidity of 85%, the image density was clear with little change in image density, and there was almost no fog.
【００３０】〈実施例６〉実施例１の安息香酸リチウム
の代わりにオルトフタル酸ナトリウムを用い以下実施例
１と同様の方法で二成分現像剤を調製し異なる環境下に
放置後繰り返し現像試験を行った。その結果実施例１と
同様に、現像開始後一万枚目の画像は気温２０℃・湿度
６０％の条件下においたものも気温３５℃・湿度８５％
の条件下においたものも画像濃度がほとんど変化せず鮮
明で、かぶりもほとんどなかった。Example 6 A two-component developer was prepared in the same manner as in Example 1 except that sodium orthophthalate was used in place of lithium benzoate of Example 1, and a development test was repeated after standing in different environments. Was. As a result, in the same manner as in Example 1, the image of the 10,000th sheet after the start of the development was obtained under the condition of the temperature of 20 ° C. and the humidity of 60%.
Under the above conditions, the image density was almost unchanged and the image was clear, and there was almost no fog.
【００３１】[0031]
【発明の効果】本発明のシクロデキストリン誘導体を含
む現像剤は耐湿性に優れ、繰り返し現像を行っても鮮明
な画像を与えることが可能である。The developer containing the cyclodextrin derivative of the present invention has excellent moisture resistance and can provide a clear image even after repeated development.
───────────────────────────────────────────────────── フロントページの続き (58)調査した分野(Int.Cl.7，ＤＢ名) G03G 9/08 ──────────────────────────────────────────────────続 き Continued on the front page (58) Field surveyed (Int.Cl. 7 , DB name) G03G 9/08
Claims (2)
のうち置換基Ｒの２５％以上がＣＨ3Ｃ6Ｈ4ＳＯ3基、或
いは、Ｃ10Ｈ7ＳＯ3基であり、ｎが６から８であり、シ
クロデキストリン誘導体を少なくとも一種類以上含有す
ることを特徴とする電子写真用トナー。 【化１】 (1) In the cyclodextrin derivative represented by the formula (1), at least 25% of the substituent R is a CH 3 C 6 H 4 SO 3 group or a C 10 H 7 SO 3 group, and n is from 6 to 8 Wherein the toner for electrophotography contains at least one kind of cyclodextrin derivative. Embedded image
ン誘導体が有機酸の金属塩かアンモニウム塩かアミン
塩、或いは無機酸の金属塩かアンモニウム塩かアミン塩
と錯体を形成している電子写真用トナー。2. The electrophotographic toner according to claim 1, wherein the cyclodextrin derivative forms a complex with a metal salt, ammonium salt or amine salt of an organic acid, or a metal salt, ammonium salt or amine salt of an inorganic acid. .
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24758992A JP3158713B2 (en) | 1992-09-17 | 1992-09-17 | Electrophotographic toner |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24758992A JP3158713B2 (en) | 1992-09-17 | 1992-09-17 | Electrophotographic toner |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06118719A JPH06118719A (en) | 1994-04-28 |
| JP3158713B2 true JP3158713B2 (en) | 2001-04-23 |
Family
ID=17165756
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP24758992A Expired - Fee Related JP3158713B2 (en) | 1992-09-17 | 1992-09-17 | Electrophotographic toner |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3158713B2 (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3373610B2 (en) * | 1993-08-23 | 2003-02-04 | オリヱント化学工業株式会社 | Chargeable resin powder and related technologies |
| DE4418842A1 (en) * | 1994-05-30 | 1995-12-07 | Hoechst Ag | Colourless, thermostable, non-toxic cyclised oligo- or poly:saccharide use as charge controller or enhancer |
| DE19517034A1 (en) * | 1995-05-10 | 1996-11-14 | Hoechst Ag | Use of inclusion compounds of ring-shaped polysaccharides as charge control agents |
| US5627002A (en) * | 1996-08-02 | 1997-05-06 | Xerox Corporation | Liquid developer compositions with cyclodextrins |
| CA2692211C (en) | 2009-12-14 | 2011-09-13 | Cellresin Technologies, Llc | Maturation or ripening inhibitor release from polymer, fiber, film, sheet or packaging |
| SI2690951T1 (en) | 2011-03-27 | 2016-02-29 | Cellresin Technologies, Llc | Cyclodextrin compositions, articles, and methods |
| US10182567B2 (en) | 2011-03-27 | 2019-01-22 | Cellresin Technologies, Llc | Cyclodextrin compositions, articles, and methods |
| US9320288B2 (en) | 2012-11-30 | 2016-04-26 | Cellresin Technologies, Llc | Controlled release compositions and methods of using |
| US9421793B2 (en) * | 2014-06-26 | 2016-08-23 | Cellresin Technologies, Llc | Electrostatic printing of cyclodextrin compositions |
-
1992
- 1992-09-17 JP JP24758992A patent/JP3158713B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH06118719A (en) | 1994-04-28 |
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