JPH02272461A - Toner for developing electrostatic charge image - Google Patents
Toner for developing electrostatic charge imageInfo
- Publication number
- JPH02272461A JPH02272461A JP1092813A JP9281389A JPH02272461A JP H02272461 A JPH02272461 A JP H02272461A JP 1092813 A JP1092813 A JP 1092813A JP 9281389 A JP9281389 A JP 9281389A JP H02272461 A JPH02272461 A JP H02272461A
- Authority
- JP
- Japan
- Prior art keywords
- toner
- parts
- formulas
- tables
- resin
- 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
Links
- -1 imide metal complex Chemical class 0.000 claims abstract description 26
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract 2
- 239000000126 substance Substances 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 abstract description 11
- 150000003949 imides Chemical class 0.000 abstract description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract description 6
- 229920005989 resin Polymers 0.000 abstract description 5
- 239000011347 resin Substances 0.000 abstract description 5
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003822 epoxy resin Substances 0.000 abstract description 2
- 239000012188 paraffin wax Substances 0.000 abstract description 2
- 229920000647 polyepoxide Polymers 0.000 abstract description 2
- 229920001225 polyester resin Polymers 0.000 abstract description 2
- 239000004645 polyester resin Substances 0.000 abstract description 2
- 239000002184 metal Substances 0.000 abstract 1
- 229920002857 polybutadiene Polymers 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 239000000843 powder Substances 0.000 description 13
- 239000000203 mixture Substances 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 229920001909 styrene-acrylic polymer Polymers 0.000 description 9
- 229920006026 co-polymeric resin Polymers 0.000 description 8
- 239000006229 carbon black Substances 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- OSNILPMOSNGHLC-UHFFFAOYSA-N 1-[4-methoxy-3-(piperidin-1-ylmethyl)phenyl]ethanone Chemical compound COC1=CC=C(C(C)=O)C=C1CN1CCCCC1 OSNILPMOSNGHLC-UHFFFAOYSA-N 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- VVOLVFOSOPJKED-UHFFFAOYSA-N copper phthalocyanine Chemical compound [Cu].N=1C2=NC(C3=CC=CC=C33)=NC3=NC(C3=CC=CC=C33)=NC3=NC(C3=CC=CC=C33)=NC3=NC=1C1=CC=CC=C12 VVOLVFOSOPJKED-UHFFFAOYSA-N 0.000 description 3
- 150000001993 dienes Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- GUYIZQZWDFCUTA-UHFFFAOYSA-N (pentadecachlorophthalocyaninato(2-))-copper Chemical compound [Cu+2].N1=C([N-]2)C3=C(Cl)C(Cl)=C(Cl)C(Cl)=C3C2=NC(C2=C(Cl)C(Cl)=C(Cl)C(Cl)=C22)=NC2=NC(C2=C(Cl)C(Cl)=C(Cl)C(Cl)=C22)=NC2=NC2=C(C(Cl)=C(C(Cl)=C3)Cl)C3=C1[N-]2 GUYIZQZWDFCUTA-UHFFFAOYSA-N 0.000 description 2
- 229920006243 acrylic copolymer Polymers 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229960002317 succinimide Drugs 0.000 description 2
- 229920005992 thermoplastic resin Polymers 0.000 description 2
- 229910000859 α-Fe Inorganic materials 0.000 description 2
- LPUUYZVKCMCHLO-UHFFFAOYSA-N 4,5,6,7-tetrachloroisoindole-1,3-dione Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)NC(=O)C2=C1Cl LPUUYZVKCMCHLO-UHFFFAOYSA-N 0.000 description 1
- IAGZAIHSURVYSD-UHFFFAOYSA-N 4,5-dimethylisoindole-1,3-dione Chemical compound CC1=CC=C2C(=O)NC(=O)C2=C1C IAGZAIHSURVYSD-UHFFFAOYSA-N 0.000 description 1
- 241000972773 Aulopiformes Species 0.000 description 1
- 241000272194 Ciconiiformes Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 235000019515 salmon Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
Landscapes
- Developing Agents For Electrophotography (AREA)
Abstract
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、静電記を濠および静電印刷等におけ
る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, electrostatic printing, electrostatic printing, and the like.
（従来の技術）
静電潜像はその静電引力によりトナーを付着せしめるこ
とにより顕像化することができ、さらに熱あるいは溶剤
、場合によっては圧力によって定着されるが、この現像
剤として、液体現像剤の池に粉末現像剤が広く一般に使
用されている。(Prior art) An electrostatic latent image can be visualized by adhering toner due to its electrostatic attraction, and is further fixed by heat or a solvent, or in some cases by pressure. Powdered developers are widely and commonly used in developer ponds.
この粉末現像剤は、天然樹脂あるいは合成？１脂に着色
剤、電荷調整剤、流動化剤等を分散させたトナーと呼ば
れる微粒子粉末と、えヤリアと呼ばれる微細な鉄粉また
はガラス粉の混合物から成る２成分系現像剤と、天然樹
脂あるいは合成樹脂に着色剤、電荷調整剤、流動化剤、
フェライト等を分散させた微粒子粉末のトナーのみから
成る１成分系現像剤とに大別することができる。Is this powder developer made of natural resin or synthetic? A two-component developer consisting of a mixture of fine particle powder called toner in which colorants, charge control agents, fluidizing agents, etc. Coloring agents, charge control agents, fluidizing agents, synthetic resins,
Developers can be broadly classified into one-component developers, which consist only of fine powder toner in which ferrite and the like are dispersed.
２成分系現像剤は、トナーをキャリアとの摩擦により荷
電せしめ、静電潜像に付着することにより顕像化され、
さらに像を定着することで現像が達成される。１成分系
現像剤は、トナーをキャリアの代わりとなるブラシ状ま
たは板状の摩擦部材との摩擦により荷電せしめ、静電現
像に付着させるものであるが、７エライＦを分散状態に
保ち、このフェライトとの相互摩擦によって荷電される
トナーもある。これらの現像用トナーは現像される静電
潜像の極性に応じて、正または負の電荷が保たれる。Two-component developers charge the toner through friction with the carrier, and the toner is visualized by adhering to the electrostatic latent image.
Development is accomplished by further fixing the image. A one-component developer charges the toner by friction with a brush-like or plate-like friction member that serves as a carrier, and causes the toner to adhere to the electrostatic developer. Some toners are charged by mutual friction with ferrite. These developing toners maintain a positive or negative charge depending on the polarity of the electrostatic latent image to be developed.
トナーの電荷を保つには、トナーの主成分である（３１
脂の摩擦帯電性を利用することが提案されているが、こ
の方法ではトナーの電荷が小さく、また、固体表面抵抗
値も大トいため、得られる画像はカブリ易く、不鮮明な
ものとなる。このため、必要な電荷を保つために、荷電
を付与する染料、顔料さらには電荷調整剤を添加するこ
とが行なわれている。To maintain the charge of the toner, the main component of the toner (31
It has been proposed to utilize the frictional charging properties of fat, but in this method, the toner has a small charge and the solid surface resistance value is also large, so the resulting images tend to fog and become unclear. For this reason, in order to maintain the necessary charge, dyes and pigments that impart charge, as well as charge control agents, are added.
（発明が解決しようとする問題点）
しかしながら、従来の電荷調整剤は一般に、構造が複雑
で安定性に乏しく、熱、機械的摩擦および衝撃、温度、
湿度条件の変化などにより、分解または変質して、電荷
調整剤としての機能が失われ易い。主た、それ自体が有
色物質であるため、その色調のトナーには適しているが
、異なる色調のトナーには適さない。さらに熱可塑性樹
脂中に均一に分散せしめることが困難なため、微粉砕し
て得られるトナー粒子間に摩擦帯電量に差異を生じると
いう欠点がある。これらの電荷調整剤の欠点を改良する
提案がいくつもあり、異なる系統の化合物が提案されて
いるが、総合的に満足できるものは見出されていない。(Problems to be Solved by the Invention) However, conventional charge control agents generally have complex structures and poor stability, and are susceptible to heat, mechanical friction and impact,
It tends to decompose or change in quality due to changes in humidity conditions and loses its function as a charge control agent. Mainly because it is a colored substance itself, it is suitable for toners of that tone, but not for toners of different tones. Furthermore, since it is difficult to uniformly disperse the toner particles in the thermoplastic resin, there is a drawback that the amount of triboelectrification varies between the toner particles obtained by pulverization. There have been a number of proposals to improve the drawbacks of these charge control agents, and different types of compounds have been proposed, but none have been found that are comprehensively satisfactory.
（問題点を解決するための手段）
本発明者等は、熱可塑性樹脂との相溶性が良好で、（３
（脂溶融温度以上の熱安定性を有し、トナー粒子に均一
で十分な電荷を付与し、カラートナー組成物の着色物質
の色特性を損なわない無色の化合物を見い出し、本発明
を完成するに至った。(Means for solving the problem) The present inventors have discovered that the compatibility with thermoplastic resin is good and (3
(To complete the present invention, we have found a colorless compound that has thermal stability above the fat melting temperature, imparts a uniform and sufficient charge to toner particles, and does not impair the color properties of the colored substance in the color toner composition.) It's arrived.
すなわち、本発明のトナーは下記−紋穴（１）（式中、
Ｍ及びＲ１は、前記と同一の意味を表わす。）で表わさ
れるイミド化合物を含有する静電荷像現像用トナーであ
る。That is, the toner of the present invention has the following formula (1) (in the formula,
M and R1 have the same meanings as above. ) is a toner for developing electrostatic images containing an imide compound represented by:
本発明で使用する一般式（１）で表わされるイミド化合
物は、下記−紋穴（Ｉｆ）で表わされる化合物（但し、
式中、Ｒ１は前記と同一の意味を表わす。）と水酸化物
を常法により反応させ高収率で得ることができる。The imide compound represented by the general formula (1) used in the present invention is a compound represented by the following - Monana (If) (however,
In the formula, R1 has the same meaning as above. ) and hydroxide in a conventional manner to obtain a high yield.
化合物Ｎｏ。Compound no.
上記反応に使用する水酸化物はｔことえば水酸化リチウ
ム、水酸化すＦリウム、水酸化カリウムなどである。The hydroxides used in the above reaction include lithium hydroxide, fluorium hydroxide, potassium hydroxide, and the like.
一般式（１）で表わされるイミド金属錯体の具体例を以
下に示す。ここで使用される化合物Ｎｏ、は実施例にお
いても共通に使用される。Specific examples of the imide metal complex represented by general formula (1) are shown below. Compound No. used here is also commonly used in Examples.
化合物Ｎｏ。Compound no.
構 泪。Structure Tears.
式 ％式％ 化合物Ｎｏ。formula %formula% Compound no.
化合物Ｎｏ。Compound no.
化合物Ｎｏ。Compound no.
構
逓
式
本発明のトナーは、−紋穴（１）で表わされるイミド化
合物の［１こ、接着性、保存性、流動性、粉砕性等を考
慮して、スチレン１３（脂、スチレン−アクリル系樹脂
、スチレン−ブタジェン＋１［ｆ、エポキシ樹脂、ポリ
エステル樹脂、パラフィンワックス等を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、顔料を用いることができるが、特に優れてい
るものとして、ペンがう、ベンジジンイエロー、キナク
ドリン、銅フタロシアニンブルー、銅フタロシアニング
リーン等が挙げられる。The structural toner of the present invention is made of styrene 13 (fat, styrene-acrylic) in consideration of adhesion, preservability, fluidity, pulverizability, etc. of the imide compound represented by Monka (1). styrene-butadiene+1[f, epoxy resin, polyester resin, paraffin wax, etc. can be used singly or as a mixture of several types.As the coloring agent, many known dyes and pigments can be used. However, particularly excellent ones include penguin, benzidine yellow, quinacridine, copper phthalocyanine blue, and copper phthalocyanine green.
本発明において、トナー組成物中に添加される一１式（
１）で表わされるイミド化合物の量は、樹脂１００重量
部に対し、一般に０．１〜１０重危部、好ましくは０．
５〜５重量部の割合で含有せしめる。In the present invention, Formula 11 (
The amount of the imide compound represented by 1) is generally 0.1 to 10 parts by weight, preferably 0.1 to 10 parts by weight, per 100 parts by weight of the resin.
It is contained in a proportion of 5 to 5 parts by weight.
本発明のイミド化合物を含有するトナーは、キャリアと
混合して２成分系現像剤を提供するが、１成分系現像剤
としても使用できる。The toner containing the imide compound of the present invention is mixed with a carrier to provide a two-component developer, but it can also be used as a one-component developer.
（実施例） 以下、＊施例によυ不兄明を詳細に説明する。(Example) Hereinafter, the υunfriendliness will be explained in detail using *example.
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.
実施例上
７タルイミド２９．４部と水酸化カリウム１３耶を水３
００部に溶解し、８０°Ｃに加温した。その後、２時間
攪はんを続け、次いで室温まで冷却した。水を留去し、
残渣を５０〜６０°Ｃで減圧乾燥して、無色粉末の化合
物Ｎｏ、１のイミド化合物３０部を得た。Example 7 29.4 parts of talimide and 13 parts of potassium hydroxide were added to 3 parts of water.
00 parts and heated to 80°C. Thereafter, stirring was continued for 2 hours, and then the mixture was cooled to room temperature. Distill water,
The residue was dried under reduced pressure at 50 to 60°C to obtain 30 parts of imide compound No. 1 as a colorless powder.
スナレンーアクリル共重合体樹脂１００部、カーボンブ
ラック１２部と、上記のようにして合成したイミド化合
物１．５部をよく混合してから加熱溶融し、冷却後、ジ
エン）ミルで微粉砕して黒色のトナーを得た。この黒色
トナーからは、カブリのない鮮明な画像が得られ、長期
間にわたる繰り返し使用にも変化のない良好な複写画像
が得られた。100 parts of Sunalene-acrylic copolymer resin, 12 parts of carbon black, and 1.5 parts of the imide compound synthesized as described above were thoroughly mixed, heated and melted, cooled, and pulverized in a diene mill. A black toner was obtained. From this black toner, a clear image without fogging was obtained, and a good copy image was obtained that did not change even after repeated use over a long period of time.
実施例２−
ジメチルフタルイミド３５部と水酸化カリウム１３耶を
水３００部に溶解し、８０℃に加温した。Example 2 - 35 parts of dimethylphthalimide and 13 parts of potassium hydroxide were dissolved in 300 parts of water and heated to 80°C.
その後、２時開攪はんそ続け、次いで室温上で冷却した
。水を留去し、残渣をＧ Ｏ−Ｇ Ｏ’Ｃでｉ減圧乾燥
して、無色粉末の化合物Ｎｏ、２のイミド化合物３４部
を得た。Thereafter, stirring was continued for 2 hours, and then the mixture was cooled to room temperature. Water was distilled off, and the residue was dried under reduced pressure with G O-G O'C to obtain 34 parts of imide compound No. 2 as a colorless powder.
スナレンーアクリル共重合体＋３１脂１００部、ベンジ
ジンイエロー７部と、上記のようにして合成したイミド
化合物１．５部をよく混合してから加熱溶融し、冷却後
、ジエン）ミルで微粉砕して黄色のトナーを得た。この
黄色トナーからは、カブリのない鮮明な画像が得られ、
長期間にわたる繰り返し使用にも変化のない良好な複写
画像が得られた。100 parts of Sunalene-acrylic copolymer +31 fat, 7 parts of benzidine yellow, and 1.5 parts of the imide compound synthesized as described above were thoroughly mixed, heated and melted, cooled, and pulverized in a diene mill. A yellow toner was obtained. This yellow toner produces clear, fog-free images.
A good copy image was obtained with no change even after repeated use over a long period of time.
実施例３
テトラクロルフタルイミド５７部と水酸化カリウム１３
部を水３００部に溶解し、８０°Ｃに加温しｔこ。その
後、２時間攪はんを続け、次いで室温まで冷却した。水
を留去し、残渣を５０〜６０’Ｃで減圧乾燥して、無色
粉末の化合物Ｎｏ、３のイミド化合物５６部を得た。Example 3 57 parts of tetrachlorophthalimide and 13 parts of potassium hydroxide
1 part was dissolved in 300 parts of water and heated to 80°C. Thereafter, stirring was continued for 2 hours, and then the mixture was cooled to room temperature. Water was distilled off, and the residue was dried under reduced pressure at 50 to 60'C to obtain 56 parts of imide compound No. 3 as a colorless powder.
スチレン−アクリル共重合体樹脂１００’ｌ、銅７りロ
シアユングリーフ６部と、上記のように合成したイミド
化合物１６５部をよく混合してから加熱溶融し、冷却後
、ジエン）ミルで微粉砕して緑色のトナーを得た。この
緑色トナーからは、カブリのない鮮明な画像が得られ、
長期間にわたる繰り返し使用にも変化のない良好な複写
画像が得られた。100'l of styrene-acrylic copolymer resin, 6 parts of Copper 7-Russian Green Leaf, and 165 parts of the imide compound synthesized above are thoroughly mixed, heated and melted, cooled, and pulverized in a diene mill. I got a green toner. This green toner provides clear images without fogging.
A good copy image was obtained with no change even after repeated use over a long period of time.
及１鮭１
４−ニトロ７タルイミド３８．４部と水酸化カリウム１
３部を水３００部に溶解し、８０℃に加温した。その後
、２時間攪はんを続゛け、次いで室温まで冷却した。、
水を留去し、残渣を５０〜６０’Ｃで減圧乾燥して、無
色の粉末の化合物Ｎｏ。and 1 salmon, 38.4 parts of 4-nitro 7-talimide and 1 part of potassium hydroxide
3 parts were dissolved in 300 parts of water and heated to 80°C. Thereafter, stirring was continued for 2 hours, and then the mixture was cooled to room temperature. ,
The water was distilled off and the residue was dried under reduced pressure at 50-60'C to obtain Compound No. 1 as a colorless powder.
４のイミド化合物３９部を得た。39 parts of imide compound No. 4 was obtained.
スチレン−アクリル共重合体樹脂１００１、銅フタロシ
アニンブルー６部と、上記のように合成したイミド化合
物１．５部をよく混合してから加熱溶融し、冷却後、ジ
ェットミルで微粉砕して青色のトナーを得た。この青色
トナーがらは、カブリのない鮮明な画像が得られ、長期
間にわたる繰９返し使用にも変化のない良好な複写画像
が得られた。Styrene-acrylic copolymer resin 1001, 6 parts of copper phthalocyanine blue, and 1.5 parts of the imide compound synthesized above are thoroughly mixed, heated and melted, cooled, and pulverized with a jet mill to produce a blue color. Got toner. With this blue toner particles, a clear image without fogging was obtained, and a good copy image was obtained with no change even after repeated use over a long period of time.
及１鮭影
７タルイミド２９．４部と水酸化リチウム８．４部を水
３００部に溶解し、８０’Ｃに加温した。その後、２時
開攪はんを続け、次いで室温まで冷却した。水を留去し
、残渣を５０〜６０°Ｃで減圧乾燥して、無色の粉末の
イミド化合物２６部を得た。29.4 parts of talimide and 8.4 parts of lithium hydroxide were dissolved in 300 parts of water and heated to 80'C. Thereafter, stirring was continued for 2 hours, and then the mixture was cooled to room temperature. Water was distilled off, and the residue was dried under reduced pressure at 50 to 60°C to obtain 26 parts of an imide compound as a colorless powder.
スチレン−アクリル共重合体樹脂１００部、カーボンブ
ラック１２部と、上記のように合成したイミド化合物１
．５部をよく混合してから加熱溶融し、冷却後、ジェッ
トミルで微粉砕して黒色のトナーを得た。この黒色トナ
ーからは、カブリのない鮮明な画像が得られ、長期間に
わたる繰り返し使用にも変化のない良好な複写画像が得
られた。100 parts of styrene-acrylic copolymer resin, 12 parts of carbon black, and imide compound 1 synthesized as above.
．． 5 parts were thoroughly mixed, heated and melted, cooled, and then finely pulverized with a jet mill to obtain a black toner. From this black toner, a clear image without fogging was obtained, and a good copy image was obtained that did not change even after repeated use over a long period of time.
尺１汁団
ツメチル７タルイミド３５部と水酸化リチウム８．４部
を水３００部に溶解し、８０’Ｃに加温した。その後、
２時間攪はんを続け、次いで室温まで冷却した。水を留
去し、残渣を５０〜６０ ’Ｃで減圧乾燥して、無色粉
末の化合物Ｎｏ、１９のイミド化合物３１部を得ｔこ。35 parts of methyl 7-talimide and 8.4 parts of lithium hydroxide were dissolved in 300 parts of water and heated to 80'C. after that,
Stirring was continued for 2 hours and then cooled to room temperature. Water was distilled off, and the residue was dried under reduced pressure at 50-60'C to obtain 31 parts of imide compound No. 19 as a colorless powder.
スチレン−アクリル共重合体樹脂１００部、ベンジジン
イエロー７部と、上記のように合成したイミド化合物１
．５部をよく混合してから加熱溶融し、冷却後、ジェッ
トミルで微粉砕して黄色のトナーを得た。この黄色トナ
ーからは、カブリのない鮮明な画像が得られ、長期間に
わたる繰り返し使用にも変化のない良好な複写画像が得
られた。100 parts of styrene-acrylic copolymer resin, 7 parts of benzidine yellow, and imide compound 1 synthesized as above.
．． 5 parts were thoroughly mixed, heated and melted, cooled and pulverized using a jet mill to obtain a yellow toner. From this yellow toner, clear images without fogging were obtained, and good copied images were obtained that did not change even after repeated use over a long period of time.
聚１汁り
す７タレンー１，８−ジカルボン酸イミド３９部と水酸
化リチウム８．４部を水３００部に溶解し、８０℃に加
温しｔこ。その後、２時間攪はんを続け、次いで室温ま
で冷却した。水を留去し、残渣を５０〜６０’Ｃで減圧
乾燥して、無色粉末のイミド化合物３６ｍを得た。39 parts of 1,8-dicarboxylic acid imide and 8.4 parts of lithium hydroxide were dissolved in 300 parts of water and heated to 80°C. Thereafter, stirring was continued for 2 hours, and then the mixture was cooled to room temperature. Water was distilled off, and the residue was dried under reduced pressure at 50 to 60'C to obtain imide compound 36m as a colorless powder.
スチレン−アクリル共重合体樹脂１００部、カーボンブ
ラック１２ｍと、上記のように合成したイミド化合物１
．５部をよく混合してから加熱溶融し、冷却後、ジェン
）ミルで微粉砕して黒色のトナーを得た。この黒色トナ
ーからは、カブリのない鮮明な画像が得られ、長期間に
わたる繰り返し使用にも変化のない良好な複写画像が得
られた。100 parts of styrene-acrylic copolymer resin, 12m of carbon black, and imide compound 1 synthesized as above.
．． 5 parts were thoroughly mixed, heated and melted, cooled, and finely pulverized in a Gen) mill to obtain a black toner. From this black toner, a clear image without fogging was obtained, and a good copy image was obtained that did not change even after repeated use over a long period of time.
実施例８
９．１０−ジヒドロアントラセン−９４０−エンド−α
β−無水フハク酸イミド５４．６部と水酸化リチウム８
．４部を水３００部に溶解し、８０°Ｃ１こ加温した。Example 8 9.10-dihydroanthracene-940-endo-α
54.6 parts of β-succinimide anhydride and 8 parts of lithium hydroxide
．． 4 parts were dissolved in 300 parts of water and heated to 80°C.
その後、２時間攪はんを続け、次いで室温まで冷却した
。水を留去し、残渣を５０〜６０°Ｃで減圧乾燥して、
無色粉末のイミド化合物４８ｍを得た。Thereafter, stirring was continued for 2 hours, and then the mixture was cooled to room temperature. Water was distilled off, the residue was dried under reduced pressure at 50-60°C,
Imide compound 48m was obtained as a colorless powder.
スチレン−アクリル共重合体樹脂１００部、銅フタロシ
アニンブルー６部と、上記のように合成したイミド化合
物１．５部をよ（混合してから加熱溶融し、冷却後、ジ
ェン）ミルで微粉砕して青色のトナーを得だ。この青色
トナーからは、カブリのない鮮明な画像が得られ、長期
Ｉｉｌにわたる繰り返し使用にも変化のない良好な複写
画像が得られた。100 parts of styrene-acrylic copolymer resin, 6 parts of copper phthalocyanine blue, and 1.5 parts of the imide compound synthesized as above were mixed and melted by heating, and after cooling, finely pulverized in a mill. I got blue toner. From this blue toner, a clear image without fogging was obtained, and a good copy image was obtained with no change even after repeated use over a long period of time.
実施例９
ナフタレン−１，８−ジカルボン酸イミド３９部と水酸
化すＦリウム８．６部を水３００部に溶解し、８０’（
：に加温した。その後、２時間攪はんを続け、次いで室
温主で冷却した。水３０（ｌに投入し、析出しｔこ固体
をろ別し、５０〜６０℃で減圧乾燥して、無色粉末のイ
ミド化合物４０部を得た。Example 9 39 parts of naphthalene-1,8-dicarboxylic acid imide and 8.6 parts of Fium hydroxide were dissolved in 300 parts of water.
: Warmed to . Thereafter, stirring was continued for 2 hours, and then the mixture was cooled to room temperature. The precipitated solid was filtered out and dried under reduced pressure at 50 to 60°C to obtain 40 parts of an imide compound as a colorless powder.
スチレン−アクリル共重合体樹脂１００部、カーボンブ
ラック１２部と、上記のように合成したイミド化合物１
．５部をよ（混合してから加熱溶融し、冷却後、ジェッ
トミルで微粉砕して黒色のトナーを得た。この黒色トナ
ーからは、カブリのない鮮明な画像が得られ、長期間に
わたる繰り返し使用にも変化のない良好な複写画像が得
られた。100 parts of styrene-acrylic copolymer resin, 12 parts of carbon black, and imide compound 1 synthesized as above.
．． 5 parts were mixed (mixed, heated and melted, cooled and pulverized with a jet mill to obtain a black toner. Clear images without fogging were obtained from this black toner, and it could be repeated over a long period of time. A good copy image was obtained with no change in use.
実施例１０
９．１０−ジヒドロアントラセン−９，１０−エンド−
αβ−無水フハク酸イミド５４．６部と水酸化すＹリウ
ム８．６部をＩ）ＭＰ６０部に溶解し、８０’Ｃに加温
した。その後、８０”Ｃで２時間攪はんを続け、次いで
室温まで冷却した。水３００部１こ投入し、析出した固
体をろ別し、５０〜ａ ｏ ’Ｃで減圧乾燥して、無色
粉末のイミド化合物５５部を得た。Example 10 9.10-dihydroanthracene-9,10-endo-
54.6 parts of αβ-succinimide anhydride and 8.6 parts of Ylium hydroxide were dissolved in 60 parts of I) MP and heated to 80'C. Thereafter, stirring was continued for 2 hours at 80"C, and then cooled to room temperature. 300 parts of water was added, the precipitated solid was filtered out, and dried under reduced pressure at 50~a.o.'C to form a colorless powder. 55 parts of an imide compound were obtained.
スチレン−アクリル共重合体樹脂１０（）部、銅フタロ
シアニングリーン６部と、上記のように合成したイミド
化合物１．５部をよ（混合してから加熱溶融し、冷却後
、ジェットミルで微粉砕して緑色のトナーを得た。この
緑色トナーからは、カブリのない鮮明な画像が得られ、
長期間にわたる繰り返し使用にも変化のない良好な複写
画像が得られた。10 parts of styrene-acrylic copolymer resin, 6 parts of copper phthalocyanine green, and 1.5 parts of the imide compound synthesized as above were mixed (mixed, heated and melted, cooled, and pulverized with a jet mill. A green toner was obtained from this green toner. Clear images without fogging were obtained from this green toner.
A good copy image was obtained with no change even after repeated use over a long period of time.
（発明の効果）
本発明１こ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 1 has excellent mechanical friction and impact stability, temperature and humidity stability, etc., 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)
し、Ｒ＿１は、 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、 ▲数式、化学式、表等があります▼、 ▲数式、化学式、表等があります▼、 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼ ▲数式、化学式、表等があります▼又は▲数式、化学式
、表等があります▼ であり、Ｒ＿２、Ｒ＿３、Ｒ＿４、Ｒ＿５、Ｒ＿６、Ｒ
＿７、Ｒ＿８、Ｒ＿９は、水素または炭素数１〜１８の
アルキル基、ハロゲン、 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、−Ｎ＿３、 −ＮＯ＿２または−ＳＯ＿３Ｈであり、これらは同一で
も異なっていてもよく、Ｒ＿１＿０は −ＣＨ＿２−、
▲数式、化学式、表等があります▼、−ＣＨ＝ＣＨ−、
▲数式、化学式、表等があります▼、 −ＣＨ＿２−ＣＨ＿２−または▲数式、化学式、表等が
あります▼ であり、Ｒ＿１＿１、Ｒ＿１＿２およびＲ＿１＿３は、
水素または炭素数１〜５のアルキル基であり、これらは
同一でも異なっていてもよい。）で表わされるイミド化
合物を含有することを特徴とする静電荷像現像用トナー
。[Claims] 1 The following general formula (I) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (I) (In the formula, M represents an alkali metal or ammonium ion, and R_1 is ▲ Numerical formulas, chemical formulas, tables, etc. There are ▼, ▲mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼ ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ and R_2, R_3, R_4, R_5, R_6, R
_7, R_8, R_9 are hydrogen or an alkyl group having 1 to 18 carbon atoms, halogen, ▲Mathematical formula, chemical formula, table, etc.▼, ▲Mathematical formula, chemical formula,
There are tables, etc. ▼, -N_3, -NO_2 or -SO_3H, which may be the same or different, R_1_0 is -CH_2-,
▲There are mathematical formulas, chemical formulas, tables, etc.▼, -CH=CH-,
▲There are mathematical formulas, chemical formulas, tables, etc.▼, -CH_2-CH_2- or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, and R_1_1, R_1_2 and R_1_3 are
It is hydrogen or an alkyl group having 1 to 5 carbon atoms, and these may be the same or different. ) A toner for developing electrostatic images, characterized by containing an imide compound represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1092813A JP2764606B2 (en) | 1989-04-14 | 1989-04-14 | Toner for developing electrostatic images |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1092813A JP2764606B2 (en) | 1989-04-14 | 1989-04-14 | Toner for developing electrostatic images |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02272461A true JPH02272461A (en) | 1990-11-07 |
| JP2764606B2 JP2764606B2 (en) | 1998-06-11 |
Family
ID=14064857
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1092813A Expired - Lifetime JP2764606B2 (en) | 1989-04-14 | 1989-04-14 | Toner for developing electrostatic images |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2764606B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5534978A (en) * | 1994-03-02 | 1996-07-09 | Fujitsu Limited | Imaging apparatus and photoconductor |
| JP2006519167A (en) * | 2003-02-27 | 2006-08-24 | エムシーエー テクノロジーズ ゲーエムベーハー | Solvent-free production method of diketopyrrolopyrrole derivative. |
-
1989
- 1989-04-14 JP JP1092813A patent/JP2764606B2/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5534978A (en) * | 1994-03-02 | 1996-07-09 | Fujitsu Limited | Imaging apparatus and photoconductor |
| JP2006519167A (en) * | 2003-02-27 | 2006-08-24 | エムシーエー テクノロジーズ ゲーエムベーハー | Solvent-free production method of diketopyrrolopyrrole derivative. |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2764606B2 (en) | 1998-06-11 |
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