JPH04306665A - Tonner for electrostatic charge image development - Google Patents
Tonner for electrostatic charge image developmentInfo
- Publication number
- JPH04306665A JPH04306665A JP3071236A JP7123691A JPH04306665A JP H04306665 A JPH04306665 A JP H04306665A JP 3071236 A JP3071236 A JP 3071236A JP 7123691 A JP7123691 A JP 7123691A JP H04306665 A JPH04306665 A JP H04306665A
- Authority
- JP
- Japan
- Prior art keywords
- group
- parts
- toner
- exemplified compound
- general formula
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims description 40
- 229920005989 resin Polymers 0.000 claims description 8
- 239000011347 resin Substances 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 239000000460 chlorine Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000003086 colorant Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 239000010936 titanium Substances 0.000 claims description 2
- 229910052726 zirconium Inorganic materials 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 description 16
- 238000000034 method Methods 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
- 239000002245 particle Substances 0.000 description 5
- 239000000969 carrier Substances 0.000 description 4
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- -1 nonanyl group Chemical group 0.000 description 4
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 108091008695 photoreceptors Proteins 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- BIIBYWQGRFWQKM-JVVROLKMSA-N (2S)-N-[4-(cyclopropylamino)-3,4-dioxo-1-[(3S)-2-oxopyrrolidin-3-yl]butan-2-yl]-2-[[(E)-3-(2,4-dichlorophenyl)prop-2-enoyl]amino]-4,4-dimethylpentanamide Chemical compound CC(C)(C)C[C@@H](C(NC(C[C@H](CCN1)C1=O)C(C(NC1CC1)=O)=O)=O)NC(/C=C/C(C=CC(Cl)=C1)=C1Cl)=O BIIBYWQGRFWQKM-JVVROLKMSA-N 0.000 description 1
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
- UXHQLGLGLZKHTC-CUNXSJBXSA-N 4-[(3s,3ar)-3-cyclopentyl-7-(4-hydroxypiperidine-1-carbonyl)-3,3a,4,5-tetrahydropyrazolo[3,4-f]quinolin-2-yl]-2-chlorobenzonitrile Chemical compound C1CC(O)CCN1C(=O)C1=CC=C(C=2[C@@H]([C@H](C3CCCC3)N(N=2)C=2C=C(Cl)C(C#N)=CC=2)CC2)C2=N1 UXHQLGLGLZKHTC-CUNXSJBXSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 229920001890 Novodur Polymers 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229920006026 co-polymeric resin Polymers 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- AYOOGWWGECJQPI-NSHDSACASA-N n-[(1s)-1-(5-fluoropyrimidin-2-yl)ethyl]-3-(3-propan-2-yloxy-1h-pyrazol-5-yl)imidazo[4,5-b]pyridin-5-amine Chemical compound N1C(OC(C)C)=CC(N2C3=NC(N[C@@H](C)C=4N=CC(F)=CN=4)=CC=C3N=C2)=N1 AYOOGWWGECJQPI-NSHDSACASA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920001909 styrene-acrylic polymer Polymers 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- KMIOJWCYOHBUJS-HAKPAVFJSA-N vorolanib Chemical compound C1N(C(=O)N(C)C)CC[C@@H]1NC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C KMIOJWCYOHBUJS-HAKPAVFJSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
Landscapes
- Developing Agents For Electrophotography (AREA)
Abstract
(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.
Description
【０００１】0001
【産業上の利用分野】本発明は電子複写機等で使用され
る、静電荷像現像用トナーに関するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a toner for developing electrostatic images used in electronic copying machines and the like.
【０００２】0002
【従来の技術】電子複写機等で使用される現像剤は、そ
の現像工程において、例えば静電荷像が形成されている
感光体等の像担持体に一旦付着せしめられ、次に転写工
程において感光体から転写紙に転写された後、定着工程
においてコピー紙面に定着される。その際、潜像保持面
上に形成される静電荷像を現像するための現像剤として
、キャリアーとトナーとから成る二成分系現像剤および
キャリアーを必要としない一成分系現像剤（磁性トナー
）が知られている。そして、従来より現像剤に帯電性を
付与するものとしてニグロシン系染料、４級アンモニウ
ム塩等の帯電制御剤やキャリアのコーティング剤等が知
られていた。2. Description of the Related Art Developers used in electronic copying machines and the like are first adhered to an image bearing member such as a photoreceptor on which an electrostatic image is formed during the development process, and then are applied to the photoreceptor during the transfer process. After being transferred from the paper to the transfer paper, it is fixed to the copy paper surface in a fixing step. At that time, the developer for developing the electrostatic charge image formed on the latent image holding surface is a two-component developer consisting of a carrier and toner, and a one-component developer (magnetic toner) that does not require a carrier. It has been known. Conventionally, charge control agents such as nigrosine dyes and quaternary ammonium salts, carrier coating agents, and the like have been known as agents that impart chargeability to developers.
【０００３】0003
【発明が解決しようとする課題】しかしながら、これら
従来の帯電性付与剤は、帯電性付与効果が必ずしも十分
ではなく特に該効果が経時変化する為に連続複写による
コピー汚れが発生し、コピー品質にが低下するという問
題点を有していた。[Problems to be Solved by the Invention] However, these conventional chargeability imparting agents do not necessarily have a sufficient chargeability imparting effect, and in particular, the effect changes over time, resulting in copy stains caused by continuous copying, resulting in poor copy quality. There was a problem in that the value decreased.
【０００４】0004
【課題を解決するための手段】そこで、本発明者等は時
間を経てもコピー汚れ等の発生しにくい高品質の静電荷
像現像用トナーを提供すべく鋭意検討を行なった結果、
特定の構造を有する化合物をトナー中に含有させること
により、これらの問題点が解決されることを見い出し、
本発明に到達した。すなわち、本発明の要旨は、少なく
とも樹脂及び着色剤を含有してなる静電荷像現像用トナ
ーにおいて、前記一般式（Ｉ）又は（ＩＩ）で表される
化合物を１種以上含有することを特徴とする静電荷像現
像用トナーに存する。[Means for Solving the Problems] Therefore, the inventors of the present invention conducted extensive studies in order to provide a high-quality toner for developing electrostatic images that is less likely to cause stains on copies over time.
We have discovered that these problems can be solved by incorporating a compound with a specific structure into the toner,
We have arrived at the present invention. That is, the gist of the present invention is that an electrostatic image developing toner containing at least a resin and a colorant is characterized in that it contains one or more compounds represented by the general formula (I) or (II). It consists in a toner for developing an electrostatic image.
【０００５】以下に本発明を詳細に説明する。本発明の
静電荷像現像用トナーは、前記請求項１に記載した一般
式（Ｉ）又は（ＩＩ）で表される化合物を１種以上含有
することが特徴である。The present invention will be explained in detail below. The electrostatic image developing toner of the present invention is characterized in that it contains one or more compounds represented by the general formula (I) or (II) described in claim 1 above.
【０００６】[0006]
【化３】[Chemical 3]
【０００７】置換基Ｒ１ ，Ｒ２ の具体例をあげれば
、メチル基、エチル基、プロピル基、ブチル基、ヘプチ
ル基、ヘキシル基、オクチル基、ノナニル基、デシル基
、ウンデシル基、ドデシル基、トリデシル基、テトラデ
シル基、ペンタデシル基、ヘキサデシル基、ヘプタデシ
ル基、ステアリル基等のアルキル基；ベンジル基等のア
ラルキル基；低級アルキル置換ベンジル基、ニトロ置換
ベンジル基、ハロゲン置換ベンジル基等の置換アラルキ
ル基が挙げられ、中でもドデシル基、トリデシル基、ス
テアリル基、ベンジル基が好ましく、Ｒ１ とＲ２ の
炭素数をたしあわせた数が１３以上が好ましい。Specific examples of substituents R1 and R2 include methyl group, ethyl group, propyl group, butyl group, heptyl group, hexyl group, octyl group, nonanyl group, decyl group, undecyl group, dodecyl group, and tridecyl group. Alkyl groups such as , tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, stearyl group; aralkyl groups such as benzyl group; substituted aralkyl groups such as lower alkyl-substituted benzyl group, nitro-substituted benzyl group, halogen-substituted benzyl group, etc. Among them, dodecyl group, tridecyl group, stearyl group, and benzyl group are preferable, and it is preferable that the total number of carbon atoms of R1 and R2 is 13 or more.
【０００８】Ａｒ１ ，Ａｒ２ は各々独立にメチル基
、エチル基、プロピル基、イソプロピル基、ｎ−ブチル
基、イソブチル基、ペンチル基、ヘキシル基、ヘプチル
基、オクチル基、デシル基、ドデシル基、テトラデシル
基、オクタデシル基等のアルキル基；ベンジル基等のア
ラルキル基；低級のアルキル置換ベンジル基、ニトロ置
換ベンジル基、ハロゲン置換ベンジル基、等の置換アラ
ルキル基を表わす。特にドデシル基、テトラデシル基、
オクタデシル基が好ましい。Ａは、チタン、ジルコニウ
ム、またはケイ素原子を表わし、Ｘは、フッ素、塩素、
または臭素原子であり、特にフッ素原子が好ましい。一
般式（Ｉ）又は（ＩＩ）で表される化合物の中で本発明
の静電荷像現像用トナーに含有せしめるのに好適なもの
の具体例としては、下記の構造式で表される化合物を挙
げることができるが、これらに限定されるものではない
。尚、下記例示化合物の式中、ＢＺとはベンゼン環を意
味し、それに対する置換基の位置は、全てｐ−位を表示
したものとする。Ar1 and Ar2 each independently represent a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a decyl group, a dodecyl group, and a tetradecyl group. , an alkyl group such as an octadecyl group; an aralkyl group such as a benzyl group; a substituted aralkyl group such as a lower alkyl-substituted benzyl group, a nitro-substituted benzyl group, a halogen-substituted benzyl group, etc. Especially dodecyl group, tetradecyl group,
Octadecyl group is preferred. A represents titanium, zirconium, or a silicon atom, and X represents fluorine, chlorine,
or a bromine atom, with a fluorine atom being particularly preferred. Among the compounds represented by general formula (I) or (II), specific examples of compounds suitable for inclusion in the toner for developing electrostatic images of the present invention include compounds represented by the following structural formula. However, it is not limited to these. In the formulas of the exemplified compounds below, BZ means a benzene ring, and the positions of substituents on it are all p-positions.
【０００９】一般式（Ｉ）の例示化合物（１）Ｒ１ ：
−Ｃ１８Ｈ３７，Ｒ２ ：−ＣＨ２ −ＢＺ，Ａ：Ｚｒ
，Ｘ：Ｆ
（２）Ｒ１ ：−Ｃ１６Ｈ３３，Ｒ２ ：−ＣＨ２ −
ＢＺ−Ｃｌ，Ａ：Ｓｉ，Ｘ：Ｆ
（３）Ｒ１ ：−Ｃ１２Ｈ２５，Ｒ２ ：−ＣＨ２ −
ＢＺ，Ａ：Ｔｉ，Ｘ：Ｃｌ
（４）Ｒ１ ：−Ｃ１２Ｈ２５，Ｒ２ ：−ＣＨ２ −
ＢＺ−ＮＯ２ ，Ａ：Ｓｉ，Ｘ：Ｆ
（５）Ｒ１ ：−Ｃ１４Ｈ２９，Ｒ２ ：−ＣＨ２ −
ＢＺ，Ａ：Ｚｒ，Ｘ：Ｂｒ
（６）Ｒ１ ：−Ｃ１８Ｈ３７，Ｒ２ ：−ＣＨ２ −
ＢＺ，Ａ：Ｓｉ，Ｘ：Ｆ
（７）Ｒ１ ：−Ｃ１８Ｈ３７，Ｒ２ ：−ＣＨ２ −
ＢＺ，Ａ：Ｔｉ，Ｘ：Ｆ
（８）Ｒ１ ：−Ｃ１６Ｈ３３，Ｒ２ ：−ＣＨ２ −
ＢＺ，Ａ：Ｚｒ，Ｘ：Ｆ
（９）Ｒ１ ：−Ｃ１２Ｈ２５，Ｒ２ ：−ＣＨ２ −
ＢＺ−Ｃｌ，Ａ：Ｔｉ，Ｘ：Ｃｌ
（１０）Ｒ１ ：−Ｃ１４Ｈ２９，Ｒ２：−ＣＨ２ −
ＢＺ−ＣＨ３ ，Ａ：Ｓｉ，Ｘ：Ｆ
（１１）Ｒ１ ：−Ｃ１４Ｈ２９，Ｒ２：−ＣＨ２ −
ＢＺ−ＮＯ２ ，Ａ：Ｔｉ，Ｘ：Ｆ
（１２）Ｒ１ ：−Ｃ１８Ｈ３７，Ｒ２：−Ｃ１８Ｈ３
７，Ａ：Ｚｒ，Ｘ：Ｆ
（１３）Ｒ１ ：−Ｃ１８Ｈ３７，Ｒ２：−Ｃ１８Ｈ３
７，Ａ：Ｓｉ，Ｘ：Ｆ
（１４）Ｒ１ ：−Ｃ１８Ｈ３７，Ｒ２：−Ｃ１８Ｈ３
７，Ａ：Ｔｉ，Ｘ：Ｆ
（１５）Ｒ１ ：−Ｃ１８Ｈ３７，Ｒ２：−ＣＨ３ ，
Ａ：Ｓｉ，Ｘ：Ｆ
（１６）Ｒ１ ：−Ｃ１８Ｈ３７，Ｒ２：−ＣＨ３ ，
Ａ：Ｚｒ，Ｘ：Ｆ
（１７）Ｒ１ ：−Ｃ１８Ｈ３７，Ｒ２：−ＣＨ３ ，
Ａ：Ｔｉ，Ｘ：ＦExemplary compound (1) R1 of general formula (I):
-C18H37,R2:-CH2-BZ,A:Zr
,X:F (2)R1:-C16H33,R2:-CH2-
BZ-Cl,A:Si,X:F (3)R1:-C12H25,R2:-CH2-
BZ, A: Ti, X: Cl (4) R1: -C12H25, R2: -CH2 -
BZ-NO2,A:Si,X:F (5)R1:-C14H29,R2:-CH2-
BZ, A: Zr, X: Br (6) R1: -C18H37, R2: -CH2 -
BZ, A: Si, X: F (7) R1: -C18H37, R2: -CH2 -
BZ,A:Ti,X:F (8)R1:-C16H33,R2:-CH2-
BZ,A:Zr,X:F (9)R1:-C12H25,R2:-CH2-
BZ-Cl,A:Ti,X:Cl (10)R1:-C14H29,R2:-CH2-
BZ-CH3,A:Si,X:F (11)R1:-C14H29,R2:-CH2-
BZ-NO2,A:Ti,X:F (12)R1:-C18H37,R2:-C18H3
7, A: Zr, X: F (13) R1: -C18H37, R2: -C18H3
7, A: Si, X: F (14) R1: -C18H37, R2: -C18H3
7, A: Ti, X: F (15) R1: -C18H37, R2: -CH3,
A: Si, X: F (16) R1: -C18H37, R2: -CH3,
A: Zr, X: F (17) R1: -C18H37, R2: -CH3,
A: Ti, X: F
【００１０】一般式（ＩＩ）の例示化合物（１８）Ａｒ
１ ：−ＣＨ２ −ＢＺ，Ａｒ２ ：−ＣＨ２ −ＢＺ
，Ａ：Ｓｉ，Ｘ：Ｆ
（１９）Ａｒ１ ：−Ｃ１６Ｈ３３，Ａｒ２ ：−Ｃ１
６Ｈ３３，Ａ：Ｔｉ，Ｘ：Ｆ
（２０）Ａｒ１ ：−Ｃ７ Ｈ１５，Ａｒ２ ：−Ｃ７
Ｈ１５，Ａ：Ｚｒ，Ｘ：Ｂｒ
（２１）Ａｒ１ ：−Ｃ１０Ｈ２１，Ａｒ２ ：−Ｃ１
０Ｈ２１，Ａ：Ｚｒ，Ｘ：Ｆ
（２２）Ａｒ１ ：−Ｃ１４Ｈ２９，Ａｒ２ ：−Ｃ１
４Ｈ２９，Ａ：Ｓｉ，Ｘ：Ｆ
（２３）Ａｒ１ ：−Ｃ１６Ｈ３３，Ａｒ２ ：−ＣＨ
２ −ＢＺ，Ａ：Ｔｉ，Ｘ：Ｂｒ
（２４）Ａｒ１ ：−Ｃ１０Ｈ２１，Ａｒ２ ：−ＣＨ
２ −ＢＺ−Ｃｌ，Ａ：Ｓｉ，Ｘ：Ｆ
（２５）Ａｒ１ ：−Ｃ７ Ｈ１５，Ａｒ２ ：−ＣＨ
２ −ＢＺ−ＮＯ２ ，Ａ：Ｔｉ，Ｘ：Ｆ
（２６）Ａｒ１ ：−Ｃ５ Ｈ１１，Ａｒ２ ：−Ｃ１
０Ｈ２１，Ａ：Ｚｒ，Ｘ：Ｆ
（２７）Ａｒ１ ：−ＣＨ３ ，Ａｒ２ ：−Ｃ１６Ｈ
３３，Ａ：Ｔｉ，Ｘ：Ｆ
（２８）Ａｒ１ ：−Ｃ３ Ｈ７ ，Ａｒ２ ：−Ｃ１
６Ｈ３３，Ａ：Ｓｉ，Ｘ：Ｆ
（２９）Ａｒ１ ：−Ｃ４ Ｈ９ ，Ａｒ２ ：−Ｃ１
４Ｈ２９，Ａ：Ｔｉ，Ｘ：Ｆ
（３０）Ａｒ１ ：−Ｃ５ Ｈ１１，Ａｒ２ ：−Ｃ１
４Ｈ２９，Ａ：Ｚｒ，Ｘ：Ｆ
（３１）Ａｒ１ ：−ＣＨ２ −ＢＺ−Ｃｌ，Ａｒ２
：−ＣＨ２ −ＢＺ−Ｃｌ，Ａ：Ｔｉ，Ｘ：Ｆ
（３２）Ａｒ１ ：−ＣＨ２ −ＢＺ−ＮＯ２ ，Ａｒ
２ ：−ＣＨ２ −ＢＺ−ＮＯ２ ，Ａ：Ｚｒ，Ｘ：Ｆ
（３３）Ａｒ１ ：−ＣＨ２ −ＢＺ−ＣＨ３ ，Ａｒ
２ ：−ＣＨ２ −ＢＺ−ＮＯ２ ，Ａ：Ｓｉ，Ｘ：Ｆ
Exemplary compound (18) of general formula (II) Ar
1:-CH2-BZ, Ar2:-CH2-BZ
,A:Si,X:F (19)Ar1:-C16H33,Ar2:-C1
6H33,A:Ti,X:F (20)Ar1:-C7 H15,Ar2:-C7
H15,A:Zr,X:Br (21)Ar1:-C10H21,Ar2:-C1
0H21,A:Zr,X:F (22)Ar1:-C14H29,Ar2:-C1
4H29,A:Si,X:F (23)Ar1:-C16H33,Ar2:-CH
2-BZ,A:Ti,X:Br (24)Ar1:-C10H21,Ar2:-CH
2-BZ-Cl,A:Si,X:F (25)Ar1:-C7 H15,Ar2:-CH
2-BZ-NO2,A:Ti,X:F (26)Ar1:-C5 H11,Ar2:-C1
0H21,A:Zr,X:F (27)Ar1:-CH3,Ar2:-C16H
33,A:Ti,X:F (28)Ar1:-C3H7,Ar2:-C1
6H33,A:Si,X:F (29)Ar1:-C4H9,Ar2:-C1
4H29,A:Ti,X:F (30)Ar1:-C5 H11,Ar2:-C1
4H29,A:Zr,X:F (31)Ar1:-CH2-BZ-Cl,Ar2
:-CH2-BZ-Cl,A:Ti,X:F (32)Ar1 :-CH2-BZ-NO2,Ar
2:-CH2-BZ-NO2, A:Zr, X:F
(33) Ar1 :-CH2-BZ-CH3, Ar
2:-CH2-BZ-NO2, A:Si, X:F
【００１１】一般式（Ｉ）又は（ＩＩ）で表される化合
物はその製造方法によらず、本発明に用いることができ
るが、以下にその具体的製造方法の一例を説明する。一
般式（Ｉ）で表される化合物は、一般には例えば下記一
般式（ＩＩＩ）[0011] The compound represented by the general formula (I) or (II) can be used in the present invention regardless of its manufacturing method, and one example of a specific manufacturing method will be explained below. The compound represented by the general formula (I) is generally, for example, the following general formula (III).
【００１２】0012
【化４】
で表されるハロゲン化四級アンモニウム塩化合物を、下
記一般式（ＩＶ）A halogenated quaternary ammonium salt compound represented by the following general formula (IV)
【００１３】Ｙ２ ＡＸ６ ・・・・〔ＩＶ〕[0013]Y2 AX6 ・・・[IV]
【００１
４】001
4]
【化５】
と水中、もしくはアルコール中で７０℃前後に加温して
反応させることにより得られる。又、一般式（ＩＩ）
におけるカチオン成分は一般に、例えば下記一般式（Ｖ
）Ａｒ′Ｙ ・・・（Ｖ）
〔式中Ａｒ′は一般式（ＩＩ）におけるＡｒ１ ，Ａｒ
２と同意義、Ｙは塩素、臭素等のハロゲン基を表わす〕
で表わされる、ハロゲン化化合物とトリエチレンジアミ
ンをジメチルホルムアミド、Ｎ−メチルピロリドン等の
反応に不活性な有機溶媒中、７０℃前後に加温して例え
ば２４時間反応させることにより得られる。It can be obtained by reacting with [Chemical formula 5] in water or alcohol by heating to around 70°C. Also, general formula (II)
The cationic component in is generally represented by, for example, the following general formula (V
)Ar'Y...(V) [In the formula, Ar' is Ar1, Ar in general formula (II)
Same meaning as 2, Y represents a halogen group such as chlorine or bromine]
It can be obtained by reacting a halogenated compound represented by the formula with triethylenediamine in an organic solvent inert to the reaction, such as dimethylformamide or N-methylpyrrolidone, at a temperature of about 70°C for, for example, 24 hours.
【００１５】本発明に、使用し得る樹脂成分としては、
静電荷像現像用トナーに適した公知の種々のものが使用
できる。例えば、スチレン系樹脂、スチレンアクリル系
共重合樹脂、ポリエステル系樹脂、エポキシ系樹脂及び
これらの混合樹脂、また、これらのアルキル側鎖にアミ
ノ基を有するもの等がある。トナー中の一般式（Ｉ）又
は（ＩＩ）で表される化合物の含有率は、樹脂１００重
量部に対して０．１〜２０重量部が好ましく、より好ま
しく０．５〜１５重量部である。[0015] Resin components that can be used in the present invention include:
Various known toners suitable for developing electrostatic images can be used. Examples include styrene resins, styrene-acrylic copolymer resins, polyester resins, epoxy resins, mixed resins thereof, and those having amino groups in their alkyl side chains. The content of the compound represented by formula (I) or (II) in the toner is preferably 0.1 to 20 parts by weight, more preferably 0.5 to 15 parts by weight, based on 100 parts by weight of the resin. .
【００１６】一般式（Ｉ）又は（ＩＩ）で表される化合
物の含有率が、少なすぎると帯電性の向上効果が期待で
きずまた過剰であるとトナーの品質が低下するので好ま
しくない。本発明で用いる着色剤としては、従来から用
いられているものであれば特に制限されるものではなく
、黒色トナーを得るには、カーボンブラック等を使用す
る。また、一般式（Ｉ）又は（ＩＩ）で表される化合物
は通常白色なので、青、赤、黄等のカラートナーに含有
せしめてもよく、この場合は相当する色の染顔料等から
なる着色剤を用いる。If the content of the compound represented by formula (I) or (II) is too low, no improvement in charging properties can be expected, and if it is excessive, the quality of the toner will deteriorate, which is not preferable. The colorant used in the present invention is not particularly limited as long as it is conventionally used, and carbon black or the like is used to obtain a black toner. Furthermore, since the compound represented by the general formula (I) or (II) is usually white, it may be included in a color toner such as blue, red, yellow, etc. In this case, it is colored with a dye or pigment of the corresponding color. using an agent.
【００１７】着色剤の含有率は、樹脂１００重量部に対
して３〜２０重量部とするのが好ましい。更に、本発明
のトナーには、一般式（Ｉ）又は（ＩＩ）で表される化
合物とは別に、公知のものを含めて他の帯電制御剤、例
えば、ニグロシン系染料、４級アンモニウム塩、ポリア
ミン樹脂等を含有せしめてもよい。その他、本発明のト
ナー構成成分として、定着性や流動性を向上させるため
、低分子量オレフィン重合体や微粉末シリカ等の添加剤
を含有せしめてもよい。The content of the colorant is preferably 3 to 20 parts by weight per 100 parts by weight of the resin. Furthermore, in addition to the compound represented by formula (I) or (II), the toner of the present invention may contain other charge control agents, including known ones, such as nigrosine dyes, quaternary ammonium salts, It may also contain a polyamine resin or the like. In addition, additives such as a low molecular weight olefin polymer and finely powdered silica may be included as the toner constituent components of the present invention in order to improve fixing properties and fluidity.
【００１８】トナーの製造法としては、上記の各成分を
ニーダー等で混練し冷却後、粉砕し分級すればよい。
又、本発明のトナーは二成分系現像剤の他に、カプセル
化トナーや重合トナー及びマグネタイト含有トナー等の
いわゆる一成分系現像剤（磁性トナー）にも適用するこ
とができる。トナーの平均粒径は５〜２０μｍが好適で
ある。本発明のトナーと混合して現像剤を形成するキャ
リアーとしては、特に制限はないが１０〜２００μｍの
平均粒径を有する鉄粉が好ましい。なお、鉄粉の粒径に
は特に制限はない。この場合、連続使用時の耐久性向上
の目的でフッ素系樹脂等をコーティングしたいわゆるコ
ーティングキャリアーも使用することができる。又、フ
ェライト系、マグネタイト系等を初めとする公知の他の
キャリアーも使用することができる。これらキャリアー
は、トナー１重量部に対して、５〜１００重量部使用す
ることが好ましい。The toner can be produced by kneading the above-mentioned components in a kneader or the like, cooling them, and then pulverizing and classifying them. Furthermore, the toner of the present invention can be applied not only to two-component developers but also to so-called one-component developers (magnetic toners) such as encapsulated toners, polymerized toners, and magnetite-containing toners. The average particle size of the toner is preferably 5 to 20 μm. The carrier to be mixed with the toner of the present invention to form a developer is not particularly limited, but iron powder having an average particle size of 10 to 200 μm is preferable. Note that there is no particular restriction on the particle size of the iron powder. In this case, a so-called coated carrier coated with a fluororesin or the like can also be used for the purpose of improving durability during continuous use. Other known carriers including ferrite carriers, magnetite carriers, etc. can also be used. It is preferable to use 5 to 100 parts by weight of these carriers per 1 part by weight of the toner.
【００１９】[0019]
【実施例】以下、実施例により本発明を更に詳細に説明
するが本発明はその要旨を超えない限り以下の実施例に
よりなんら制限されるものではない。なお、下記実施例
中単に「部」とあるのはいずれも「重量部」を意味する
ものとする。[Examples] The present invention will be explained in more detail with reference to Examples below, but the present invention is not limited to the following Examples in any way unless it exceeds the gist thereof. In addition, in the following examples, the term "parts" simply means "parts by weight."
【００２０】実施例−１
スチレン系樹脂 １００部
（三洋化成社製、商品名ＳＢＭ−６００）カーボンブラ
ック １０部
（三菱化成（株）製＃４４）
例示化合物（１） ２部
上記の材料を配合混練し、粉砕分級して平均粒子径１１
μｍの黒色トナーを得た。Example-1 Styrenic resin 100 parts (manufactured by Sanyo Kasei Co., Ltd., trade name SBM-600) Carbon black 10 parts (Mitsubishi Kasei Corporation #44) Exemplary compound (1) 2 parts Blended with the above materials Knead, crush and classify to obtain an average particle size of 11
A black toner of μm was obtained.
【００２１】このトナー５部と平均粒径約１００μｍの
フッ素系樹脂コーティングキャリアー１００部とを混合
、攪拌して現像剤を作製した。次いでこの現像剤を有機
光導電体を感光体とする複写機で実写したところ、白地
部の地汚れ、いわゆるカブリの少ない鮮明なコピーが得
られた。
実施例−２
帯電制御剤として、例示化合物（１）２部のかわりに例
示化合物（６）を２部使用する以外は、実施例−１と全
く同様にしたところ、実施例−１と同様に良好なコピー
が得られた。A developer was prepared by mixing and stirring 5 parts of this toner and 100 parts of a fluororesin coated carrier having an average particle size of about 100 μm. When this developer was then used in a copying machine using an organic photoconductor as a photoreceptor, clear copies were obtained with little background smudge, or so-called fog, in the white background. Example-2 The same procedure as in Example-1 was carried out except that 2 parts of Exemplified Compound (6) was used instead of 2 parts of Exemplified Compound (1) as a charge control agent. A good copy was obtained.
【００２２】実施例−３
帯電制御剤として例示化合物（１）２部のかわりに例示
化合物（７）を３部使用する以外は実施例−１と全く同
様にしたところ、実施例−１と同様に良好なコピーが得
られた。
実施例−４
帯電制御剤として例示化合物（１）２部のかわりに例示
化合物（１２）を２部使用する以外は、実施例−１と全
く同様にしたところ、実施例−１と同様に良好なコピー
が得られた。Example 3 The same procedure as in Example 1 was carried out except that 3 parts of Exemplified Compound (7) was used instead of 2 parts of Exemplified Compound (1) as a charge control agent. A good copy was obtained. Example-4 The same procedure as in Example-1 was performed except that 2 parts of Exemplified Compound (12) was used instead of 2 parts of Exemplified Compound (1) as a charge control agent, and the results were as good as in Example-1. A copy was obtained.
【００２３】実施例−５
帯電制御剤として例示化合物（１）２部のかわりに例示
化合物（１３）を２部使用する以外は、実施例−１と全
く同様にしたところ、実施例−１と同様に良好なコピー
が得られた。
実施例−６
帯電制御剤として例示化合物（１）２部のかわりに例示
化合物（１４）を２部使用する以外は、実施例−１と全
く同様にしたところ、実施例−１と同様に良好なコピー
が得られた。Example 5 The same procedure as in Example 1 was carried out except that 2 parts of Exemplified Compound (13) was used instead of 2 parts of Exemplified Compound (1) as a charge control agent. Good copies were also obtained. Example-6 The same procedure as in Example-1 was performed except that 2 parts of Exemplified Compound (14) was used instead of 2 parts of Exemplified Compound (1) as a charge control agent, and the results were as good as in Example-1. A copy was obtained.
【００２４】実施例−７
帯電制御剤として、例示化合物（１）２部のかわりに例
示化合物（１５）を５部使用する以外は、実施例−１と
全く同様にしたところ、実施例−１と同様に良好なコピ
ーが得られた。
実施例−８
帯電制御剤として、例示化合物（１）２部のかわりに例
示化合物（１６）を４部使用する以外は実施例−１と全
く同様にしたところ、実施例−１と同様に良好なコピー
が得られた。Example 7 Example 1 was carried out in exactly the same manner as in Example 1, except that 5 parts of Exemplified Compound (15) was used as a charge control agent instead of 2 parts of Exemplified Compound (1). A good copy was obtained as well. Example-8 The same procedure as in Example-1 was performed except that 4 parts of Exemplified Compound (16) was used instead of 2 parts of Exemplified Compound (1) as a charge control agent, and the results were as good as in Example-1. A copy was obtained.
【００２５】実施例−９
帯電制御剤として例示化合物（１）２部のかわりに例示
化合物（１７）を６部使用する以外は実施例−１と全く
同様にしたところ、実施例−１と同様に良好なコピーが
得られた。
実施例−１０
帯電制御剤として例示化合物（１）２部のかわりに例示
化合物（２９）を３部使用する以外は実施例−１と全く
同様にしたところ、実施例−１と同様に良好なコピーが
得られた。Example 9 The same procedure as in Example 1 was carried out except that 6 parts of Exemplified Compound (17) was used instead of 2 parts of Exemplified Compound (1) as a charge control agent. A good copy was obtained. Example-10 The same procedure as Example-1 was carried out except that 3 parts of Exemplified Compound (29) was used instead of 2 parts of Exemplified Compound (1) as a charge control agent. As a result, similar to Example-1, good results were obtained. A copy was obtained.
【００２６】実施例−１１
帯電制御剤として例示化合物（１）２部のかわりに例示
化合物（３２）を３部使用する以外は実施例−１と全く
同様にしたところ、実施例−１と同様に良好なコピーが
得られた。
実施例−１２
帯電制御剤として例示化合物（１）２部のかわりに例示
化合物（３３）を２部使用する以外は実施例−１と全く
同様にしたところ、実施例−１と同様に良好なコピーが
得られた。Example 11 The same procedure as in Example 1 was carried out except that 3 parts of Exemplified Compound (32) was used instead of 2 parts of Exemplified Compound (1) as a charge control agent. A good copy was obtained. Example-12 The same procedure as Example-1 was carried out except that 2 parts of Exemplified Compound (33) was used instead of 2 parts of Exemplified Compound (1) as a charge control agent. As a result, similar to Example-1, good results were obtained. A copy was obtained.
【００２７】比較例−１
材料として例示化合物（１）を用いなかった以外は実施
例−１と同様にして現像剤を製造し実写に供した所、カ
ブリの多いコピー品質の悪いコピーが得られた。Comparative Example-1 A developer was produced in the same manner as in Example-1 except that the exemplified compound (1) was not used as a material, and when it was used for actual copying, copies with poor quality were obtained with a lot of fog. Ta.
【００２８】[0028]
【発明の効果】本発明の静電荷像現像用トナーは、連続
複写によるコピーの汚れ等の発生しない高品質の静電荷
像現像用トナーである。Effects of the Invention The toner for developing electrostatic images of the present invention is a high quality toner for developing electrostatic images that does not cause stains on copies due to continuous copying.
Claims (1)
る静電荷像現像用トナーにおいて、下記一般式（Ｉ）ま
たは（ＩＩ） で表される化合物を１種以上含有するこ
とを特徴とする静電荷像現像用トナー。 【化１】 【化２】 （式中、Ｒ１ ，Ｒ２ ，Ａｒ１ ，Ａｒ２ はそれぞ
れ置換もしくは未置換のアルキル基または置換もしくは
未置換のアラルキル基を表し、Ａはチタン，ジルコニウ
ム、又はケイ素原子を表し、Ｘはフッ素，塩素、又は臭
素原子を表す。）[Claim 1] An electrostatic image developing toner comprising at least a resin and a colorant, characterized in that it contains one or more compounds represented by the following general formula (I) or (II): Toner for developing electrostatic images. [Chemical 1] [Chemical 2] (wherein R1, R2, Ar1, Ar2 each represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aralkyl group, and A represents a titanium, zirconium, or silicon atom. , X represents a fluorine, chlorine, or bromine atom.)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3071236A JPH04306665A (en) | 1991-04-03 | 1991-04-03 | Tonner for electrostatic charge image development |
| EP91114929A EP0475263B1 (en) | 1990-09-12 | 1991-09-04 | Electrostatic image-developing toner |
| DE69125899T DE69125899T2 (en) | 1990-09-12 | 1991-09-04 | Toner for developing electrostatic images |
| US07/757,211 US5166030A (en) | 1990-09-12 | 1991-09-10 | Electrostatic image-developing toner containing a quaternary ammonium charge controlling agent |
| AU83796/91A AU8379691A (en) | 1990-09-12 | 1991-09-10 | Electrostatic image-developing toner |
| CA002051162A CA2051162A1 (en) | 1990-09-12 | 1991-09-11 | Electrostatic image-developing toner |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3071236A JPH04306665A (en) | 1991-04-03 | 1991-04-03 | Tonner for electrostatic charge image development |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04306665A true JPH04306665A (en) | 1992-10-29 |
Family
ID=13454861
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3071236A Pending JPH04306665A (en) | 1990-09-12 | 1991-04-03 | Tonner for electrostatic charge image development |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04306665A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5545502A (en) * | 1992-12-14 | 1996-08-13 | Mitsubishi Chemical Corporation | Electrostatic image-developing toner |
-
1991
- 1991-04-03 JP JP3071236A patent/JPH04306665A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5545502A (en) * | 1992-12-14 | 1996-08-13 | Mitsubishi Chemical Corporation | Electrostatic image-developing toner |
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