JPS58111049A - Metallic complex salt compound and toner for electrophotography containing said compound - Google Patents
Metallic complex salt compound and toner for electrophotography containing said compoundInfo
- Publication number
- JPS58111049A JPS58111049A JP56209271A JP20927181A JPS58111049A JP S58111049 A JPS58111049 A JP S58111049A JP 56209271 A JP56209271 A JP 56209271A JP 20927181 A JP20927181 A JP 20927181A JP S58111049 A JPS58111049 A JP S58111049A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- complex salt
- represent
- toner
- salt compound
- 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
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
- G03G9/09—Colouring agents for toner particles
- G03G9/0906—Organic dyes
- G03G9/091—Azo dyes
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Photoreceptors In Electrophotography (AREA)
- Developing Agents For Electrophotography (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は金属錯塩化合物およびこの化合物の使用法Ｋｌ
ｌする。DETAILED DESCRIPTION OF THE INVENTION The present invention provides a metal complex compound and a method of using the compound.
I do it.
さらに詳ＪＩＫは、本発明の第一の発明は、一般（式中
、ｘｌおよびｘｓは水素原子、低級アル中ル基。In more detail, JIK explains that the first invention of the present invention is a general (formula, in which xl and xs are hydrogen atoms, lower alkyl groups.
低級アルコ命シ基、ニトロ基またはハｑゲン厘子を表わ
し、ｘｌとＸｍ４！同じであっても異なっていてもよ（
、ｍおよびｄは１〜Ｓの整数を表わし、Ｒ凰およびＲ３
はハロゲン原子を表わし、Ｒ１と−は同じであっても異
なり【もよ＜ｓ”およびｎ′は１〜！Ｉの整数を表わし
、Ｒ３およびＲ４は水素原子またはニトロ基を表わし、
Ｍはりａムまたはコバルト原子な表わし、に■は水素ナ
トリウム、カリウムまたはアンモニウムイオンを表わす
。）で表わされる新規な金属錯塩化合物である。さらに
、纂二の発明は、この化合物な含有する電子写真トナー
！ある。Represents a lower alkyl group, a nitro group, or a halogen group, and xl and Xm4! It doesn't matter if it's the same or different (
, m and d represent integers from 1 to S, R 凰 and R3
represents a halogen atom, R1 and - may be the same or different, and n' represents an integer from 1 to !I, R3 and R4 represent a hydrogen atom or a nitro group,
M represents am or cobalt atom, and ■ represents sodium hydrogen, potassium or ammonium ion. ) is a novel metal complex compound represented by Furthermore, Shinji's invention is an electrophotographic toner containing this compound! be.
本発明の第一の発明の金属錯塩化合物は、下記一般式
（式中、Ｒ１、”＊＊ ＲＩｓ ”４、ｎおよび思′は
、ＩＩＮＣ定義した通りである。）で表わされるジアゾ
成分を常法によりジアゾ化し、とのジアゾ化物を、下記
一般式
（式中、ｘｌ、）５． ｃｍおよびｄはＷＩＫ定義した
通りである。）で表わされるアゾ成分と常法に従いカッ
プリングするととにより、下記一般式（式中、Ｘｌ、
Ｘｌ、Ｒ１，Ｒ１，Ｒ＄、Ｒ４，ｖｒ 、 ｍ’、 ｔ
ｍおよびｄはＩｒＫ定義した通りである。）で表わされ
る峰ノアゾ化合物を合成し１次にこのモノ１ゾ化合物な
水あるいは有横溶謀中常法によリフロム仕付与剤あるい
はコバルト化付与剤で加熱処理することにより％＾収率
で得ることができる０本発明で出いられる上記一般式（
２）で表わされるジアゾ成分としては、例えば５−タａ
ロー２−ア（ノフェノール％４−タロｏ −２−アミノ
フェノール、５−グａムー２−１イノフェノール、４−
曹一ドー２−１ｉノフェノール％へ５−シタａｏ −２
−１ζノフェノール、４．６−ジ゛りｏ ａ −２−ア
（ノフェノール、へ４．６−）リクロロー２−１イノフ
ェノール、６−り０ロー４−ニトロ−２−アζノフエノ
ール、４−りｏ ａ −５−ニトロ−２−１（ノフェノ
ール、４−りａロー６−ニトロ−２−ア（ノフェノール
、６−プロムー４−ニドＥ２−２−アミノフェノール等
があげられる。The metal complex salt compound of the first aspect of the present invention always contains a diazo component represented by the following general formula (wherein R1, "** RIs" 4, n and '' are as defined by IINC). The diazotized product is converted into a diazotized product according to the following general formula (in the formula, xl)5. cm and d are as defined by WIK. ) by coupling with an azo component represented by the following general formula (wherein, Xl,
Xl, R1, R1, R$, R4, vr, m', t
m and d are as defined by IrK. ) is synthesized, and then this mono-monozo compound is heated with water or a refloming agent or a cobaltization agent using a conventional method to obtain a yield of %^. 0 The above general formula (
As the diazo component represented by 2), for example, 5-taa
rho2-a(nophenol%4-talo-2-aminophenol, 5-guamo-2-1inophenol, 4-
Soichi Do 2-1i Nophenol% to 5-Sita ao-2
-1ζinophenol, 4.6-di-a-2-a(nophenol, 4.6-)lichloro-2-1inophenol, 6-di-o-4-nitro-2-aζnophenol, Examples include 4-ri-a-5-nitro-2-1(nophenol), 4-ri-a-6-nitro-2-a(nophenol), 6-promo-4-nidoE2-2-aminophenol, and the like.
本発明の第２の発明は、下記一般式
（式中、Ｒ１、Ｒ８、Ｒ，、Ｒ，、ｘ、、 ｘ、、ｍ、
ａ／二臆。The second invention of the present invention is based on the following general formula (wherein, R1, R8, R,, R,, x,, x,, m,
a/Two cows.
ｎ’、Ｍおよびに■は上で定義した・通りである。）で
表わされる金属錯塩化合物な含有する電子写真用トナー
である。n', M and ■ are as defined above. ) is an electrophotographic toner containing a metal complex compound represented by:
金属錯塩化合物な含有する電子トナーについては１例え
ば、持分＠４ｌ−２０１５ｉＳ、特公昭４５−１７９５
５および特公昭４５−２７５９４号公報等により既知で
あるが、本発明の一般式（１）で表わされる金属錯塩化
合物を含有するトナーはこれら公報に記載のものに比較
して、帯電性において優れており、また変異原性試験（
工−ムズテスト）においても陰性を示すものである。さ
らにまた本二明の金属錯塩化合物は、耐熱性、耐水性。Regarding electronic toners containing metal complex compounds, for example, 1.
5 and Japanese Patent Publication No. 45-27594, the toner containing the metal complex compound represented by the general formula (1) of the present invention has superior charging properties compared to those described in these publications. and mutagenicity test (
It also shows a negative result in the engineering test). Furthermore, the metal complex salt compound of Nimei is heat resistant and water resistant.
耐光性に優れていることから各種樹脂の着色剤および木
工等の塗料として好適に使用することができる。Due to its excellent light resistance, it can be suitably used as a coloring agent for various resins and as a paint for woodworking, etc.
以下実施例により本発明の詳細な説明するが。The present invention will be explained in detail below with reference to Examples.
部とは１重量部であ□る。Part means 1 part by weight.
実施例１
１４４部の４−夕０ロー２−１（ノフェノールな２６部
の濃塩酸および水４００部と共にかきまぜた俵、氷冷し
０〜５Ｃとし、亜硝酸ナトリ３五４９部を加え、ｊｌ温
で２時間かきまぜてジアゾ化した。このジアゾ化物なＯ
〜５Ｃで水３００部。Example 1 144 parts of 4-2-1 bales (stirred with 26 parts of nophenolic concentrated hydrochloric acid and 400 parts of water, cooled on ice to 0-5C, added 3549 parts of sodium nitrite, The diazotization was carried out by stirring for 2 hours at Jl temperature.This diazotized O
~300 parts water at 5C.
１０部の水酸化ナトリウムおよび２部５部の５−ヒトｃ
１ｄＰシー２−ナフトー０−１ニジジッドの混合液に注
入しカップリング反応な行った俵、次の構造式を有する
モノアゾ化合物を単離した。10 parts sodium hydroxide and 2 parts 5 parts 5-human c
A monoazo compound having the following structural formula was isolated by injecting it into a mixture of 1 dP C2-naphthol 0-1 dizidide and carrying out a coupling reaction.
このモノアゾ化合物のペーストを１２０ＩＫのエチレン
グリコールに溶解し、５部の水酸化ナトリウムおよび１
７．４部のりＯムサリチル酸ナトリウムを加え、１１０
〜１２０Ｃで５時間かきまぜクロム化を行った俵、５０
Ｃまで冷却し、内容物にｔｏｓのｍ鐙を加え、コンゴレ
ッド酸性として常温で生成物ｋｃＩ別単離し、５０〜６
０Ｃ滅１乾燥して下記式で示される黒色黴看末のクロム
錯塩化合物４８部な得た。This monoazo compound paste was dissolved in 120 IK ethylene glycol, 5 parts sodium hydroxide and 1
Add 7.4 parts of glue O sodium musalicylate, and make 110
~Bales chromed by stirring at 120C for 5 hours, 50
Cool to C, add tos m stirrup to the contents, and isolate the product kcI separately at room temperature as Congo red acid.
The mixture was dried at 0C to obtain 48 parts of a black mold-like chromium complex compound represented by the following formula.
このクロム錯塩化合物をジメチル本ル五ア（ドに溶解さ
せると黒色（最大吸収波長５６８ｓｓｎ）を呈した。When this chromium complex salt compound was dissolved in dimethyl chloride, it exhibited a black color (maximum absorption wavelength 568ssn).
このクロム錯塩化合物を電子写真トナーの着色および電
荷制御剤として用いたところ、このトナーからは、カプ
リのない鮮明な画像、長期間にわたるくり返し使用にも
変化のない安定な複写画像を得ることができた。When this chromium complex salt compound was used as a coloring and charge control agent for electrophotographic toner, it was possible to obtain clear images without capri and stable copied images that did not change even after repeated use over a long period of time. Ta.
またポリスチレン系、ポリエステル系、ポリエチレン系
樹脂の着色剤として使用した場合、耐水耐光性に富み、
鮮明な色調を有する黒色の着色樹脂を得ることができた
。In addition, when used as a coloring agent for polystyrene, polyester, and polyethylene resins, it has excellent water and light resistance.
A black colored resin with a clear color tone could be obtained.
実施例２
υ
のモノアゾ化合物４６部を２５０部のエチレングリコー
ルに溶解し、２０部の濃硫酸および４９部の４０％硫酸
クロム水溶液を加え、９５〜１１０Ｃで２時間かきまぜ
タロム化を行った。Example 2 46 parts of the monoazo compound υ was dissolved in 250 parts of ethylene glycol, 20 parts of concentrated sulfuric acid and 49 parts of a 40% chromium sulfate aqueous solution were added, and the mixture was stirred at 95 to 110 C for 2 hours to perform taromization.
次に内容物を室温まで放冷し、この中に実施例１で得た
モノアゾ化合物４４部および水酸化ナト９９１８０部を
加え、９５〜１００Ｃで３時間かきまぜ、実施例１に準
じ後処理を実施して下記式で示される黒色黴桧末のりａ
ム錯塩化合物９０部な得た。Next, the contents were allowed to cool to room temperature, 44 parts of the monoazo compound obtained in Example 1 and 99,180 parts of sodium hydroxide were added thereto, stirred at 95 to 100 C for 3 hours, and post-treated according to Example 1. Black cypress powder paste a shown by the following formula
90 parts of a complex salt compound were obtained.
このクロム錯塩化合物なジメチルホルムア建ドに溶解さ
せると黒色（最大吸収波長５７５ｎａｓ）を呈した。When this chromium complex salt compound was dissolved in dimethylformamide, it exhibited a black color (maximum absorption wavelength 575 nas).
このクロム錯塩化合物な電子写真トナーの着色および電
荷制御剤として用いたところ、このトナーからは、カプ
リのない鮮明な画像、長期間にわたるくり返し使用にも
変化のない安定な複写画像な得ることができた。When this chromium complex compound was used as a coloring and charge control agent in electrophotographic toner, it was possible to obtain clear images without capri and stable reproduced images that did not change even after repeated use over a long period of time. Ta.
マタボリスチレン系、ポリエステル系、ボ暢エチレン系
樹脂の着色剤とＬ−ｃｆ用した場合、耐水、耐光性に富
み、鮮明な色ａｔ有する黒色の着色樹脂な得ることがで
きた。When L-CF was used with a matabori styrene-based, polyester-based, or bouncy ethylene-based resin colorant, a black colored resin with excellent water resistance and light resistance and a clear color at could be obtained.
以下本実施例と同様の方法によつ【、金属錯塩化合物を
得た。A metal complex salt compound was obtained in the same manner as in this example.
実施例１０
１ａ９部の５−二トＤ−４−りｃＩＨ−２−７ｆノフエ
ノールを実施例１と同様にしてジアゾ化し。Example 10 9 parts of 1a of 5-di-D-4-lycIH-2-7f nophenol was diazotized in the same manner as in Example 1.
２＆５部の５−ヒドロ中シー２−ナフトアニリドとカッ
プリングして次の構造式な有するモノアゾ化合物を単一
した。Coupling with 2 & 5 parts of 2-naphthanilide in 5-hydro prepared a monoazo compound having the following structural formula.
得られたモノアゾ化合物のベーストを実施例１と同様に
処理して下記式
で示される黒色値粉末のクロム錯塩化合物４５１１を得
た。The obtained base of the monoazo compound was treated in the same manner as in Example 1 to obtain chromium complex salt compound 4511 as a black value powder represented by the following formula.
このクロム錯塩化合物をジメチルホルム１（ドに溶解す
ると黒色（最大吸収＃ＩＬ長５８９ｕｍ）をこのクロム
塩化合物をポリスチレン系、ボリエへ
ステル糸、ポリエチレン系、ポリアクリル１＃、、ポリ
クレタｙｊｉ＆樹脂の着色剤として使用した場合。When this chromium complex salt compound is dissolved in dimethylform 1 (de), it becomes black (maximum absorption #IL length 589 um). When used as an agent.
耐水、耐光性に富み、鮮明な色調を有する黒色の着色樹
脂を得ることができた。A black colored resin with excellent water resistance and light resistance and a clear color tone could be obtained.
またこのクロム錯塩化合物を電子写真トナーの着色およ
び電荷制御剤として用いたところ、このトナーからは、
カプリのない鮮明なＩＬ長期関にわたるくり返し使用に
も変化のない安定な禎写画曽な得ることができた。In addition, when this chromium complex salt compound was used as a coloring and charge control agent for electrophotographic toner, the toner produced
I was able to obtain a clear IL image with no capri, which was stable and unaltered even after repeated use over a long period of time.
以下１本実施例と同様の方法によって、金属錯塩化合物
を得た。A metal complex salt compound was obtained in the same manner as in this example.
Claims (1)
、低級、アルコ命シ基、ニトロ基マたはハロゲン原子を
豪わし、ｘｌとｘ怠は肯じであっても異なっていてもよ
（、ｍおよびｄは１〜Ｓの整数を表わし％ Ｒ１および
Ｒｓはハロゲン原子を表わし、ＲＩと１．は肯じであっ
ても異なっていてもよい、１Ｂおよび鳳′は１〜Ｓの整
数を表わしｂ Ｒ１および１１４は水素原子またはニド
ａ基を表わし１Ｍはクロムまたはコバルト原子を表わし
、Ｋ■は水嵩、ナトリウム、カリウムまたはアンモニク
ムイオンを褒わす、）で表わされる金属錯塩化合物。 ２下記一般式 （式中、ｘ哀およびｘｌは水素原子、低級アル中ル基。 低級アルコ命シ基、ニトロ基またはハロゲン原子を表わ
し、ｘｌとＸｓは同じであっても異なってもよ（１ｍお
よびｄは１〜５の整数を表わし、Ｒ１およびＲｓはハロ
ゲン原子を褒わし、Ｒ１とＲ，は崗じ″１％ｂつても異
なっていてもよい、１１＃よびｎ′は１〜Ｓの整数を表
わし、ＲｓおよびＩＩ４は水素原子または品トロ基な表
わし、Ｍはクロムまたはコバルト電子を表わし、にΦは
水素、ナトリウム、力Ｖラムまたはアンモニウムイオν
を表わす、）で表わされる金属錯塩化合物を含有するこ
とを特徴とする電子写真用トナー。[Scope of Claims] The following general formula (wherein XI and may be the same or different (, m and d represent integers from 1 to S, % R1 and Rs represent halogen atoms, RI and 1 may be the same or different) , 1B and O' represent integers from 1 to S, R1 and 114 represent a hydrogen atom or a group, 1M represents a chromium or cobalt atom, and K represents a water volume, sodium, potassium or ammonium ion. A metal complex compound represented by the following general formula (where x and xl represent a hydrogen atom, a lower alkyl group, a lower alkyl group, a nitro group, or a halogen atom, and xl and Xs are the same). (1m and d represent integers from 1 to 5, R1 and Rs represent halogen atoms, R1 and R may be the same or different by 1%, 11 # and n' represent an integer from 1 to S, Rs and II4 represent a hydrogen atom or a hydrogen atom, M represents a chromium or cobalt electron, and Φ represents hydrogen, sodium, force V ram or ammonium ion ν
An electrophotographic toner characterized by containing a metal complex compound represented by ).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56209271A JPS58111049A (en) | 1981-12-25 | 1981-12-25 | Metallic complex salt compound and toner for electrophotography containing said compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56209271A JPS58111049A (en) | 1981-12-25 | 1981-12-25 | Metallic complex salt compound and toner for electrophotography containing said compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58111049A true JPS58111049A (en) | 1983-07-01 |
| JPS6361347B2 JPS6361347B2 (en) | 1988-11-29 |
Family
ID=16570176
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56209271A Granted JPS58111049A (en) | 1981-12-25 | 1981-12-25 | Metallic complex salt compound and toner for electrophotography containing said compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58111049A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61101558A (en) * | 1984-10-23 | 1986-05-20 | Hodogaya Chem Co Ltd | Metal complex salt compound and toner for electrophotography |
| JPS61155464A (en) * | 1984-12-28 | 1986-07-15 | Hodogaya Chem Co Ltd | Metal complex salt compound and toner for electrophotography |
| JPS6311952A (en) * | 1986-07-03 | 1988-01-19 | Canon Inc | Dry type toner for electrophotography |
| JPS6375077A (en) * | 1986-09-18 | 1988-04-05 | Hodogaya Chem Co Ltd | Resin powder coating composition for electrostatic coating |
| JPH02105864A (en) * | 1988-08-31 | 1990-04-18 | Basf Ag | Preparation of 1:2-chromium complex azo dye solution |
| EP1426830A1 (en) * | 2002-12-06 | 2004-06-09 | Orient Chemical Industries, Ltd. | Charge control agent and toner for electrostatic image development |
| WO2014092125A1 (en) | 2012-12-13 | 2014-06-19 | 保土谷化学工業株式会社 | Production method for charge control agent |
-
1981
- 1981-12-25 JP JP56209271A patent/JPS58111049A/en active Granted
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61101558A (en) * | 1984-10-23 | 1986-05-20 | Hodogaya Chem Co Ltd | Metal complex salt compound and toner for electrophotography |
| JPH043432B2 (en) * | 1984-10-23 | 1992-01-23 | ||
| JPH0475263B2 (en) * | 1984-12-28 | 1992-11-30 | ||
| JPS61155464A (en) * | 1984-12-28 | 1986-07-15 | Hodogaya Chem Co Ltd | Metal complex salt compound and toner for electrophotography |
| JPS6311952A (en) * | 1986-07-03 | 1988-01-19 | Canon Inc | Dry type toner for electrophotography |
| JPH0547828B2 (en) * | 1986-07-03 | 1993-07-19 | Canon Kk | |
| JPS6375077A (en) * | 1986-09-18 | 1988-04-05 | Hodogaya Chem Co Ltd | Resin powder coating composition for electrostatic coating |
| JPH02105864A (en) * | 1988-08-31 | 1990-04-18 | Basf Ag | Preparation of 1:2-chromium complex azo dye solution |
| EP1426830A1 (en) * | 2002-12-06 | 2004-06-09 | Orient Chemical Industries, Ltd. | Charge control agent and toner for electrostatic image development |
| US7094513B2 (en) | 2002-12-06 | 2006-08-22 | Orient Chemical Industries, Ltd. | Charge control agent and toner for electrostatic image development |
| WO2014092125A1 (en) | 2012-12-13 | 2014-06-19 | 保土谷化学工業株式会社 | Production method for charge control agent |
| US9056884B2 (en) | 2012-12-13 | 2015-06-16 | Hodogaya Chemical Co., Ltd. | Process for producing a charge control agent |
| KR20150097490A (en) | 2012-12-13 | 2015-08-26 | 호도가야 가가쿠 고교 가부시키가이샤 | Production method for charge control agent |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6361347B2 (en) | 1988-11-29 |
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