JPH047748B2 - - Google Patents
Info
- Publication number
- JPH047748B2 JPH047748B2 JP25186A JP25186A JPH047748B2 JP H047748 B2 JPH047748 B2 JP H047748B2 JP 25186 A JP25186 A JP 25186A JP 25186 A JP25186 A JP 25186A JP H047748 B2 JPH047748 B2 JP H047748B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- water
- aluminum
- orthophthalodinitrile
- chlorophthalocyanine
- 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
Links
- 238000006243 chemical reaction Methods 0.000 claims description 19
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 12
- 229910052782 aluminium Inorganic materials 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- HUVXQFBFIFIDDU-UHFFFAOYSA-N aluminum phthalocyanine Chemical compound [Al+3].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 HUVXQFBFIFIDDU-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、アルミクロロフタロシアニンの製造
法に関するものである。
〔従来の技術〕
アルミクロロフタロシアニンは、近年、レーザ
−プリンター等に使用される有機光電導体の電荷
発生層の材料として注目されている。その製造法
としては、オルソフタロジニトリルと塩化アルミ
ニウムを加熱反応させる方法が一般的である。従
来法では、単にオルソフタロジニトリルと塩化ア
ルミとを混合して、加熱反応させる。
〔発明が解決しようとする問題点〕
従来法の如き反応手法では、反応のコントロー
ルができない。即ち極端な場合反応が全く進行し
ない場合があつたり、反応が暴走的に起り、塩酸
ガスが突沸状態で飛び出す等の欠点があつた。そ
の結果として反応生成物の再現性が低かつた。
〔問題点を解決するための手段〕
本発明者等は、安定に制御できるアルミクロロ
フタロシアニンを製造する方法を鋭意検討の結
果、反応系に適度な水を共存させる時、反応が極
めて円滑に進み、反応の制御が可能となり、又、
共存水の管理を強化すると極めて再現性も高い事
を見い出し、本発明を完成させるに到つた。
即ち、本発明は、オルソフタロジニトリルと塩
化アルミニウムとを反応せしめてアルミクロロフ
タロシアニンを製造する際、反応系中に所定量の
水を共存させる事を特徴とするアルミクロロフタ
ロシアニンの製造法に関するものである。
その製造は、一般にオルソフタロジニトリル、
塩化アルミニウム、及び水を反応器中に添加し
て、その後反応器を180〜250℃に加熱することに
よつて行う。その際添加する水の量は、原料中の
オルソフタロジニトリル、塩化アルミニウム、及
びその他共存物中に含まれる水を考慮する事が必
要であり、反応系中の水と添加する水の総量が
1.6〜2.2重量％となる量とする。水の総量が1.6重
量％以下の場合、反応が全く進行しないか、仮に
反応が進行しても収率が低い方向である。又、
2.2重量％以上の場合、反応が速やかに反応しす
ぎて暴走反応をおこし制御不能となる為好ましく
ない方向である。オルソフタロジニトリルと塩化
アルミニウムとの仕込み比率は、モル比で８：１
〜２：１が好ましく、最適比率は４：１である。
なお反応は上記の如く通常３成分のみで反応させ
る事が好ましいが、反応を緩慢にする為に、反応
生成物であるアルミクロロフタロシアニン、アル
キルベンゼン、キノリン等の高沸点有機物、塩化
ナトリウム等の無機物を共存させることも有り得
る。
上記の如く得られたアルミクロロフタロシアニ
ンは、脂肪族炭化水素、芳香族炭化水素、アルコ
ール等の単独溶媒若しくは混合溶媒で洗浄して、
アルミクロロフタロシアニンを得る。得られたア
ルミクロロフタロシアニンのクロロ含有量は、
6.2〜12.0重量％、アルミ含有量は3.8〜4.4重量％
となる。
〔本発明の効果〕
以上の如く、反応系中に水を共存させる事によ
り、反応制御可能で且つ再現性のある工業的に実
施可能なアルミフタロシアニンの製造法を確立し
た。
〔実施例〕
実施例
１のガラス製の容器にオルソフタロジニトリ
ル100ｇ、塩化アルミニウム25ｇを添加、ついで
表−１に示す所定量の水を添加する。マントルヒ
ーターにより徐々に180℃まで昇温反応させた。
得られた反応生成物をトルエンで洗浄し、未反応
の原料を除去した。その結果を表−１に示す。
また、水を添加しない場合の結果も併記する。
なお、原料中に含まれる水の量はカールフイツ
シヤー水分計によりその量を求めた。
【表】DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a method for producing aluminum chlorophthalocyanine. [Prior Art] Aluminum lophthalocyanine has recently attracted attention as a material for charge generation layers of organic photoconductors used in laser printers and the like. A common method for producing it is to heat-react orthophthalodinitrile and aluminum chloride. In the conventional method, orthophthalodinitrile and aluminum chloride are simply mixed and reacted by heating. [Problems to be solved by the invention] Reactions cannot be controlled using conventional reaction techniques. That is, in extreme cases, the reaction may not proceed at all, or the reaction may occur runaway, resulting in disadvantages such as hydrochloric acid gas ejecting in a bumping state. As a result, the reproducibility of the reaction products was low. [Means for Solving the Problems] As a result of intensive study on a method for producing aluminum chlorophthalocyanine that can be stably controlled, the present inventors have found that when an appropriate amount of water is coexisting in the reaction system, the reaction proceeds extremely smoothly. , it becomes possible to control the reaction, and
We have discovered that the reproducibility is extremely high when we strengthen the management of coexisting water, and have completed the present invention. That is, the present invention relates to a method for producing aluminum chlorophthalocyanine, which is characterized in that a predetermined amount of water is allowed to coexist in the reaction system when producing aluminum chlorophthalocyanine by reacting orthophthalodinitrile and aluminum chloride. It is. Its production generally involves orthophthalodinitrile,
This is done by adding aluminum chloride and water into the reactor and then heating the reactor to 180-250°C. The amount of water added at this time needs to take into consideration the water contained in orthophthalodinitrile, aluminum chloride, and other coexisting substances in the raw materials, and the total amount of water in the reaction system and water added must be
The amount should be 1.6 to 2.2% by weight. When the total amount of water is 1.6% by weight or less, the reaction does not proceed at all, or even if the reaction does proceed, the yield tends to be low. or,
If the amount is 2.2% by weight or more, the reaction will be too rapid, causing a runaway reaction and becoming uncontrollable, which is not preferable. The molar ratio of orthophthalodinitrile and aluminum chloride is 8:1.
~2:1 is preferred, with the optimum ratio being 4:1.
As mentioned above, it is usually preferable to carry out the reaction with only three components, but in order to slow down the reaction, high-boiling point organic substances such as aluminum chlorophthalocyanine, alkylbenzene, and quinoline, and inorganic substances such as sodium chloride, which are reaction products, are added. It is possible for them to coexist. The aluminum chlorophthalocyanine obtained as described above is washed with a single solvent or a mixed solvent such as an aliphatic hydrocarbon, an aromatic hydrocarbon, or an alcohol.
Obtain aluminophthalocyanine. The chloro content of the obtained aluminum chlorophthalocyanine is
6.2~12.0wt%, aluminum content is 3.8~4.4wt%
becomes. [Effects of the Invention] As described above, by coexisting water in the reaction system, an industrially practicable method for producing aluminum phthalocyanine that can control the reaction and is reproducible has been established. [Example] 100 g of orthophthalodinitrile and 25 g of aluminum chloride are added to the glass container of Example 1, and then a predetermined amount of water shown in Table 1 is added. The reaction temperature was gradually raised to 180°C using a mantle heater.
The obtained reaction product was washed with toluene to remove unreacted raw materials. The results are shown in Table-1. The results when no water was added are also shown. The amount of water contained in the raw materials was determined using a Karl Fischer moisture meter. 【table】
Claims (1)
とを反応せしめてアルミクロロフタロシアニンを
製造する際、反応系中に水を共存させることを特
徴とするアルミクロロフタロシアニンの製造法。 ２ 共存させる水の量が1.6〜2.2重量％である特
許請求の範囲第１項記載のアルミクロロフタロシ
アニンの製造法。[Scope of Claims] 1. A method for producing aluminum chlorophthalocyanine, which comprises allowing water to coexist in the reaction system when producing aluminum chlorophthalocyanine by reacting orthophthalodinitrile and aluminum chloride. 2. The method for producing aluminum chlorophthalocyanine according to claim 1, wherein the amount of water coexisting is 1.6 to 2.2% by weight.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25186A JPS62158284A (en) | 1986-01-07 | 1986-01-07 | Production of aluminum chlorophthalocyanin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25186A JPS62158284A (en) | 1986-01-07 | 1986-01-07 | Production of aluminum chlorophthalocyanin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62158284A JPS62158284A (en) | 1987-07-14 |
| JPH047748B2 true JPH047748B2 (en) | 1992-02-12 |
Family
ID=11468722
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP25186A Granted JPS62158284A (en) | 1986-01-07 | 1986-01-07 | Production of aluminum chlorophthalocyanin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62158284A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6133862B2 (en) | 2011-08-03 | 2017-05-24 | サン ケミカル コーポレイション | Phthalocyanine synthesis |
| EP3303480B1 (en) | 2015-06-04 | 2022-03-09 | Sun Chemical Corporation | Chlorinated copper phthalocyanine pigments |
-
1986
- 1986-01-07 JP JP25186A patent/JPS62158284A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62158284A (en) | 1987-07-14 |
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