JPH0588218B2 - - Google Patents
Info
- Publication number
- JPH0588218B2 JPH0588218B2 JP6904185A JP6904185A JPH0588218B2 JP H0588218 B2 JPH0588218 B2 JP H0588218B2 JP 6904185 A JP6904185 A JP 6904185A JP 6904185 A JP6904185 A JP 6904185A JP H0588218 B2 JPH0588218 B2 JP H0588218B2
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- aromatic amino
- amino derivative
- formula
- derivative represented
- 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
- -1 aromatic amino derivative Chemical class 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 150000005171 halobenzenes Chemical class 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 108091008695 photoreceptors Proteins 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- 229910052711 selenium Inorganic materials 0.000 description 3
- 239000011669 selenium Substances 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- UDHAWRUAECEBHC-UHFFFAOYSA-N 1-iodo-4-methylbenzene Chemical compound CC1=CC=C(I)C=C1 UDHAWRUAECEBHC-UHFFFAOYSA-N 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 238000005282 brightening Methods 0.000 description 1
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 1
- 229940045348 brown mixture Drugs 0.000 description 1
- 230000002925 chemical effect Effects 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Photoreceptors In Electrophotography (AREA)
Description
技術分野
本発明は新規な芳香族アミノ誘導体及びその製
造法に関する。
従来技術
従来、電子写真方式おいて使用される感光体の
有機光導電性素材としてポリ−Ｎ−ビニルカルバ
ゾールをはじめ数多くの材料が提案されている。
ここにいう「電子写真方式」とは一般に光導電
性の感光体を、まず暗所で例えばコロナ放電など
により帯電せしめ、ついで露光部のみの電荷を選
択的に放電させることにより静電潜像を得て、こ
の潜像部をトナーなどを用いた現像手段で可視化
して画像を形成するようにした画像形成法の一つ
である。このような電子写真方式における感光体
に要求される基本的な特性としては、１）暗所に
おいて適当な電位に帯電されること、２）暗所に
おける電荷の放電が少ないこと、３）光照射によ
り速やかに電荷を放電すること、などが挙げられ
る。しかし、従来の光導電性有機材料はこれらの
要求をかならずしも満足していないのが実状であ
る。
一方、セレンや酸化亜鉛は光導電性無機材料と
して知られており、中でもセレンは広く実用に供
されている。しかし、最近電子写真のプロセスの
点から、感光体に対する種々の要求、即ち一例と
して前述の基本的特性に加えて、例えばその形状
についても可撓性のあるベルト状の感光体などが
要求されるようになつてきている。しか、セレン
の場合は一般にこのような形状のものに作成する
ことは困難である。
目 的
電子写真用の有機光導電性素材、蛍光増白剤と
して使用することができ、特に電子写真用の上記
要望を満足する有機光導電性材料として有用な芳
香族アミノ誘導体及びその製造法を提供すること
である。
構 成
第１の発明は一般式（）
TECHNICAL FIELD The present invention relates to a novel aromatic amino derivative and a method for producing the same. BACKGROUND OF THE INVENTION Conventionally, many materials including poly-N-vinylcarbazole have been proposed as organic photoconductive materials for photoreceptors used in electrophotography. The "electrophotographic method" referred to here generally means that a photoconductive photoreceptor is first charged in a dark place by, for example, corona discharge, and then the electrostatic latent image is formed by selectively discharging the charge only in the exposed areas. This is one of the image forming methods in which an image is formed by visualizing this latent image using a developing means using toner or the like. The basic characteristics required of a photoreceptor in such an electrophotographic method are 1) to be charged to an appropriate potential in a dark place, 2) to have little discharge of charge in a dark place, and 3) to be able to withstand light irradiation. Examples include discharging charges more quickly. However, the reality is that conventional photoconductive organic materials do not necessarily satisfy these requirements. On the other hand, selenium and zinc oxide are known as photoconductive inorganic materials, and among them selenium is widely used in practical use. However, in recent years, various requirements have been placed on photoreceptors in terms of the electrophotographic process. For example, in addition to the above-mentioned basic characteristics, a flexible belt-like photoreceptor is also required in terms of shape. It's starting to look like this. However, in the case of selenium, it is generally difficult to make it into such a shape. Purpose: To provide an aromatic amino derivative that can be used as an organic photoconductive material for electrophotography and a fluorescent brightening agent, and is particularly useful as an organic photoconductive material that satisfies the above requirements for electrophotography, and a method for producing the same. It is to provide. Configuration The first invention is the general formula ()
【化】
（式中Ｘは、酸素原子、硫黄原子を表わす。）
で表わされる芳香族アミノ誘導体であり、第２の
発明は一般式（）[C] (In the formula, X represents an oxygen atom or a sulfur atom.)
The second invention is an aromatic amino derivative represented by the general formula ()
【化】
（式中Ｘは酸素原子、硫黄原子を表わす。）で
表わされる。アミノ誘導体と下記一般式（）[Chemical formula] (In the formula, X represents an oxygen atom or a sulfur atom.) Amino derivatives and the following general formula ()
【化】
（式中Ｙはハロゲン原子を表わす。）で表わさ
れるハロベンゼン誘導体とを反応させることを特
徴とする下記一般式（）[Chemical formula] The following general formula () is characterized by reacting with a halobenzene derivative represented by (in the formula, Y represents a halogen atom)
【化】
（式中Ｘは一般式（）に同じ）で表わされる
芳香族アミノ誘導体の製造法である。
前記一般式（）ならびに（）中メチル基の
置換位置はメタおよびパラである。
本発明の芳香族アミノ誘導体（）は、一般式
（）で表わされるアミノ誘導体と一般式（）
で表わされるハロベンゼン誘導体とを、塩基性触
媒と、銅触媒の存在下、100℃から250℃程度の温
度において反応させることによつて製造される。
塩基性触媒としては、苛性ソーダ、苛性カリ、無
水炭酸ナリウム、無水炭酸カリウムなどを挙げる
ことができる。銅触媒としては銅粉、酸化銅、あ
るいは臭化銅、ヨー化銅などのハロゲン化銅を挙
げることができる。
反応は無溶媒、あるいは溶媒を使用しても良
い。使用する反応溶媒としてはトルエン、キシレ
ン、クロルベンゼン、Ｏ−ジクロルベンゼン、ニ
トロベンゼンなどのベンゼン系溶媒、Ｎ，Ｎ−ジ
メチルホルムアミド、Ｎ−メチルピロリドン、
１，３−ジメチル−２−イミダゾリジノン、ジメ
チルスルホキシドなどを挙げることができる。中
でも極性溶媒、例えばニトロベンゼン、１，３−
ジメチル−２−イミダゾリジノン、及びジメチル
スルホキシドが好適である。
反応温度は１）使用する溶媒の塩基性触媒に対
する安定性、２）縮合成分（一般式（）及び
（）の化合物）の反応性、３）前記塩基触媒中
における縮合剤としての反応性によつて広範囲に
選択することができる。例えば極性溶媒を用いる
ときは実際には100℃から250℃、好ましくは150
℃から250℃である。
しかし、反応時間の短縮又は活性の低い縮合剤
を使用するときはさらに高い温度でも良い。この
ようにして得られる本発明にかかわる新規な芳香
族アミノ誘導体を例示すれば、次の通りである。This is a method for producing an aromatic amino derivative represented by the formula (wherein X is the same as the general formula ()). The substitution positions of the methyl group in the general formulas () and () are meta and para. The aromatic amino derivative () of the present invention comprises an amino derivative represented by the general formula () and an amino derivative represented by the general formula ().
It is produced by reacting a halobenzene derivative represented by with a basic catalyst in the presence of a copper catalyst at a temperature of about 100°C to 250°C.
Examples of the basic catalyst include caustic soda, caustic potash, anhydrous sodium carbonate, anhydrous potassium carbonate, and the like. Examples of the copper catalyst include copper powder, copper oxide, and copper halides such as copper bromide and copper iodide. The reaction may be carried out without a solvent or with a solvent. The reaction solvents used include benzene solvents such as toluene, xylene, chlorobenzene, O-dichlorobenzene, and nitrobenzene, N,N-dimethylformamide, N-methylpyrrolidone,
Examples include 1,3-dimethyl-2-imidazolidinone and dimethyl sulfoxide. Among them, polar solvents such as nitrobenzene, 1,3-
Dimethyl-2-imidazolidinone and dimethyl sulfoxide are preferred. The reaction temperature depends on 1) the stability of the solvent used against the basic catalyst, 2) the reactivity of the condensation components (compounds of general formulas () and ()), and 3) the reactivity as a condensing agent in the basic catalyst. You can choose from a wide range of options. For example, when using polar solvents, it is actually 100°C to 250°C, preferably 150°C.
℃ to 250℃. However, when the reaction time is shortened or a condensing agent with low activity is used, a higher temperature may be used. Examples of the novel aromatic amino derivatives according to the present invention obtained in this way are as follows.
【化】[ka]
【化】
実施例 １
攪拌機を有した、500mlの三口丸底フラスコに、
４，4′−ジアミノジフエニルエーテル20.0g（0.1モ
ル）、４−ヨードトルエン87.2ｇ（0.4モル）、無
水炭酸カリウム55.3ｇ（0.4モル）、銅粉1.0ｇおよ
び200mlのニトロベンゼンを装入した。この混合
物を共沸により水を除去しながら、200〜210℃に
８時間加熱攪拌を行つた。
反応後、濾過によつて無水炭酸カリウムと銅粉
を除き、次いで水蒸気蒸留によつて、ニトロベン
ゼンを除く、残留油状物をトルエンに溶解し、ト
ルエン溶液を無水硫酸マグネシウムで乾燥した。
そして、トルエン留去後、この褐色混合物をシ
リカゲル（ワコーゲルＣ−200）500ｇとシクロヘ
キサン（溶出剤）を用いて、カラムクロマトにか
け、淡黄色の結晶36.7ｇ（収率65.5％）を得た。
酢酸エチル−エタノールの混合溶媒から再結晶し
て、４，4′−ビス（Ｎ，Ｎ−ジ−Ｐ−トリルアミ
ノ）ジフエニルエーテルの純品を得た。融点
134.0〜6.0℃であつた。赤外線吸収スペクトル
（KBr錠剤法）を図に示した。[C] Example 1 In a 500 ml three-necked round bottom flask equipped with a stirrer,
20.0 g (0.1 mol) of 4,4'-diaminodiphenyl ether, 87.2 g (0.4 mol) of 4-iodotoluene, 55.3 g (0.4 mol) of anhydrous potassium carbonate, 1.0 g of copper powder, and 200 ml of nitrobenzene were charged. This mixture was heated and stirred at 200 to 210° C. for 8 hours while removing water by azeotropy. After the reaction, anhydrous potassium carbonate and copper powder were removed by filtration, then nitrobenzene was removed by steam distillation, the residual oil was dissolved in toluene, and the toluene solution was dried over anhydrous magnesium sulfate. After distilling off the toluene, this brown mixture was subjected to column chromatography using 500 g of silica gel (Wako Gel C-200) and cyclohexane (eluent) to obtain 36.7 g of pale yellow crystals (yield: 65.5%).
Recrystallization from a mixed solvent of ethyl acetate and ethanol yielded pure 4,4'-bis(N,N-di-P-tolylamino)diphenyl ether. melting point
The temperature was 134.0-6.0℃. The infrared absorption spectrum (KBr tablet method) is shown in the figure.
【表】
実施例 ２〜４
実施例１と同様にして得られた芳香族アミノ誘
導体について表１に示す。[Table] Examples 2 to 4 Aromatic amino derivatives obtained in the same manner as in Example 1 are shown in Table 1.
【化】
効 果
以上の説明から明らかなように本発明に係る芳
香族アミノ誘導体は新規な化合物であつて、特に
電子写真用有機光導電性材料として有効なもので
ある。[Chemical Effect] As is clear from the above explanation, the aromatic amino derivative according to the present invention is a new compound, and is particularly effective as an organic photoconductive material for electrophotography.
図は４，4′−ビス（Ｎ，Ｎ−ジ−Ｐ−トリルア
ミノ）ジフエニルエーテルの赤外線吸収スペクト
ル図である。
The figure is an infrared absorption spectrum diagram of 4,4'-bis(N,N-di-P-tolylamino)diphenyl ether.
Claims (1)
示される芳香族アミノ誘導体。 ２ 一般式（） 【化】 （式中Ｘは酸素原子、硫黄原子を表わす。）で
表わされるアミノ誘導体と下記一般式（） 【式】 （式中Ｙはハロゲン原子を表す。）で表わされ
るハロベンゼン誘導体とを反応させることを特徴
とする下記一般式（） 【化】 （式中Ｘは前記に同じ） で表わされる芳香族アミノ誘導体の製造方法。[Claims] 1. An aromatic amino derivative represented by the general formula () (wherein, X represents an oxygen atom or a sulfur atom). 2 An amino derivative represented by the general formula () [formula] (wherein X represents an oxygen atom or a sulfur atom) and the following general formula () [formula] (wherein Y represents a halogen atom) A method for producing an aromatic amino derivative represented by the following general formula () (wherein X is the same as above), which comprises reacting the aromatic amino derivative with a halobenzene derivative.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6904185A JPS61229849A (en) | 1985-04-03 | 1985-04-03 | Aromatic amino derivative and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6904185A JPS61229849A (en) | 1985-04-03 | 1985-04-03 | Aromatic amino derivative and production thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61229849A JPS61229849A (en) | 1986-10-14 |
| JPH0588218B2 true JPH0588218B2 (en) | 1993-12-21 |
Family
ID=13391104
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6904185A Granted JPS61229849A (en) | 1985-04-03 | 1985-04-03 | Aromatic amino derivative and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61229849A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01136160A (en) * | 1987-11-24 | 1989-05-29 | Canon Inc | Electrophotographic sensitive body |
| JPH01136161A (en) * | 1987-11-24 | 1989-05-29 | Canon Inc | Electrophotographic sensitive body |
-
1985
- 1985-04-03 JP JP6904185A patent/JPS61229849A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61229849A (en) | 1986-10-14 |
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