JPS6339842A - Bis (4-diphenylaminophenyl)ether and production thereof - Google Patents
Bis (4-diphenylaminophenyl)ether and production thereofInfo
- Publication number
- JPS6339842A JPS6339842A JP18272486A JP18272486A JPS6339842A JP S6339842 A JPS6339842 A JP S6339842A JP 18272486 A JP18272486 A JP 18272486A JP 18272486 A JP18272486 A JP 18272486A JP S6339842 A JPS6339842 A JP S6339842A
- Authority
- JP
- Japan
- Prior art keywords
- ether
- diphenylaminophenyl
- bis
- potassium carbonate
- copper
- 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
- CIEDPTNTMUYRJI-UHFFFAOYSA-N n,n-diphenyl-4-[4-(n-phenylanilino)phenoxy]aniline Chemical compound C=1C=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1OC(C=C1)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 CIEDPTNTMUYRJI-UHFFFAOYSA-N 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims abstract description 18
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims abstract description 16
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910000027 potassium carbonate Inorganic materials 0.000 claims abstract description 9
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052802 copper Inorganic materials 0.000 claims abstract description 6
- 239000010949 copper Substances 0.000 claims abstract description 6
- 239000002904 solvent Substances 0.000 claims abstract description 4
- VHEGXFQQYZIMMF-UHFFFAOYSA-N 1-iodo-4-(4-iodophenoxy)benzene Chemical compound C1=CC(I)=CC=C1OC1=CC=C(I)C=C1 VHEGXFQQYZIMMF-UHFFFAOYSA-N 0.000 claims abstract 3
- 239000000126 substance Substances 0.000 claims 2
- -1 4-diphenylaminophenyl Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 10
- 238000006243 chemical reaction Methods 0.000 abstract description 5
- 239000000463 material Substances 0.000 abstract description 4
- 239000003054 catalyst Substances 0.000 abstract description 3
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 108091008695 photoreceptors Proteins 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical class C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0601—Acyclic or carbocyclic compounds
- G03G5/0618—Acyclic or carbocyclic compounds containing oxygen and nitrogen
Landscapes
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Photoreceptors In Electrophotography (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明ハ、新規なビス（４−ジフェニルアミノフェニル
）エーテルおよびその製法に関する。DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a novel bis(4-diphenylaminophenyl) ether and a method for producing the same.
（＠明の構成）
本発明の化合物は１文献未載の新規化合物であって、構
造式（１）
で示されるビス（４−ジフェニルアミノフェニル）エー
テルである。該化合物は、有機感光体（ＤＰＣ）のキャ
リア輸送剤（ＣＴ材）として有用である。(@Ming Structure) The compound of the present invention is a novel compound that has not been described in any literature, and is a bis(4-diphenylaminophenyl) ether represented by the structural formula (1). The compound is useful as a carrier transport agent (CT material) for an organic photoreceptor (DPC).
類似の化合物としてトリフェニルアミン２量体が知られ
ているが、この化合物と同様の作用効果が認められる。Triphenylamine dimer is known as a similar compound, and effects similar to those of this compound are observed.
本発明のｆと金物は、以下に示す方法によって失透する
ことができる。The f and hardware of the present invention can be devitrified by the method shown below.
（Ｉ）
上記の式に示すように、４．４’−ショートジフェニル
エーテルとジフェニルアミンおヨヒ炭酸カリウム全反応
させることにより１本発明の化合物（１）が製造される
。この反応においては、溶媒としてニトロベンゼンを用
い、触媒として銅を用いる。(I) As shown in the above formula, the compound (1) of the present invention is produced by completely reacting 4,4'-short diphenyl ether with diphenylamine and potassium carbonate. In this reaction, nitrobenzene is used as a solvent and copper is used as a catalyst.
この方法において、４．４’−ショートフェニルエーテ
ルとジフェニルアミンおよび炭酸カリウムの使用割合は
特に限定されず、広い範囲から適宜選択されるが、収率
よく本発明の化合物を得るにハ、 ’ ＋ ”−ショー
トジフェニルエーテルに対して、ジフェニルアミンと炭
酸カリウムを等モ／？Ｊｌないし過剰モル量用いるのが
よく、好ましくは４．４′−ショートジフェニルエーテ
ルに対し／テ。In this method, the proportions of 4,4'-short phenyl ether, diphenylamine, and potassium carbonate to be used are not particularly limited and may be appropriately selected from a wide range, but in order to obtain the compound of the present invention in good yield. - It is preferable to use diphenylamine and potassium carbonate in equimolar to molar excess amounts relative to 4,4'-short diphenyl ether, preferably in molar excess relative to 4,4'-short diphenyl ether.
ジフェニルアミン全２〜４倍モル、炭酸カリウムを１〜
４倍モルである。2 to 4 times the total amount of diphenylamine, 1 to 4 times the mole of potassium carbonate
It is 4 times the mole.
ま九、触媒である銅の量は特に限定されるものではない
が、好ましくは４．４′−ショートジフェニルエーテル
に対して０．１〜１倍モル使用するのがよい。４．４′
−ショートジフェニルエーテルのニトロベンゼンに対す
る量に特に限定はないが。(9) The amount of copper as a catalyst is not particularly limited, but it is preferably used in an amount of 0.1 to 1 mole based on 4,4'-short diphenyl ether. 4.4'
- There is no particular limitation on the amount of short diphenyl ether relative to nitrobenzene.
好１ Ｌ ＜ ハ’ Ｉ”−ショートジフェニルエーテ
ル／ニトロベンゼン（重量比）の値が１．０以下である
のがよい。上記の反応は、一般に１００〜３００Ｃ，好
ましくは１００〜２００Ｃの温度で行なわれ、１〜２日
で完結する。It is preferable that the value of 1 L <H'I''-short diphenyl ether/nitrobenzene (weight ratio) is 1.0 or less. The above reaction is generally carried out at a temperature of 100 to 300C, preferably 100 to 200C. , completed in 1 to 2 days.
反る終了後は常法にしたがい５例えば、濾過。After the warp is finished, follow the usual method (5), for example, filtration.
濃縮、結晶化、再結品等１適常の分離手段で１反応液か
ら本発明の化合物金得ることができる。The compound gold of the present invention can be obtained from one reaction solution by a suitable separation method such as concentration, crystallization, or re-crystallization.
（実施例） 次に、実施例によシ本発明を芒らに具体的に説明する。(Example) Next, the present invention will be specifically explained using examples.
空冷冷却管を設けＬ５００ｍｌの容器に ４ 、４’−
ショートジフェニルエーテル３０ｆ、ジフェニルアミン
２８−８７ 、炭酸カリウム３０ｔ、銅７１゜ニトロベ
ンゼン２００９′ｆｒ：仕込み、１９０Ｃ，３０時間攪
拌しながら反応させた。反応液に６５７のテトラヒドロ
フランを加え、塩類の結晶全濾過し。4,4'- in a L500ml container with an air cooling condenser tube.
Short diphenyl ether 30f, diphenylamine 28-87, potassium carbonate 30t, copper 71° nitrobenzene 2009'fr were charged and reacted at 190C for 30 hours with stirring. 657 tetrahydrofuran was added to the reaction solution, and all salt crystals were filtered.
テトラヒドロフランとＴＨＦの大部分を留去し。Most of the tetrahydrofuran and THF were distilled off.
アセトンを加え冷所に放置し九ところ、２４ｖのビス（
４−ジフェニルアミノフェニル）エーテルを得友（収率
９（１９６，単離収率６７％）。Add acetone, leave it in a cool place, and then connect it with a 24V screw (
4-diphenylaminophenyl) ether (yield 9 (196, 67% isolated yield)).
生成物のマススペクトルはＭ ５０４ｉ示し。The mass spectrum of the product shows M504i.
融点は１５７〜１５８Ｃである。生成物の赤外線吸収ス
ペクトル（日本分光ＩＲＡ−１型、ＫＢｒペレット）訃
よび１８ｃ ＮＭＲスペクトル（ＪＥＯＬ ＦＸ−９
０Ｑ、溶媒ＴＨＦ−ｄ、）を、それぞれ図面に示した。The melting point is 157-158C. Infrared absorption spectrum of product (JASCO IRA-1 type, KBr pellet) and 18c NMR spectrum (JEOL FX-9
0Q, solvent THF-d,) are shown in the drawing, respectively.
（発明の効果）
本発明によれば ４ 、４’−ショートジフェニルエー
テルとジフェニルアミンおよび炭酸カリウムを反１δさ
せることにより、有機感光体のキャリア輸送材として有
用な構造式（Ｉ）で示されるビス（４−ジフェニルアミ
ノフェニル）エーテルｔ 容易Ｋ ’４ることができる
。(Effects of the Invention) According to the present invention, bis(4) represented by the structural formula (I), which is useful as a carrier transport material for organic photoreceptors, is produced by diluting 4,4'-short diphenyl ether, diphenylamine, and potassium carbonate by 1 delta. -diphenylaminophenyl) ether t can be easily K'4.
第１図は実施例によシ得られた化合物の′３ＣＮＭＲス
ペクトル、第２図は同赤外線吸収スペクトルである。FIG. 1 shows the '3CNMR spectrum of the compound obtained in Example, and FIG. 2 shows the infrared absorption spectrum of the same.
Claims (2)
テル。(1) Structural formula (I) ▲Mathematical formulas, chemical formulas, tables, etc.▼Bis(4-diphenylaminophenyl) ether shown by (I).
ロベンゼンを溶媒として、炭酸カリウムおよび銅の存在
下、ジフエニルアミンと反応させることを特徴とする構
造式（ I ） ▲数式、化学式、表等があります▼（ I ） で示されるビス（４−ジフエニルアミノフエニル）エー
テルの製法。(2) Structural formula (I) characterized by reacting 4,4'-diiododiphenyl ether with diphenylamine in the presence of potassium carbonate and copper using nitrobenzene as a solvent ▲There are mathematical formulas, chemical formulas, tables, etc.▼ A method for producing bis(4-diphenylaminophenyl) ether represented by (I).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18272486A JPS6339842A (en) | 1986-08-05 | 1986-08-05 | Bis (4-diphenylaminophenyl)ether and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18272486A JPS6339842A (en) | 1986-08-05 | 1986-08-05 | Bis (4-diphenylaminophenyl)ether and production thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6339842A true JPS6339842A (en) | 1988-02-20 |
Family
ID=16123335
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18272486A Pending JPS6339842A (en) | 1986-08-05 | 1986-08-05 | Bis (4-diphenylaminophenyl)ether and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6339842A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5338633A (en) * | 1991-05-23 | 1994-08-16 | Mitsubishi Kasei Corporation | Electrophotographic photoreceptor |
| KR20220148774A (en) * | 2019-12-09 | 2022-11-07 | (주) 카스윈 | Two-head simultaneous manufacturing device for inner and outer of work |
-
1986
- 1986-08-05 JP JP18272486A patent/JPS6339842A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5338633A (en) * | 1991-05-23 | 1994-08-16 | Mitsubishi Kasei Corporation | Electrophotographic photoreceptor |
| KR20220148774A (en) * | 2019-12-09 | 2022-11-07 | (주) 카스윈 | Two-head simultaneous manufacturing device for inner and outer of work |
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