JPS6136023B2 - - Google Patents
Info
- Publication number
- JPS6136023B2 JPS6136023B2 JP8011677A JP8011677A JPS6136023B2 JP S6136023 B2 JPS6136023 B2 JP S6136023B2 JP 8011677 A JP8011677 A JP 8011677A JP 8011677 A JP8011677 A JP 8011677A JP S6136023 B2 JPS6136023 B2 JP S6136023B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- lower alkoxy
- compound
- ethylcarbazole
- 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
- -1 disazo compound Chemical class 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 28
- 108091008695 photoreceptors Proteins 0.000 description 14
- 238000000034 method Methods 0.000 description 12
- 239000000463 material Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000000862 absorption spectrum Methods 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- FZNXRFYRXBFQMX-UHFFFAOYSA-N (4-nitrophenyl)methylphosphonic acid Chemical compound OP(O)(=O)CC1=CC=C([N+]([O-])=O)C=C1 FZNXRFYRXBFQMX-UHFFFAOYSA-N 0.000 description 3
- QXZQSVXTSRPYJJ-UHFFFAOYSA-N 4-[2-[6-[2-(4-aminophenyl)ethenyl]-9-ethylcarbazol-3-yl]ethenyl]aniline Chemical compound C1=C2C3=CC(C=CC=4C=CC(N)=CC=4)=CC=C3N(CC)C2=CC=C1C=CC1=CC=C(N)C=C1 QXZQSVXTSRPYJJ-UHFFFAOYSA-N 0.000 description 3
- YUYGLHDPWGWFQB-UHFFFAOYSA-N 9-ethylcarbazole-3,6-dicarbaldehyde Chemical compound O=CC1=CC=C2N(CC)C3=CC=C(C=O)C=C3C2=C1 YUYGLHDPWGWFQB-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 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
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229910052711 selenium Inorganic materials 0.000 description 3
- 239000011669 selenium Substances 0.000 description 3
- LIZRSSDYPJIIFZ-UHFFFAOYSA-N 9-ethyl-3,6-bis[2-(4-nitrophenyl)ethenyl]carbazole Chemical compound C1=C2C3=CC(C=CC=4C=CC(=CC=4)[N+]([O-])=O)=CC=C3N(CC)C2=CC=C1C=CC1=CC=C([N+]([O-])=O)C=C1 LIZRSSDYPJIIFZ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HOQAPVYOGBLGOC-UHFFFAOYSA-N 1-ethyl-9h-carbazole Chemical compound C12=CC=CC=C2NC2=C1C=CC=C2CC HOQAPVYOGBLGOC-UHFFFAOYSA-N 0.000 description 1
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 1
- JFGQHAHJWJBOPD-UHFFFAOYSA-N 3-hydroxy-n-phenylnaphthalene-2-carboxamide Chemical compound OC1=CC2=CC=CC=C2C=C1C(=O)NC1=CC=CC=C1 JFGQHAHJWJBOPD-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- SRKRSWKCLVMJRZ-UHFFFAOYSA-N [S-2].S.[SeH2].[Cd+2] Chemical compound [S-2].S.[SeH2].[Cd+2] SRKRSWKCLVMJRZ-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920006038 crystalline resin Polymers 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- OKVJWADVFPXWQD-UHFFFAOYSA-N difluoroborinic acid Chemical compound OB(F)F OKVJWADVFPXWQD-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001470 polyketone Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 229920002102 polyvinyl toluene Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- Photoreceptors In Electrophotography (AREA)
- Indole Compounds (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8011677A JPS5414967A (en) | 1977-07-05 | 1977-07-05 | Novel disazo compound and its preparation |
| US05/921,086 US4251614A (en) | 1977-07-05 | 1978-06-30 | Novel disazo compounds, process for the preparation of same and application of said disazo compounds and analogues thereof to electrophotographic sensitive materials |
| DE2829606A DE2829606C3 (de) | 1977-07-05 | 1978-07-05 | Bisazoverbindungen, Verfahren zu ihrer Herstellung und deren Verwendung für die Herstellung von elektrophotographischen Aufzeichnungsmaterialien |
| US06/152,061 US4293492A (en) | 1977-07-05 | 1980-05-20 | Disazo compounds derived from 3,6-bis(styryl)-9-ethylcarbazole |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8011677A JPS5414967A (en) | 1977-07-05 | 1977-07-05 | Novel disazo compound and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5414967A JPS5414967A (en) | 1979-02-03 |
| JPS6136023B2 true JPS6136023B2 (US06650917-20031118-M00005.png) | 1986-08-15 |
Family
ID=13709211
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8011677A Granted JPS5414967A (en) | 1977-07-05 | 1977-07-05 | Novel disazo compound and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5414967A (US06650917-20031118-M00005.png) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0412892Y2 (US06650917-20031118-M00005.png) * | 1986-07-31 | 1992-03-26 |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5632458A (en) * | 1979-08-28 | 1981-04-01 | Asahi Glass Co Ltd | 3,6-distyrylcarbazole derivative and its preparation |
| DE3447685A1 (de) * | 1983-12-28 | 1985-07-18 | Ricoh Co., Ltd., Tokio/Tokyo | Disazoverbindungen, verfahren zu ihrer herstellung und ein diese verbindungen enthaltendes elektrophotographisches element |
| WO2005054957A1 (ja) | 2003-12-01 | 2005-06-16 | Ricoh Company, Ltd. | 電子写真感光体、画像形成方法、画像形成装置、画像形成装置用プロセスカートリッジ |
| EP2000856B1 (en) | 2007-06-04 | 2011-02-02 | Ricoh Company, Ltd. | Electrophotographic photoreceptor, image forming apparatus, and process cartridge |
| JP5386884B2 (ja) | 2007-09-10 | 2014-01-15 | 株式会社リコー | ナフタレンテトラカルボン酸ジイミド誘導体、及び該ナフタレンテトラカルボン酸ジイミド誘導体を用いた電子写真感光体 |
| EP2078988B1 (en) | 2008-01-10 | 2013-06-26 | Ricoh Company, Ltd. | Image forming apparatus and image forming method |
| US8173343B2 (en) | 2008-07-15 | 2012-05-08 | Ricoh Company, Ltd. | Electrophotographic photoconductor, image forming apparatus using the same, and process cartridge |
| JP5401933B2 (ja) | 2008-11-10 | 2014-01-29 | 株式会社リコー | 電子写真感光体、および該電子写真感光体を用いた画像形成方法、画像形成装置、画像形成装置用プロセスカートリッジ |
| JP5403350B2 (ja) | 2009-09-10 | 2014-01-29 | 株式会社リコー | 電子写真感光体、電子写真方法、電子写真装置、並びに電子写真装置用プロセスカートリッジ |
| JP5477625B2 (ja) | 2009-09-10 | 2014-04-23 | 株式会社リコー | 電子写真感光体、画像形成装置及びプロセスカートリッジ |
| JP5652641B2 (ja) | 2010-07-07 | 2015-01-14 | 株式会社リコー | 電子写真感光体及び画像形成装置、画像形成装置用プロセスカートリッジ |
| JP5903999B2 (ja) | 2011-06-16 | 2016-04-13 | 株式会社リコー | 感光体ドラム、画像形成装置、画像形成方法、及びプロセスカートリッジ |
| JP6095107B2 (ja) | 2013-01-29 | 2017-03-15 | 高砂香料工業株式会社 | トリフェニルアミン誘導体、並びにそれを用いた電荷輸送材料及び電子写真感光体 |
| KR102125518B1 (ko) | 2016-02-08 | 2020-06-22 | 다카사고 고료 고교 가부시키가이샤 | 트리페닐아민 유도체, 그것을 사용하여 생성된 전하 수송 재료 및 전자 사진 감광체 |
-
1977
- 1977-07-05 JP JP8011677A patent/JPS5414967A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0412892Y2 (US06650917-20031118-M00005.png) * | 1986-07-31 | 1992-03-26 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5414967A (en) | 1979-02-03 |
