DE3336595A1 - Neue bisazo-verbindungen, verfahren zu ihrer herstellung und unter verwendung dieser bisazo-verbindungen hergestellte elektrophotographische aufzeichnungsmaterialien - Google Patents
Neue bisazo-verbindungen, verfahren zu ihrer herstellung und unter verwendung dieser bisazo-verbindungen hergestellte elektrophotographische aufzeichnungsmaterialienInfo
- Publication number
- DE3336595A1 DE3336595A1 DE19833336595 DE3336595A DE3336595A1 DE 3336595 A1 DE3336595 A1 DE 3336595A1 DE 19833336595 DE19833336595 DE 19833336595 DE 3336595 A DE3336595 A DE 3336595A DE 3336595 A1 DE3336595 A1 DE 3336595A1
- Authority
- DE
- Germany
- Prior art keywords
- radical
- group
- recording material
- carbon atoms
- electrophotographic recording
- 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
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- 238000004519 manufacturing process Methods 0.000 title description 16
- -1 alkyl radical Chemical class 0.000 claims description 136
- 125000000217 alkyl group Chemical group 0.000 claims description 46
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 37
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
- 239000000126 substance Substances 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 27
- 125000005843 halogen group Chemical group 0.000 claims description 26
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 25
- 150000003254 radicals Chemical class 0.000 claims description 22
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 18
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- WQOWBWVMZPPPGX-UHFFFAOYSA-N 2,6-diaminoanthracene-9,10-dione Chemical compound NC1=CC=C2C(=O)C3=CC(N)=CC=C3C(=O)C2=C1 WQOWBWVMZPPPGX-UHFFFAOYSA-N 0.000 claims description 4
- 125000001725 pyrenyl group Chemical group 0.000 claims description 4
- FNIATMYXUPOJRW-UHFFFAOYSA-N cyclohexylidene Chemical class [C]1CCCCC1 FNIATMYXUPOJRW-UHFFFAOYSA-N 0.000 claims description 3
- PWAPCRSSMCLZHG-UHFFFAOYSA-N cyclopentylidene Chemical compound [C]1CCCC1 PWAPCRSSMCLZHG-UHFFFAOYSA-N 0.000 claims description 3
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 11
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims 3
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 2
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 2
- REHHBTUVMSHZNT-UHFFFAOYSA-N bromocyclohexatriene Chemical compound BrC1=CC=C=C[CH]1 REHHBTUVMSHZNT-UHFFFAOYSA-N 0.000 claims 2
- GPKUICFDWYEPTK-UHFFFAOYSA-N methoxycyclohexatriene Chemical compound COC1=CC=C=C[CH]1 GPKUICFDWYEPTK-UHFFFAOYSA-N 0.000 claims 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 2
- VHPJXYDOOWUMBR-UHFFFAOYSA-N 1,2-dichlorocyclohexa-1,3,5-triene Chemical compound ClC1=C[C]=CC=C1Cl VHPJXYDOOWUMBR-UHFFFAOYSA-N 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 1
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 claims 1
- 125000005577 anthracene group Chemical group 0.000 claims 1
- 235000021190 leftovers Nutrition 0.000 claims 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 1
- 239000010410 layer Substances 0.000 description 85
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 10
- 125000001309 chloro group Chemical group Cl* 0.000 description 10
- 229910052782 aluminium Inorganic materials 0.000 description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
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- 239000011230 binding agent Substances 0.000 description 7
- 125000001246 bromo group Chemical group Br* 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- 238000000862 absorption spectrum Methods 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
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- 238000006243 chemical reaction Methods 0.000 description 4
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
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- RILZRCJGXSFXNE-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]ethanol Chemical compound OCCC1=CC=C(OC(F)(F)F)C=C1 RILZRCJGXSFXNE-UHFFFAOYSA-N 0.000 description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/021—Disazo dyes characterised by two coupling components of the same type
-
- 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
- G03G5/0664—Dyes
- G03G5/0675—Azo dyes
- G03G5/0679—Disazo dyes
- G03G5/0683—Disazo dyes containing polymethine or anthraquinone groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Photoreceptors In Electrophotography (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17741982A JPS5966460A (ja) | 1982-10-08 | 1982-10-08 | 新規なジスアゾ化合物およびその製造方法 |
| JP231083A JPS59127050A (ja) | 1983-01-12 | 1983-01-12 | 電子写真用感光体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3336595A1 true DE3336595A1 (de) | 1984-04-12 |
| DE3336595C2 DE3336595C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1987-06-11 |
Family
ID=26335657
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19833336595 Granted DE3336595A1 (de) | 1982-10-08 | 1983-10-07 | Neue bisazo-verbindungen, verfahren zu ihrer herstellung und unter verwendung dieser bisazo-verbindungen hergestellte elektrophotographische aufzeichnungsmaterialien |
Country Status (3)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3515177A1 (de) * | 1984-04-27 | 1985-11-07 | Ricoh Co., Ltd., Tokio/Tokyo | Elektrophotographische originaldruckform und verfahren zur herstellung von druckplatten |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4537844A (en) * | 1982-10-08 | 1985-08-27 | Ricoh Co. Ltd. | Electrophotographic element containing disazo compound |
| US4833052A (en) * | 1988-08-02 | 1989-05-23 | Xerox Corporation | Bisazo photoconductive imaging members |
| FR2889954B1 (fr) * | 2005-08-26 | 2007-10-19 | Oreal | Colorants mixtes cationiques comprenant un chromophore anthraquinone et leur utilisation en colorant capillaire |
| JP5571387B2 (ja) | 2007-01-11 | 2014-08-13 | クリティカル・アウトカム・テクノロジーズ・インコーポレイテッド | 癌の治療のための化合物および方法 |
| EP2008995B1 (en) | 2007-06-29 | 2013-09-11 | Ricoh Company, Ltd. | Azo compound and method of preparing the azo compound |
| EP2225226B1 (en) | 2007-12-26 | 2016-08-17 | Critical Outcome Technologies, Inc. | Compounds and their use in a method for treatment of cancer |
| CA2999321A1 (en) | 2008-07-17 | 2010-01-21 | Critical Outcome Technologies Inc. | Thiosemicarbazone inhibitor compounds and cancer treatment methods |
| CA2999435A1 (en) | 2010-04-01 | 2011-10-06 | Critical Outcome Technologies Inc. | Compounds and method for treatment of hiv |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2412076A1 (de) * | 1973-03-16 | 1974-09-26 | Ciba Geigy Ag | Neue disazopigmente und verfahren zu deren herstellung |
| JPS56143437A (en) * | 1980-04-11 | 1981-11-09 | Ricoh Co Ltd | Electrophotographic receptor |
| US4440845A (en) * | 1981-06-08 | 1984-04-03 | Ricoh Co., Ltd. | Disazo compound, method of making same and electrophotographic element using same |
| JPS5935935B2 (ja) * | 1981-06-08 | 1984-08-31 | 株式会社リコー | 新規なジスアゾ化合物およびその製造方法 |
| US4537844A (en) * | 1982-10-08 | 1985-08-27 | Ricoh Co. Ltd. | Electrophotographic element containing disazo compound |
| US4546554A (en) * | 1982-11-30 | 1985-10-15 | Cissell Manufacturing Company | Clothes dryer having variable position motor and moisture sensor |
-
1983
- 1983-09-28 US US06/536,924 patent/US4537844A/en not_active Expired - Lifetime
- 1983-10-07 DE DE19833336595 patent/DE3336595A1/de active Granted
- 1983-10-10 GB GB08327020A patent/GB2131041B/en not_active Expired
-
1985
- 1985-06-20 US US06/747,150 patent/US4656257A/en not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3515177A1 (de) * | 1984-04-27 | 1985-11-07 | Ricoh Co., Ltd., Tokio/Tokyo | Elektrophotographische originaldruckform und verfahren zur herstellung von druckplatten |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2131041A (en) | 1984-06-13 |
| DE3336595C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1987-06-11 |
| GB8327020D0 (en) | 1983-11-09 |
| US4656257A (en) | 1987-04-07 |
| GB2131041B (en) | 1986-07-02 |
| US4537844A (en) | 1985-08-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| 8128 | New person/name/address of the agent |
Representative=s name: SCHWABE, H., DIPL.-ING. SANDMAIR, K., DIPL.-CHEM. |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |