DE1230031B - Process for the preparation of derivatives of naphthalene-1, 4, 5, 8-tetracarboxylic acid diimide - Google Patents
Process for the preparation of derivatives of naphthalene-1, 4, 5, 8-tetracarboxylic acid diimideInfo
- Publication number
- DE1230031B DE1230031B DEF43093A DEF0043093A DE1230031B DE 1230031 B DE1230031 B DE 1230031B DE F43093 A DEF43093 A DE F43093A DE F0043093 A DEF0043093 A DE F0043093A DE 1230031 B DE1230031 B DE 1230031B
- Authority
- DE
- Germany
- Prior art keywords
- tetracarboxylic acid
- naphthalene
- group
- derivatives
- preparation
- 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
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- RJCHVBHJXJDUNL-UHFFFAOYSA-N 5,8-dicarbamoylnaphthalene-1,4-dicarboxylic acid Chemical class C1=CC(C(O)=O)=C2C(C(=N)O)=CC=C(C(O)=N)C2=C1C(O)=O RJCHVBHJXJDUNL-UHFFFAOYSA-N 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 6
- -1 derivatives of naphthalene-1,4,5,8-tetracarboxylic acid imide Chemical class 0.000 claims description 4
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 125000005277 alkyl imino group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 150000000000 tetracarboxylic acids Chemical class 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- YTVNOVQHSGMMOV-UHFFFAOYSA-N naphthalenetetracarboxylic dianhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=C2C(=O)OC(=O)C1=C32 YTVNOVQHSGMMOV-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 2
- 229910000071 diazene Inorganic materials 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- OLAPPGSPBNVTRF-UHFFFAOYSA-N naphthalene-1,4,5,8-tetracarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1C(O)=O OLAPPGSPBNVTRF-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- DCDXFJZEEYCWFT-UHFFFAOYSA-N NN=C(O)C1=CC=C(C=2C(=CC=C(C1=2)C(=O)O)C(=O)O)C(O)=NN Chemical compound NN=C(O)C1=CC=C(C=2C(=CC=C(C1=2)C(=O)O)C(=O)O)C(O)=NN DCDXFJZEEYCWFT-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 206010034133 Pathogen resistance Diseases 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229960004909 aminosalicylic acid Drugs 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 230000002475 laxative effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- MKQLBNJQQZRQJU-UHFFFAOYSA-N morpholin-4-amine Chemical compound NN1CCOCC1 MKQLBNJQQZRQJU-UHFFFAOYSA-N 0.000 description 1
- VHPLSRUYMRRUFN-UHFFFAOYSA-N n-naphthalen-1-ylpyridine-4-carboxamide Chemical compound C=1C=CC2=CC=CC=C2C=1NC(=O)C1=CC=NC=C1 VHPLSRUYMRRUFN-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000001549 tubercolostatic effect Effects 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
Verfahren zur Herstellung von Derivaten des Naphthalin-1,4,5,8-tetracarbonsäurediimids Es wurde gefunden, daß Derivate des Naphthalin-1,4,5,8-tetracarbonsäurediimids der allgemeinen Formel in der R1 ein Wasserstoffatom, eine Methylgruppe oder eine Dialkylaminoalkylgruppe und R2 ein Wasserstoffatom, eine Methylgruppe, eine Dialkylaminoalkylgruppe oder den Acylrest der Isonicotinsäure bedeutet oder R1 und R2 zusammen eine gegebenenfalls durch ein Sauerstoff- oder Schwefelatom oder eine Alkyliminogruppe mit 1 bis 4 Kohlenstoffatomen unterbrochene Alkylengruppe darstellen, gute Wirkung gegen Tuberkulose und Amöben-, Lamblien- und Oxyuren-Infektionen besitzen.Process for the preparation of derivatives of naphthalene-1,4,5,8-tetracarboxylic acid diimide It has been found that derivatives of naphthalene-1,4,5,8-tetracarboxylic acid diimide of the general formula in which R1 is a hydrogen atom, a methyl group or a dialkylaminoalkyl group and R2 is a hydrogen atom, a methyl group, a dialkylaminoalkyl group or the acyl radical of isonicotinic acid, or R1 and R2 together are an alkylene group optionally interrupted by an oxygen or sulfur atom or an alkylimino group with 1 to 4 carbon atoms represent, have a good effect against tuberculosis and amoebic, lamblia and oxyuric infections.
Die Verbindungen beeinflussen als solche oder in Form ihrer Salze mit nicht toxischen anorganischen oder organischen Säuren die genannten Infektionen günstig. Im Vergleich dazu sind die bekannten nicht basischen Imide der Naphthalin- 1 ,4,5,8-tetracarbonsäure [deutsche Patentschrift 552 760; Liebigs Ann. d. Chem., 531, S. 1 (1937); Helv. chim. acta, 21, 5. 1466 (1938); USA.-Patentschrift 2914531] unwirksam. The compounds affect as such or in the form of their salts the infections mentioned with non-toxic inorganic or organic acids cheap. In comparison, the well-known non-basic imides of the naphthalene 1, 4,5,8-tetracarboxylic acid [German patent specification 552 760; Liebigs Ann. d. Chem., 531, p. 1 (1937); Helv. Chim. acta, 21, p. 1466 (1938); U.S. Patent 2914531] ineffective.
Die neuen Verbindungen haben außerdem laxierende Wirkung. Die erfindungsgemäß
erhältlichen Verbindungen zeichnen sich durch eine gute Wirkung gegenüber solchen
Tuberkelbazillen aus, die gegen eine Behandlung durch Isonicotinsäurehydrazid (INH)
und Thiosemicarbazon resistent geworden sind. Sie zeigen auch gegenüber anderen
klinisch bedeutsamen Tuberkulostatika, wie Streptomycin und p-Aminosalicylsäure,
keine Kreuzresistanz. In der folgenden Aufstellung sind die minimalen Hemmkonzentrationen
von verschiedenen Verfahrensprodukten in γ/ml Eimedium, die für eine Unterdrückung
des Wachstums von gegen INH-resistenten Mykobakterien erforderlich waren, im Vergleich
zur Hemmkonzentration des Isonicotinsäurehydrazids aufgeführt. Die Versuche wurden.an
einem Laborstamm (125) durchgeführt, der ursprünglich aus Patientenmaterial isoliert
worden war.
Die Umsetzung wird in Gegenwart eines Lösungsmittels oder in der Schmelze durchgeführt. Als besonders günstig hat sich die Verwendung von Toluol und Xylol als Lösungsmittel erwiesen. Bei der bei Siedetemperatur rasch verlaufenden Reaktion läßt sich das entstehende Wasser durch azeotrope Destillation am Wasserabscheider in einfacher Weise entfernen. The reaction is carried out in the presence of a solvent or in the Melt carried out. The use of toluene has proven to be particularly favorable and xylene proved to be solvents. In the case of the rapidly running at boiling point The resulting water can be reacted by azeotropic distillation on a water separator easily remove.
Beispiel 1 a) 15 g Naphthalin- 1,4,5, 8-tetracarbonsäuredianhydrid werden in 250 ccm Chlorbenzol suspendiert und unter Rühren zum Sieden erwärmt. Man tropft 23 g N,N-Bis-(ß-diäthylaminoäthyl)-hydrazin ein und kocht 1 Stunde unter Rückfluß. Nach dem Erkalten wird mit verdünnter Essigsäure extrahiert, die essigsauren Auszüge alkalisch gestellt und mit Chloroform ausgeschüttelt. Nach dem Trocknen und Eindampfen hinterbleibt ein Ol, das nach einiger Zeit kristallisiert. Example 1 a) 15 g of naphthalene-1,4,5,8-tetracarboxylic acid dianhydride are suspended in 250 ccm of chlorobenzene and heated to the boil while stirring. Man drops 23 g of N, N-bis (ß-diethylaminoethyl) hydrazine and boils under for 1 hour Reflux. After cooling, it is extracted with dilute acetic acid, the acetic acid Extracts made alkaline and extracted with chloroform. After drying and evaporation, an oil remains which crystallizes after a while.
Zur Charakterisierung der erhaltenen Verbindung fällt man aus Äthanol das Maleinat aus, das sich aus Athanol umkristallisieren läßt. Man erhält 14 g N,N'-Bis-[bis-(ß-diäthylaminoäthyl)-amino]-naphthalin-1,4,5,8-tetracarbonsäurediimid-maleinat; F. 184 bis 186"C. b) In analoger Weise erhält man N,N'-Bis-[ß-diäthylaminoäthylamino] - naphthalin - 1,4,5,8 - tetracarbonsäurediimid; F. 187 bis 188"C. To characterize the compound obtained, it is precipitated from ethanol the maleate, which can be recrystallized from ethanol. 14 g of N, N'-bis [bis (ß-diethylaminoethyl) amino] naphthalene-1,4,5,8-tetracarboxylic acid diimide maleate are obtained; F. 184 to 186 "C. b) N, N'-bis [ß-diethylaminoäthylamino] is obtained in an analogous manner - naphthalene - 1,4,5,8 - tetracarboxylic acid diimide; F. 187 to 188 "C.
Beispiel 2 13,4 g Naphthalin- 1,4, 5,8-tetracarbonsäuredianhydrid werden in 80 ccm Dimethylformamid auf 100"C erwärmt. Man tropft unter Rühren langsam 6 ccm Hydrazinhydrat ein und rührt weitere 2 Stunden bei Zimmertemperatur. Nach dem Erkalten wird abgesaugt, der Rückstand mit Äthanol gewaschen, anschließend mit der zehnfachen Menge gesättigter Sodalösung auf dem Wasserbad erwärmt, wieder abfiltriert und neutral gewaschen. Nach dem Trocknen erhält man 10 g N,N'-Diaminonaphthalin-1,4,5,8-tetracarbonsäurediimid, das oberhalb 250"C schmilzt. Example 2 13.4 g of naphthalene-1,4,5,8-tetracarboxylic acid dianhydride are heated to 100 ° C. in 80 cc of dimethylformamide. It is slowly added dropwise with stirring 6 cc hydrazine hydrate and stir for a further 2 hours at room temperature. To the cooling is suctioned off, the residue washed with ethanol, then with ten times the amount of saturated soda solution heated on a water bath, filtered off again and washed neutral. After drying, 10 g of N, N'-diaminonaphthalene-1,4,5,8-tetracarboxylic acid diimide are obtained, that melts above 250 "C.
Beispiel 3 21 g Naphthalin- 1 ,4,5,8-tetracarbonsäuredianhydiid und 27 g Isonicotinsäurehydrazid werden gemischt und etwa 1 Stunde auf 260"C zum Schmelzen erhitzt. Nach dem Erkalten wird in Dimethylformamid gelöst und durch Eintropfen in Äthanol ausgefällt; man erhält 20 g N,N'-Bis-(isonicotinoylamino) - naphthalin - 1,4,5,8- tetracarbonsäurediimid; E. >360°C. Example 3 21 g of naphthalene-1, 4,5,8-tetracarboxylic acid dianhydride and 27 g of isonicotinic hydrazide are mixed and allowed to melt at 260 "C for about 1 hour heated. After cooling, it is dissolved in dimethylformamide and added dropwise precipitated in ethanol; 20 g of N, N'-bis (isonicotinoylamino) naphthalene are obtained - 1,4,5,8-tetracarboxylic acid diimide; E.> 360 ° C.
Beispiel 4 a) 13,4 g Naphthalin-1,4,5,8-tetracarbonsäureanhydrid werden in 100 ml Äthanol mit 11,2 gN-Aminomorpholin 6 Stunden unter Rückfluß gekocht. Man saugt nach demErkalten ab und wäscht mit Methanol. Example 4 a) 13.4 g of naphthalene-1,4,5,8-tetracarboxylic acid anhydride are refluxed for 6 hours in 100 ml of ethanol with 11.2 g of N-aminomorpholine. After cooling, it is suctioned off and washed with methanol.
Man erhält 20 g N,N'-Dimorpholino-naphthalin-1,4,5,8-tetracarbonsäurediimid; F. >260°C. b) In analoger Weise erhält man das N,N'-Bis-(dimethylamino)-naphthalin-1 ,4,5,84etracarbonsäurediimid; F. >260°C.20 g of N, N'-dimorpholino-naphthalene-1,4,5,8-tetracarboxylic acid diimide are obtained; F.> 260 ° C. b) N, N'-bis (dimethylamino) naphthalene-1 is obtained in an analogous manner , 4,5,84etracarboxylic acid diimide; F.> 260 ° C.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF43093A DE1230031B (en) | 1964-06-05 | 1964-06-05 | Process for the preparation of derivatives of naphthalene-1, 4, 5, 8-tetracarboxylic acid diimide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF43093A DE1230031B (en) | 1964-06-05 | 1964-06-05 | Process for the preparation of derivatives of naphthalene-1, 4, 5, 8-tetracarboxylic acid diimide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1230031B true DE1230031B (en) | 1966-12-08 |
Family
ID=7099397
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF43093A Pending DE1230031B (en) | 1964-06-05 | 1964-06-05 | Process for the preparation of derivatives of naphthalene-1, 4, 5, 8-tetracarboxylic acid diimide |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1230031B (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0031065A3 (en) * | 1979-12-20 | 1982-01-20 | Bayer Ag | Naphthaline-tetracarbonic acid diimides as electrical semiconductors and photoconductors |
| US5468583A (en) * | 1994-12-28 | 1995-11-21 | Eastman Kodak Company | Cyclic bis-dicarboximide electron transport compounds for electrophotography |
| US5767268A (en) * | 1995-05-05 | 1998-06-16 | Hoffmann-La Roche Inc. | Sulfuric acid esters of amino sugars |
| EP2000856A1 (en) | 2007-06-04 | 2008-12-10 | Ricoh Company, Ltd. | Electrophotographic photoreceptor, image forming apparatus, and process cartridge |
| EP2033961A1 (en) | 2007-09-10 | 2009-03-11 | Ricoh Company, Ltd. | Naphthalenetetracarboxylic acid diimide derivative and electrophotographic photoconductor having the same |
| JP2009193045A (en) * | 2008-01-17 | 2009-08-27 | Ricoh Co Ltd | Electrophotographic equipment |
| JP2009198624A (en) * | 2008-02-20 | 2009-09-03 | Ricoh Co Ltd | Electrophotographic photoreceptor, image forming device, full-color image forming device and process cartridge |
| JP2010039123A (en) * | 2008-08-04 | 2010-02-18 | Ricoh Co Ltd | Electrophotographic photoreceptor, image forming apparatus, full-color image forming apparatus, and process cartridge |
| JP2010048876A (en) * | 2008-08-19 | 2010-03-04 | Ricoh Co Ltd | Image forming apparatus |
| DE102013003680A1 (en) | 2013-02-28 | 2014-09-11 | LMU Universität München Department Chemie | Chromophors arranged as 'metatoms': building blocks for molecular metamaterials |
-
1964
- 1964-06-05 DE DEF43093A patent/DE1230031B/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0031065A3 (en) * | 1979-12-20 | 1982-01-20 | Bayer Ag | Naphthaline-tetracarbonic acid diimides as electrical semiconductors and photoconductors |
| US5468583A (en) * | 1994-12-28 | 1995-11-21 | Eastman Kodak Company | Cyclic bis-dicarboximide electron transport compounds for electrophotography |
| US5767268A (en) * | 1995-05-05 | 1998-06-16 | Hoffmann-La Roche Inc. | Sulfuric acid esters of amino sugars |
| EP2000856A1 (en) | 2007-06-04 | 2008-12-10 | Ricoh Company, Ltd. | Electrophotographic photoreceptor, image forming apparatus, and process cartridge |
| US8110326B2 (en) | 2007-06-04 | 2012-02-07 | Ricoh Company Limited | Electrophotographic photoreceptor, image forming apparatus, and process cartridge |
| EP2033961A1 (en) | 2007-09-10 | 2009-03-11 | Ricoh Company, Ltd. | Naphthalenetetracarboxylic acid diimide derivative and electrophotographic photoconductor having the same |
| US8232031B2 (en) | 2007-09-10 | 2012-07-31 | Ricoh Company, Ltd. | Naphthalenetetracarboxylic acid diimide derivative and electrophotographic photoconductor having the same |
| JP2009193045A (en) * | 2008-01-17 | 2009-08-27 | Ricoh Co Ltd | Electrophotographic equipment |
| JP2009198624A (en) * | 2008-02-20 | 2009-09-03 | Ricoh Co Ltd | Electrophotographic photoreceptor, image forming device, full-color image forming device and process cartridge |
| JP2010039123A (en) * | 2008-08-04 | 2010-02-18 | Ricoh Co Ltd | Electrophotographic photoreceptor, image forming apparatus, full-color image forming apparatus, and process cartridge |
| JP2010048876A (en) * | 2008-08-19 | 2010-03-04 | Ricoh Co Ltd | Image forming apparatus |
| DE102013003680A1 (en) | 2013-02-28 | 2014-09-11 | LMU Universität München Department Chemie | Chromophors arranged as 'metatoms': building blocks for molecular metamaterials |
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