JPS6126904B2 - - Google Patents
Info
- Publication number
- JPS6126904B2 JPS6126904B2 JP6411979A JP6411979A JPS6126904B2 JP S6126904 B2 JPS6126904 B2 JP S6126904B2 JP 6411979 A JP6411979 A JP 6411979A JP 6411979 A JP6411979 A JP 6411979A JP S6126904 B2 JPS6126904 B2 JP S6126904B2
- Authority
- JP
- Japan
- Prior art keywords
- hydrazone compound
- photoreceptor
- charge
- reaction
- present
- 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 hydrazone compound Chemical class 0.000 claims description 21
- 238000004519 manufacturing process Methods 0.000 claims description 8
- QGJXVBICNCIWEL-UHFFFAOYSA-N 9-ethylcarbazole-3-carbaldehyde Chemical compound O=CC1=CC=C2N(CC)C3=CC=CC=C3C2=C1 QGJXVBICNCIWEL-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 108091008695 photoreceptors Proteins 0.000 description 24
- 239000010410 layer Substances 0.000 description 16
- 239000000463 material Substances 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 206010034972 Photosensitivity reaction Diseases 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 230000036211 photosensitivity Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 239000011669 selenium Substances 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SQMOOVFBFVTTGF-UHFFFAOYSA-N 1-benzyl-1-phenylhydrazine Chemical compound C=1C=CC=CC=1N(N)CC1=CC=CC=C1 SQMOOVFBFVTTGF-UHFFFAOYSA-N 0.000 description 1
- FGRBYDKOBBBPOI-UHFFFAOYSA-N 10,10-dioxo-2-[4-(N-phenylanilino)phenyl]thioxanthen-9-one Chemical compound O=C1c2ccccc2S(=O)(=O)c2ccc(cc12)-c1ccc(cc1)N(c1ccccc1)c1ccccc1 FGRBYDKOBBBPOI-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 206010034960 Photophobia Diseases 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000002800 charge carrier Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000005496 eutectics Effects 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 208000013469 light sensitivity Diseases 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000728 polyester Polymers 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
- 229920000642 polymer Polymers 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical class C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003068 static effect Effects 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- G03G5/0622—Heterocyclic compounds
- G03G5/0624—Heterocyclic compounds containing one hetero ring
- G03G5/0627—Heterocyclic compounds containing one hetero ring being five-membered
- G03G5/0629—Heterocyclic compounds containing one hetero ring being five-membered containing one hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Photoreceptors In Electrophotography (AREA)
- Indole Compounds (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6411979A JPS55154955A (en) | 1979-05-24 | 1979-05-24 | Novel hydrazone compound and its preparation |
| CA352,269A CA1125771A (en) | 1979-05-24 | 1980-05-20 | Hydrazone compounds and process for preparing the same |
| DE19803019395 DE3019395A1 (de) | 1979-05-24 | 1980-05-21 | 9-aethylcarbazol-3-aldehyd-1-methyl- 1-phenylhydrazon und -1-benzyl-1-phenylhydrazon, verfahren zur herstellung dieser verbindungen und ihre verwendung |
| FR8011518A FR2457285A1 (fr) | 1979-05-24 | 1980-05-23 | Nouvelles hydrazones utiles comme transporteurs de charges et leur procede de preparation |
| GB8017231A GB2055803B (en) | 1979-05-24 | 1980-05-27 | Hydrazones of 9-ethylcarbazole-3-aldehydes and their use in electrophotography |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6411979A JPS55154955A (en) | 1979-05-24 | 1979-05-24 | Novel hydrazone compound and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55154955A JPS55154955A (en) | 1980-12-02 |
| JPS6126904B2 true JPS6126904B2 (US20100012521A1-20100121-C00001.png) | 1986-06-23 |
Family
ID=13248850
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6411979A Granted JPS55154955A (en) | 1979-05-24 | 1979-05-24 | Novel hydrazone compound and its preparation |
Country Status (5)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6338805A (ja) * | 1986-07-31 | 1988-02-19 | 関西電力株式会社 | ボイラ−のスプレ−水注入制御装置 |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2088074B (en) * | 1980-09-26 | 1984-12-19 | Copyer Co | Electrophotographic photosensitive member |
| GB2096134B (en) * | 1981-02-03 | 1985-07-17 | Canon Kk | Heterocyclic hydrazones for use in electrophotographic photosensitive members |
| JPS5865275A (ja) * | 1981-10-14 | 1983-04-18 | Asahi Glass Co Ltd | 新規なヒドラゾン化合物及びその製造法 |
| US4456671A (en) * | 1981-12-23 | 1984-06-26 | Canon Kabushiki Kaisha | Electrophotographic photosensitive member having a photosensitive layer containing a hydrazone compound |
| JPS58199353A (ja) * | 1982-05-17 | 1983-11-19 | Canon Inc | 電子写真感光体 |
| JPS61107248A (ja) * | 1984-10-31 | 1986-05-26 | Canon Inc | 積層型電子写真感光体 |
| JPS61109056A (ja) * | 1984-11-01 | 1986-05-27 | Mitsubishi Chem Ind Ltd | 積層型電子写真感光体 |
| JP2002014478A (ja) | 2000-06-30 | 2002-01-18 | Hodogaya Chem Co Ltd | 電子製品材料の精製方法 |
| US6824939B2 (en) | 2001-12-11 | 2004-11-30 | Ricoh Company Limited | Electrophotographic image forming method and apparatus |
| WO2008078699A1 (ja) | 2006-12-26 | 2008-07-03 | Asahi Kasei E-Materials Corporation | 印刷版用樹脂組成物 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5546760A (en) * | 1978-09-29 | 1980-04-02 | Ricoh Co Ltd | Electrophotographic photoreceptor |
-
1979
- 1979-05-24 JP JP6411979A patent/JPS55154955A/ja active Granted
-
1980
- 1980-05-20 CA CA352,269A patent/CA1125771A/en not_active Expired
- 1980-05-21 DE DE19803019395 patent/DE3019395A1/de not_active Ceased
- 1980-05-23 FR FR8011518A patent/FR2457285A1/fr active Pending
- 1980-05-27 GB GB8017231A patent/GB2055803B/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6338805A (ja) * | 1986-07-31 | 1988-02-19 | 関西電力株式会社 | ボイラ−のスプレ−水注入制御装置 |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2055803A (en) | 1981-03-11 |
| JPS55154955A (en) | 1980-12-02 |
| DE3019395A1 (de) | 1980-11-27 |
| GB2055803B (en) | 1983-07-06 |
| FR2457285A1 (fr) | 1980-12-19 |
| CA1125771A (en) | 1982-06-15 |
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