DE1058836B - Material fuer elektrophotographische Reproduktion - Google Patents
Material fuer elektrophotographische ReproduktionInfo
- Publication number
- DE1058836B DE1058836B DEK29014A DEK0029014A DE1058836B DE 1058836 B DE1058836 B DE 1058836B DE K29014 A DEK29014 A DE K29014A DE K0029014 A DEK0029014 A DE K0029014A DE 1058836 B DE1058836 B DE 1058836B
- Authority
- DE
- Germany
- Prior art keywords
- formula
- oxdiazole
- paper
- solution
- acid
- 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
- 239000000463 material Substances 0.000 title claims description 10
- 229920005989 resin Polymers 0.000 claims description 44
- 239000011347 resin Substances 0.000 claims description 44
- 239000000243 solution Substances 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- FUSNOPLQVRUIIM-UHFFFAOYSA-N 4-amino-2-(4,4-dimethyl-2-oxoimidazolidin-1-yl)-n-[3-(trifluoromethyl)phenyl]pyrimidine-5-carboxamide Chemical compound O=C1NC(C)(C)CN1C(N=C1N)=NC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 FUSNOPLQVRUIIM-UHFFFAOYSA-N 0.000 claims description 15
- 239000012493 hydrazine sulfate Substances 0.000 claims description 15
- 229910000377 hydrazine sulfate Inorganic materials 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 11
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 9
- 239000000155 melt Substances 0.000 claims description 9
- 238000002844 melting Methods 0.000 claims description 9
- 230000008018 melting Effects 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 229920003023 plastic Polymers 0.000 claims description 7
- 239000004033 plastic Substances 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 5
- 238000001953 recrystallisation Methods 0.000 claims description 5
- YDIYEOMDOWUDTJ-UHFFFAOYSA-N 4-(dimethylamino)benzoic acid Chemical compound CN(C)C1=CC=C(C(O)=O)C=C1 YDIYEOMDOWUDTJ-UHFFFAOYSA-N 0.000 claims description 4
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 claims description 4
- LNYTUARMNSFFBE-UHFFFAOYSA-N 4-(diethylazaniumyl)benzoate Chemical compound CCN(CC)C1=CC=C(C(O)=O)C=C1 LNYTUARMNSFFBE-UHFFFAOYSA-N 0.000 claims description 3
- 239000006229 carbon black Substances 0.000 claims description 3
- 239000000025 natural resin Substances 0.000 claims description 3
- 239000006104 solid solution Substances 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 239000004801 Chlorinated PVC Substances 0.000 claims description 2
- 229920000457 chlorinated polyvinyl chloride Polymers 0.000 claims description 2
- 239000011521 glass Substances 0.000 claims description 2
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 6
- 235000019441 ethanol Nutrition 0.000 claims 5
- 239000007795 chemical reaction product Substances 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 2
- 239000000084 colloidal system Substances 0.000 claims 2
- SWXFMMWYVSYQGF-UHFFFAOYSA-N 4-(ethylamino)benzoic acid Chemical compound CCNC1=CC=C(C(O)=O)C=C1 SWXFMMWYVSYQGF-UHFFFAOYSA-N 0.000 claims 1
- MJZXFMSIHMJQBW-UHFFFAOYSA-N 4-[5-(4-aminophenyl)-1,3,4-oxadiazol-2-yl]aniline Chemical compound C1=CC(N)=CC=C1C1=NN=C(C=2C=CC(N)=CC=2)O1 MJZXFMSIHMJQBW-UHFFFAOYSA-N 0.000 claims 1
- YIYBPEDZAUFQLO-UHFFFAOYSA-N 4-amino-3-chlorobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1Cl YIYBPEDZAUFQLO-UHFFFAOYSA-N 0.000 claims 1
- 240000000972 Agathis dammara Species 0.000 claims 1
- 206010034972 Photosensitivity reaction Diseases 0.000 claims 1
- 239000011324 bead Substances 0.000 claims 1
- 238000005266 casting Methods 0.000 claims 1
- 238000005660 chlorination reaction Methods 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- JVICFMRAVNKDOE-UHFFFAOYSA-M ethyl violet Chemical compound [Cl-].C1=CC(N(CC)CC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC)=C1C=CC(=[N+](CC)CC)C=C1 JVICFMRAVNKDOE-UHFFFAOYSA-M 0.000 claims 1
- 238000001640 fractional crystallisation Methods 0.000 claims 1
- 230000036211 photosensitivity Effects 0.000 claims 1
- 239000004800 polyvinyl chloride Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 239000011888 foil Substances 0.000 description 11
- 239000000843 powder Substances 0.000 description 9
- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 238000009833 condensation Methods 0.000 description 7
- 230000005494 condensation Effects 0.000 description 7
- 239000000975 dye Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 229920003002 synthetic resin Polymers 0.000 description 7
- 239000000057 synthetic resin Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 5
- 239000004071 soot Substances 0.000 description 5
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 4
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 4
- NKHOUDMZYQDBQE-UHFFFAOYSA-N 4-(cyclopentylamino)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1CCCC1 NKHOUDMZYQDBQE-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 229920000137 polyphosphoric acid Polymers 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 3
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 3
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 description 3
- 229960000907 methylthioninium chloride Drugs 0.000 description 3
- 230000035515 penetration Effects 0.000 description 3
- 239000002985 plastic film Substances 0.000 description 3
- 230000011514 reflex Effects 0.000 description 3
- 230000033458 reproduction Effects 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
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- 239000013078 crystal Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002688 maleic acid derivatives Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000004888 n-propyl amino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 229920006255 plastic film Polymers 0.000 description 2
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- 235000019422 polyvinyl alcohol Nutrition 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- GUEIZVNYDFNHJU-UHFFFAOYSA-N quinizarin Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 description 2
- 229940043267 rhodamine b Drugs 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
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- 230000035945 sensitivity Effects 0.000 description 2
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
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- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- MXODCLTZTIFYDV-UHFFFAOYSA-L zinc;1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylate Chemical compound [Zn+2].C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C([O-])=O.C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C([O-])=O MXODCLTZTIFYDV-UHFFFAOYSA-L 0.000 description 2
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- 235000009508 confectionery Nutrition 0.000 description 1
- CEJANLKHJMMNQB-UHFFFAOYSA-M cryptocyanin Chemical compound [I-].C12=CC=CC=C2N(CC)C=CC1=CC=CC1=CC=[N+](CC)C2=CC=CC=C12 CEJANLKHJMMNQB-UHFFFAOYSA-M 0.000 description 1
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- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- JBBPTUVOZCXCSU-UHFFFAOYSA-L dipotassium;2',4',5',7'-tetrabromo-4,7-dichloro-3-oxospiro[2-benzofuran-1,9'-xanthene]-3',6'-diolate Chemical compound [K+].[K+].O1C(=O)C(C(=CC=C2Cl)Cl)=C2C21C1=CC(Br)=C([O-])C(Br)=C1OC1=C(Br)C([O-])=C(Br)C=C21 JBBPTUVOZCXCSU-UHFFFAOYSA-L 0.000 description 1
- 238000005421 electrostatic potential Methods 0.000 description 1
- YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 description 1
- SEACYXSIPDVVMV-UHFFFAOYSA-L eosin Y Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 SEACYXSIPDVVMV-UHFFFAOYSA-L 0.000 description 1
- IINNWAYUJNWZRM-UHFFFAOYSA-L erythrosin B Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C([O-])=C(I)C=C21 IINNWAYUJNWZRM-UHFFFAOYSA-L 0.000 description 1
- 229940011411 erythrosine Drugs 0.000 description 1
- 235000012732 erythrosine Nutrition 0.000 description 1
- 239000004174 erythrosine Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 208000013469 light sensitivity Diseases 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- QWYZFXLSWMXLDM-UHFFFAOYSA-M pinacyanol iodide Chemical compound [I-].C1=CC2=CC=CC=C2N(CC)C1=CC=CC1=CC=C(C=CC=C2)C2=[N+]1CC QWYZFXLSWMXLDM-UHFFFAOYSA-M 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- AZJPTIGZZTZIDR-UHFFFAOYSA-L rose bengal Chemical compound [K+].[K+].[O-]C(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C([O-])=C(I)C=C21 AZJPTIGZZTZIDR-UHFFFAOYSA-L 0.000 description 1
- 229940081623 rose bengal Drugs 0.000 description 1
- 229930187593 rose bengal Natural products 0.000 description 1
- STRXNPAVPKGJQR-UHFFFAOYSA-N rose bengal A Natural products O1C(=O)C(C(=CC=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 STRXNPAVPKGJQR-UHFFFAOYSA-N 0.000 description 1
- AXMCIYLNKNGNOT-UHFFFAOYSA-M sodium;3-[[4-[(4-dimethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)-[4-[ethyl-[(3-sulfonatophenyl)methyl]amino]phenyl]methyl]-n-ethylanilino]methyl]benzenesulfonate Chemical compound [Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](C)C)C=2C=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 AXMCIYLNKNGNOT-UHFFFAOYSA-M 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- -1 sulfo- Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000001016 thiazine dye Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- JEVGKYBUANQAKG-UHFFFAOYSA-N victoria blue R Chemical compound [Cl-].C12=CC=CC=C2C(=[NH+]CC)C=CC1=C(C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 JEVGKYBUANQAKG-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C07D271/107—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with two aryl or substituted aryl radicals attached in positions 2 and 5
-
- 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
- G03G5/0605—Carbocyclic compounds
- G03G5/0607—Carbocyclic compounds containing at least one non-six-membered ring
-
- 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
- G03G5/0631—Heterocyclic compounds containing one hetero ring being five-membered containing two hetero atoms
-
- 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
- G03G5/0666—Dyes containing a methine or polymethine group
- G03G5/0668—Dyes containing a methine or polymethine group containing only one methine or polymethine group
- G03G5/067—Dyes containing a methine or polymethine group containing only one methine or polymethine group containing hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Photoreceptors In Electrophotography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL217825D NL217825A (en)) | 1956-06-04 | ||
| BE558078D BE558078A (en)) | 1956-06-04 | ||
| NL99369D NL99369C (en)) | 1956-06-04 | ||
| LU35193D LU35193A1 (en)) | 1956-06-04 | ||
| DEK29014A DE1058836B (de) | 1956-06-04 | 1956-06-04 | Material fuer elektrophotographische Reproduktion |
| US662319A US3189447A (en) | 1956-06-04 | 1957-05-29 | Electrophotographic material and method |
| GB17519/57A GB851218A (en) | 1956-06-04 | 1957-06-03 | Improvements in or relating to photographic reproduction |
| FR1176457D FR1176457A (fr) | 1956-06-04 | 1957-06-03 | Matériel pour la reproduction électrophotographique |
| CH360899D CH360899A (de) | 1956-06-04 | 1957-06-03 | Material für elektrophotographische Reproduktion |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK29014A DE1058836B (de) | 1956-06-04 | 1956-06-04 | Material fuer elektrophotographische Reproduktion |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1058836B true DE1058836B (de) | 1959-06-04 |
Family
ID=7218378
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEK29014A Pending DE1058836B (de) | 1956-06-04 | 1956-06-04 | Material fuer elektrophotographische Reproduktion |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3189447A (en)) |
| BE (1) | BE558078A (en)) |
| CH (1) | CH360899A (en)) |
| DE (1) | DE1058836B (en)) |
| FR (1) | FR1176457A (en)) |
| GB (1) | GB851218A (en)) |
| LU (1) | LU35193A1 (en)) |
| NL (2) | NL217825A (en)) |
Cited By (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1193363B (de) * | 1961-01-28 | 1965-05-20 | Kalle Ag | Photoleitfaehige Schicht fuer elektro-photographische Zwecke |
| DE2336094A1 (de) * | 1973-07-16 | 1975-02-06 | Hoechst Ag | Elektrophotographisches aufzeichungsmaterial |
| DE2715714A1 (de) * | 1976-04-12 | 1977-10-13 | Ricoh Kk | 1,3,4-oxadiazolderivate sowie diese enthaltende elektrophotographische aufzeichnungsmaterialien |
| DE2659709A1 (de) * | 1976-12-31 | 1978-07-13 | Hoechst Ag | 1,3,4-oxadiazole, verfahren zu ihrer herstellung und ihre verwendung |
| DE3246250A1 (de) * | 1981-12-14 | 1983-06-16 | Fuji Photo Film Co., Ltd., Minami-Ashigara, Kanagawa | Photoleitfaehige zusammensetzungen und elektrophotographische aufzeichnungsmaterialien |
| DE3414791A1 (de) * | 1983-04-18 | 1984-10-18 | Canon K.K., Tokio/Tokyo | Fotoleitfaehiges aufzeichnungselement und traeger fuer das fotoleitfaehige aufzeichnungselement |
| EP0125481A1 (de) * | 1983-04-15 | 1984-11-21 | Hoechst Aktiengesellschaft | Elektrophotographisches Aufzeichnungsmaterial |
| EP0127862A1 (de) * | 1983-05-31 | 1984-12-12 | Hoechst Aktiengesellschaft | Elektrophotographisches Aufzeichnungsmaterial |
| US4492747A (en) * | 1980-06-30 | 1985-01-08 | Hoechst Aktiengesellschaft | Flexible laminatable photosensitive layer |
| US4533612A (en) * | 1983-04-27 | 1985-08-06 | Basf Aktiengesellschaft | Electrophotographic recording materials containing special charge carrier-transporting compounds |
| US4556621A (en) * | 1983-07-05 | 1985-12-03 | Basf Aktiengesellschaft | Electrophotographic recording material containing a metal-1,3-diketone complex |
| US4559285A (en) * | 1983-07-05 | 1985-12-17 | Basf Aktiengesellschaft | Electrophotographic recording materials containing a metal acetylacetonate |
| US4739053A (en) * | 1983-02-09 | 1988-04-19 | Basf Aktiengesellschaft | 2H-v-triazolo[4-5-d]pyrimidines |
| US4906541A (en) * | 1987-11-28 | 1990-03-06 | Basf Aktiengesellschaft | Electrophotographic recording element containing a naphtholactam dye sensitizer |
| US5132189A (en) * | 1989-09-07 | 1992-07-21 | Fuji Electric Co., Ltd. | Photoconductor for electrophotography |
| US5178981A (en) * | 1990-03-08 | 1993-01-12 | Fuji Electric Co., Ltd. | Photoconductor for electrophotography with a charge generating substance comprising a polycyclic and azo compound |
| US5286590A (en) * | 1989-06-06 | 1994-02-15 | Fuji Electric Co., Ltd. | Bisazo photoconductor for electrophotography |
| US5316881A (en) * | 1991-12-27 | 1994-05-31 | Fuji Electric Co., Ltd. | Photoconductor for electrophotgraphy containing benzidine derivative |
| DE3890861C2 (de) * | 1987-10-07 | 1994-10-13 | Fuji Electric Co Ltd | Elektrophotographisches Auzeichnungsmaterial |
| US5368966A (en) * | 1992-05-14 | 1994-11-29 | Fuji Electric Co., Ltd. | Photosensitive member for electrophotography with indole derivative |
| US5393627A (en) * | 1992-02-12 | 1995-02-28 | Fuji Electric Co., Ltd. | Photoconductor for electrophotography |
| EP1515191A2 (en) | 2003-09-05 | 2005-03-16 | Xerox Corporation | Dual charge transport layer and photoconductive imaging member including the same |
Families Citing this family (131)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE585419A (en)) * | 1958-12-19 | |||
| NL129066C (en)) * | 1959-01-07 | |||
| NL266999A (en)) * | 1959-08-04 | |||
| US3287120A (en) * | 1961-07-24 | 1966-11-22 | Azoplate Corp | Process for the sensitization of photoconductors |
| DE1250736B (en)) * | 1962-10-13 | |||
| DE1265582B (de) * | 1963-10-12 | 1968-04-04 | Kalle Ag | Elektrophotographisches Aufzeichnungsmaterial zur Herstellung von Bildern oder Flachdruckformen |
| DE2160812C2 (de) * | 1971-12-08 | 1982-04-15 | Hoechst Ag, 6000 Frankfurt | Elektrophotographisches Aufzeichnungsmaterial |
| US3873312A (en) * | 1973-05-04 | 1975-03-25 | Eastman Kodak Co | Photoconductive composition and elements containing a styryl amino group containing photoconductor |
| US3873311A (en) * | 1973-05-04 | 1975-03-25 | Eastman Kodak Co | Aggregate photoconductive compositions and elements containing a styryl amino group containing photoconductor |
| US4157913A (en) * | 1976-04-12 | 1979-06-12 | Ricoh Co., Ltd. | Derivatives of 1,3,4-oxadiazole and electrophotographic elements containing same |
| US4192677A (en) * | 1976-05-18 | 1980-03-11 | Ricoh Co., Ltd. | 1,3,4-Oxadiazole derivatives and use thereof |
| US4141729A (en) * | 1976-05-18 | 1979-02-27 | Ricoh Company, Ltd. | 1,3,4-Oxadiazole derivatives and electrophotographic plates containing same |
| US4055420A (en) * | 1977-01-27 | 1977-10-25 | Xerox Corporation | Single phase organic photoconductive composition |
| US4399206A (en) | 1980-10-06 | 1983-08-16 | Canon Kabushiki Kaisha | Disazo electrophotographic photosensitive member |
| JPS57148750A (en) * | 1981-03-11 | 1982-09-14 | Konishiroku Photo Ind Co Ltd | Electrophotographic receptor |
| DE3210576A1 (de) * | 1982-03-23 | 1983-10-06 | Hoechst Ag | Elektrophotographisches aufzeichnungsmaterial |
| JPS5942352A (ja) | 1982-09-01 | 1984-03-08 | Fuji Photo Film Co Ltd | ジスアゾ化合物、それを含む光導電性組成物及び電子写真感光体 |
| DE3404365A1 (de) * | 1984-02-08 | 1985-08-08 | Hoechst Ag, 6230 Frankfurt | Elektrophotographisches aufzeichnungsmaterial |
| DE3409888A1 (de) * | 1984-03-17 | 1985-09-19 | Hoechst Ag, 6230 Frankfurt | Lichtempfindliches aufzeichnungsmaterial und dessen verwendung in einem verfahren zum herstellen einer druckform oder einer gedruckten schaltung |
| DE3417951A1 (de) * | 1984-05-15 | 1985-11-21 | Hoechst Ag, 6230 Frankfurt | Elektrophotographisches aufzeichnungsmaterial |
| NL8402705A (nl) * | 1984-09-05 | 1986-04-01 | Oce Nederland Bv | Ladingstransporterende verbindingen en fotogeleidende elementen voorzien van dergelijke ladingstransporterende verbindingen. |
| DE3506436A1 (de) * | 1985-02-23 | 1986-08-28 | Hoechst Ag, 6230 Frankfurt | Neue sulfonhaltige styrolderivate, verfahren zu deren herstellung und deren verwendung |
| DE3509147A1 (de) * | 1985-03-14 | 1986-09-18 | Hoechst Ag, 6230 Frankfurt | Elektrophotographisches aufzeichnungsmaterial |
| DE3513747A1 (de) * | 1985-04-17 | 1986-10-23 | Hoechst Ag, 6230 Frankfurt | Elektrophotographisches aufzeichnungsmaterial |
| EP0238095A1 (en) * | 1986-03-20 | 1987-09-23 | Minolta Camera Kabushiki Kaisha | Photosensitive member composed of charge transporting layer and charge generating layer |
| JPH0693124B2 (ja) * | 1986-05-12 | 1994-11-16 | ミノルタ株式会社 | 感光体 |
| DE3706880A1 (de) * | 1987-03-04 | 1988-09-15 | Hoechst Ag | 4-chloroxazol-derivate, verfahren zu ihrer herstellung und ihre verwendung |
| US5000831A (en) * | 1987-03-09 | 1991-03-19 | Minolta Camera Kabushiki Kaisha | Method of production of amorphous hydrogenated carbon layer |
| DE3813459A1 (de) * | 1987-04-24 | 1988-11-10 | Minolta Camera Kk | Funktionsmaessig geteiltes photoempfindliches element |
| DE3814105C2 (de) * | 1987-04-27 | 1999-02-04 | Minolta Camera Kk | Elektrophotographisches Aufzeichnungsmaterial |
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| US4886720A (en) * | 1987-08-31 | 1989-12-12 | Minolta Camera Kabushiki Kaisha | Photosensitive medium having a styryl charge transport material |
| JP2717569B2 (ja) * | 1989-02-23 | 1998-02-18 | コニカ株式会社 | 感光体 |
| US5130603A (en) | 1989-03-20 | 1992-07-14 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device |
| US5198318A (en) * | 1989-06-06 | 1993-03-30 | Fuji Electric Co., Ltd. | Bisazo photoconductor for electrophotography |
| JPH03255453A (ja) * | 1990-01-17 | 1991-11-14 | Fuji Electric Co Ltd | 電子写真用感光体 |
| US5294510A (en) * | 1990-06-14 | 1994-03-15 | Minolta Camera Kabushiki Kaisha | Photosensitive member containing specific coumarin fluorescent bleaching agent |
| JPH04119360A (ja) * | 1990-09-11 | 1992-04-20 | Fuji Electric Co Ltd | 電子写真用感光体 |
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| US5443922A (en) * | 1991-11-07 | 1995-08-22 | Konica Corporation | Organic thin film electroluminescence element |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1730505A (en) * | 1928-01-30 | 1929-10-08 | Hart Russell | Photo-electric cell |
| FR1008598A (fr) * | 1948-04-30 | 1952-05-19 | Onera (Off Nat Aerospatiale) | Procédé pour l'enregistrement graphique ou l'inscription dirccte en matériaux pour la mise en oeuvre de ce procédé |
| US2663636A (en) * | 1949-05-25 | 1953-12-22 | Haloid Co | Electrophotographic plate and method of producing same |
| US2765304A (en) * | 1952-05-21 | 1956-10-02 | Ciba Ltd | New ox-diazole compounds and process for their manufacture |
| US2825814A (en) * | 1953-07-16 | 1958-03-04 | Haloid Co | Xerographic image formation |
| US2800559A (en) * | 1953-07-23 | 1957-07-23 | Nat Res Dev | Electrical semi-conductors comprising organo metallic compounds and process of producing same |
-
0
- NL NL99369D patent/NL99369C/xx active
- BE BE558078D patent/BE558078A/xx unknown
- NL NL217825D patent/NL217825A/xx unknown
- LU LU35193D patent/LU35193A1/xx unknown
-
1956
- 1956-06-04 DE DEK29014A patent/DE1058836B/de active Pending
-
1957
- 1957-05-29 US US662319A patent/US3189447A/en not_active Expired - Lifetime
- 1957-06-03 FR FR1176457D patent/FR1176457A/fr not_active Expired
- 1957-06-03 GB GB17519/57A patent/GB851218A/en not_active Expired
- 1957-06-03 CH CH360899D patent/CH360899A/de unknown
Cited By (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1193363B (de) * | 1961-01-28 | 1965-05-20 | Kalle Ag | Photoleitfaehige Schicht fuer elektro-photographische Zwecke |
| DE2336094A1 (de) * | 1973-07-16 | 1975-02-06 | Hoechst Ag | Elektrophotographisches aufzeichungsmaterial |
| DE2715714A1 (de) * | 1976-04-12 | 1977-10-13 | Ricoh Kk | 1,3,4-oxadiazolderivate sowie diese enthaltende elektrophotographische aufzeichnungsmaterialien |
| DE2659709A1 (de) * | 1976-12-31 | 1978-07-13 | Hoechst Ag | 1,3,4-oxadiazole, verfahren zu ihrer herstellung und ihre verwendung |
| US4492747A (en) * | 1980-06-30 | 1985-01-08 | Hoechst Aktiengesellschaft | Flexible laminatable photosensitive layer |
| DE3246250A1 (de) * | 1981-12-14 | 1983-06-16 | Fuji Photo Film Co., Ltd., Minami-Ashigara, Kanagawa | Photoleitfaehige zusammensetzungen und elektrophotographische aufzeichnungsmaterialien |
| US4739053A (en) * | 1983-02-09 | 1988-04-19 | Basf Aktiengesellschaft | 2H-v-triazolo[4-5-d]pyrimidines |
| EP0125481A1 (de) * | 1983-04-15 | 1984-11-21 | Hoechst Aktiengesellschaft | Elektrophotographisches Aufzeichnungsmaterial |
| US4528256A (en) * | 1983-04-15 | 1985-07-09 | Hoechst Aktiengesellschaft | Electrophotographic recording material with condensation product |
| DE3414791A1 (de) * | 1983-04-18 | 1984-10-18 | Canon K.K., Tokio/Tokyo | Fotoleitfaehiges aufzeichnungselement und traeger fuer das fotoleitfaehige aufzeichnungselement |
| US4533612A (en) * | 1983-04-27 | 1985-08-06 | Basf Aktiengesellschaft | Electrophotographic recording materials containing special charge carrier-transporting compounds |
| EP0127862A1 (de) * | 1983-05-31 | 1984-12-12 | Hoechst Aktiengesellschaft | Elektrophotographisches Aufzeichnungsmaterial |
| US4562134A (en) * | 1983-05-31 | 1985-12-31 | Hoechst Aktiengesellschaft | Electrophotographic material with cyanine sensitizer with betaine group |
| US4559285A (en) * | 1983-07-05 | 1985-12-17 | Basf Aktiengesellschaft | Electrophotographic recording materials containing a metal acetylacetonate |
| US4556621A (en) * | 1983-07-05 | 1985-12-03 | Basf Aktiengesellschaft | Electrophotographic recording material containing a metal-1,3-diketone complex |
| DE3890861C2 (de) * | 1987-10-07 | 1994-10-13 | Fuji Electric Co Ltd | Elektrophotographisches Auzeichnungsmaterial |
| US4906541A (en) * | 1987-11-28 | 1990-03-06 | Basf Aktiengesellschaft | Electrophotographic recording element containing a naphtholactam dye sensitizer |
| US5286590A (en) * | 1989-06-06 | 1994-02-15 | Fuji Electric Co., Ltd. | Bisazo photoconductor for electrophotography |
| US5292608A (en) * | 1989-06-06 | 1994-03-08 | Fugi Electric Co., Ltd. | Bisazo photoconductor for electrophotography |
| US5292602A (en) * | 1989-06-06 | 1994-03-08 | Fugi Electric Co., Ltd. | Bisazo photoconductor for electrophotography |
| US5132189A (en) * | 1989-09-07 | 1992-07-21 | Fuji Electric Co., Ltd. | Photoconductor for electrophotography |
| US5178981A (en) * | 1990-03-08 | 1993-01-12 | Fuji Electric Co., Ltd. | Photoconductor for electrophotography with a charge generating substance comprising a polycyclic and azo compound |
| US5316881A (en) * | 1991-12-27 | 1994-05-31 | Fuji Electric Co., Ltd. | Photoconductor for electrophotgraphy containing benzidine derivative |
| US5393627A (en) * | 1992-02-12 | 1995-02-28 | Fuji Electric Co., Ltd. | Photoconductor for electrophotography |
| US5368966A (en) * | 1992-05-14 | 1994-11-29 | Fuji Electric Co., Ltd. | Photosensitive member for electrophotography with indole derivative |
| EP1515191A2 (en) | 2003-09-05 | 2005-03-16 | Xerox Corporation | Dual charge transport layer and photoconductive imaging member including the same |
Also Published As
| Publication number | Publication date |
|---|---|
| NL99369C (en)) | |
| CH360899A (de) | 1962-03-15 |
| FR1176457A (fr) | 1959-04-10 |
| GB851218A (en) | 1960-10-12 |
| BE558078A (en)) | |
| US3189447A (en) | 1965-06-15 |
| LU35193A1 (en)) | |
| NL217825A (en)) |
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