US3871884A - Photoconductive complex with hydroxy-nitrobenzoic acids and triarylmethane dyes - Google Patents
Photoconductive complex with hydroxy-nitrobenzoic acids and triarylmethane dyes Download PDFInfo
- Publication number
- US3871884A US3871884A US207981A US20798171A US3871884A US 3871884 A US3871884 A US 3871884A US 207981 A US207981 A US 207981A US 20798171 A US20798171 A US 20798171A US 3871884 A US3871884 A US 3871884A
- Authority
- US
- United States
- Prior art keywords
- hydroxy
- photoconductive
- acid
- charge transfer
- transfer reaction
- 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 - Lifetime
Links
- 239000001003 triarylmethane dye Substances 0.000 title description 2
- KPDBKQKRDJPBRM-UHFFFAOYSA-N 602-00-6 Chemical class OC(=O)C1=CC=CC(O)=C1[N+]([O-])=O KPDBKQKRDJPBRM-UHFFFAOYSA-N 0.000 title 1
- 239000000463 material Substances 0.000 claims abstract description 30
- 238000006276 transfer reaction Methods 0.000 claims abstract description 17
- 239000000975 dye Substances 0.000 claims abstract description 15
- WWWFHFGUOIQNJC-UHFFFAOYSA-N 2-hydroxy-3-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1O WWWFHFGUOIQNJC-UHFFFAOYSA-N 0.000 claims abstract description 7
- PPDRLQLKHRZIJC-UHFFFAOYSA-N 5-nitrosalicylic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1O PPDRLQLKHRZIJC-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 13
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 claims description 10
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 8
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 claims description 7
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 claims description 6
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 claims description 6
- 229960001506 brilliant green Drugs 0.000 claims description 4
- HXCILVUBKWANLN-UHFFFAOYSA-N brilliant green cation Chemical compound C1=CC(N(CC)CC)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](CC)CC)C=C1 HXCILVUBKWANLN-UHFFFAOYSA-N 0.000 claims description 4
- 239000013078 crystal Substances 0.000 claims description 4
- 239000004014 plasticizer Substances 0.000 claims description 4
- 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 claims description 4
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 claims description 3
- LAXBNTIAOJWAOP-UHFFFAOYSA-N 2-chlorobiphenyl Chemical compound ClC1=CC=CC=C1C1=CC=CC=C1 LAXBNTIAOJWAOP-UHFFFAOYSA-N 0.000 claims description 3
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 125000006267 biphenyl group Chemical group 0.000 claims description 3
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 claims description 3
- HSUIVCLOAAJSRE-UHFFFAOYSA-N bis(2-methoxyethyl) benzene-1,2-dicarboxylate Chemical compound COCCOC(=O)C1=CC=CC=C1C(=O)OCCOC HSUIVCLOAAJSRE-UHFFFAOYSA-N 0.000 claims description 3
- ZXJXZNDDNMQXFV-UHFFFAOYSA-M crystal violet Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1[C+](C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 ZXJXZNDDNMQXFV-UHFFFAOYSA-M 0.000 claims description 3
- 229960002380 dibutyl phthalate Drugs 0.000 claims description 3
- 229940107698 malachite green Drugs 0.000 claims description 3
- FDZZZRQASAIRJF-UHFFFAOYSA-M malachite green Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](C)C)C=C1 FDZZZRQASAIRJF-UHFFFAOYSA-M 0.000 claims description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 3
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 claims description 3
- LWFUFLREGJMOIZ-UHFFFAOYSA-N 3,5-dinitrosalicylic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O LWFUFLREGJMOIZ-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 14
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 abstract description 14
- 230000035945 sensitivity Effects 0.000 abstract description 14
- 238000002156 mixing Methods 0.000 abstract description 9
- 239000000243 solution Substances 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 206010034972 Photosensitivity reaction Diseases 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- -1 benzoic acid derivative compound Chemical class 0.000 description 2
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 230000036211 photosensitivity Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- AXMCIYLNKNGNOT-UHFFFAOYSA-N sodium;3-[[4-[(4-dimethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)-[4-[ethyl-[(3-sulfophenyl)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-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- 229920001756 Polyvinyl chloride acetate Polymers 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000004776 molecular orbital Methods 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- SRYYCRXKYKWXDQ-PTGKCMAJSA-N success Chemical compound O([C@H]1CCC[C@@H](OC(=O)C[C@H]2[C@@H]3C=C[C@@H]4C[C@H](C[C@H]4[C@@H]3C=C2C(=O)[C@@H]1C)O[C@H]1[C@@H]([C@H](OC)[C@@H](OC)[C@H](C)C1)OC)CC)[C@H]1CC[C@H](N(C)C)[C@@H](C)O1 SRYYCRXKYKWXDQ-PTGKCMAJSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 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
- G03G5/07—Polymeric photoconductive materials
- G03G5/071—Polymeric photoconductive materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
- G03G5/072—Polymeric photoconductive materials obtained by reactions only involving carbon-to-carbon unsaturated bonds comprising pending monoamine groups
- G03G5/073—Polymeric photoconductive materials obtained by reactions only involving carbon-to-carbon unsaturated bonds comprising pending monoamine groups comprising pending carbazole groups
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/001—Electric or magnetic imagery, e.g., xerography, electrography, magnetography, etc. Process, composition, or product
- Y10S430/10—Donor-acceptor complex photoconductor
Definitions
- Photoconductive materials for electrophotography have been formed by blending a molecular compound produced by a charge transfer reaction of poly-N- vinylcarbazole and tetrachloro-p-benzoquinone, with at least one compound selected from the group consisting of 2,hydroxy-3,S-dinitrobenzoic acid, 2- hydroxy-3-nitrobenzoic acid and 2-hydroxy-5- nitrobenzoic acid, and with at least one triarylmethane dyestuff.
- These photoconductive materials for electrophotography are not only characterized by high sensitivity and excellent image quality, but they also can be ABSTRACT easily cast into films and possess good transparency.
- Inorganic materials such as selenium or zinc oxide
- organic materials such as poly-N-vinyl carbazole systems or polyacetylnaphthylene systems
- the organic photoconductive materials in particular have been considered to be especially attractive industrially, since they can be easily cast into films, they possess high flexibility which renders them easily handleable, and they can be formed at relatively low costs.
- the conventional organic materials 'used for this purpose have demonstrated several undesirable defects which have prevented the attainment of higher image quality, and higher photosensitivity.
- poly-N-vinyl carbazole has good spectral sensitivity in the ultraviolet region, its degree of sensitivity is so low that it has insufficient electrophotographic sensitivity under incandescent light exposure.
- Attempts have been made to improve this sensitivity by blending a small amount of tetrachloro-p-benzoquinone as a sensitizer, with the poly-N-vinyl carbazole, in order to shift the spectral sensitivity to the visible regions and at the same time to intensify the photosensitivity.
- these attempts have not been entirely successful, since they have resulted in compositions possessing rather poor resolution, and which are characterized by nonuniformity of image, strong edge effects, and staining of the non-imaged parts.
- an organic photoconductive material for electrophotography which is not only characterized by high sensitivity and excellent image quality, but also by easy film castability for films and good transparency.
- a photoconductive material for electrophotography formed by blending a molecular compound produced by a charge transfer reaction of poly- N-vinyl carbazole and tetrachloro-p-benzoquinone, with at least one compound selected from the group consisting of 2-hydroxy-3,S-dinitrobenzoic acid, 2- hydroxy-3-nitrobenzoic acid and 2-hydroxy-5- nitrobenzoic acid, and with at least one triarylmethane dyestufl'.
- a solution of poly-N-vinyl carbazole and a solution of tetrachloro p-benzoquinone is prepared. Both solutions are heated slightly and the poly-N-vinyl carbazole solution is added to the tetrachloro-p-benzoquinone solution while stirring vigorously. Stirring is continued for several hours and the combined solutions are concentrated slowly and left for several hours at room temperature. A non-soluble solvent, such as methylalcohol, is then added slowly to the mixed solution, while stirring, until a deep blue violet-colored deposit is produced as a fine suspension in the solution.
- the separated, refined and dried'deposit will be the charge transfer reaction product of poly-'N-vinylcarbazole and tetrachloro-p-benzoquinone.
- the reaction may conveniently be carried out at temperatures of about 50C. and in such solvents as chloroform.
- a benzoic acid derivative compound such as 2-hydroxy-3,S-dinitrobenzoic acid, 2-hydroxy-3- nitrobenzoic acid or 2-hydroxy-5-nitrobenzoic acid, is then mixed and blended with the molecular charge transfer reaction product in a ratio of 05-10 parts by weight of the benzoic acid derivative per parts of charge transfer reaction product.
- Suitable triarylmethane dyestuffs which can be used for this purpose include crystal violet, Brilliant-green, Victoria blue, Methyl violet, Malachite green, Acid violet 68, etc.
- the photoconductive material of this invention can be further blended with p-ter-phenyl, diphenyl, diphenylchloride, dibutylphthalate, dimethylglycolphthalate, triphenylphosphate, methylnaphthalene or dioctylphthalate, etc. as a plasticizer to improve its filmforming capability.
- the charge transfer reaction product is a high molecular weight compound, which possesses good film formability and good flexibility even without the optional plasticizer, and it possesses good transparency and high sensitivity throughout the visible region. It is highly photoconductive itself, without any other additive, but when it is blended with one of the abovementioned benzoic acid derivatives, and at least one triarylmethane dyestuff, it becomes even more highly sensitive. Surprisingly, when this product is blended with only the benzoic acid derivative or with only the triarylmethane dyestuff separately, the degree of sensitivity and image quality tends to be lower, rather than improved.
- the photoconductive film produced by the photoconductive material of this invention can be formed with good homogeneity and is characterized by good image reproducibility when exposed through any colored original incandescent light or other visible rays, and can form an image of good resolution and high uniformity. Moreover, when thesubstratum is moderately transparent, the image formed can be used as a socalled secondary master, as a substitute for a negative or a semitransparent master, Le, a diazo master or a copy master.
- the reason why the photoconductive material of this invention has such'good photographic characterisitcs is not'fully understood, but seems to be explainable as follows:
- the charge transfer reaction product is formed from poly-N-vinylcarbazole and the tetrachloro-pbenzoquinone, which effectively overlap each other in molecular orbital electronic states. This is believed to have some effect in increasing the sensitivity. When this product is combined with the benzoic acid derivative and the triarylmethane dyestuff, the sensitivity becomes even greater.
- the charge transfer reaction product which forms the matrix of the system is a high molecular weight material which possesses good miscibility in the blend and permits'the formation of a smooth and homogeneous photoconductive film.
- solution A chloroform solution of poly-N-vinylcarbazole (hereinafter referred to as solution A) was prepared by dissolving 4.0 g. of poly-N-vinylcarbazole in 1.4 l. of
- solution B Another benzoquinone solution (hereinafter referred to as solution B) was prepared by dissolving 4,9 g. of tetrachlorop-benzoquinone in 1.0 l. of chloroform.
- Solution A was heated to a temperature of 50C. and was added dropwise into solution B which was also heated to a temperature of 50C.
- the mixing was accompanied by vigorous stirring. After the mixing of solutions A and B, stirring was continued for 3 hours and the temperature was maintained at 50C.
- the mixed solution was then concentrated slowly to a volume of 1 liter, and was left for 24 hours at room temperature.
- chloroform solution of tetrachloro-p violet-colored deposit was produced as a fine. suspension in the solution. This deposit was separated from the solution, refined and dried. This was identified as a molecular compound produced by acharge. transfer reaction of poly-N-vinylcarbazoleand tetrachloro-pbenzoquinone.
- photosensitive plates for electrophotography were prepared, and these plates'were given a positive electric charge by ordinary corona-discharge methods from a 5' kV. source.
- the plates were then exposed with incandescent light through an original, master by means of photographic enlarger, and were developed by cascading the toner.
- the optimum exposure described here means the so-called optimum exposure required to obtain a faithful duplication ofthe original master of good resolution or good contrast, uniform image, stainlessness of the non-imaged portions and to produce acopy ofgood image quality without edge effects.
- 6 raphy comprising a blend of a. a molecular charge transfer reaction product of poly-N-vinylcarbazole and tetrachloro-pbenzoquinone,
- At least one benzoic acid derivative selected from the group consisting of 2-hydroxy-3,5- dinitrobenzoic acid, 2-hydroxy-3-nitrobenzoic acid and 2-hydroxy-5-nitrobenzoic acid, and
- the photoconductive material of this invention is consisting of Crystal violet, Brilliant-green. Victoria blue, Methyl-violet, Malachite-green and Acid-violet 6B.
- the photocondutive material ofclaim l which further contains a plasticizer selected from the group ,consisting of p-ter-phenyl, diphenyl, diphenylchloride, dibutylphthalate, dimethylglycolphthalate, triphenylphosphate, methylnaphthalene and dioctylphthalate.
- a plasticizer selected from the group ,consisting of p-ter-phenyl, diphenyl, diphenylchloride, dibutylphthalate, dimethylglycolphthalate, triphenylphosphate, methylnaphthalene and dioctylphthalate.
- the photoconductive material of claim 1 which contains 0.05-2 parts by weight of a triarylmethane dyestuff per parts by weight of said charge transfer reaction product.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Photoreceptors In Electrophotography (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP45111880A JPS4927705B1 (en, 2012) | 1970-12-16 | 1970-12-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3871884A true US3871884A (en) | 1975-03-18 |
Family
ID=14572454
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US207981A Expired - Lifetime US3871884A (en) | 1970-12-16 | 1971-12-14 | Photoconductive complex with hydroxy-nitrobenzoic acids and triarylmethane dyes |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US3871884A (en, 2012) |
| JP (1) | JPS4927705B1 (en, 2012) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4088483A (en) * | 1974-02-13 | 1978-05-09 | Minolta Camera Kabushiki Kaisha | Electrophotographic plate with charge transport overlayer |
| US4302521A (en) * | 1979-07-16 | 1981-11-24 | Konishiroku Photo Industry Co., Ltd. | Photosensitive element for electrophotography |
| US4562133A (en) * | 1983-10-13 | 1985-12-31 | Yeda Research And Development Company Limited | Polymers photoconductive in the near infra-red |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3037861A (en) * | 1957-09-07 | 1962-06-05 | Kalle Ag | Electrophotographic reproduction material |
| US3159483A (en) * | 1959-07-14 | 1964-12-01 | Azoplate Corp | Process for the preparation of electrophotographic reversed images |
| US3162532A (en) * | 1959-06-25 | 1964-12-22 | Azoplate Corp | Photoconductive layers for electrophotographic purposes |
| US3287120A (en) * | 1961-07-24 | 1966-11-22 | Azoplate Corp | Process for the sensitization of photoconductors |
| US3421891A (en) * | 1964-06-18 | 1969-01-14 | Matsushita Electric Ind Co Ltd | Electrophotographic materials comprising brominated poly-n-vinyl carbazoles |
-
1970
- 1970-12-16 JP JP45111880A patent/JPS4927705B1/ja active Pending
-
1971
- 1971-12-14 US US207981A patent/US3871884A/en not_active Expired - Lifetime
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3037861A (en) * | 1957-09-07 | 1962-06-05 | Kalle Ag | Electrophotographic reproduction material |
| US3162532A (en) * | 1959-06-25 | 1964-12-22 | Azoplate Corp | Photoconductive layers for electrophotographic purposes |
| US3159483A (en) * | 1959-07-14 | 1964-12-01 | Azoplate Corp | Process for the preparation of electrophotographic reversed images |
| US3287120A (en) * | 1961-07-24 | 1966-11-22 | Azoplate Corp | Process for the sensitization of photoconductors |
| US3421891A (en) * | 1964-06-18 | 1969-01-14 | Matsushita Electric Ind Co Ltd | Electrophotographic materials comprising brominated poly-n-vinyl carbazoles |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4088483A (en) * | 1974-02-13 | 1978-05-09 | Minolta Camera Kabushiki Kaisha | Electrophotographic plate with charge transport overlayer |
| US4302521A (en) * | 1979-07-16 | 1981-11-24 | Konishiroku Photo Industry Co., Ltd. | Photosensitive element for electrophotography |
| US4562133A (en) * | 1983-10-13 | 1985-12-31 | Yeda Research And Development Company Limited | Polymers photoconductive in the near infra-red |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4927705B1 (en, 2012) | 1974-07-19 |
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