US3935009A
Expired / Lapsed
US
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Electrophotographic reproduction element of an aniline compound electron acceptor
Assignee: Canon Production Printing Holding BV
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Filing: 1974-02-06
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Granted: 1976-01-27
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Expires: 1994-02-06
Abstract
Abstract Reproduction elements coated with organic photoconductors are made with improved and/or more widely selectable electrophotographic properties by employing in the photoconductive coating a donor-acceptor complex composed of a known organic electron donor having photo- or semiconductor properties, e.g. a poly-N-vinylcarbazole or polyvinylpyrene, and a N-(fluoren-9-ylidene)-aniline compound as an activating electron acceptor. Especially effective as the electron acceptor are certain new compounds, namely, p- and m-nitro-N-(2,4,7-trinitrofluoren-9-ylidene)-aniline and p-methylsulfonyl-N-(2,4,7-trinitrofluoren-9-ylidene)-aniline.
Inventors
- 👤 Gerardus J. Crommentuyn
- 👤 Johannes H. A. Kuiper
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 08:13
CPC Classifications
G; G03; G03G; G03G5/00; G03G5/02; G03G5/04; G03G5/06; G03G5/0601; G03G5/0612; G03G5/0618; G03G5/062
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
110 words
An electrophotographic reproduction element comprising a support having on it a photoconductive coating layer which contains a donor-acceptor complex formed of an electron donor having photo- or semiconductor properties and an electron acceptor, wherein the electron acceptor is a compound of the formula ##SPC3## in which R represents one or more moieties selected from the group consisting of hydrogen and halogen atoms and lower alkyl, lower alkoxy, nitro, cyano, carboxylic acid, carboxylic ester, sulfonic acid, sulfonic ester, alkylsulfinyl, alkylsulfonyl and trifluoromethyl substituents and R' and R" each represents a hydrogen atom or one or more nitro groups but at least one of R' and R" is not a hydrogen atom.
Claim 2
Dependent Claim
110 words
An electrophotographic reproduction element comprising a support having on it a photoconductive coating layer which contains a donor-acceptor complex formed of an electron donor having photo- or semiconductor properties and an electron acceptor, wherein the electron acceptor is a compound of the formula ##SPC3## in which R represents one or more moieties selected from the group consisting of hydrogen and halogen atoms and lower alkyl, lower alkoxy, nitro, cyano, carboxylic acid, carboxylic ester, sulfonic acid, sulfonic ester, alkylsulfinyl, alkylsulfonyl and trifluoromethyl substituents and R' and R" each represents a hydrogen atom or one or more nitro groups but at least one of R' and R" is not a hydrogen atom.
Claim 3
Dependent Claim
14 words
An electrophotographic reproduction element according to claim 1, wherein R is a methoxy group.
Claim 4
Dependent Claim
28 words
An electrophotographic reproduction element according to claim 1, wherein R is selected from the group consisting of nitro, halogen, trifluoromethyl and methylsulfonyl substituents or is a hydrogen atom.
Claim 5
Dependent Claim
32 words
An electrophotographic reproduction element according to claim 1, wherein R is in the para or meta position relative to the nitrogen atom which forms the link between the fluorene and benzene residues.
Claim 6
Dependent Claim
18 words
An electrophotographic reproduction element according to claim 1, wherein the electron acceptor is p- or m-nitro-N-(2,4,7-trinitrofluoren-9-ylidene)-aniline or p-methylsulfonyl-N-(2,4,7-trinitrofluoren-9-ylidene)-aniline.
Claim 7
Dependent Claim
114 words
A photoconductive composition for use in the coating layer of an electrophotographic reproduction element, comprising in admixture an organic electron donor having photo- or semiconductive properties and an organic electron acceptor that forms a donor-acceptor complex with said donor, said acceptor being a compound of the formula ##SPC4## in which R represents one or more moieties selected from the group consisting of hydrogen and halogen atoms and lower alkyl, lower alkoxy, nitro, cyano, carboxylic acid, carboxylic ester, sulfonic acid, sulfonic ester, alkylsulfinyl, alkylsulfonyl and trifluoromethyl substituents and R' and R" each represents a hydrogen atom or one or more nitro groups but at least one of R' and R" is not a hydrogen atom.
Claim 8
Dependent Claim
114 words
A photoconductive composition for use in the coating layer of an electrophotographic reproduction element, comprising in admixture an organic electron donor having photo- or semiconductive properties and an organic electron acceptor that forms a donor-acceptor complex with said donor, said acceptor being a compound of the formula ##SPC4## in which R represents one or more moieties selected from the group consisting of hydrogen and halogen atoms and lower alkyl, lower alkoxy, nitro, cyano, carboxylic acid, carboxylic ester, sulfonic acid, sulfonic ester, alkylsulfinyl, alkylsulfonyl and trifluoromethyl substituents and R' and R" each represents a hydrogen atom or one or more nitro groups but at least one of R' and R" is not a hydrogen atom.
Claim 9
Dependent Claim
45 words
A compound of the formula ##SPC5## in which R is a nitro, trifluoromethyl or methyl sulfonyl group and R' and R" each is a hydrogen atom or one or more nitro groups, but at least one of R' and R" is not a hydrogen atom.
Claim 10
Dependent Claim
45 words
A compound of the formula ##SPC5## in which R is a nitro, trifluoromethyl or methyl sulfonyl group and R' and R" each is a hydrogen atom or one or more nitro groups, but at least one of R' and R" is not a hydrogen atom.
Claim 11
Dependent Claim
17 words
A compound according to claim 7, selected from the group consisting of p- or m-nitro-N-(2,4,7-trinitrofluoren-9-ylidene)-aniline and p-methylsulfonyl-N-(2,4,7-trinitrofluoren-9-ylidene)-aniline.
Claim 12
Dependent Claim
18 words
An electrophotographic reproduction element according to claim 1, carrying an electrophotographic image on the photoconductive coating layer thereof.
Claim 13
Dependent Claim
19 words
An electrophotographic reproduction element according to claim 1, said electron donor being a poly-N-vinyl carbazole or a polyvinyl pyrene.
Claim 14
Dependent Claim
54 words
An electrophotographic reproduction element according to claim 1, said electron donor being a poly-N-vinyl carbazole or a polyvinyl pyrene and said electron acceptor being p- or m-nitro-N-(2,4,7-trinitrofluoren-9-ylidene)-aniline or p-methylsulfonyl-N-(2,4,7-trinitrofluorene-9-ylidene)-aniline, said acceptor being present in a molar ratio of between 0.02 and 1 to the amount of such donor calculated to the monomeric unit thereof.
Claim 15
Dependent Claim
50 words
An electrophotographic reproduction element according to claim 1, said electron donor being a poly-N-vinyl carbazole or a polyvinyl pyrene and said electron acceptor being p-nitro-N-(2,4, 7-trinitrofluorene-9-ylidene)-aniline and being present in a molar ratio of between 0.02 and 1 to the amount of said donor calculated to the monomeric unit thereof.
Claim 16
Dependent Claim
18 words
A photoconductive composition according to claim 6, said electron donor being a poly-N-vinyl carbazole or a polyvinyl pyrene.
Claim 17
Dependent Claim
54 words
A photoconductive composition according to claim 6, said electron donor being a poly-N-vinyl carbazole or a polyvinyl pyrene and said electron acceptor being p- or m-nitro-N-(2,4,7-trinitrofluorene-9-ylidene)- aniline or p-methylsulfonyl-N-(2,4,7-trinitrofluoren-9-ylidene)-aniline, said acceptor being present in a molar ratio of between 0.02 and 1 to the amount of said donor calculated to the monomeric unit thereof.
Claim 18
Dependent Claim
49 words
A photoconductive composition according to claim 6, said electron donor being a poly-N-vinyl carbazole or a polyvinyl pyrene and said electron acceptor being p-nitro-N-(2,4, 7-trinitrofluorene-9-ylidene)-aniline and being present in a molar ratio of between 0.02 and 1 to the amount of said donor calculated to the monomeric unit thereof.
Claim 19
Dependent Claim
8 words
A compound according to claim 7, namely, p-nitro-N-(2,4,7-trinitrofluorene-9-ylidene)-aniline.
References Cited (Backward Citations)
US3037861A
Cited
US3617271A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-01-26 | 1979-07-28 | 1980-01-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-01-26 | 1983-07-28 | 1984-01-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-01-26 | 1987-07-28 | 1988-01-27 | $7700.00 | Window Closed / Lapsed |