US4606986A
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US
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Electrophotographic elements containing unsymmetrical squaraines
Assignee: Xerox Corp
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Filing: 1985-04-05
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Granted: 1986-08-19
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Expires: 2005-04-05
Abstract
Abstract An unsymmetrical squaraine composition, process for synthesizing the unsymmetrical squaraine composition, devices containing the unsymmetrical squaraine composition, and methods of using the devices. The process for synthesizing the unsymmetrical squaraine composition comprises forming a mixture comprising squaric acid, a long chain primary alcohol, a first tertiary amine, and a second tertiary aromatic amine different from the first tertiary aromatic amine, and heating the mixture in vacuo below the boiling points of the primary alcohol, the first tertiary amine and the second tertiary aromatic amine to form an unsymmetrical squaraine composition. The novel unsymmetrical squaraine composition synthesized by this process may be used in electrostatographic imaging members comprising a supporting substrate and a photoconductive layer comprising the novel unsymmetrical squaraine composition. These electrostatographic imaging members may be utilized in an electrostatographic imaging processes.
Inventors
- 👤 John F. Yanus
- 👤 William W. Limburg
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 16:22
CPC Classifications
G; G03; G03G; G03G5/00; G03G5/02; G03G5/04; G03G5/06
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
176 words
An electrostatographic imaging member comprising a supporting substrate and a photoconductive layer comprising from about 5 percent and about 100 percent by volume of an unsymmetrical squaraine composition having the formula: ##STR6## wherein R 1 , R 2 , R 5 and R 6 are independently selected from the group consisting of alkyl radicals having 1 to 4 carbon atoms, phenyl radicals, and radicals having the formula: ##STR7## and R 3 , R 4 , R 7 and R 8 are independently selected from the group consisting of H, CH 3 , CH 2 CH 3 , CF 3 , F, Cl, Br, and COOH, wherein at least one of R 3 and R 4 are different than R 7 and R 8 if R 7 and R 8 are located on the same relative position on the aromatic ring as R 3 and R 4 and wherein R 9 is selected from the group consisting of H, alkyl radicals having from 1 to 4 carbon atoms, F, Cl, Br, COOH, CN and CF 3 .
Claim 2
Dependent Claim
176 words
An electrostatographic imaging member comprising a supporting substrate and a photoconductive layer comprising from about 5 percent and about 100 percent by volume of an unsymmetrical squaraine composition having the formula: ##STR6## wherein R 1 , R 2 , R 5 and R 6 are independently selected from the group consisting of alkyl radicals having 1 to 4 carbon atoms, phenyl radicals, and radicals having the formula: ##STR7## and R 3 , R 4 , R 7 and R 8 are independently selected from the group consisting of H, CH 3 , CH 2 CH 3 , CF 3 , F, Cl, Br, and COOH, wherein at least one of R 3 and R 4 are different than R 7 and R 8 if R 7 and R 8 are located on the same relative position on the aromatic ring as R 3 and R 4 and wherein R 9 is selected from the group consisting of H, alkyl radicals having from 1 to 4 carbon atoms, F, Cl, Br, COOH, CN and CF 3 .
Claim 3
Dependent Claim
180 words
An electrostatographic imaging member comprising a supporting substrate, a photoconductive layer comprising from about 5 percent and about 100 percent by volume of an unsymmetrical squaraine composition having the formula: ##STR8## wherein R 1 , R 2 , R 5 and R 6 are independently selected from the group consisting of alkyl radicals having 1 to 4 carbon atoms, phenyl radicals, and radicals having the formula: ##STR9## and R 3 , R 4 , R 7 and R 8 are independently selected from the group consisting of H, CH 3 , CH 2 CH 3 , CF 3 , F, Cl, Br, and COOH, wherein at least one of R 3 and R 4 are different than R 7 and R 8 if R 7 and R 8 are located on the same relative position on the aromatic ring as R 3 and R 4 and wherein R 9 is selected from the group consisting of H, alkyl radicals having from 1 to 4 carbon atoms, F, Cl, Br, COOH, CN and CF 3 , and a charge transport layer.
Claim 4
Dependent Claim
180 words
An electrostatographic imaging member comprising a supporting substrate, a photoconductive layer comprising from about 5 percent and about 100 percent by volume of an unsymmetrical squaraine composition having the formula: ##STR8## wherein R 1 , R 2 , R 5 and R 6 are independently selected from the group consisting of alkyl radicals having 1 to 4 carbon atoms, phenyl radicals, and radicals having the formula: ##STR9## and R 3 , R 4 , R 7 and R 8 are independently selected from the group consisting of H, CH 3 , CH 2 CH 3 , CF 3 , F, Cl, Br, and COOH, wherein at least one of R 3 and R 4 are different than R 7 and R 8 if R 7 and R 8 are located on the same relative position on the aromatic ring as R 3 and R 4 and wherein R 9 is selected from the group consisting of H, alkyl radicals having from 1 to 4 carbon atoms, F, Cl, Br, COOH, CN and CF 3 , and a charge transport layer.
Claim 5
Dependent Claim
47 words
An electrostatographic imaging member in accordance with claim 2 wherein said squaraine composition is dispersed in a resin binder in an amount of from about 30 percent by weight to about 50 percent by weight squaraine based on the weight of said squaraine and said resin binder.
Claim 6
Dependent Claim
20 words
An electrostatographic imaging member in accordance with claim 2 wherein said hole transport layer comprises a diamine hole transport material.
Claim 7
Dependent Claim
37 words
An electrostatographic imaging member in accordance with claim 4 wherein said diamine hole transport material is dispersed in a resinous binder in an amount of from about 10 percent by weight to about 75 percent by weight.
Claim 8
Dependent Claim
26 words
An electrostatographic imaging member in accordance with claim 5 wherein said resinous binder for said diamine hole transport material is a polycarbonate, polyester or vinyl polymer.
Claim 9
Dependent Claim
59 words
An electrostatographic imaging member in accordance with claim 4 wherein said diamine hole transport material comprises molecules of the formula: ##STR10## dispersed in a highly insulating and transport organic resinous material wherein X is selected from the group consisting of ortho (CH 3 ), meta (CH 3 ), para (CH 3 ), ortho (Cl), meta (Cl), and para (Cl).
Claim 10
Dependent Claim
17 words
An electrostatographic imaging member in accordance with claim 7 wherein said diamine hole transport material comprises N,N'-diphenyl-N,N'-bis(3-methylphenyl)-[1,1-biphenyl]-4,4'-diamine.
Claim 11
Dependent Claim
18 words
An electrostatographic imaging member in accordance with claim 2 wherein said supporting substrate comprises an electrically conductive metal.
Claim 12
Dependent Claim
30 words
An electrostatographic imaging member in accordance with claim 2 comprising a supporting substrate, a metal oxide hole blocking layer, a photoconductive layer comprising said squaraine and a hole transport layer.
Claim 13
Dependent Claim
33 words
An electrostatographic imaging member in accordance with claim 2 comprising a supporting substrate, a metal oxide hole blocking layer, an adhesive layer, a photoconductive layer comprising said squaraine and a hole transport layer.
Claim 14
Dependent Claim
38 words
An electrostatographic imaging member in accordance with claim 2 comprising a supporting substrate, a metal oxide hole blocking layer, an adhesive layer, a photoconductive layer comprising said squaraine and a transport layer comprising a diamine hole transport material.
Claim 15
Dependent Claim
234 words
An electrostatographic imaging process comprising (a) providing an electrostatographic imaging member comprising an electrostatographic imaging memvber having an imaging surface, said imaging member comprising a supporting substrate and a photoconductive layer comprising from about 5 percent and about 100 percent by volume of an unsymmetrical squaraine composition having the formula: ##STR11## wherein R 1 , R 2 , R 5 and R 6 are independently selected from the group consisting of alkyl radicals having 1 to 4 carbon atoms, phenyl radicals, and radicals having the formula: ##STR12## and R 3 , R 4 , R 7 and R 8 are independently selected from the group consisting of H, CH 3 , CH 2 CH 3 , CF 3 , F, Cl, Br, and COOH, wherein at least one of R 3 and R 4 are different than R 7 and R 8 if R 7 and R 8 are located on the same relative position on the aromatic ring as R 3 and R 4 and wherein R 9 is selected from the group consisting of H, alkyl radicals having from 1 to 4 carbon atoms, F, Cl, Br, COOH, CN and CF 3 , (b) depositing in the dark a substantially uniform electrostatic charge on said imaging surface and (c) exposing said imaging surface to activating radiation in image configuration to selectively discharge said uniform electrostatic charge thereby forming an electrostatic latent image.
Claim 16
Dependent Claim
234 words
An electrostatographic imaging process comprising (a) providing an electrostatographic imaging member comprising an electrostatographic imaging memvber having an imaging surface, said imaging member comprising a supporting substrate and a photoconductive layer comprising from about 5 percent and about 100 percent by volume of an unsymmetrical squaraine composition having the formula: ##STR11## wherein R 1 , R 2 , R 5 and R 6 are independently selected from the group consisting of alkyl radicals having 1 to 4 carbon atoms, phenyl radicals, and radicals having the formula: ##STR12## and R 3 , R 4 , R 7 and R 8 are independently selected from the group consisting of H, CH 3 , CH 2 CH 3 , CF 3 , F, Cl, Br, and COOH, wherein at least one of R 3 and R 4 are different than R 7 and R 8 if R 7 and R 8 are located on the same relative position on the aromatic ring as R 3 and R 4 and wherein R 9 is selected from the group consisting of H, alkyl radicals having from 1 to 4 carbon atoms, F, Cl, Br, COOH, CN and CF 3 , (b) depositing in the dark a substantially uniform electrostatic charge on said imaging surface and (c) exposing said imaging surface to activating radiation in image configuration to selectively discharge said uniform electrostatic charge thereby forming an electrostatic latent image.
References Cited (Backward Citations)
US3121006A
Cited
BE763540A
Cited
US3838059A
Cited
US3824099A
Cited
US4123270A
Cited
US4265990A
Cited
US4251612A
Cited
US4353971A
Cited
US4481270A
Cited
US4486520A
Cited
US4508803A
Cited
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1989-08-18 | 1990-02-17 | 1990-08-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-08-18 | 1994-02-17 | 1994-08-19 | $3760.00 | Window Closed / Lapsed |
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