US4514481A
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4H-Thiopyran-1,1-dioxide and electrophotographic layers and elements comprising same
Assignee: Eastman Kodak Co
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Filing: 1984-03-09
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Granted: 1985-04-30
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Expires: 2004-03-09
Abstract
Abstract Novel 4H-thiopyran-1,1-dioxides are disclosed. They are useful as electron transporters in electrophotographic layers and elements.
Inventors
- 👤 Michael Scozzafava
- 👤 Chin H. Chen
- 👤 George A. Reynolds
- 👤 Jerome H. Perlstein
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 13:14
CPC Classifications
C; C07; C07D; C07D409/00; C07D409/02; C07D409/04; C07D335/00; C07D335/02; G; G03; G03G; G03G5/00; G03G5/02; G03G5/04; G03G5/06; G03G5/0622; G03G5/0624; G03G5/0635; G03G5/0637
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
49 words
An electrophotographic layer comprising an electrically insulating binder, and an electron donor characterized in that the composition also comprises a 4H-thiopyran-1,1-dioxide having (a) an electron withdrawing group in the 4-position and (b) a half wave reduction potential more positive than -0.5 volts as measured against a saturated calomel electrode.
Claim 2
Dependent Claim
49 words
An electrophotographic layer comprising an electrically insulating binder, and an electron donor characterized in that the composition also comprises a 4H-thiopyran-1,1-dioxide having (a) an electron withdrawing group in the 4-position and (b) a half wave reduction potential more positive than -0.5 volts as measured against a saturated calomel electrode.
Claim 3
Dependent Claim
73 words
The layer of claim 1 wherein the 4H-thiopyran-1,1-dioxide has the structure ##STR11## wherein R 3 represents an electron withdrawing group; R 1 and R 5 each independently represents alkyl or aryl; R 2 and R 4 each independently represents hydrogen or an alkoxy carbonyl group; or R 1 and R 2 or R 4 and R 5 together with the carbon atoms to which they are attached form a fused unsaturated 6-membered ring.
Claim 4
Dependent Claim
60 words
The layer of claim 2 wherein R 3 represents oxo, dicyanomethylene, indandionemethylene or cyanoethoxycarbonylmethylene; R 1 and R 5 each independently represents phenyl, methyl or t-butyl; R 2 and R 4 each independently represents hydrogen or methoxycarbonyl; or R 1 and R 2 taken together with the carbon atoms to which they are attached form a fused 6-member unsaturated ring.
Claim 5
Dependent Claim
19 words
The layer of claim 2 wherein the 4H-thiopyran-1,1-dioxide is selected from the group consisting of 4-dicyanomethylene-2,6-diphenyl-4H-thiopyran-1,1-dioxide, 2,6-di-tert-butyl-4-dicyanomethylene-4H-thiopyran-1,1-dioxide and 2,6-dimethyl-4-dicyanomethylene-4H-thiopyram-4-one-1,1-dioxide.
Claim 6
Dependent Claim
26 words
The layer of claim 2 comprising from 0.01 to 50 weight percent of the electron donor and from 10 to 50 weight percent of the 4H-thiopyran-1,1-dioxide.
Claim 7
Dependent Claim
51 words
An electrophotographic element comprising a charge-generating electrophotographic layer in electrical contact with a charge-transport layer characterized in that the charge-transport layer comprises a 4H-thiopyran-1,1-dioxide having (a) an electron withdrawing group in the 4-position and (b) a half wave potential more positive than -0.5 volts as measured against a saturated calomel electrode.
Claim 8
Dependent Claim
51 words
An electrophotographic element comprising a charge-generating electrophotographic layer in electrical contact with a charge-transport layer characterized in that the charge-transport layer comprises a 4H-thiopyran-1,1-dioxide having (a) an electron withdrawing group in the 4-position and (b) a half wave potential more positive than -0.5 volts as measured against a saturated calomel electrode.
Claim 9
Dependent Claim
74 words
The electrophotographic element of claim 6 wherein the 4H-thiopyran-1,1-dioxide has the structure ##STR12## wherein R 3 represents an electron withdrawing group; R 1 and R 5 each independently represents alkyl or aryl; R 2 and R 4 each independently represents hydrogen or an alkoxy carbonyl group; or R 1 and R 2 or R 4 and R 5 together with the carbon atoms to which they are attached form a fused unsaturated 6-membered ring.
Claim 10
Dependent Claim
20 words
The electrophotograpnic element of claim 6 wherein the 4H-thiopyran-1,1-dioxide is selected from the group consisting of 4-dicyanomethylene-2,6-diphenyl-4H-thiopyran-1,1-dioxide, 2,6-di-tert-butyl-4-dicyanomethylene-4H-thiopyran-1,1-dioxide and 2,6-dimethyl-4-dicyanomethylene-4H-thiopyran-4-one-1,1-dioxide.
Claim 11
Dependent Claim
48 words
The electrophotographic element of claims 6 or 7 wherein the charge-generating layer is selected from the group consisting of a selenium layer, a chloroindiumphthalocyanine chloride layer and a heterogeneous conductive layer and the charge-transport layer comprises a 4H-thiopyran-1,1-dioxide selected from the group consisting of 4-dicyanomethylene-2,6-diphenyl-4H-thiopyran-1,1-dioxide, 2,6-di-tert-butyl-4-dicyanomethylene-4H-thiopyran-1,1-dioxide and 2,6-dimethyl-4-dicyanomethylene-4H-thiopyran-4-one-1,1-dioxide.
Claim 12
Dependent Claim
20 words
The electrophotographic elements of claims 6 or 7 wherein the charge-transport layer comprises from 10 to 50 weight percent 4H-thiopyran-1,1-dioxide.
Claim 13
Dependent Claim
30 words
A 4H-thiopyran-1,1-dioxide having an electron withdrawing group other than oxo in the 4-position and a half wave reduction potential more positive than -0.5 volts as measured against a calomel electrode.
Claim 14
Dependent Claim
30 words
A 4H-thiopyran-1,1-dioxide having an electron withdrawing group other than oxo in the 4-position and a half wave reduction potential more positive than -0.5 volts as measured against a calomel electrode.
Claim 15
Dependent Claim
73 words
The compound of claim 11 having the structure ##STR13## wherein R 3 represents an electron withdrawing group other than oxo; R 1 and R 5 each independently represents alkyl or aryl; R 2 and R 4 each independently represents hydrogen or an alkoxy carbonyl group; or R 1 and R 2 or R 4 and R 5 together with the carbon atoms to which they are attached form a fused unsaturated 6-membered ring.
Claim 16
Dependent Claim
58 words
The compound of claim 12 wherein R 3 represents dicyanomethylene, indandionemethylene, cyanoethoxycarbonylmethylene; R 1 and R 5 each independently represents phenyl, methyl and t-butyl; R 2 and R 4 each independently represents hydrogen or methoxycarbonyl; or R 4 and R 5 taken together with the carbon atoms to which they are attached form a fused 6-member unsaturated ring.
Claim 17
Dependent Claim
15 words
The compound of claim 12 selected from the group consisting of 4-dicyanomethylene-2,6-diphenyl-4H-thiopyran-1,1-dioxide, 2,6-di-tertbutyl-4-dicyanomethylene-4H-thiopyran-1,1-dioxide and 2,6-dimethyl-4-dicyanomethylene-4H-thiopyran-4-one-1,1-dioxide.
References Cited (Backward Citations)
US3905814A
Cited
US4105446A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-04-29 | 1988-10-29 | 1989-04-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-04-29 | 1992-10-29 | 1993-04-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-04-29 | 1996-10-29 | 1997-04-30 | $7700.00 | Window Closed / Lapsed |