US4365085A
Expired / Lapsed
US
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Bicyclic reductone developing agents
Assignee: Polaroid Corp
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Filing: 1979-02-05
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Granted: 1982-12-21
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Expires: 1999-02-05
Abstract
Abstract The present invention relates to novel bicyclic compounds useful as photographic silver halide developing agents, to the preparation of these compounds and to photographic products, processes and compositions employing the same. The subject compounds may be represented by the formula ##STR1## wherein R 1 and R 2 , the same or different, each represents hydrogen, a hydrocarbon moiety, preferably an alkyl group, --COOH or --COOR 1 wherein R 1 is an alkyl group; R 3 and R 4 , the same or different, each represent hydrogen or an alkyl group, R 5 represents hydrogen or --COR 2 wherein R 2 is an alkyl group; R 6 represents hydrogen when R 5 is hydrogen and represents hydrogen or --OCOR 3 wherein R 3 is an alkyl group the same as R 2 when R 5 represents --COR 2 ; X represents --OH, --NH 2 or --NHCOR 4 wherein R 4 represents an alkyl group the same as R 2 ; Y represents --OH or --OCOR 5 wherein R 5 represents an alkyl group the same as R 2 ; and Z represents ═O or ═NCOR 6 wherein R 6 is an alkyl group the same as R 2 .
Inventors
- 👤 James R. Bartels-Keith
- 👤 Eva R. Karger
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 20:17
CPC Classifications
G; G03; G03C; G03C8/00; G03C8/32; G03C8/36; G03C5/00; G03C5/26; G03C5/29; G03C5/30
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
197 words
A compound of the formula ##STR9## wherein R 1 and R 2 , the same or different, each represent hydrogen, an alkyl group, --COOH or --COOR 1 wherein R 1 is an alkyl group; R 3 and R 4 , the same or different, each represent hydrogen or an alkyl group, R 5 represents hydrogen or --COR 2 wherein R 2 is an alkyl group containing 1-6 carbon atoms; R 6 represents hydrogen when R 5 is hydrogen and represents hydrogen or --OCOR 3 wherein R 3 is an alkyl group the same as R 2 when R 5 represents --COR 2 provided that when R 6 is --OCOR 3 , Y is --OCOR 5 ; X represents --OH or --NH 2 when Y is --OH or X represents --NHCOR 4 wherein R 4 represents an alkyl group the same as R 2 when Y is --OCOR 5 ; Y represents --OH or --OCOR 5 wherein R 5 represents an alkyl group the same as R 2 ; and Z represents O when Y is --OH or NCOR 6 wherein R 6 is an alkyl group the same as R 2 when Y is --OCOR 5 .
Claim 2
Dependent Claim
197 words
A compound of the formula ##STR9## wherein R 1 and R 2 , the same or different, each represent hydrogen, an alkyl group, --COOH or --COOR 1 wherein R 1 is an alkyl group; R 3 and R 4 , the same or different, each represent hydrogen or an alkyl group, R 5 represents hydrogen or --COR 2 wherein R 2 is an alkyl group containing 1-6 carbon atoms; R 6 represents hydrogen when R 5 is hydrogen and represents hydrogen or --OCOR 3 wherein R 3 is an alkyl group the same as R 2 when R 5 represents --COR 2 provided that when R 6 is --OCOR 3 , Y is --OCOR 5 ; X represents --OH or --NH 2 when Y is --OH or X represents --NHCOR 4 wherein R 4 represents an alkyl group the same as R 2 when Y is --OCOR 5 ; Y represents --OH or --OCOR 5 wherein R 5 represents an alkyl group the same as R 2 ; and Z represents O when Y is --OH or NCOR 6 wherein R 6 is an alkyl group the same as R 2 when Y is --OCOR 5 .
Claim 3
Dependent Claim
17 words
A compound as defined in claim 1 wherein said R 1 and R 2 are the same.
Claim 4
Dependent Claim
16 words
A compound as defined in claim 2 wherein said R 1 and R 2 are hydrogen.
Claim 5
Dependent Claim
16 words
A compound as defined in claim 1 wherein R 3 and R 4 are the same.
Claim 6
Dependent Claim
15 words
A compound as defined in claim 4 wherein R 3 and R 4 are hydrogen.
Claim 7
Dependent Claim
20 words
A compound as defined in claim 1 wherein said R 5 represents --COR 2 and said R 6 represents hydrogen.
Claim 8
Dependent Claim
17 words
A compound as defined in claim 1 wherein said R 5 and R 6 each represent hydrogen.
Claim 9
Dependent Claim
3 words
The compound ##STR10##
Claim 10
Dependent Claim
3 words
The compound ##STR10##
Claim 11
Dependent Claim
3 words
The compound ##STR11##
Claim 12
Dependent Claim
3 words
The compound ##STR11##
Claim 13
Dependent Claim
3 words
The compound ##STR12##
Claim 14
Dependent Claim
3 words
The compound ##STR12##
Claim 15
Dependent Claim
3 words
The compound ##STR13##
Claim 16
Dependent Claim
3 words
The compound ##STR13##
Claim 17
Dependent Claim
215 words
A process of preparing certain bicyclic compounds which comprises hydrogenating a mixture of (a) a bicyclic nitronate salt of the formula ##STR14## wherein R 1 and R 2 , the same or different, each represent hydrogen, an alkyl group, --COOH or --COOR 1 wherein R 1 is an alkyl group; R 3 and R 4 , the same or different, each represent hydrogen or an alkyl group; and R 7 and R 8 taken separately each represent alkyl groups containing 1 to 6 carbon atoms and taken together represent the atoms necessary to complete a saturated 5 or 6 member heterocyclic moiety and (b) an anhydride of a monocarboxylic alkanoic acid by introducing hydrogen at a pressure of between about 40 and 50 lbs per square inch in the presence of a hydrogenation catalyst at ambient temperature to yield (c) the corresponding acylated bicyclic compound of the formula ##STR15## wherein R 2 is an alkyl group containing 1-6 carbon atoms; R is hydrogen or --OCOR 3 wherein R 3 is an alkyl group the same as R 2 ; R 4 , R 5 and R 6 each are alkyl groups the same as R 2 ; and R 1 , R 2 , R 3 and R 4 have the same meaning given above.
Claim 18
Dependent Claim
215 words
A process of preparing certain bicyclic compounds which comprises hydrogenating a mixture of (a) a bicyclic nitronate salt of the formula ##STR14## wherein R 1 and R 2 , the same or different, each represent hydrogen, an alkyl group, --COOH or --COOR 1 wherein R 1 is an alkyl group; R 3 and R 4 , the same or different, each represent hydrogen or an alkyl group; and R 7 and R 8 taken separately each represent alkyl groups containing 1 to 6 carbon atoms and taken together represent the atoms necessary to complete a saturated 5 or 6 member heterocyclic moiety and (b) an anhydride of a monocarboxylic alkanoic acid by introducing hydrogen at a pressure of between about 40 and 50 lbs per square inch in the presence of a hydrogenation catalyst at ambient temperature to yield (c) the corresponding acylated bicyclic compound of the formula ##STR15## wherein R 2 is an alkyl group containing 1-6 carbon atoms; R is hydrogen or --OCOR 3 wherein R 3 is an alkyl group the same as R 2 ; R 4 , R 5 and R 6 each are alkyl groups the same as R 2 ; and R 1 , R 2 , R 3 and R 4 have the same meaning given above.
Claim 19
Dependent Claim
18 words
A process as defined in claim 12 wherein said catalyst is palladium-on-carbon in combination with a zinc salt.
Claim 20
Dependent Claim
68 words
A process as defined in claim 12 which includes the additional step of hydrolyzing said acylated bicyclic compound (c) wherein R represents hydrogen by refluxing with an aqueous solution of hydroxide to yield (d) the alkaline hydrolysis product of the formula ##STR16## wherein R 1 and R 2 are hydrogen, alkyl or --COOH and R 3 , R 4 and R 2 have the same meaning given above.
Claim 21
Dependent Claim
75 words
A process as defined in claim 12 which includes the additional step of hydrolyzing said acylated bicyclic compound (c) wherein said R is hydrogen by refluxing in 2 N to 4 N aqueous hydrochloric acid to give the acid hydrolysis product of the formula ##STR17## wherein X' is --OH or --NH 2 , R 1 and R 2 are hydrogen, alkyl or --COOH and R 3 and R 4 have the same meaning given above.
References Cited (Backward Citations)
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Cited
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Cited
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-12-20 | 1986-06-21 | 1986-12-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-12-20 | 1990-06-21 | 1990-12-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-12-20 | 1994-06-21 | 1994-12-21 | $7700.00 | Window Closed / Lapsed |