EP0200354A2
Expired / Lapsed
EP
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Pyrazolo [3,2-c]-s-triazole photographic couplers, their use, synthesis and intermediates therefore
Assignee: Kodak Ltd
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Filing: 1986-03-26
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Granted: —
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Expires: 2006-03-26
Abstract
Abstract Novel pyrazolo[3,2-c]-s-triazole compounds of the general formula: wherein R 1 is an aryl or substituted aryl group; R 2 is a tertiary alkyl group, which may be substituted; and I R 3 and =CHR 4 are moieties which are displaced when the coupler reacts with the oxidation product of a primary aromatic amino photographic silver halide color developing agent, give image dyes of good light stability upon undergoing that reaction. That light stability can be enhanced by certain tetraalkoxybenzenes. A novel synthesis of the compounds is provided, together with necessary intermediate compounds.
Inventors
- 👤 Paul Richard Buckland
- 👤 Llewellyn James Leyshon
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-03 21:35
CPC Classifications
C; C07; C07D; C07D487/00; C07D487/02; C07D487/04; G; G03; G03C; G03C7/00; G03C7/30; G03C7/305; G03C7/30511; G03C7/30517; G03C7/30529; G03C7/32; G03C7/36; G03C7/38; G03C7/381; G03C7/382; G03C7/3825; G03C7/3835
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
77 words
A photographic element comprising a support bearing a photographic silver halide emulsion layer and incorporated in the emulsion layer or a layer adjacent thereto, a 1-H -pyrazolo[3,2,-c]-s-triazole dye-forming coupler, characterized in that the coupler is a compound of the formula: wherein R, is unsubstituted aryl or substituted aryl; R 2 is unsubstituted tertiary alkyl or substituted tertiary alkyl; R 3 and CHR, are individually moieties that are displaced when the coupler reacts with oxidized color developing agent.
Claim 2
Dependent Claim
77 words
A photographic element comprising a support bearing a photographic silver halide emulsion layer and incorporated in the emulsion layer or a layer adjacent thereto, a 1-H -pyrazolo[3,2,-c]-s-triazole dye-forming coupler, characterized in that the coupler is a compound of the formula: wherein R, is unsubstituted aryl or substituted aryl; R 2 is unsubstituted tertiary alkyl or substituted tertiary alkyl; R 3 and CHR, are individually moieties that are displaced when the coupler reacts with oxidized color developing agent.
Claim 3
Dependent Claim
45 words
A photographic element as in claim 1 wherein R, is a phenyl or naphthyl group, which is optionally substituted; R 2 is tertiary alkyl containing 4 to 20 carbon atoms; R3 is hydrogen, halogen, carboxy or aryloxy; and R, is an aryl or heterocyclic group.
Claim 4
Dependent Claim
19 words
A photographic element as in claim 1 wherein the coupler is water-insoluble and nondiffusible in a hydrophilic colloid layer.
Claim 5
Dependent Claim
24 words
A photographic element as in claim 2 wherein R2 is t-butyl and R, is one of the following: wherein Z is a ballast group.
Claim 6
Dependent Claim
13 words
A photographic element as in claim 1 comprising an alkoxybenzene dye image stabilizer.
Claim 7
Dependent Claim
27 words
A photographic element as in claim 1 comprising a 1, 2, 4, 5-tetraalkoxybenzene dye image stabilizer in which each alkoxy group contains 1 to 20 carbon atoms.
Claim 8
Dependent Claim
13 words
A photographic element as in claim 1 comprising 1, 2, 3, 4-tetrabutoxy benzene.
Claim 9
Independent Claim
75 words
A method of forming a photographic image dye by reacting oxidized primary amino photographic silver halide color developing agent with a 1-H - pyrazolo[3,2-c]-s-triazole dye-forming coupler characterized in that the coupler is a compound of the formula: wherein R, is unsubstituted aryl or substituted aryl; R 2 is unsubstituted tertiary alkyl or substituted tertiary alkyl; R 3 and CHR 4 are individually moieties that are displaced when the coupler reacts with oxidized color developing agent.
Claim 10
Independent Claim
75 words
A method of forming a photographic image dye by reacting oxidized primary amino photographic silver halide color developing agent with a 1-H - pyrazolo[3,2-c]-s-triazole dye-forming coupler characterized in that the coupler is a compound of the formula: wherein R, is unsubstituted aryl or substituted aryl; R 2 is unsubstituted tertiary alkyl or substituted tertiary alkyl; R 3 and CHR 4 are individually moieties that are displaced when the coupler reacts with oxidized color developing agent.
Claim 11
Dependent Claim
17 words
A method according to claim 8 wherein the color developing agent is a p-phenylenediamine color developing agent.
Claim 12
Dependent Claim
23 words
A method according to claim 8 wherein R is t-butyl and R, is one of the following: wherein Z is a ballast group.
Claim 13
Dependent Claim
43 words
A 1-H-pyrazolo[3,2-c]-s-triazole coupler of the formula: wherein R, is unsubstituted aryl or substituted aryl; R 2 is unsubstituted tertiary alkyl or substituted tertiary alkyl; R 3 and CHR 4 are individually moieties that are displaced when the coupler reacts with oxidized color developing.
Claim 14
Dependent Claim
43 words
A 1-H-pyrazolo[3,2-c]-s-triazole coupler of the formula: wherein R, is unsubstituted aryl or substituted aryl; R 2 is unsubstituted tertiary alkyl or substituted tertiary alkyl; R 3 and CHR 4 are individually moieties that are displaced when the coupler reacts with oxidized color developing.
Claim 15
Dependent Claim
25 words
A 1-H-pyrazolo[3,2-c]-s-triazole coupler as in claim 13 wherein R 2 is t-butyl and R, is one of the following: wherein Z is a ballast group.
Claim 16
Dependent Claim
22 words
A 1-H-pyrazolo-[3,2-c]-s-triazole coupler which is: or wherein X is moiety that is displaced when the coupler reacts with oxidized color developing agent.
Claim 17
Dependent Claim
22 words
A 1-H-pyrazolo-[3,2-c]-s-triazole coupler which is: or wherein X is moiety that is displaced when the coupler reacts with oxidized color developing agent.
Claim 18
Independent Claim
171 words
A method of preparing a pyrazolo-[3,-2-c]-s-triazole coupler represented by the formula: wherein R, is unsubstituted aryl or substituted aryl; R 2 is unsubstituted tertiary alkyl or substituted tertiary alkyl; R 3 and R4 are individually hydrogen or a coupling-off group, said method comprising the steps (i) reacting a compound (IV) of the formula R 2 COC(CN) = C(SCH 3 ) 2 with t-butyl carbazate to form a compound (VI) of the formula: then (ii) reacting compound (VI) from step (i) with hydrazine hydrate to form a pyrazole (VII) of the formula: (iii) treating pyrazole (VII) from step (ii) with concentrated acid to form a 3(5)-hydrazinopyrazole salt (VIII) from pyrazole (VII); (iv) reacting the 3(5)-hydrazinopyrazole salt (VIII) from step (iii) with an aromatic aldehyde (IX) or aromatic acid chloride to form product (X); and, (v) effecting ring closure of the product (X) from step (iv) to form a compound (XI) of the formula: wherein Ar is unsubstituted or substituted aryl; (vi) removing the cyano group from compound - (XI) from step (v).
Claim 19
Independent Claim
171 words
A method of preparing a pyrazolo-[3,-2-c]-s-triazole coupler represented by the formula: wherein R, is unsubstituted aryl or substituted aryl; R 2 is unsubstituted tertiary alkyl or substituted tertiary alkyl; R 3 and R4 are individually hydrogen or a coupling-off group, said method comprising the steps (i) reacting a compound (IV) of the formula R 2 COC(CN) = C(SCH 3 ) 2 with t-butyl carbazate to form a compound (VI) of the formula: then (ii) reacting compound (VI) from step (i) with hydrazine hydrate to form a pyrazole (VII) of the formula: (iii) treating pyrazole (VII) from step (ii) with concentrated acid to form a 3(5)-hydrazinopyrazole salt (VIII) from pyrazole (VII); (iv) reacting the 3(5)-hydrazinopyrazole salt (VIII) from step (iii) with an aromatic aldehyde (IX) or aromatic acid chloride to form product (X); and, (v) effecting ring closure of the product (X) from step (iv) to form a compound (XI) of the formula: wherein Ar is unsubstituted or substituted aryl; (vi) removing the cyano group from compound - (XI) from step (v).
Claim 20
Dependent Claim
29 words
A method as in claim 19 comprising, after said step (vi), (vii) introducing a substituent R 3 or = CHR4 into the 7-position of the product of step (vi).
Claim 21
Dependent Claim
20 words
A pyrazolo [3,2-c]-s-triazole represented by the formula: wherein R 2 is tertiary alkyl, and Ar is unsubstituted or substituted aryl.
Claim 22
Dependent Claim
20 words
A pyrazolo [3,2-c]-s-triazole represented by the formula: wherein R 2 is tertiary alkyl, and Ar is unsubstituted or substituted aryl.
Claim 23
Dependent Claim
6 words
A pyrazolo [3,2-c]-s-triazole that is: or
Claim 24
Dependent Claim
6 words
A pyrazolo [3,2-c]-s-triazole that is: or
Claim 25
Dependent Claim
38 words
A dye represented by the formula: wherein R, is unsubstituted aryl or substituted aryl; R 2 is unsubstituted tertiary alkyl or substituted tertiary alkyl; and = N-(DOX) is a moiety derived from an oxidized photographic color developing agent.
Claim 26
Dependent Claim
38 words
A dye represented by the formula: wherein R, is unsubstituted aryl or substituted aryl; R 2 is unsubstituted tertiary alkyl or substituted tertiary alkyl; and = N-(DOX) is a moiety derived from an oxidized photographic color developing agent.
Claim 27
Dependent Claim
4 words
A dye that is
Claim 28
Dependent Claim
4 words
A dye that is
References Cited (Backward Citations)
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