US4183754A
Expired / Lapsed
US
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Photographic products and processes employing nondiffusible 1-arylazo-4-isoquinolinol dye-releasing compounds
Assignee: Eastman Kodak Co
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Filing: 1978-10-10
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Granted: 1980-01-15
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Expires: 1998-10-10
Abstract
Abstract Photographic elements, diffusion transfer assemblages and processes are described which employ a novel nondiffusible compound having a releasable 1-arylazo-4-isoquinolinol dye moiety. The compound contains: (a) in the ortho position of the arylazo moiety a metal chelating group, a salt thereof or a hydrolyzable precursor thereof; and (b) a ballasted carrier moiety which is capable of releasing the diffusible azo dye under alkaline conditions. The dye is transferred imagewise to an image-receiving layer where it is contacted with metal ions to form a metal-complexed azo dye transfer image of excellent stability.
Inventors
- 👤 Derek D. Chapman
- 👤 James A. Friday
- 👤 James Elwood
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 17:43
CPC Classifications
C; C09; C09B; C09B45/00; G; G03; G03C; G03C8/00; G03C8/02; G03C8/08; G03C8/10; Y; Y10; Y10S; Y10S430/00; Y10S430/137; Y10S430/156; Y10S430/159; Y10S534/00; Y10S534/02
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
53 words
A nondiffusible compound having at least one diffusible 1-arylazo-4-isoquinolinol dye moiety, said compound containing: (a) in the ortho position of the arylazo moiety a metal chelating group, a salt thereof or a hydrolyzable precursor thereof; and (b) a ballasted carrier moiety which is capable of releasing said diffusible azo dye under alkaline conditions.
Claim 2
Dependent Claim
53 words
A nondiffusible compound having at least one diffusible 1-arylazo-4-isoquinolinol dye moiety, said compound containing: (a) in the ortho position of the arylazo moiety a metal chelating group, a salt thereof or a hydrolyzable precursor thereof; and (b) a ballasted carrier moiety which is capable of releasing said diffusible azo dye under alkaline conditions.
Claim 3
Dependent Claim
143 words
The compound of claim 1 which has the formula: ##STR24## wherein: G is a metal chelating group, a salt thereof or a hydrolyzable precursor thereof; a group which together with ##STR25## is CAR, said CAR being bonded to the benzene ring through the oxygen of said ##STR26## group; or a group which together with SO 2 NH is CAR, said CAR being bonded to the benzene ring through the SO 2 NH group; G 1 is a hydroxy group, a salt thereof, or a hydrolyzable precursor thereof; or a group which together with ##STR27## is CAR, said CAR being bonded to the isoquinoline ring through the oxygen of said ##STR28## group; CAR represents said ballasted carrier moiety; and t is an integer of 0 or 1, with the proviso that the compound contains at least one but not more than two CAR groups.
Claim 4
Dependent Claim
57 words
The compound of claim 2 wherein G 1 is a hydrolyzable precursor comprising an acyloxy group having the formula --OCOR 1 , --OCOOR 1 , or --OCON(R 1 ) 2 , wherein each R 1 is an alkyl group having 1 to about 8 carbon atoms or an aryl group having 6 to about 12 carbon atoms.
Claim 5
Dependent Claim
60 words
The compound of claim 2 wherein G is hydroxy; amino; carboxy; sulfonamido; sulfamoyl; a fused nitrogen-containing ring; or a hydrolyzable ester group having the formula --OCOR 1 , --OCOOR 1 , or --COOR 1 , wherein R 1 is an alkyl group having 1 to about 8 carbon atoms or an aryl group having 6 to about 12 carbon atoms.
Claim 6
Dependent Claim
81 words
The compound of claim 2 wherein said CAR is a group having the formula: (Ballast-Carrier-Link)-- wherein: (a) Ballast is an organic ballasting radical of such molecular size and configuration as to render said compound nondiffusible in a photographic element during development in an alkaline processing composition; (b) Carrier is an oxidiable acyclic, carbocyclic or heterocyclic moiety; and (c) Link represents a group which, upon oxidation of said carrier moiety, is capable of being hydrolytically cleaved to release said diffusible azo dye.
Claim 7
Dependent Claim
40 words
The compound of claim 5 wherein the Carrier moiety contains atoms according to the following configuration: a(--C═C).sub.b -- wherein: b is a positive integer of 1 to 2; and a represents the radicals OH, SH, NH--, or hydrolyzable precursors thereof.
Claim 8
Dependent Claim
333 words
The compound of claim 2 wherein said CAR is a group having the formula: ##STR29## wherein: (a) Ballast is an organic ballasting radical of such molecular size and configuration as to render said compound nondiffusible in a photographic element during development in an alkaline processing composition; (b) D is OR 2 or NHR 3 wherein R 2 is hydrogen or a hydrolyzable moiety and R 3 is hydrogen or a substituted or unsubstituted alkyl group of 1 to 22 carbon atoms; (c) Y represents the atoms necessary to complete a benzene nucleus, a naphthalene nucleus, or a 5 to 7 membered heterocyclic ring; (d) j is a positive integer of 1 to 2 and is 2 when D is OR 2 or NHR 3 when R 3 is hydrogen or an alkyl group of less than 8 carbon atoms; and (e) L in a linking group which is [X--(NR 4 --J) q ] m -- or X--J--NR 4 -- wherein: (i) X represents a bivalent linking group of the formula --R 5 --L' n --R 5 p -- where each R 5 can be the same or different and each represents an alkylene radical having 1 to about 8 carbon atoms; a phenylene radical; or a substituted phenylene radical having 6 to about 9 carbon atoms; (ii) L' represents a bivalent radical selected from oxy, carbonyl, carboxamido, carbamoyl, sulfonamido, ureylene, sulfamoyl, sulfinyl or sulfonyl; (iii) n is an integer of 0 or 1; (iv) p is 1 when n equals 1 and p is 1 or 0 when n equals 0, provided that when p is 1 the carbon content of the sum of both R 5 radicals does not exceed 14 carbon atoms; (v) R 4 represents a hydrogen atom, or an alkyl radical having 1 to about 6 carbon atoms; (vi) J represents a bivalent radical selected from sulfonyl or carbonyl; (vii) q represents an integer of 0 or 1; and (viii) m represents an integer of 0, 1 or 2.
Claim 9
Dependent Claim
28 words
The compound of claim 7 wherein D is OH, j is 2, Y is a naphthalene nucleus, G is OH, G 1 is OH and t is 1.
Claim 10
Dependent Claim
31 words
The compound of claim 2 wherein said CAR is capable of releasing said diffusible azo dye as an inverse function of development of a silver halide emulsion layer under alkaline conditions.
Claim 11
Dependent Claim
117 words
The compound of claim 9 wherein said CAR is a group having the formula: ##STR30## wherein: Ballast is an organic ballasting radical of such molecular size and configuration as to render said compound nondiffusible in a photographic element during said development in an alkaline processing composition; W 1 represents at least the atoms necessary to complete a quinone nucleus; r is a positive integer of 1 or 2; R 6 is an alkyl radical having 1 to about 40 carbon atoms or an aryl radical having 6 to about 40 carbon atoms; and k is a positive integer of 1 to 2 and is 2 when R 6 is a radical of less than 8 carbon atoms.
Claim 12
Dependent Claim
73 words
The compound of claim 9 wherein said CAR is a group having the formula: ##STR31## wherein: Ballast is an organic ballasting radical of such molecular size and configuration as to render said compound nondiffusible in a photographic element during said development in an alkaline processing composition; W 2 represents at least the atoms necessary to complete a benzene nucleus; and R 7 is an alkyl radical having 1 to about 4 carbon atoms.
Claim 13
Dependent Claim
73 words
The compound of claim 9 wherein said CAR is a group having the formula: ##STR32## wherein: Ballast is an organic ballasting radical of such molecular size and configuration as to render said compound nondiffusible in a photographic element during said development in an alkaline processing composition; W 2 represents at least the atoms necessary to complete a benzene nucleus; and R 7 is an alkyl radical having 1 to about 4 carbon atoms.
Claim 14
Dependent Claim
125 words
The compound of claim 9 wherein said CAR is a group having the formula: ##STR33## wherein: Ballast is an organic ballasting radical of such molecular size and configuration as to render said compound nondiffusible in a photographic element during said development in an alkaline processing composition; W 2 represents at least the atoms necessary to complete a benzene nucleus; r is a positive integer of 1 to 2; R 6 is an alkyl radical having 1 to about 40 carbon atoms or an aryl radical having 6 to about 40 carbon atoms; k is a positive integer of 1 to 2 and is 2 when R 6 is a radical of less than 8 carbon atoms; and K is OH or a hydrolyzable precursor thereof.
Claim 15
Dependent Claim
19 words
The compound of claim 1 wherein said compound has the formula: ##STR34## wherein CAR represents said ballasted carrier moiety.
Claim 16
Dependent Claim
10 words
The compound of claim 1 which has the formula: ##STR35##
Claim 17
Dependent Claim
31 words
A photographic element comprising a support having thereon a coordination complex of a polyvalent metal ion and a compound having the following formula: ##STR36## wherein G is a metal chelating group.
Claim 18
Dependent Claim
31 words
A photographic element comprising a support having thereon a coordination complex of a polyvalent metal ion and a compound having the following formula: ##STR36## wherein G is a metal chelating group.
Claim 19
Dependent Claim
24 words
The photographic element of claim 16 wherein the metal ion is nickel (II), copper (II), zinc (II), platinum (II), palladium (II) or cobalt (II).
Claim 20
Dependent Claim
23 words
A coordination complex of a polyvalent metal ion and a compound having the following formula: ##STR37## wherein G is a metal chelating group.
Claim 21
Dependent Claim
23 words
A coordination complex of a polyvalent metal ion and a compound having the following formula: ##STR37## wherein G is a metal chelating group.
Claim 22
Dependent Claim
23 words
The complex of claim 18 wherein the metal ion is nickel (II), copper (II), zinc (II), platinum (II), palladium (II) or cobalt (II).
References Cited (Backward Citations)
US2508404A
Cited
US3377337A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-01-14 | 1983-07-16 | 1984-01-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-01-14 | 1987-07-16 | 1988-01-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-01-14 | 1991-07-16 | 1992-01-15 | $7700.00 | Window Closed / Lapsed |