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US4273708A Expired / Lapsed US ⏱️ 0.0 years remaining

Carbonyl-substituted cyan azo dye-providing materials

Assignee: Eastman Kodak Co
•
Filing: 1979-06-06
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Granted: 1981-06-16
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Expires: 1999-06-06
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Abstract

Abstract Cyan azo dye-providing compounds have the formula: ##STR1## wherein: R 1 is selected from the group consisting of aryl, alkyl or NR 11 R 12 wherein R 11 is alkyl or aryl and R 12 is alkyl, or R 11 and R 12 , taken together with the nitrogen atom to which they are attached, is a heterocyclic group; X is --CO-- or --SO 2 --; R 3 is --COOH or --CAR and is attached in the meta or para position to X in the benzene ring; R is alkyl; ##STR2## can be taken together with R and the nitrogen atom to which it is attached to form a heterocyclic ring unsubstituted or substituted with a carboxy group; and CAR is a carrier moiety which, as a function of oxidation under alkaline conditions, releases a diffusible dye, with the proviso that the compound contains at least one CAR group and, excepting when R and R 2 form a heterocyclic group and X is --SO 2 --, must contain at least one carboxy group. The compounds are particularly useful in photographic elements and more particularly useful in image transfer film units.

Inventors

  • 👤 Kenneth N. Kilminster
  • 👤 Colin Holstead

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-02 06:39
CPC Classifications
C; C09; C09B; C09B29/00; C09B29/24; C09B29/28; G; G03; G03C; G03C8/00; G03C8/02; G03C8/08; G03C8/10; Y; Y10; Y10S; Y10S534/00; Y10S534/02

Claims Analysis

Total Claims: 12
Claim 1
Independent Claim 184 words
A nondiffusible compound which releases a cyan dye, said compound having a formula as follows: ##STR41## wherein: R 1 is selected from the group consisting of aryl, alkyl and NR 11 R 12 wherein R 11 is alkyl or aryl and R 12 is alkyl, or R 11 and R 12 , taken together with the nitrogen atom to which they are attached, is a heterocyclic group; X is --CO-- or --SO 2 --; R 3 is --COOH or --CAR and is attached in the meta or para position to X in the benzene ring; R is alkyl; R 2 is ##STR42## or taken together with R and the nitrogen atom to which it is attached form a heterocyclic ring, unsubstituted or substituted with a carboxy group; and CAR is a ballasted carrier moiety which, as a function of oxidation under alkaline conditions, releases said cyan dye, with the proviso that the compound must contain at least one CAR moiety and, except when R and R 2 form a heterocyclic group and X is --SO 3 --, must contain at least one carboxy group.
Claim 2
Dependent Claim 184 words
A nondiffusible compound which releases a cyan dye, said compound having a formula as follows: ##STR41## wherein: R 1 is selected from the group consisting of aryl, alkyl and NR 11 R 12 wherein R 11 is alkyl or aryl and R 12 is alkyl, or R 11 and R 12 , taken together with the nitrogen atom to which they are attached, is a heterocyclic group; X is --CO-- or --SO 2 --; R 3 is --COOH or --CAR and is attached in the meta or para position to X in the benzene ring; R is alkyl; R 2 is ##STR42## or taken together with R and the nitrogen atom to which it is attached form a heterocyclic ring, unsubstituted or substituted with a carboxy group; and CAR is a ballasted carrier moiety which, as a function of oxidation under alkaline conditions, releases said cyan dye, with the proviso that the compound must contain at least one CAR moiety and, except when R and R 2 form a heterocyclic group and X is --SO 3 --, must contain at least one carboxy group.
Claim 3
Dependent Claim 74 words
A compound as described in claim 1 wherein CAR has 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 during development in an alkaline processing composition; (b) Carrier is an oxidizable 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 cyan dye.
Claim 4
Dependent Claim 42 words
A compound as described in claim 2 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 5
Dependent Claim 338 words
A compound as described in claim 1 wherein said carrier moiety is a group having the formula: ##STR43## wherein: (a) Ballast is an organic ballasting radical of such molecular size and configuration as to render said compound nondiffusible during development in an alkaline processing composition; (b) D is ortho or para to --NHSO 2 L-- and comprises OR 4 or NHR 5 , wherein R 4 is hydrogen or a hydrolyzable moiety and R 5 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 4 or when R 5 is hydrogen or an alkyl group of less than 8 carbon atoms; and (e) L is a linking group which is [X--(NR 6 --J) q ] m -- or X--J--NR 6 -- wherein: (i) X represents a bivalent linking group of the formula --R 7 --L' n --R 7 p -- where each R 7 is 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; 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 7 radicals does not exceed 14 carbon atoms; (v) R 6 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 6
Dependent Claim 20 words
A compound as described in claim 4 wherein D is OH, j is 2, and Y is a naphthalene nucleus.
Claim 7
Dependent Claim 26 words
A compound as described in claim 1 wherein R 1 is alkyl, R 2 is ##STR44## X is --SO 2 -- and R 3 is --CAR.
Claim 8
Dependent Claim 99 words
A cyan dye having a formula as follows: ##STR45## wherein: R 1 is selected from the group consisting of aryl, alkyl and NR 11 R 12 wherein R 11 is alkyl or aryl and R 12 is alkyl, or R 11 and R 12 , taken together with the nitrogen atom to which they are attached, is a heterocyclic group; X is --CO-- or --SO 2 --; R is alkyl; R 2 is ##STR46## or taken together with R and the nitrogen atom to which it is attached form a heterocyclic ring, unsubstituted or substituted with a carboxy group.
Claim 9
Dependent Claim 99 words
A cyan dye having a formula as follows: ##STR45## wherein: R 1 is selected from the group consisting of aryl, alkyl and NR 11 R 12 wherein R 11 is alkyl or aryl and R 12 is alkyl, or R 11 and R 12 , taken together with the nitrogen atom to which they are attached, is a heterocyclic group; X is --CO-- or --SO 2 --; R is alkyl; R 2 is ##STR46## or taken together with R and the nitrogen atom to which it is attached form a heterocyclic ring, unsubstituted or substituted with a carboxy group.
Claim 10
Dependent Claim 22 words
A dye as described in claim 7 wherein R 1 is alkyl, R 2 is ##STR47## and X is --SO 2 .
Claim 11
Dependent Claim 7 words
A cyan dye having the formula: ##STR48##
Claim 12
Dependent Claim 7 words
A cyan dye having the formula: ##STR48##

References Cited (Backward Citations)

US3929760A Cited
US4013635A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1984-06-15 1984-12-15 1985-06-16 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-06-15 1988-12-15 1989-06-16 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-06-15 1992-12-15 1993-06-16 $7700.00 Window Closed / Lapsed

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