Nondiffusible compounds having a releasable azo dye moiety

• US 4,272,434 A
• Filed: 03/23/1979
• Issued: 06/09/1981
• Est. Priority Date: 09/10/1976
• Status: Expired due to Term

• Current Assignee: Eastman Kodak Company
• Original Assignee: Eastman Kodak Company
• Inventors: Bailey, Joseph, Johnston, Linda G., Mijovic, Miroslav V., Baigrie, Brian D.
• Primary Examiner(s): Higel, Floyd D.
• Application Number:
  US06/023,430
• Time in Patent Office: 809 Days
• Field of Search: 260/152, 260/155, 260/156, 260/157, 260/158, 260/162, 260/163
• US Class Current: 534/648
• CPC Class Codes: G03C 8/10 of dyes or their precursors

Abstract

Photographic elements, diffusion transfer assemblages and processes are described which employ a nondiffusible compound having a releasable azo dye moiety having the formula: ##STR1## wherein: Z represents the atoms necessary to complete an aromatic carbocyclic or heterocyclic nucleus having at least one ring of 5 to 7 atoms;

Z'"'"' is an aromatic carbocyclic or heterocyclic nucleus having at least one ring of 5 to 7 atoms, the Z'"'"' having, in a position adjacent to the point of attachment to the azo linkage, either (a) a nitrogen atom in the ring of the nucleus which acts as a chelating site, or (b) a carbon atom in the ring of the nucleus having directly attached thereto a nitrogen atom which acts as a chelating site;

G is a metal chelating group, a salt thereof or a hydrolyzable precursor thereof; the compound also containing a ballasted carrier moiety which will release 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.

Claims

1. A nondiffusible compound having a releasable azo dye moiety, said compound having the following formula:

##STR28## wherein;

Z represents the atoms necessary to complete an aromatic carbocyclic or heterocyclic nucleus having at least one ring of 5 to 7 atoms;

Z'"'"' is an aromatic carbocyclic or heterocyclic nucleus having at least one ring of 5 to 7 atoms, said Z'"'"' having, in a position adjacent to the point of attachment to the azo linkage, either (a) a nitrogen atom in said ring of said nucleus which acts as a chelating site, or (b) a carbon atom in said ring of said nucleus having directly attached thereto a nitrogen atom which acts as a chelating site;

G is a metal chelating group, a salt thereof or a hydrolyzable precursor thereof;

said compound also containing a ballasted carrier moiety which will release said diffusible azo dye under alkaline conditions.

2. The compound of claim 1 wherein Z represents the atoms necessary to complete a phenyl group and Z'"'"' represents a pyrazolotriazole nucleus.

3. The compound of claim 1 wherein Z represents the atoms necessary to complete a phenyl group and Z'"'"' represents a pyridinol nucleus.

4. The compound of claim 1 wherein G is hydroxy;

amino;

carboxy;

sulfonamido;

sulfamoyl;

a hydrolyzable ester group having the formula --OCOR¹, --OCOOR¹, --OCON(R¹)₂ or --COOR¹, wherein R¹ is alkyl having 1 to about 4 carbon atoms or aryl having 6 to about 8 carbon atoms, or a group which together with ##STR29## is said ballasted carrier moiety, said ballasted carrier moiety being attached to said Z nucleus through the oxygen of said ##STR30##

5. The compound of claim 1 wherein said ballasted carrier moiety is a group having the formula:

space="preserve" listing-type="equation">(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 oxidizable cyclic, 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 arylazo-pyrazolotriazole dye.

6. The compound of claim 5 wherein the Carrier moiety contains atoms according to the following configuration:

space="preserve" listing-type="equation">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.

7. The compound of claim 1 wherein said ballasted carrier moiety is a group having the formula:

##STR31## 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 OR² or NHR³ wherein R² is hydrogen or a hydrolyzable moiety and R³ is hydrogen or substituted or unsubstituted alkyl 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 OR² or when R³ is hydrogen or alkyl of less than 8 carbon atoms; and

(e) L is a linking group which is [X--(NR⁴ --J)_q ]_m -- or X--J--NR⁴ -- wherein;

(i) X represents a bivalent linking group of the formula --R⁵ --L'"'"'_n --R⁵_p -- where each R⁵ can be the same or different and each represents alkylene having 1 to about 8 carbon atoms;

phenylene;

or substituted phenylene 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 R⁵ radicals does not exceed 14 carbon atoms;

(v) R⁴ represents hydrogen, or alkyl 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.

8. The compound of claim 7 wherein D is OH, j is 2, Y is a naphthalene nucleus, and G is OH.

9. The compound of claim 1 wherein said ballasted carrier moiety will release said diffusible azo dye as an inverse function of development of a silver halide emulsion layer under alkaline conditions.

10. The compound of claim 9 wherein said ballasted carrier moiety 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;

W¹ represents the atoms necessary to complete a quinone nucleus;

r is a positive integer of 1 or 2;

R⁶ is alkyl having 1 to about 40 carbon atoms or aryl having 6 to about 40 carbon atoms; and

k is a positive integer of 1 to 2 and is 2 when R⁶ has less than 8 carbon atoms.

11. The compound of claim 9 wherein said ballasted carrier moiety 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;

W² represents at least the atoms necessary to complete a benzene nucleus; and

R⁷ is alkyl having 1 to about 4 carbon atoms.

12. The compound of claim 9 wherein said ballasted carrier moiety is a group having the formula:

##STR34## 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;

W² represents at least the atoms necessary to complete a benzene nucleus; and

R⁷ is alkyl having 1 to about 4 carbon atoms.

13. The compound of claim 9 wherein said ballasted carrier moiety is a group having the formula:

##STR35## 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;

W² represents at least the atoms necessary to complete a benzene nucleus;

r is a positive integer of 1 or 2;

R⁶ is alkyl having 1 to about 40 carbon atoms or aryl having 6 to about 40 carbon atoms;

k is a positive integer of 1 to 2 and is 2 when R⁶ has less than 8 carbon atoms; and

K is OH or a hydrolyzable precursor thereof.

14. The compound of claim 1 which has a releasable 7-arylazo-pyrazolotriazole 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 will release said diffusible arylazopyrazolotriazole dye under alkaline conditions.

15. The compound of claim 14 which has the formula:

##STR36## wherein;

G is a metal chelating group, a salt thereof or a hydrolyzable precursor thereof;

or a group which together with ##STR37## is CAR, said CAR group being attached to the phenyl group through the oxygen of said ##STR38## CAR represents said ballasted carrier moiety; and

s is 1 to 2 except when G is a group which together with ##STR39## is CAR, in which case s is 0.

16. The compound of claim 15 which is:

##STR40##

17. The compound of claim 1 which has a releasable 6-arylazo-3-pyridinol 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 will release said diffusible 6-arylazo-3-pyridinol dye under alkaline conditions.

18. The compound of claim 17 which has the formula:

##STR41## wherein;

G is a metal chelating group, a salt thereof or a hydrolyzable precursor thereof;

CAR represents said ballasted carrier moiety; and

t is a positive integer of 1 to 2.

19. The compound of claim 18 wherein the phenyl group is substituted with a nitro group para to the azo linkage, said CAR is attached to the pyridine ring, and the pyridine ring is substituted in the 2-position with an amino group.

20. The compound of claim 19 which has the formula:

##STR42##

21. The compound of claim 19 which has the formula:

##STR43##