Method of processing a photographic element containing electron transfer agent releasing couplers

• US 6,929,905 B2
• Filed: 12/20/2001
• Issued: 08/16/2005
• Est. Priority Date: 12/20/2001
• Status: Expired due to Fees

• Current Assignee: Eastman Kodak Company
• Original Assignee: Eastman Kodak Company
• Inventors: Gordon, Stuart T., Arcus, Robert A., Lunt, Sharon R., Southby, David T.
• Primary Examiner(s): Le, Hoa Van
• Application Number:
  US10/028,132
• Publication Number:
  US 20030175628A1
• Time in Patent Office: 1,335 Days
• Field of Search: 430/361
• US Class Current: 430/361
• CPC Class Codes: G03C 2001/03511 Bromide content
• CPC Class Codes: G03C 2200/52 Rapid processing
• CPC Class Codes: G03C 7/3022 Materials with specific emulsion characteristics, e.g. thickness of the layers, silver content, shape of AgX grains
• CPC Class Codes: G03C 7/30558 Heterocyclic group G03C7/30552 takes precedence
• CPC Class Codes: G03C 7/407 Development processes or agents therefor G03C7/3244 takes precedence

Abstract

A method of processing a silver bromoiodide photographic element comprising contacting the photographic element with a color developer for less than 120 seconds; wherein the photographic element comprises a support and more than one dye forming unit, and wherein the dye forming unit closest to the support contains an electron transfer agent releasing compound represented by the formula:
CAR-(L)_n-ETA
wherein:

• • CAR is a carrier moiety which is capable of releasing -(L)n-ETA on reaction with oxidized developing agent;
  • L is a divalent linking group, n is 0, 1, or 2; and
  • ETA is a releasable 1-aryl-3-pyrazolidinone electron transfer agent having a calculated log partition coefficient (c log P) greater than or equal to 2.40 bonded to L or CAR through either the nitrogen atom in the 2-position or the oxygen attached to the 3-position of the pyrazolidinone ring.

Claims

1. A method of processing a silver bromoiodide photographic element comprising contacting the photographic element with a color developer for 20 to 120 seconds;

wherein the photographic element comprises a support and more than one dye forming unit, and wherein the least light sensitive layer of the dye forming unit closest to the support contains about 6 μ

mole/m² to about 500 μ

mole/m² of an electron transfer agent releasing compound represented by the formula;

CAR-(L)_n-ETA

wherein;

CAR is a carrier moiety which is capable of releasing -(L)_n-ETA on reaction with oxidized developing agent;

L is a divalent linking group, with the proviso that L is not —

O —

CO—

;

n is 0, 1, or 2; and

ETA is a releasable 1-aryl-3-pyrazolidinone electron transfer agent having a calculated log partition coefficient (c log P) greater than or equal to 2.40 bonded to L or CAR through either the nitrogen atom in the 2-position or the oxygen attached to the 3-position of the pyrazolidinone ring.

2. The method of claim 1 wherein ETA is represented by Formulas I or II

wherein:

R² and R³ each independently represents hydrogen, a substituted or unsubstituted alkyl group having from 1 to 12 carbon atoms, CH₂OR⁷ or CH₂OC(O)R⁷ where R⁷ is a substituted or unsubstituted alkyl, aryl, or a heteroatom containing group;

R⁴ and R⁵ each independently represents hydrogen, a substituted or unsubstituted alkyl group having from 1 to 8 carbon atoms or a substituted or unsubstituted aryl group having from 6 to 10 carbon atoms;

R⁶ is a substituent; and

m is 0 to 5;

wherein when m is greater than 1, the R⁶ substituents may form a carbocyclic or heterocyclic ring.

3. The method of claim 2 wherein R² and R³ are independently alkyl, CH₂OR⁷ or CH₂OC(O)R⁷ groups containing 3 to 8 carbon atoms;

R⁴ and R⁵ are hydrogen, R⁶ is independently a halogen, a substituted or unsubstituted alkyl group having from 1 to 8 carbon atoms, a substituted or unsubstituted alkoxy group having from 1 to 8 carbon atoms, an amido, sulfonamido, ester, cyano, sulfone, carbamoyl, uriedo group, or a heteroatom containing group or ring.

4. The method of claim 2 wherein R⁴ and R⁵ are hydrogen;

and R^2, R^3, and R⁶ are as represented in the following table;

TABLEETA No.R²R³R⁶1CH₃CH₂OC(O)iPrH2CH₃CH₂OC(O)tBuH3CH₃CH₂OC(O)Etp-CH₃4CH₃CH₂OC(O)Et3,4-dimethyl5HCH₂OC₄H₉-np-OCH₃6CH₃CH₂OC(O)CH₂—

O—

(CH₂)₂S(CH₂)₂SMeH

5. The method of claim 1 wherein CAR is a coupler moiety.

6. The method of claim 5 wherein the coupler moiety is a phenol or naphthol coupler moiety.

7. The method of claim 6 wherein the coupler moiety is represented by the structures:

where R¹² and R¹³ are independently a ballast group, a hydrogen, or a substituted or unsubstituted alkyl or aryl group, R¹¹ is a halogen atom, an alkyl group having from 1 to 4 carbon atoms or an alkoxy group having from 1 to 4 carbon atoms, and w is 1 or 2.

8. The method of claim 1 wherein the ETA has a calculated log partition coefficient (c log P) between and including 2.40 and 3.50.

9. The method of claim 1 wherein the dye forming unit closest to the support is the red dye forming unit.

10. The method of claim 1 wherein the silver bromoiodide photographic element is contacted with the color developer for 100 seconds or less.

11. The method of claim 1 wherein the silver bromoiodide photographic element is contacted with the color developer for 60 seconds or less.

20. The method of claim 1 wherein the dye forming unit closest to the support contains a development inhibitor releasing compound.

12. A method of processing a silver bromoiodide photographic element comprising contacting the photographic element with a color developer for 20 to 100 seconds;

wherein the photographic element comprises a support and more than one dye forming unit, and wherein the least sensitive layer of the dye forming unit closest to the support contains about 6 μ

mole/m² to about 500 μ

mole/m² of an electron transfer agent releasing compound represented by the formula;

CAR-(L)_n-ETA

wherein;

CAR is a coupler moiety which is capable of releasing -(L)_n-ETA on reaction with oxidized developing agent;

L is a divalent linking group, with the proviso that L is not —

O—

CO—

;

n is 0, 1, or 2; and

ETA is a releasable 1-aryl-3-pyrazolidinone electron transfer agent having a calculated log partition coefficient (c log P) greater than or equal to 2.40 wherein ETA is represented by the formulas;

wherein;

R² and R³ each independently represents hydrogen, a substituted or unsubstituted alkyl group having from 1 to 12 carbon atoms, CH₂OR⁷ or CH₂OC(O)R⁷ where R⁷ is a substituted or unsubstituted alkyl, aryl or a heteroatom containing group;

R⁴ and R⁵ each independently represents hydrogen, a substituted or unsubstituted alkyl group having from 1 to 8 carbon atoms or a substituted or unsubstituted aryl group having from 6 to 10 carbon atoms;

R⁶ is independently a substituent; and

m is 0 to 5 wherein when m is greater than 1, the R⁶ substituents may form a carbocyclic or heterocyclic ring.

13. The photographic element of claim 12 wherein R2 and R3 are independently alkyl, CH2OR7 or CH2OC(O)R7 groups containing 3 to 8 carbon atoms;

R4 and R5 are hydrogen; and

R6 is independently a halogen, a substituted or unsubstituted alkyl group having from 1 to 8 carbon atoms, a substituted or unsubstituted alkoxy group having from 1 to 8 carbon atoms, an amido, sulfonamido, ester, cyano, sulfone, carbamoyl, uriedo group, or a heteroatom containing group or ring.

14. The photographic element of claim 12 wherein R⁴ and R⁵ are hydrogen;

and R^2, R³ and R⁶ are as represented in the following Table;

TABLEETANo.R²R³R⁶1CH₃CH₂OC(O)iPrH2CH₃CH₂OC(O)tBuH3CH₃CH₂OC(O)Etp-CH₃4CH₃CH₂OC(O)Et3,4-dimethyl5HCH₂OC₄H_9-np-OCH₃6CH₃CH₂OC(O)CH₂—

O—

(CH₂)₂S(CH₂)₂SMeH

15. The method of claim 12 wherein the coupler moiety is a phenol or naphthol coupler moiety.

16. The method of claim 12 wherein the dye forming unit closest to the support is the red dye forming unit.

17. The photographic element of claim 16 wherein the ETA has a calculated log partition coefficient (c log P) between and including 2.40 and 3.50.

18. The method of claim 12 wherein the electron transfer agent releasing compound is contained in the least light sensitive layer of the dye forming unit.

19. The method of claim 12 wherein the silver bromoiodide photographic element is contacted with the color developer for 60 seconds or less.

21. The method of claim 12 wherein the dye forming unit closest to the support contains a development inhibitor releasing compound.