Claims
- 1. A photographic element comprising a support, and a silver halide emulsion layer having associated therewith a molecule which is a one-equivalent coupler having the structure
- COUP--(CONNECT).sub.n' --(T).sub.m --DYE
- wherein
- n' is 0or 1,
- m is 0, 1, or 2,
- COUP is a coupler moiety,
- CONNECT is a group attached to a coupling site of the coupler that connects the coupler to either the timing group T or directly to the dye, if attached directly to the dye it remains permanently attached to the dye after the dye is released from COUP,
- T is a timing group, which is cleaved from the dye during processing,
- DYE is a dye having the following structure, ##STR26## wherein, R.sub.1 =H, a removable timing group, or a removable blocking group, wherein removable denotes that after processing, R.sub.1 is hydrogen, so that the dye remains substantially or completely ionized in the element,
- R.sub.2 =one or more substituents, which ensure that the oxygen auxochrome group remains ionized after processing of the element,
- n=1, 2, 3 or 4,
- X=O or N; wherein if X is N then it is part of a heterocyclic ring that forms part of the dye chromophore, ##STR27## represents a carbon containing ring or ring system, R.sub.3 =one or more substituents, which may be located anywhere along the ring or ring system, the ##STR28## indicates that if X is N, then it is part of the ring or ring system; with the proviso that the substituent R.sub.2 and R.sub.3 and the ring or ring system are selected so that the dye has a pKa below about five so that the dye remains fully ionized or substantially ionized in the processed photographic element such that the dye retains the desired hue;
- and with the further proviso that the molecule may optionally contain one or more ballast groups,
- wherein said dye is a yellow dye, or a cyan dye, or has the structure ##STR29## wherein, R.sub.10 and R.sub.11 are independently selected from a substituted alkyl, substituted alkyloxy or substituted phenyl group.
- 2. A photographic element as claimed in claim 1, wherein R.sub.2 is an electron withdrawing group.
- 3. A photographic element as claimed in claim 2, wherein an R.sub.2 substituent is present in both the 2 and 6 positions, both R.sub.2 substituents being electron-withdrawing groups, which may be the same or different.
- 4. A photographic element as claimed in claim 3, wherein said electron-withdrawing groups are selected from nitro, Cl, CN, SO.sub.2 N(R').sub.2, CON(R').sub.2, CO.sub.2 R', wherein R' is hydrogen or an alkyl or aryl group.
- 5. A photographic element as claimed in claim 4, wherein said electron withdrawing groups are selected from the group consisting of Cl, SO.sub.2 NH(t--Bu), and C(O)NH2.
- 6. A photographic element as claimed in claim 1, wherein said dye has a pKa of below 4.
- 7. A photographic element as claimed in claim 1, wherein said dye has the structure ##STR30## wherein, R.sub.4 and R.sub.5 are selected from --NHCOR' or --NHCON(R').sub.2, wherein R' is hydrogen or a substituted or unsubstituted alkyl group or substituted or unsubstituted phenyl group.
- 8. A photographic element as claimed in claim 1 when said dye has the structure ##STR31## wherein, R.sub.6 is an electron-withdrawing group, and
- R.sub.7 is a group capable of hydrogen bond donation to the imine nitrogen.
- 9. A photographic element as claimed in claim 8, wherein
- R.sub.6 is selected from the group consisting of Cl, SO.sub.2 N(R').sub.2, CN, SO.sub.2 R', CON(R').sub.2, CO.sub.2 R', and CONHR', wherein R' is hydrogen or an alkyl or phenyl group either of which may be substituted or unsubstituted, and
- R.sub.7 is OH or an NH acidic group selected from the group consisting of --NHCOR', --NHCON(R').sub.2, --NHSO.sub.2 R', and --NHSO.sub.2 N(R').sub.2, wherein R' is as defined for R.sub.6.
- 10. A photographic element as claimed in claim 1, wherein said dye has the structure ##STR32## wherein, X=--CONHR' or --SO.sub.2 N(R').sub.2, wherein R' is an alkyl or phenyl group, either of which may be substituted or unsubstituted.
- 11. A photographic element as claimed in claim 1, wherein said dye is selected from the following compounds A-F: ##STR33##
- 12. A photographic element as claimed in claim 1, wherein said COUP is a universal coupler.
- 13. A photographic element as claimed in claim 1, wherein said COUP is a pyrazolotriazole.
- 14. A photographic element as claimed in claim 13, wherein COUP is a 1H-pyrazolo (1,5-b) (1,2,4 ) triazole or 1H-pyrazolo (2,3,-c) (1,2,4) triazole.
- 15. A photographic element as claimed in claim 1, wherein no mordant is present in the element.
- 16. A photographic element as claimed in claim 1, wherein the DYE is a yellow dye.
- 17. A photographic element as claimed in claim 1, wherein the DYE is a cyan dye.
- 18. A photographic element as claimed in claim 1, wherein the DYE is a magenta dye.
- 19. A photographic element as claimed in claim 1, wherein a ballast group is attached to a portion of the molecule which is intended to remain in the film after reaction with oxidized silver halide developer.
- 20. A photographic element as claimed in claim 1, wherein COUP is other than a magenta dye-forming coupler.
- 21. A photographic element as claimed in claim 1, wherein the DYE remains substantially in the layer in the element in which it is generated.
- 22. A photographic element comprising a support, and a silver halide emulsion layer having associated therewith a molecule which is a one-equivalent coupler having the structure
- COUP--(CONNECT).sub.n' --(T).sub.m --DYE
- wherein
- n' is 0 or 1,
- m is 0, 1, or 2,
- COUP is a 1H-pyrazolo (2,3-C)(1,2,4)triazole,
- CONNECT is a group attached to a coupling site of the coupler that connects the coupler to either the timing group T or directly to the dye, if attached directly to the dye it remains permanently attached to the dye after the dye is released from COUP,
- T is a timing group, which is cleaved from the dye during processing,
- DYE is a dye having the following structure, ##STR34## wherein, R.sub.l =H, a removable timing group, or a removable blocking group, wherein removable denotes that after processing, R.sub.l is hydrogen, so that the dye remains substantially or completely ionized in the element,
- R.sub.2 =one or more substituents, which ensure that the oxygen auxochrome group remains ionized after processing of the element,
- n=1, 2, 3 or 4,
- X=O or N; wherein if X is N then it is part of a heterocyclic ring that forms part of the dye chromophore, ##STR35## represents a carbon containing ring or ring system, R.sub.3 =one or more substituents, which may be located anywhere along the ring or ring system,
- the ##STR36## indicates that if X is N, then it is part of the ring or ring system; with the proviso that the substituents R.sub.2 and R.sub.3 and the ring or ring system are selected so that the dye has a pKa below about five so that the dye remains fully ionized or substantially ionized in the processed photographic element such that the dye retains the desired hue;
- and with the further proviso that the molecule may optionally contain one or more ballast groups.
- 23. A multicolor photographic element comprising a support bearing a cyan dye image-forming unit comprising at least one red-sensitive silver halide emulsion layer having associated therewith at least one cyan dye-forming coupler, a magenta dye image-forming unit comprising at least one green-sensitive silver halide emulsion layer having associated therewith at least one magenta dye-forming coupler and a yellow dye image-forming unit comprising at least one blue-sensitive silver halide emulsion layer having associated therewith at least one yellow dye forming coupler, wherein the element further comprises a molecule having a structure
- COUP--(CONNECT).sub.n'--( T).sub.m --DYE
- wherein
- n' is 0 or 1,
- m is 0, 1, or 2,
- COUP is a coupler moiety,
- CONNECT is a group attached to a coupling site of the coupler that connects the coupler to either the timing group T or directly to the dye, if attached directly to the dye it remains permanently attached to the dye after the dye is released from COUP,
- T is a timing group, which is cleaved from the dye during processing,
- DYE is a dye having the following structure, ##STR37## wherein, R.sub.1 =H, a removable timing group, or a removable blocking group, wherein removable denotes that after processing, R.sub.1 is hydrogen, so that the dye remains substantially or completely ionized in the element,
- R.sub.2 =one or more substituents, which ensure that the oxygen auxochrome group remains ionized after processing of the element,
- n=1, 2, 3 or 4,
- X=O or N; wherein if X is N then it is part of a heterocyclic ring that forms part of the dye chromophore, ##STR38## represents a carbon containing ring or ring system, R.sub.3 =one or more substituents, which may be located anywhere along the ring or ring system,
- the indicates that if X is N, then it is part of the ring or ring system;
- with the proviso that the substituents R.sub.2 and R.sub.3 and the ring or ring system are selected so that the dye has a pKa below about five so that the dye remains fully ionized or substantially ionized in the processed photographic element such that the dye retains the desired hue;
- and with the further proviso that the molecule may optionally contain one or more ballast groups,
- wherein said dye is a yellow dye, or a cyan dye, or has the structure ##STR39## wherein, R.sub.10 and R.sub.11 are independently selected from a substituted alkyl, substituted alkyloxy or substituted phenyl group.
- 24. A process for developing an image in a photographic element comprising a support and a silver halide emulsion containing an image-wise distribution of developable silver halide grains, said process comprising the step of developing said element with a silver halide color developing agent in the presence of a molecule having a structure
- COUP--(CONNECT).sub.n' --(T).sub.m --DYE
- wherein
- n' is 0 or 1,
- m is 0, 1, or 2,
- COUP is a coupler moiety,
- CONNECT is a group attached to a coupling site of the coupler that connects the coupler to either the timing group T or directly to the dye, if attached directly to the dye it remains permanently attached to the dye after the dye is released from COUP,
- T is a timing group, which is cleaved from the dye during processing,
- DYE is a dye having the following structure, ##STR40## wherein, R.sub.2 =H, a removable timing group, or a removable blocking group, wherein removable denotes that after processing, R.sub.1 is hydrogen, so that the dye remains substantially or completely ionized in the element,
- R.sub.2 =one or more substituents, which ensure that the oxygen auxochrome group remains ionized after processing of the element,
- n=1, 2, 3 or 4,
- X=O or N; wherein if X is N then it is part of a heterocyclic ring that forms part of the dye chromophore, ##STR41## represents a carbon containing ring or ring system, R.sub.3 =one or more substituents, which may be located anywhere along the ring or ring system,
- the ##STR42## indicates that if X is N, then it is part of the ring or ring system; with the proviso that the substituents R.sub.2 and R.sub.3 and the ring or ring system are selected so that the dye has a pKa below about five so that the dye remains fully ionized or substantially ionized in the processed photographic element such that the dye retains the desired hue;
- and with the further proviso that the molecule may optionally contain one or more ballast groups,
- wherein said dye is a yellow dye, or a cyan dye, or has the structure ##STR43## wherein, R.sub.10 and R.sub.11 are independently selected from a substituted alkyl, substituted alkyloxy or substituted phenyl group.
- 25. A photographic silver halide emulsion containing a molecule
- COUP--(CONNECT).sub.n' --(T).sub.m --DYE
- wherein
- n' is 0 or 1,
- m is 0, 1, or 2,
- COUP is a coupler moiety,
- CONNECT is a group attached to a coupling site of the coupler that connects the coupler to either the timing group T or directly to the dye, if attached directly to the dye it remains permanently attached to the dye after the dye is released from COUP,
- T is a timing group, which is cleaved from the dye during processing,
- DYE is a dye having the following structure, ##STR44## wherein R.sub.1 =H, a removable timing group, or a removable blocking group, wherein removable denotes that after processing, R.sub.1 is hydrogen, so that the dye remains substantially or completely ionized in the element,
- R.sub.2 -one or more substituents, which ensure that the oxygen auxochrome group remains ionized after processing of the element,
- n=1, 2, 3 or 4,
- X=O or N; wherein if X is N then it is part of a heterocyclic ring that forms part of the dye chromophore, ##STR45## represents a carbon containing ring or ring system, R.sub.3 =one or more substituents, which may be located anywhere along the ring or ring system,
- the ##STR46## indicates that if X is N, then it is part of the ring or ring system; with the proviso that the substituents R.sub.2 and R.sub.3 and the ring or ring system are selected so that the dye has a pKa below about five so that the dye remains fully ionized or substantially ionized in the processed photographic element such that the dye retains the desired hue;
- and with the further proviso that the molecule may optionally contain one or more ballast groups,
- wherein said dye is a yellow dye, or a cyan dye, or has the structure ##STR47## wherein, R.sub.10 and R.sub.11 are independently selected from a substituted alkyl, substituted alkyloxy or substituted phenyl group.
- 26. A photographic element comprising a support, and a silver halide emulsion layer having associated therewith a molecule which is a one-equivalent coupler having the structure
- COUP--(CONNECT).sub.n' --(T).sub.m --DYE
- wherein
- n' is 0 or 1,
- m is 0, 1, or 2,
- COUP is a coupler moiety,
- CONNECT is a group attached to a coupling site of the coupler that connects the coupler to either the timing group T or directly to the dye, if attached directly to the dye it remains permanently attached to the dye after the dye is released from COUP,
- T is a timing group, which is cleaved from the dye during processing,
- DYE is a dye having the following structure, ##STR48## wherein, .sub. = H, a removable timing group, or a removable blocking group, wherein removable denotes that after processing, R.sub.l is hydrogen, so that the dye remains substantially or completely ionized in the element,
- R.sub.2 =one or more substituents, which ensure that the oxygen auxochrome group remains ionized after processing of the element,
- n=1, 2, 3 or 4,
- X=O or N; wherein if X is N then it is part of a heterocyclic ring that forms part of the dye chromophore, ##STR49## represents a carbon containing ring or ring system, R.sub.3 =one or more substituents, which may be located anywhere along the ring or ring system,
- the ##STR50## indicates that if X is N, then it is part of the ring or ring system; with the proviso that the substituents R.sub.2 and R.sub.3 and the ring or ring system are selected so that the dye has a pKa below about five so that the dye remains fully ionized or substantially ionized in the processed photographic element such that the dye retains the desired hue;
- and with the further proviso that the molecule may optionally contain one or more ballast groups,
- wherein the DYE remains substantially in the layer in the element in which it is generated, and wherein COUP is other than a pyrazoloazole magenta dye-forming coupler.
- 27. A photographic element as claimed in claim 26, wherein said dye has the structure ##STR51## wherein, R.sub.8 is selected from NR'.sub.2, NH--Ph--R', NHCOR', or NH--Ph--NH--SO.sub.2 R', wherein R' is hydrogen or an alkyl or phenyl group, either of which may be substituted or unsubstituted, and
- R.sub.9 is a substituted phenyl group.
- 28. A photographic element as claimed in claim 26, wherein said dye is selected from the following compounds (K)-(O) ##STR52##
Parent Case Info
This application is a continuation, of application Ser. No. 07/897,713, filed Jun. 12, 1992.
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Entry |
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Continuations (1)
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Number |
Date |
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Parent |
897713 |
Jun 1992 |
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