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US 5,612,173 AGranted
One equivalent couplers and low PKA release dyes
AssigneeEastman Kodak Company
InventorsGary S. Proehl, Stephen P. Singer, J. Michael Buchanan
Life of this patent
Estimating the term…
Abstract
A photographic element containing a dye which when released from a coupler has a sufficiently low pKa, generally less than about 5, such that the dye remains substantially or fully ionized during coating of the film and in the produced film, results in an element containing a dye which has the desired hue without the use of additional additives, such as mordants, to keep the dye ionized. The dye is also useful in photographic elements without release from a coupler, for example, as a filter dye.
Claims28
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.
12 more elements
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.
12 more elements
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.
13 more elements
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.
13 more elements
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.
13 more elements
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.
13 more elements
Dependencies are inferred from the claim text.