Aryloxy substituted photographic couplers and photographic elements and processes employing same

Claim 2

A photographic element comprising a support and a silver halide emulsion having associated therewith a dye-forming coupler having the structure: ##STR61## where: COUP represents a dye-forming coupler moiety substituted in its coupling position with the remainder of the structure; X represents the atoms to complete a phenyl nucleus free of groups which are capable of undergoing coupling; R is hydrogen or one or more substituents selected from the group consisting of halogen, alkyl, alkoxy, nitro, cyano, carboxy, alkoxycarbonyl, aryloxycarbonyl, alkylsulfonyl, arylsulfonyl, amido, carbamoyl, sulfonamido and sulfamoyl; R 1 is hydrogen or alkyl of 1 to 4 carbon atoms; m is 0 to 4; and A is a moiety containing a polarizable carbonyl, sulfonyl or phosphinyl group free of photographic dye groups and photographic reagent groups which are released during photographic processing.

Claim 3

A photographic element comprising a support and a silver halide emulsion having associated therewith a dye-forming coupler having the structure: ##STR62## where: COUP represents a dye-forming coupler moiety substituted in its coupling position with the remainder of the structure; X represents the atoms to complete a phenyl nucleus free of groups which are capable of undergoing coupling; R is hydrogen or one or more substituents selected from halogen, alkyl, alkoxy, nitro, cyano, carboxy, alkoxycarbonyl, aryloxycarbonyl, alkylsulfonyl, arylsulfonyl, amido (--NR 1 COR 2 ), carbamoyl (--CONR 3 R 4 ), sulfonamido (--NR 1 SO 2 R 2 ) and sulfamoyl (--SO 2 NR 3 R 4 ); m is 0 to 4; and A is a moiety containing a polarizable carbonyl, sulfonyl or phosphinyl group selected from ##STR63## R 1 is hydrogen or alkyl of 1 to 4 carbon atoms; R 2 is hydrogen, alkyl or aryl; R 3 and R 4 are each, individually, hydrogen, alky, aryl or heterocyclyl, or together R 3 and R 4 complete a heterocyclic ring with the nitrogen atom to which they are attached; and each R 5 is, individually, alkyl, alkoxy, aryl or aryloxy.

Claim 4

A photographic element comprising a support and a silver halide emulsion having associated therewith a dye-forming coupler having the structure: ##STR62## where: COUP represents a dye-forming coupler moiety substituted in its coupling position with the remainder of the structure; X represents the atoms to complete a phenyl nucleus free of groups which are capable of undergoing coupling; R is hydrogen or one or more substituents selected from halogen, alkyl, alkoxy, nitro, cyano, carboxy, alkoxycarbonyl, aryloxycarbonyl, alkylsulfonyl, arylsulfonyl, amido (--NR 1 COR 2 ), carbamoyl (--CONR 3 R 4 ), sulfonamido (--NR 1 SO 2 R 2 ) and sulfamoyl (--SO 2 NR 3 R 4 ); m is 0 to 4; and A is a moiety containing a polarizable carbonyl, sulfonyl or phosphinyl group selected from ##STR63## R 1 is hydrogen or alkyl of 1 to 4 carbon atoms; R 2 is hydrogen, alkyl or aryl; R 3 and R 4 are each, individually, hydrogen, alky, aryl or heterocyclyl, or together R 3 and R 4 complete a heterocyclic ring with the nitrogen atom to which they are attached; and each R 5 is, individually, alkyl, alkoxy, aryl or aryloxy.

Claim 5

A photographic element of claim 2 wherein: m is 0 or 1; R is hydrogen or is a para position substituent selected from carboxy, alkoxy, alkoxycarbonyl, hydroxyalkyl and hydroxyalkylsulfamoyl; R 1 is hydrogen; A is --NHCOR 2 , --CONR 3 R 4 , --SO 2 R 2 , --NHSO 2 R 2 or --SO 2 NR 3 R 4 ; R 2 is alkyl or hydroxyalkyl of 1 to 4 carbon atoms; and one of R 3 and R 4 is hydrogen and the other is alkyl or hydroxyalkyl of 1 to 4 carbon atoms.

Claim 6

A photographic element of claim 1 or 2 wherein COUP is an acetoacetanilide yellow dye-forming coupler moiety.

Claim 7

A photographic element of claim 1 or 2 wherein COUP is a phenol or naphthol cyan dye-forming coupler moiety.

Claim 8

A photographic element of claim 1 or 2 wherein COUP is a pyrazolone or pyrazolotriazole magenta dye-forming coupler moiety.

Claim 9

A photographic element of claim 1 wherein the dye-forming coupler has one of the structures: ##STR64##

Claim 10

A photographic element of claim 1 wherein the dye-forming coupler has one of the structures: ##STR65##

Claim 11

a multicolor photographic element comprising a support bearing a cyan dye image-forming unit comprised of 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, at least one of the dye-forming couplers being a coupler of claim 1 or 2.

Claim 12

A process of developing an image in a photographic element comprising a support and a silver halide emulsion containing an imagewise distribution of developable silver halide grains, the process comprising the step of developing the element with a silver halide color developing agent in the presence of a dye-forming coupler having the structure: ##STR66## where: COUP represents a dye-forming coupler moiety substituted in its coupling position with the remainder of the structure; X represents the atoms to complete a phenyl nucleus free of groups which are capable of undergoing coupling; R is hydrogen or one or more substituents selected from the group consisting of halogen, alkyl, alkoxy, nitro, cyano, carboxy, alkoxycarbonyl, aryloxycarbonyl, alkylsulfonyl, arylsulfonyl, amido, carbamoyl, sulfonamido and sulfamoyl; R 1 is hydrogen or alkyl of 1 to 4 carbon atoms; m is 0 to 4; and A is a moiety containing a polarizable carbonyl, sulfonyl or phosphinyl group free of photographic dye groups and photographic reagent groups which are released during photographic processing.

Claim 13

A process of developing an image in a photographic element comprising a support and a silver halide emulsion containing an imagewise distribution of developable silver halide grains, the process comprising the step of developing the element with a silver halide color developing agent in the presence of a dye-forming coupler having the structure: ##STR66## where: COUP represents a dye-forming coupler moiety substituted in its coupling position with the remainder of the structure; X represents the atoms to complete a phenyl nucleus free of groups which are capable of undergoing coupling; R is hydrogen or one or more substituents selected from the group consisting of halogen, alkyl, alkoxy, nitro, cyano, carboxy, alkoxycarbonyl, aryloxycarbonyl, alkylsulfonyl, arylsulfonyl, amido, carbamoyl, sulfonamido and sulfamoyl; R 1 is hydrogen or alkyl of 1 to 4 carbon atoms; m is 0 to 4; and A is a moiety containing a polarizable carbonyl, sulfonyl or phosphinyl group free of photographic dye groups and photographic reagent groups which are released during photographic processing.

Claim 14

A process of developing an image in a photographic element comprising a support and a silver halide emulsion containing an imagewise distribution of developable silver halide grains, the process comprising the step of developing the element with a silver halide color developing agent in the presence of a dye-forming coupler having the structure: ##STR67## where: COUP represents a dye-forming coupler moiety substituted in its coupling position with the remainder of the structure; X represents the atoms to complete a phenyl nucleus free of groups which are capable of undergoing coupling; m is 0 to 4; R is hydrogen or one or more substituents selected from halogen, alkyl, alkoxy, nitro, cyano, carboxy, alkoxycarbonyl, aryloxycarbonyl, alkylsulfonyl, arylsulfonyl, amido (--NR 1 COR 2 ), carbamoyl (--CONR 3 R 4 ), sulfonamido (--NR 1 SO 2 R 2 ) and sulfamoyl (--SO 2 NR 3 R 4 ); A is a moiety containing a polarizable carbonyl, sulfonyl or phosphinyl group selected from ##STR68## R 1 is hydrogen or alkyl of 1 to 4 carbon atoms; R 2 is hydrogen, alkyl or aryl; R 3 and R 4 are each, individually, hydrogen, alkyl, aryl or heterocyclyl, or together R 3 and R 4 complete a heterocyclic ring with the nitrogen atom to which they are attached; and each R 5 is, individually, alkyl, alkoxy, aryl or aryloxy.

Claim 15

A process of developing an image in a photographic element comprising a support and a silver halide emulsion containing an imagewise distribution of developable silver halide grains, the process comprising the step of developing the element with a silver halide color developing agent in the presence of a dye-forming coupler having the structure: ##STR67## where: COUP represents a dye-forming coupler moiety substituted in its coupling position with the remainder of the structure; X represents the atoms to complete a phenyl nucleus free of groups which are capable of undergoing coupling; m is 0 to 4; R is hydrogen or one or more substituents selected from halogen, alkyl, alkoxy, nitro, cyano, carboxy, alkoxycarbonyl, aryloxycarbonyl, alkylsulfonyl, arylsulfonyl, amido (--NR 1 COR 2 ), carbamoyl (--CONR 3 R 4 ), sulfonamido (--NR 1 SO 2 R 2 ) and sulfamoyl (--SO 2 NR 3 R 4 ); A is a moiety containing a polarizable carbonyl, sulfonyl or phosphinyl group selected from ##STR68## R 1 is hydrogen or alkyl of 1 to 4 carbon atoms; R 2 is hydrogen, alkyl or aryl; R 3 and R 4 are each, individually, hydrogen, alkyl, aryl or heterocyclyl, or together R 3 and R 4 complete a heterocyclic ring with the nitrogen atom to which they are attached; and each R 5 is, individually, alkyl, alkoxy, aryl or aryloxy.

Claim 16

A process of claim 11 wherein: m is 0 or 1; R is hydrogen or is a para position substituent selected from carboxy, alkoxy, alkoxycarbonyl, hydroxyalkyl and hydroxyalkylsulfamoyl; R 1 is hydrogen; A is --NHCOR 2 , --CONR 3 R 4 , --SO 2 R 2 , --NHSO 2 R 2 or --SO 2 NR 3 R 4 ; R 2 is alkyl or hydroxyalkyl of 1 to 4 carbon atoms; and one of R 3 and R 4 is hydrogen and the other is alkyl or hydroxyalkyl of 1 to 4 carbon atoms.

Claim 17

A process of claim 10 or 11 wherein COUP is an acetoacetanilide yellow dye-forming coupler moiety.

Claim 18

A process of claim 10 or 11 wherein COUP is a phenol or naphthol cyan dye-forming coupler moiety.

Claim 19

A process of claim 10 or 11 wherein COUP is a pyrazolone or pyrazolotriazole magenta dye-forming coupler moiety.

Claim 20

A photographic silver halide emulsion containing a dye-forming coupler having the structure: ##STR69## where: COUP represents a dye-forming coupler moiety substituted in its coupling position with the remainder of the structure; X represents the atoms to complete a phenyl nucleus free of groups which are capable of undergoing coupling; R is hydrogen or one or more substituents selected from the group consisting of halogen, alkyl, alkoxy, nitro, cyano, carboxy, alkoxycarbonyl, aryloxycarbonyl, alkylsulfonyl, arylsulfonyl, amido, carbamoyl, sulfonamido and sulfamoyl; R 1 is hydrogen or alkyl of 1 to 4 carbon atoms; m is 0 to 4; and A is a moiety containing a polarizable carbonyl, sulfonyl or phosphinyl group free of photographic dye groups and photographic reagent groups which are released during photographic processing.

Claim 21

A photographic silver halide emulsion containing a dye-forming coupler having the structure: ##STR69## where: COUP represents a dye-forming coupler moiety substituted in its coupling position with the remainder of the structure; X represents the atoms to complete a phenyl nucleus free of groups which are capable of undergoing coupling; R is hydrogen or one or more substituents selected from the group consisting of halogen, alkyl, alkoxy, nitro, cyano, carboxy, alkoxycarbonyl, aryloxycarbonyl, alkylsulfonyl, arylsulfonyl, amido, carbamoyl, sulfonamido and sulfamoyl; R 1 is hydrogen or alkyl of 1 to 4 carbon atoms; m is 0 to 4; and A is a moiety containing a polarizable carbonyl, sulfonyl or phosphinyl group free of photographic dye groups and photographic reagent groups which are released during photographic processing.

Claim 22

A photographic silver halide emulsion containing a dye-forming coupler having the structure: ##STR70## where: COUP represents a dye-forming coupler moiety substituted in its coupling position with the remainder of the structure; X represents the atoms to complete a phenyl nucleus free of groups which are capable of undergoing coupling; m is 0 to 4; R is hydrogen or one or more substituents selected from the group consisting of halogen, alkyl, alkoxy, nitro, cyano, carboxy, alkoxycarbonyl, aryloxycarbonyl, alkylsulfonyl, arylsulfonyl, amido, carbamoyl, sulfonamido and sulfamoyl; R 1 is hydrogen or alkyl of 1 to 4 carbon atoms; and A is a moiety containing a polarizable carbonyl, sulfonyl or phosphinyl group free of photographic dye groups and photographic reagent groups which are released during photographic processing.

Claim 23

A photographic silver halide emulsion containing a dye-forming coupler having the structure: ##STR70## where: COUP represents a dye-forming coupler moiety substituted in its coupling position with the remainder of the structure; X represents the atoms to complete a phenyl nucleus free of groups which are capable of undergoing coupling; m is 0 to 4; R is hydrogen or one or more substituents selected from the group consisting of halogen, alkyl, alkoxy, nitro, cyano, carboxy, alkoxycarbonyl, aryloxycarbonyl, alkylsulfonyl, arylsulfonyl, amido, carbamoyl, sulfonamido and sulfamoyl; R 1 is hydrogen or alkyl of 1 to 4 carbon atoms; and A is a moiety containing a polarizable carbonyl, sulfonyl or phosphinyl group free of photographic dye groups and photographic reagent groups which are released during photographic processing.

Claim 24

An emulsion of claim 17 wherein: m is 0 or 1; R is hydrogen or is a para position substituent selected from carboxy, alkoxy, alkoxycarbonyl, hydroxyalkyl and hydroxyalkylsulfamoyl; R 1 is hydrogen; A is --NHCOR 2 , --CONR 3 R 4 , --SO 2 R 2 , --NHSO 2 R 2 or --SO 2 NR 3 R 4 ; R 2 is alkyl or hydroxyalkyl of 1 to 4 carbon atoms; and one of R 3 and R 4 is hydrogen and the other is alkyl or hydroxyalkyl of 1 to 4 carbon atoms.