Color-forming carboxamidonaphthalene dye precursor and carboximide dye in photographic material and process

Claim 2

In a photographic element comprising a support having thereon, in reactive association, photographic silver halide and a carboxamido color-forming dye precursor which is imagewise converted upon exposure and processing of said element to a dye; the improvement comprising: as said dye precursor, a 4-(4'-secondary or tertiary-amino)anilino-1-carboxamidonaphthalene color-forming dye precursor which forms a naphthoquinoneimide dye.

Claim 3

In a photographic element comprising a support having thereon, in reactive association, photographic silver halide and a carboxamido color-forming dye precursor which is imagewise converted upon exposure and processing of said element to a dye; the improvement comprising: as said dye precursor, a carboxamido color-forming dye precursor represented by the formula: ##STR39## wherein: R 1 is alkyl containing 1 to 25 carbon atoms, cycloalkyl containing 5 to 8 carbon atoms, aryl containing 6 to 25 carbon atoms, alkoxy containing 1 to 25 carbon atoms, aryloxy containing 6 to 25 carbon atoms, ##STR40## or a 5 or 6 member heterocyclic group; R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 are individually hydrogen, alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, alkoxy containing 1 to 25 carbon atoms, arylsulfonyl containing 6 to 25 carbon atoms, chlorine, bromine, carbamoyl, sulfamoyl, carboxy, and carboxamido; R 8 is hydrogen, alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, acyl containing 2 to 25 carbon atoms, or carbamoyl containing 2 to 25 carbon atoms; R 9 is alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, acyl containing 2 to 25 carbon atoms, or carbamoyl; R 10 and R 11 are individually hydrogen, alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, a carbocyclic group containing 6 to 8 carbon atoms, or taken together represent the atoms necessary to complete a 5 or 6 member heterocyclic ring; R 12 , R 13 , R 14 , and R 15 are individually hydrogen, alkyl containing 1 to 25 carbon atoms, cyano, sulfamoyl, chlorine, carboxamido, sulfonamido, bromine and alkoxy containing 1 to 25 carbon atoms.

Claim 4

In a photographic element comprising a support having thereon, in reactive association, photographic silver halide and a carboxamido color-forming dye precursor which is imagewise converted upon exposure and processing of said element to a dye; the improvement comprising: as said dye precursor, a carboxamido color-forming dye precursor represented by the formula: ##STR39## wherein: R 1 is alkyl containing 1 to 25 carbon atoms, cycloalkyl containing 5 to 8 carbon atoms, aryl containing 6 to 25 carbon atoms, alkoxy containing 1 to 25 carbon atoms, aryloxy containing 6 to 25 carbon atoms, ##STR40## or a 5 or 6 member heterocyclic group; R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 are individually hydrogen, alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, alkoxy containing 1 to 25 carbon atoms, arylsulfonyl containing 6 to 25 carbon atoms, chlorine, bromine, carbamoyl, sulfamoyl, carboxy, and carboxamido; R 8 is hydrogen, alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, acyl containing 2 to 25 carbon atoms, or carbamoyl containing 2 to 25 carbon atoms; R 9 is alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, acyl containing 2 to 25 carbon atoms, or carbamoyl; R 10 and R 11 are individually hydrogen, alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, a carbocyclic group containing 6 to 8 carbon atoms, or taken together represent the atoms necessary to complete a 5 or 6 member heterocyclic ring; R 12 , R 13 , R 14 , and R 15 are individually hydrogen, alkyl containing 1 to 25 carbon atoms, cyano, sulfamoyl, chlorine, carboxamido, sulfonamido, bromine and alkoxy containing 1 to 25 carbon atoms.

Claim 5

A photographic element as in claim 1 also comprising a binder.

Claim 6

A photographic element as in claim 1 also comprising a silver halide developing agent.

Claim 7

A photographic element as in claim 1 wherein said color-forming dye precursor consists essentially of a compound represented by the formula: ##STR41## wherein R 16 is alkyl containing 1 to 25 carbon atoms; aryl containing 6 to 25 carbon atoms, alkoxy containing 1 to 25 carbon atoms, aryloxy containing 6 to 25 carbon atoms, or ##STR42## R 17 is hydrogen, alkyl containing 1 to 25 carbon atoms, or acyl containing 2 to 25 carbon atoms; R 18 is alkyl containing 1 to 25 carbon atoms or acyl containing 2 to 25 carbon atoms; R 19 is hydrogen or alkyl containing 1 to 25 carbon atoms; R 20 is hydrogen, carboxamido or alkyl containing 1 to 25 carbon atoms,; and, R 21 and R 22 are individually hydrogen, alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms or together are the atoms necessary to complete a 5 or 6 member heterocylic group.

Claim 8

A photographic element as in claim 1 wherein said color-forming dye precursor consists essentially of a compound represented by the formula: ##STR43##

Claim 9

A photographic element as in claim 1 wherein said color-forming dye precursor consists essentially of a compound represented by the formula: ##STR44##

Claim 10

A photographic element as in claim 1 wherein said color-forming dye precursor consists essentially of a compound represented by the formula: ##STR45##

Claim 11

A photographic element as in claim 1 wherein said color-forming dye precursor consists essentially of a compound represented by the formula: ##STR46##

Claim 12

A photographic element as in claim 1 also comprising in reactive association, in binder, with said photosensitive silver halide, a cross-oxidizing, photographic silver halide developing agent.

Claim 13

A photographic element as in claim 1 also comprising in reactive association, in binder, with said photosensitive silver halide, a 3-pyrazolidone, photographic silver halide developing agent.

Claim 14

In a photographic element comprising a support having thereon, in a gelatino binder, in reactive association, photographic silver halide and a carboxamido color-forming dye precursor, the improvement comprising: as said dye precursor, a color-forming dye precursor represented by the formula: ##STR47##

Claim 15

In a photographic element comprising a support having thereon, in a gelatino binder, in reactive association, photographic silver halide and a carboxamido color-forming dye precursor, the improvement comprising: as said dye precursor, a color-forming dye precursor represented by the formula: ##STR47##

Claim 16

In a photographic element comprising a support having thereon, in a gelatino binder, in reactive association, a photographic silver halide gelatino emulsion and a carboxamido color-forming dye precursor, the improvement comprising: as said dye precursor, a color-forming dye precursor represented by the formula: ##STR48##

Claim 17

In a photographic element comprising a support having thereon, in a gelatino binder, in reactive association, a photographic silver halide gelatino emulsion and a carboxamido color-forming dye precursor, the improvement comprising: as said dye precursor, a color-forming dye precursor represented by the formula: ##STR48##

Claim 18

In a photographic element comprising a support having thereon, in a gelatino binder, in reactive association, photographic silver halide and a carboxamido color-forming dye precursor, the improvement comprising: as said dye precursor, a color-forming dye precursor represented by the formula: ##STR49##

Claim 19

In a photographic element comprising a support having thereon, in a gelatino binder, in reactive association, photographic silver halide and a carboxamido color-forming dye precursor, the improvement comprising: as said dye precursor, a color-forming dye precursor represented by the formula: ##STR49##

Claim 20

In a photographic composition comprising a photographic silver halide and a carboxamido color-forming dye precursor; the improvement comprising: as said dye precursor, a 4-(4'-secondary or tertiary-amino)anilino-1-carboxamidonaphthalene color-forming dye precursor which forms a naphthoquinoneimide dye.

Claim 21

In a photographic composition comprising a photographic silver halide and a carboxamido color-forming dye precursor; the improvement comprising: as said dye precursor, a 4-(4'-secondary or tertiary-amino)anilino-1-carboxamidonaphthalene color-forming dye precursor which forms a naphthoquinoneimide dye.

Claim 22

In a photographic composition comprising photographic silver halide and a carboxamido color-forming dye precursor; the improvement comprising: as said dye precursor, a carboxamido color-forming dye precursor represented by the formula: ##STR50## wherein: R 1 is alkyl containing 1 to 25 carbon atoms, cycloalkyl containing 5 to 8 carbon atoms, aryl containing 6 to 25 carbon atoms, alkoxy containing 1 to 25 carbon atoms, aryloxy containing 6 to 25 carbon atoms, ##STR51## or a 5 or 6 member heterocyclic group; R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 are individually hydrogen, alkyl containing 1 to 25 carbon atoms, alkoxy containing 1 to 25 carbon atoms, nitro, arylsulfonyl containing 6 to 25 carbon atoms, chlorine, bromine, carbamoyl, sulfamoyl, carboxy, and carboxamido; R 8 is hydrogen, alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, acyl containing 2 to 25 carbon atoms, or carbamoyl containing 2 to 25 carbon atoms; R 9 is alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, acyl containing 2 to 25 carbon atoms, or carbamoyl; R 10 and R 11 are individually hydrogen, alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, a carbocyclic group containing 6 to 8 carbon atoms, or taken together represent the atoms necessary to complete a 5 or 6 member heterocyclic ring; R 12 , R 13 , R 14 , and R 15 are individually hydrogen, alkyl containing 1 to 25 carbon atoms, cyano, sulfamoyl, chlorine, bromine, carboxamido, sulfonamido, and alkoxy containing 1 to 25 carbon atoms.

Claim 23

In a photographic composition comprising photographic silver halide and a carboxamido color-forming dye precursor; the improvement comprising: as said dye precursor, a carboxamido color-forming dye precursor represented by the formula: ##STR50## wherein: R 1 is alkyl containing 1 to 25 carbon atoms, cycloalkyl containing 5 to 8 carbon atoms, aryl containing 6 to 25 carbon atoms, alkoxy containing 1 to 25 carbon atoms, aryloxy containing 6 to 25 carbon atoms, ##STR51## or a 5 or 6 member heterocyclic group; R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 are individually hydrogen, alkyl containing 1 to 25 carbon atoms, alkoxy containing 1 to 25 carbon atoms, nitro, arylsulfonyl containing 6 to 25 carbon atoms, chlorine, bromine, carbamoyl, sulfamoyl, carboxy, and carboxamido; R 8 is hydrogen, alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, acyl containing 2 to 25 carbon atoms, or carbamoyl containing 2 to 25 carbon atoms; R 9 is alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, acyl containing 2 to 25 carbon atoms, or carbamoyl; R 10 and R 11 are individually hydrogen, alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, a carbocyclic group containing 6 to 8 carbon atoms, or taken together represent the atoms necessary to complete a 5 or 6 member heterocyclic ring; R 12 , R 13 , R 14 , and R 15 are individually hydrogen, alkyl containing 1 to 25 carbon atoms, cyano, sulfamoyl, chlorine, bromine, carboxamido, sulfonamido, and alkoxy containing 1 to 25 carbon atoms.

Claim 24

A photographic composition as in claim 15 also comprising a binder.

Claim 25

A photographic composition as in claim 15 also comprising a silver halide developing agent.

Claim 26

A photographic composition as in claim 15 wherein said color-forming dye precursor consists essentially of a compound represented by the formula: ##STR52##

Claim 27

A photographic composition as in claim 15 wherein said color-forming dye precursor consists essentially of a compound represented by the formula: ##STR53##

Claim 28

A photographic composition as in claim 15 wherein said color-forming dye precursor consists essentially of a compound represented by the formula: ##STR54##

Claim 29

A photographic composition as in claim 15 wherein said color-forming dye precursor consists essentially of a compound represented by the formula: ##STR55##

Claim 30

A photographic composition as in claim 15 also comprising a cross-oxidizing, photographic silver halide developing agent.

Claim 31

A photographic composition as in claim 15 also comprising a 3-pyrazolidone, photographic silver halide developing agent.

Claim 32

In a photographic composition comprising, in a binder, photographic silver halide and a carboxamido color-forming dye precursor; the improvement comprising: as said dye precursor, a color-forming dye precursor represented by the formula: ##STR56##

Claim 33

In a photographic composition comprising, in a binder, photographic silver halide and a carboxamido color-forming dye precursor; the improvement comprising: as said dye precursor, a color-forming dye precursor represented by the formula: ##STR56##

Claim 34

In a photographic composition comprising, in a binder, photographic silver halide and a carboxamido color-forming dye precursor; the improvement comprising: as said dye precursor, a color-forming dye precursor represented by the formula: ##STR57##

Claim 35

In a photographic composition comprising, in a binder, photographic silver halide and a carboxamido color-forming dye precursor; the improvement comprising: as said dye precursor, a color-forming dye precursor represented by the formula: ##STR57##

Claim 36

In a photographic composition comprising, in a binder, photographic silver halide and a carboxamido color-forming dye precursor; the improvement comprising: as said dye precursor, a color-forming dye precursor represented by the formula: ##STR58##

Claim 37

In a photographic composition comprising, in a binder, photographic silver halide and a carboxamido color-forming dye precursor; the improvement comprising: as said dye precursor, a color-forming dye precursor represented by the formula: ##STR58##

Claim 38

A process of producing a negative dye image and a negative silver image in an exposed photographic element comprising a support having thereon, in reactive association, in binder, photographic silver halide color-forming 4-(4'-secondary or tertiary-amino)anilino-1-carboxamidonaphthalene dye precursor which is converted upon processing of said element to a naphthoquinoneimide dye by cross-oxidation by means of a cross-oxidizing silver halide developing agent; said process comprising the step: (A) developing said photographic element in an alkaline, cross-oxidizing, photographic silver halide developer composition to produce a negative naphthoqinoneimide dye image and silver image.

Claim 39

A process of producing a negative dye image and a negative silver image in an exposed photographic element comprising a support having thereon, in reactive association, in binder, photographic silver halide color-forming 4-(4'-secondary or tertiary-amino)anilino-1-carboxamidonaphthalene dye precursor which is converted upon processing of said element to a naphthoquinoneimide dye by cross-oxidation by means of a cross-oxidizing silver halide developing agent; said process comprising the step: (A) developing said photographic element in an alkaline, cross-oxidizing, photographic silver halide developer composition to produce a negative naphthoqinoneimide dye image and silver image.

Claim 40

A process of producing a negative dye image and a negative silver image in an exposed photographic element comprising a support having thereon, in reactive association, in binder, photographic silver halide and a color-forming 4-(4'-secondary or tertiary-amino)anilino-1-carboxamidonaphthalene dye precursor represented by the formula: ##STR59## wherein: R 1 is alkyl containing 1 to 25 carbon atoms, cycloalkyl containing 5 to 8 carbon atoms, aryl containing 6 to 25 carbon atoms, alkoxy containing 1 to 25 carbon atoms, aryloxy containing 6 to 25 carbon atoms, ##STR60## or a 5 or 6 member heterocyclic group; R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 are individually hydrogen, alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, alkoxy containing 1 to 25 carbon atoms, arylsulfonyl containing 6 to 25 carbon atoms, chlorine, bromine, carbamoyl, sulfamoyl, carboxy, and carboxamido; R 8 is hydrogen, alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, acyl containing 2 to 25 carbon atoms, or carbamoyl containing 2 to 25 carbon atoms; R 9 is alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, acyl containing 2 to 25 carbon atoms, or carbamoyl; R 10 and R 11 are individually hydrogen, alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, a carbocyclic group containing 6 to 8 carbon atoms, or taken together represent the atoms necessary to complete a 5 or 6 member heterocyclic ring; R 14 , R 15 , R 16 , and R 17 are individually hydrogen, alkyl containing 1 to 25 carbon atoms, cyano, sulfamoyl, chlorine, carboxamido, sulfonamido, bromine and alkoxy containing 1 to 25 carbon atoms; wherein said dye precursor is converted upon processing of said element to a dye by cross-oxidation by means of a cross-oxidizing silver halide developing agent, said process comprising the step: (A) developing said photographic element in an alkaline, cross-oxidizing, photographic silver halide developer composition comprising a 3-pyrazolidone cross-oxidizing silver halide developing agent to produce a negative dye image and silver image.

Claim 41

A process of producing a negative dye image and a negative silver image in an exposed photographic element comprising a support having thereon, in reactive association, in binder, photographic silver halide and a color-forming 4-(4'-secondary or tertiary-amino)anilino-1-carboxamidonaphthalene dye precursor represented by the formula: ##STR59## wherein: R 1 is alkyl containing 1 to 25 carbon atoms, cycloalkyl containing 5 to 8 carbon atoms, aryl containing 6 to 25 carbon atoms, alkoxy containing 1 to 25 carbon atoms, aryloxy containing 6 to 25 carbon atoms, ##STR60## or a 5 or 6 member heterocyclic group; R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 are individually hydrogen, alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, alkoxy containing 1 to 25 carbon atoms, arylsulfonyl containing 6 to 25 carbon atoms, chlorine, bromine, carbamoyl, sulfamoyl, carboxy, and carboxamido; R 8 is hydrogen, alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, acyl containing 2 to 25 carbon atoms, or carbamoyl containing 2 to 25 carbon atoms; R 9 is alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, acyl containing 2 to 25 carbon atoms, or carbamoyl; R 10 and R 11 are individually hydrogen, alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, a carbocyclic group containing 6 to 8 carbon atoms, or taken together represent the atoms necessary to complete a 5 or 6 member heterocyclic ring; R 14 , R 15 , R 16 , and R 17 are individually hydrogen, alkyl containing 1 to 25 carbon atoms, cyano, sulfamoyl, chlorine, carboxamido, sulfonamido, bromine and alkoxy containing 1 to 25 carbon atoms; wherein said dye precursor is converted upon processing of said element to a dye by cross-oxidation by means of a cross-oxidizing silver halide developing agent, said process comprising the step: (A) developing said photographic element in an alkaline, cross-oxidizing, photographic silver halide developer composition comprising a 3-pyrazolidone cross-oxidizing silver halide developing agent to produce a negative dye image and silver image.

Claim 42

A process as in claim 29 of producing a negative dye image and a negative silver image in an exposed photographic element comprising a support having thereon, in reactive association, in binder, photographic silver halide and a color-forming dye precursor represented by the formula: ##STR61## said process comprising the step: (A) developing said photographic element in an aqueous, alkaline, cross-oxidizing photographic silver halide developer solution comprising a cross-oxidizing photographic silver halide developing agent consisting essentially of 4-methyl-4-hydroxymethyl-1-phenyl-3-pyrazolidone.

Claim 43

A process as in claim 29 of producing a negative dye image and a negative silver image in an exposed photographic element comprising a support having thereon, in reactive association, in binder, photographic silver halide and a color-forming dye precursor represented by the formula: ##STR62## said process comprising the step: (A) developing said photographic element in an aqueous, alkaline, cross-oxidizing photographic silver halide developer solution comprising a cross-oxidizing photographic silver halide developing agent consisting essentially of 4-methyl-4-hydroxymethyl-1-phenyl-3-pyrazolidone.

Claim 44

A process as in claim 29 of producing a negative dye image and a negative silver image in an exposed photographic element comprising a support having thereon, in reactive association, in binder, photographic silver halide and a color-forming dye precursor represented by the formula: ##STR63## said process comprising the step: (A) developing said photographic element in an aqueous, alkaline, cross-oxidizing photographic silver halide developer solution comprising a cross-oxidizing photographic silver halide developing agent consisting essentially of 4-methyl-4-hydroxymethyl-1-phenyl-3-pyrazolidone.

Claim 45

A process as in claim 29 of producing a negative dye image and a negative silver image in an exposed photographic element comprising a support having thereon, in reactive association, in binder, photographic silver halide and a color-forming dye precursor represented by the formula: ##STR64## said process comprising the step of: (A) developing said photographic element in an aqueous, alkaline, cross-oxidizing photographic silver halide developer solution comprising a cross-oxidizing photographic silver halide developing agent consisting essentially of 4-methyl-4-hydroxymethyl-1-phenyl-3-pyrazolidone.

Claim 46

A process of producing a positive, dye image in an imagewise exposed photographic element comprising a support having thereon, in reactive association, in binder, photographic silver halide and a color-forming 4-(4'-secondary or tertiary-amino)anilino-1-carboxamidonaphthalene which is converted upon processing of said element to a naphthoquinoneimide dye by cross-oxidation by means of a cross-oxidizing photographic silver halide developing agent; said process comprising the steps: (A) developing a silver image in said photographic element by means of an alkaline, photographic silver halide developer in the absence of a cross-oxidizing, photographic silver halide developing agent; (B) fogging the resulting element; (C) producing a dye image in the photographic element by means of an alkaline, cross-oxidizing, photographic silver halide developer; and (D) bleaching and fixing the photographic element by means of a silver halide bleaching and fixing solution; to produce a positive dye image in the photographic element.

Claim 47

A process of producing a positive, dye image in an imagewise exposed photographic element comprising a support having thereon, in reactive association, in binder, photographic silver halide and a color-forming 4-(4'-secondary or tertiary-amino)anilino-1-carboxamidonaphthalene which is converted upon processing of said element to a naphthoquinoneimide dye by cross-oxidation by means of a cross-oxidizing photographic silver halide developing agent; said process comprising the steps: (A) developing a silver image in said photographic element by means of an alkaline, photographic silver halide developer in the absence of a cross-oxidizing, photographic silver halide developing agent; (B) fogging the resulting element; (C) producing a dye image in the photographic element by means of an alkaline, cross-oxidizing, photographic silver halide developer; and (D) bleaching and fixing the photographic element by means of a silver halide bleaching and fixing solution; to produce a positive dye image in the photographic element.

Claim 48

A process as in claim 34 wherein said fogging is performed by means of a uniform flash exposure.

Claim 49

A process as in claim 34 wherein said photographic element after step (A) and before step (B) is treated by means of a photographic development stop bath.

Claim 50

A process as in claim 34 of producing a positive dye image in an imagewise exposed photographic element comprising a support having thereon, in reactive association, in binder, (a) photosensitive silver halide, and (b) a color-forming 4-(4'-secondary or tertiary-amino)anilino-1-carboxamidonaphthalene dye precursor consisting essentially of a compound represented by the formula: ##STR65## said process comprising the steps: (A) developing said photographic element in an alkaline, photographic developer in the absence of a cross-oxidizing, photographic silver halide developing agent; (B) treating the photographic element by means of a photographic development stop bath; (C) fogging the resulting element; (D) producing a dye image in the photographic element by means of an alkaline, cross-oxidizing, photographic silver halide developer comprising an alkaline solution of 4-methyl-4-hydroxymethyl-1-phenyl-3-pyrazolidone; and then (E) bleaching and fixing the photographic element in a silver halide bleaching and fixing solution.

Claim 51

A process as in claim 34 of producing a positive dye image in an imagewise exposed photographic element comprising a support having thereon, in reactive association, in binder, (a) photosensitive silver halide, and (b) a color-forming 4-(4'-secondary or tertiary-amino)anilino-1-carboxamidonaphthalene dye precursor consisting essentially of a compound represented by the formula: ##STR66## said process comprising the steps: (A) developing said photographic element in an alkaline, photographic developer in the absence of a cross-oxidizing, photographic silver halide developing agent; (B) treating the photographic element by means of a photographic development stop bath; (C) fogging the resulting element; (D) producing a dye image in the photographic element by means of an alkaline, cross-oxidizing, photographic silver halide developer comprising an alkaline solution of 4-methyl-4-hydroxymethyl-1-phenyl-3-pyrazolidone; and then (E) bleaching and fixing the photographic element in a silver halide bleaching and fixing solution.

Claim 52

A process of producing a negative dye image in an exposed photographic element comprising a support having thereon, in reactive association, in binder, photographic silver halide and a color-forming 4-(4'-secondary or tertiary-amino)anilino-1-carboxamidonaphthalene dye precursor which is converted upon processing of said element to a naphthoquinoneimide dye by cross-oxidation by means of a cross-oxidizing silver halide developing agent, said process comprising: (A) developing said photographic element in an alkaline, cross-oxidizing, photographic silver halide developer composition to produce a negative dye image and silver image; then (B) removing at least part of the silver image from the photographic element.

Claim 53

A process of producing a negative dye image in an exposed photographic element comprising a support having thereon, in reactive association, in binder, photographic silver halide and a color-forming 4-(4'-secondary or tertiary-amino)anilino-1-carboxamidonaphthalene dye precursor which is converted upon processing of said element to a naphthoquinoneimide dye by cross-oxidation by means of a cross-oxidizing silver halide developing agent, said process comprising: (A) developing said photographic element in an alkaline, cross-oxidizing, photographic silver halide developer composition to produce a negative dye image and silver image; then (B) removing at least part of the silver image from the photographic element.

Claim 54

A process of producing a negative dye image in an exposed photographic element comprising a support having thereon, in reactive association, in binder, photographic silver halide and a color-forming 4-(4'-secondary or tertiary-amino)anilino-1-caraboxamidonaphthalene represented by the formula: ##STR67## wherein: R 1 is alkyl containing 1 to 25 carbon atoms, cycloalkyl containing 5 to 8 carbon atoms, aryl containing 6 to 25 carbon atoms, alkoxy containing 1 to 25 carbon atoms, aryloxy containing 6 to 25 carbon atoms, ##STR68## or a 5 or 6 member heterocyclic group; R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 are individually hydrogen, alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, alkoxy containing 1 to 25 carbon atoms, arylsulfonyl containing 6 to 25 carbon atoms, chlorine, bromine, carbamoyl, sulfamoyl, carboxy, and carboxamido; R 8 is hydrogen, alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, acyl containing 2 to 25 carbon atoms, or carbamoyl containing 2 to 25 carbon atoms; R 9 is alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, acyl containing 2 to 25 carbon atoms, or carbamoyl; R 10 and R 11 are individually hydrogen, alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, a carbocyclic group containing 6 to 8 carbon atoms, or taken together represent the atoms necessary to complete a 5 or 6 member heterocyclic ring; R 12 , R 13 , R 14 , and R 15 are individually hydrogen, alkyl containing 1 to 25 carbon atoms, cyano, sulfamoyl, chlorine, carboxamido, sulfonamido, bromine and alkoxy containing 1 to 25 carbon atoms; said process comprising: (A) developing said photographic element in an alkaline, cross-oxidizing, photographic silver halide developer composition to produce a negative dye image and silver image; then (B) removing at least part of the silver image from the photographic element.

Claim 55

A process of producing a negative dye image in an exposed photographic element comprising a support having thereon, in reactive association, in binder, photographic silver halide and a color-forming 4-(4'-secondary or tertiary-amino)anilino-1-caraboxamidonaphthalene represented by the formula: ##STR67## wherein: R 1 is alkyl containing 1 to 25 carbon atoms, cycloalkyl containing 5 to 8 carbon atoms, aryl containing 6 to 25 carbon atoms, alkoxy containing 1 to 25 carbon atoms, aryloxy containing 6 to 25 carbon atoms, ##STR68## or a 5 or 6 member heterocyclic group; R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 are individually hydrogen, alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, alkoxy containing 1 to 25 carbon atoms, arylsulfonyl containing 6 to 25 carbon atoms, chlorine, bromine, carbamoyl, sulfamoyl, carboxy, and carboxamido; R 8 is hydrogen, alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, acyl containing 2 to 25 carbon atoms, or carbamoyl containing 2 to 25 carbon atoms; R 9 is alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, acyl containing 2 to 25 carbon atoms, or carbamoyl; R 10 and R 11 are individually hydrogen, alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, a carbocyclic group containing 6 to 8 carbon atoms, or taken together represent the atoms necessary to complete a 5 or 6 member heterocyclic ring; R 12 , R 13 , R 14 , and R 15 are individually hydrogen, alkyl containing 1 to 25 carbon atoms, cyano, sulfamoyl, chlorine, carboxamido, sulfonamido, bromine and alkoxy containing 1 to 25 carbon atoms; said process comprising: (A) developing said photographic element in an alkaline, cross-oxidizing, photographic silver halide developer composition to produce a negative dye image and silver image; then (B) removing at least part of the silver image from the photographic element.

Claim 56

A process as in claim 39 of producing a negative dye image in an exposed photographic element comprising a support having thereon, in reactive association, in binder, photographic silver halide and a color-forming dye precursor represented by the formula: ##STR69## said process comprising: (A) developing said photographic element in an alkaline, cross-oxidizing, photographic silver halide developer composition to produce a negative dye image and silver image; then (B) removing at least part of the silver image from the photographic element.

Claim 57

A process of producing a positive dye image and a positive silver image in an imagewise exposed photographic element comprising a support having thereon, in reactive association, in binder, (a) direct-positive photographic silver halide, and (b) a color-forming 4-(4'-secondary or tertiaryamino)-anilino-1-carboxamidonaphthalene dye precursor which is converted upon processing of said element to a naphthoquinoneimide dye by cross-oxidation by means of a cross-oxidizing silver halide developing agent, said process comprising: (A) developing said photographic element in an alkaline, cross-oxidizing photographic silver halide developing composition; then (B) fixing the resulting photographic element to produce a positive dye image and a positive silver image.

Claim 58

A process of producing a positive dye image and a positive silver image in an imagewise exposed photographic element comprising a support having thereon, in reactive association, in binder, (a) direct-positive photographic silver halide, and (b) a color-forming 4-(4'-secondary or tertiaryamino)-anilino-1-carboxamidonaphthalene dye precursor which is converted upon processing of said element to a naphthoquinoneimide dye by cross-oxidation by means of a cross-oxidizing silver halide developing agent, said process comprising: (A) developing said photographic element in an alkaline, cross-oxidizing photographic silver halide developing composition; then (B) fixing the resulting photographic element to produce a positive dye image and a positive silver image.

Claim 59

A process as in claim 42 of producing a positive dye image and a positive silver image in an imagewise exposed photographic element comprising a support having thereon, in binder, (a) direct-positive photographic silver halide, and (b) a color-forming dye precursor represented by the formula: ##STR70## said precursor comprising: (A) developing said photographic element in an alkaline, cross-oxidizing photographic silver halide developing composition; then (B) fixing the resulting photographic element to produce a positive dye image and a positive silver image.

Claim 60

A process as in claim 42 of producing a positive dye image and a positive silver image in an imagewise exposed photographic element comprising a support having thereon, in binder, (a) direct-positive photographic silver halide, and (b) a color-forming dye precursor represented by the formula: ##STR71## said process comprising: (A) developing said photographic element in an alkaline, cross-oxidizing photographic silver halide developing composition; then (B) fixing the resulting photographic element to produce a positive dye image and a positive silver image.

Claim 61

In a photographic silver halide processing composition for producing a dye enhanced silver image comprising: (a) a cross-oxidizing photographic silver halide developing agent, and (b) a color-forming dye precursor, the improvement comprising: as said dye precursor, a 4-(4'-secondary or tertiary-amino)anilino-1-carboxamidonaphthalene color-forming dye precursor which forms a naphthoquinoneimide dye.

Claim 62

In a photographic silver halide processing composition for producing a dye enhanced silver image comprising: (a) a cross-oxidizing photographic silver halide developing agent, and (b) a color-forming dye precursor, the improvement comprising: as said dye precursor, a 4-(4'-secondary or tertiary-amino)anilino-1-carboxamidonaphthalene color-forming dye precursor which forms a naphthoquinoneimide dye.

Claim 63

In a photographic silver halide processing composition for producing a dye enhanced silver image comprising: (a) a cross-oxidizing photographic silver halide developing agent, and (b) a color-forming dye precursor, the improvement comprising: as said dye precursor, a 4-(4'-secondary or tertiary-amino)anilino-1-carboxamidonaphthalene represented by the formula: ##STR72## R 1 is alkyl containing 1 to 25 carbon atoms, cycloalkyl containing 5 to 8 carbon atoms, aryl containing 6 to 25 carbon atoms, alkoxy containing 1 to 25 carbon atoms, aryloxy containing 6 to 25 carbon atoms, ##STR73## or a 5 or 6 member heterocyclic group; R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 are individually hydrogen, alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, alkoxy containing 1 to 25 carbon atoms, arylsulfonyl containing 6 to 25 carbon atoms, chlorine, bromine, carbamoyl, sulfamoyl, carboxy, and carboxamido; R 8 is hydrogen, alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, acyl containing 2 to 25 carbon atoms, or carbamoyl containing 2 to 25 carbon atoms; R 9 is alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, acyl containing 2 to 25 carbon atoms, or carbamoyl; R 10 and R 11 are individually hydrogen, alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, a carbocyclic group containing 6 to 8 carbon atoms, or taken together represent the atoms necessary to complete a 5 or 6 member heterocyclic ring; R 12 , R 13 , R 14 , and R 15 are individually hydrogen, alkyl containing 1 to 25 carbon atoms, cyano, sulfamoyl, chlorine, carboxamido, sulfonamido, bromine and alkoxy containing 1 to 25 carbon atoms.

Claim 64

In a photographic silver halide processing composition for producing a dye enhanced silver image comprising: (a) a cross-oxidizing photographic silver halide developing agent, and (b) a color-forming dye precursor, the improvement comprising: as said dye precursor, a 4-(4'-secondary or tertiary-amino)anilino-1-carboxamidonaphthalene represented by the formula: ##STR72## R 1 is alkyl containing 1 to 25 carbon atoms, cycloalkyl containing 5 to 8 carbon atoms, aryl containing 6 to 25 carbon atoms, alkoxy containing 1 to 25 carbon atoms, aryloxy containing 6 to 25 carbon atoms, ##STR73## or a 5 or 6 member heterocyclic group; R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 are individually hydrogen, alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, alkoxy containing 1 to 25 carbon atoms, arylsulfonyl containing 6 to 25 carbon atoms, chlorine, bromine, carbamoyl, sulfamoyl, carboxy, and carboxamido; R 8 is hydrogen, alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, acyl containing 2 to 25 carbon atoms, or carbamoyl containing 2 to 25 carbon atoms; R 9 is alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, acyl containing 2 to 25 carbon atoms, or carbamoyl; R 10 and R 11 are individually hydrogen, alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, a carbocyclic group containing 6 to 8 carbon atoms, or taken together represent the atoms necessary to complete a 5 or 6 member heterocyclic ring; R 12 , R 13 , R 14 , and R 15 are individually hydrogen, alkyl containing 1 to 25 carbon atoms, cyano, sulfamoyl, chlorine, carboxamido, sulfonamido, bromine and alkoxy containing 1 to 25 carbon atoms.

Claim 65

A photographic silver halide processing composition as in claim 45 wherein said dye precursor comprises a compound represented by the formula: ##STR74##

Claim 66

A photographic silver halide processing composition as in claim 45 wherein said dye precursor comprises a compound represented by the formula: ##STR75##

Claim 67

A photographic silver halide processing composition as in claim 45 wherein said dye precursor comprises a compound represented by the formula: ##STR76##

Claim 68

A photographic silver halide processing composition as in claim 45 wherein said dye precursor comprises a compound represented by the formula: ##STR77##

Claim 69

An exposed and processed photographic element comprising a support having thereon an image comprising a dye represented by the formula: ##STR78## wherein: R 1 is alkyl containing 1 to 25 carbon atoms, cycloalkyl containing 5 to 8 carbon atoms, aryl containing 6 to 25 carbon atoms, alkoxy containing 1 to 25 carbon atoms, aryloxy containing 6 to 25 carbon atoms, ##STR79## or a 5 or 6 member heterocyclic group; R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 are individually hydrogen, alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, alkoxy containing 1 to 25 carbon atoms, arylsulfonyl containing 6 to 25 carbon atoms, chlorine, bromine, carbamoyl, sulfamoyl, carboxy, sulfonamido; and carboxamido; R 8 is hydrogen, alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, acyl containing 2 to 25 carbon atoms, or carbamoyl containing 2 to 25 carbon atoms; R 9 is alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, acyl containing 2 to 25 carbon atoms, or carbamoyl; R 10 and R 11 are individually hydrogen, alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, a carbocyclic group containing 6 to 8 carbon atoms, or taken together represents the atoms necessary to complete a 5 or 6 member heterocyclic ring; R 12 , R 13 , R 14 , and R 15 are individually hydrogen, alkyl containing 1 to 25 carbon atoms, cyano, sulfamoyl, chlorine, carboxamido, sulfonamido, bromine and alkoxy containing 1 to 25 carbon atoms.

Claim 70

An exposed and processed photographic element comprising a support having thereon an image comprising a dye represented by the formula: ##STR78## wherein: R 1 is alkyl containing 1 to 25 carbon atoms, cycloalkyl containing 5 to 8 carbon atoms, aryl containing 6 to 25 carbon atoms, alkoxy containing 1 to 25 carbon atoms, aryloxy containing 6 to 25 carbon atoms, ##STR79## or a 5 or 6 member heterocyclic group; R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 are individually hydrogen, alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, alkoxy containing 1 to 25 carbon atoms, arylsulfonyl containing 6 to 25 carbon atoms, chlorine, bromine, carbamoyl, sulfamoyl, carboxy, sulfonamido; and carboxamido; R 8 is hydrogen, alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, acyl containing 2 to 25 carbon atoms, or carbamoyl containing 2 to 25 carbon atoms; R 9 is alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, acyl containing 2 to 25 carbon atoms, or carbamoyl; R 10 and R 11 are individually hydrogen, alkyl containing 1 to 25 carbon atoms, aryl containing 6 to 25 carbon atoms, a carbocyclic group containing 6 to 8 carbon atoms, or taken together represents the atoms necessary to complete a 5 or 6 member heterocyclic ring; R 12 , R 13 , R 14 , and R 15 are individually hydrogen, alkyl containing 1 to 25 carbon atoms, cyano, sulfamoyl, chlorine, carboxamido, sulfonamido, bromine and alkoxy containing 1 to 25 carbon atoms.

Claim 71

An exposed and processed photographic element as in claim 50 also comprising a binder.

Claim 72

An exposed and processed photographic element as in claim 50 also comprising a silver image.

Claim 73

An exposed and processed photographic element as in claim 51 comprising a support having thereon, in binder, an image comprising a dye represented by the formula: ##STR80##

Claim 74

An exposed and processed photographic element as in claim 51 comprising a support having thereon, in binder, an image comprising a dye represented by the formula: ##STR81##

Claim 75

An exposed and processed photographic element as in claim 51 comprising a support having thereon an image comprising a dye represented by the formula: ##STR82##

Claim 76

An exposed and processed photographic element as in claim 51 comprising a support having thereon an image comprising a dye represented by the formula: ##STR83##