Photographic emulsions, elements and processes utilizing release compounds

Claim 2

A photographic element comprising a support, at least one silver halide emulsion layer and a photographic coupler containing a coupler moiety, a photographic dye or reagent, containing a hetero atom from Group VA or VIA of the periodic table having a negative valence of 2 or 3 and a timing group joining the coupler moiety and the photographic dye or reagent, the timing means comprising a nucleophilic group attached to the coupler moiety at a position from which it is capable of being displaced as a result of reaction of the coupler moiety with oxidized color developing agent, an electrophilic group attached to said hetero atom in the photographic dye or reagent and capable of being displaced therefrom by said nucleophilic group after said nucleophilic group is displaced from said coupler moiety, and a linking group spatially relating the nucleophilic group and the electrophilic group to undergo, after cleavage of the bond between the timing group and the coupler moiety, an intramolecular nucleophilic displacement reaction which cleaves the bond between the photographic dye or reagent and the timing group.

Claim 3

A photographic element comprising a support, at least one silver halide emulsion layer and a photographic coupler represented by the structure: ##STR89## where: COUP is a coupler moiety; PUG is a photographic dye or reagent containing a hetero atom from Group VA or VIA of the periodic table having a negative valence of 2 or 3; Nu is a nucleophilic group containing an electron rich oxygen, sulfur or nitrogen atom, Nu being attached to a position on COUP from which it will be displaced upon reaction of COUP with oxidized color developing agent; E is an electrophilic group containing an electron deficient carbonyl, thiocarbonyl, phosphinyl or thiophosphinyl moiety, E being attached to said hetero atom in PUG and being displaceable therefrom by Nu after Nu is displaced from COUP; and X is a linking group for spatially relating Nu and E, upon displacement of Nu from COUP, to undergo an intramolecular nucleophilic displacement reaction with the formation of a three- to seven-membered ring and thereby release PUG.

Claim 4

A photographic element comprising a support, at least one silver halide emulsion layer and a photographic coupler represented by the structure: ##STR89## where: COUP is a coupler moiety; PUG is a photographic dye or reagent containing a hetero atom from Group VA or VIA of the periodic table having a negative valence of 2 or 3; Nu is a nucleophilic group containing an electron rich oxygen, sulfur or nitrogen atom, Nu being attached to a position on COUP from which it will be displaced upon reaction of COUP with oxidized color developing agent; E is an electrophilic group containing an electron deficient carbonyl, thiocarbonyl, phosphinyl or thiophosphinyl moiety, E being attached to said hetero atom in PUG and being displaceable therefrom by Nu after Nu is displaced from COUP; and X is a linking group for spatially relating Nu and E, upon displacement of Nu from COUP, to undergo an intramolecular nucleophilic displacement reaction with the formation of a three- to seven-membered ring and thereby release PUG.

Claim 5

A photographic element of claim 2, wherein PUG contains an oxygen, sulfur or heterocyclic nitrogen atom by which it is attached to E.

Claim 6

A photographic element of claim 2 wherein Nu contains an electron rich oxygen or sulfur atom; E contains an electron deficient carbonyl or thiocarbonyl group; PUG contains an oxgen or sulfur atom by which it is attached to E.

Claim 7

A photographic element of claim 2 wherein X is alkylene or an arylene linking group.

Claim 8

A photographic element of claim 2 wherein COUP is a coupler moiety which yields a colored product on reaction with oxidized color developing agent.

Claim 9

A photographic element of claim 2 wherein COUP is a coupler moiety which yields a colorless product on reaction with oxidized color developing agent.

Claim 10

A photographic element of claim 2 wherein PUG is a development inhibitor.

Claim 11

A photographic element of claim 2 wherein PUG is a dye or dye precursor.

Claim 12

A photographic element of claim 2 wherein PUG is a coupler.

Claim 13

A photographic element of claim 2 wherein PUG is a developing agent.

Claim 14

A photographic element of claim 2 wherein PUG is a bleach inhibitor.

Claim 15

A photographic element comprising a support and at least one silver halide emulsion layer having associated therewith a photographic coupler represented by the formula: ##STR90## where: COUP is a coupler moiety; Nu is a nucleophilic group attached to the coupling position of COUP, selected from the group consisting of ##STR91## where R is hydrogen, alkyl of 1 to 20 carbon atoms aryl of 6 to 20 carbon atoms; Z represents the atoms necessary to complete a mono- or bicyclic aromatic or heterocyclic ring system containing 5 to 10 ring atoms; E is an electrophilic group selected from the group consisting of ##STR92## where each R is independently hydrogen, alkyl of 1 to 20 carbon atoms or aryl of 6 to 20 carbon atoms; n is an integer of 0 to 4 such that the ring formed upon reaction of the nucleophilic center of Nu with the electrophilic center of E contains 5 to 6 members; and PUG is a photograhic dye or reagent containing a hetero atom from Group VA or VIA of the periodic table having a negative valence of 2 or 3 through which it is attached to a position on E from which it will be displaced upon nucleophilic attack of Nu at the electrophilic center in E.

Claim 16

A photographic element comprising a support and at least one silver halide emulsion layer having associated therewith a photographic coupler represented by the formula: ##STR90## where: COUP is a coupler moiety; Nu is a nucleophilic group attached to the coupling position of COUP, selected from the group consisting of ##STR91## where R is hydrogen, alkyl of 1 to 20 carbon atoms aryl of 6 to 20 carbon atoms; Z represents the atoms necessary to complete a mono- or bicyclic aromatic or heterocyclic ring system containing 5 to 10 ring atoms; E is an electrophilic group selected from the group consisting of ##STR92## where each R is independently hydrogen, alkyl of 1 to 20 carbon atoms or aryl of 6 to 20 carbon atoms; n is an integer of 0 to 4 such that the ring formed upon reaction of the nucleophilic center of Nu with the electrophilic center of E contains 5 to 6 members; and PUG is a photograhic dye or reagent containing a hetero atom from Group VA or VIA of the periodic table having a negative valence of 2 or 3 through which it is attached to a position on E from which it will be displaced upon nucleophilic attack of Nu at the electrophilic center in E.

Claim 17

A photographic element of claim 13 wherein COUP is a coupler moiety which yields a colored product on reaction with oxidized color developing agent.

Claim 18

A photographic element of claim 13 wherein COUP is a coupler moiety which yields a colorless or neutral product on reaction with oxidized color developing agent.

Claim 19

A photographic element comprising a support and at least one silver halide emulsion layer having associated therewith a photographic coupler represented by the structure ##STR93## where: COUP is a coupler moiety; Z 2 is oxygen, or sulfur and is attached to the coupling position of COUP; n is 0 or 1; R 3 is hydrogen or alkyl of 1 to 4 carbon atoms or aryl of 6 to 10 carbon atoms; PUG is a photographic dye or reagent containing an oxygen or sulfur atom by which it is attached to the carbonyl group; and X 1 is hydrogen, halogen, cyano, nitro, alkyl of 1 to 20 carbon atoms, --OR 4 , --COOR 4 , --CONHR 4 , --NHCOR 4 , --NHSO 2 R 4 , --SO 2 NHR 4 or SO 2 R 4 where R 4 is hydrogen, alkyl of 1 to 20 carbon atoms or aryl of 6 to 20 carbon atoms.

Claim 20

A photographic element comprising a support and at least one silver halide emulsion layer having associated therewith a photographic coupler represented by the structure ##STR93## where: COUP is a coupler moiety; Z 2 is oxygen, or sulfur and is attached to the coupling position of COUP; n is 0 or 1; R 3 is hydrogen or alkyl of 1 to 4 carbon atoms or aryl of 6 to 10 carbon atoms; PUG is a photographic dye or reagent containing an oxygen or sulfur atom by which it is attached to the carbonyl group; and X 1 is hydrogen, halogen, cyano, nitro, alkyl of 1 to 20 carbon atoms, --OR 4 , --COOR 4 , --CONHR 4 , --NHCOR 4 , --NHSO 2 R 4 , --SO 2 NHR 4 or SO 2 R 4 where R 4 is hydrogen, alkyl of 1 to 20 carbon atoms or aryl of 6 to 20 carbon atoms.

Claim 21

A photographic element of claim 16 wherein COUP is a ballasted yellow-dye-forming coupler.

Claim 22

A photographic element of claim 16 wherein COUP is a ballasted cyan dye forming coupler.

Claim 23

A photographic element of claim 16 wherein COUP is a ballasted magenta dye forming coupler.

Claim 24

A photographic element of claim 16 wherein COUP forms a colorless reaction product on reaction with oxidized color developing agent.

Claim 25

A photographic element of claim 16 wherein PUG is a mercaptotetrazole or benzotriazole development inhibitor.

Claim 26

A photographic element comprising a support and at least one silver halide emulsion layer having associated therewith a photographic coupler represented by the structure: ##STR94## where: Z is oxygen or sulfur; X is hydrogen, nitro, alkoxycarbonyl, sulfonamido or carbonamido; n is 0 or 1; R 3 is alkyl of 1 to 4 carbon atoms and R is phenyl or alkyl of 1 to 4 carbon atoms.

Claim 27

A photographic element comprising a support and at least one silver halide emulsion layer having associated therewith a photographic coupler represented by the structure: ##STR94## where: Z is oxygen or sulfur; X is hydrogen, nitro, alkoxycarbonyl, sulfonamido or carbonamido; n is 0 or 1; R 3 is alkyl of 1 to 4 carbon atoms and R is phenyl or alkyl of 1 to 4 carbon atoms.

Claim 28

A photographic element comprising a support and at least one silver halide emulsion layer having associated therewith a photographic coupler represented by the structure: ##STR95## where: COUP is a coupler moiety; Z 1 is oxygen or sulfur and is attached to the coupling position of COUP; n is 2 or 3; R 3 is hydrogen, alkyl of 1 to 4 carbon atoms or aryl of 6 to 10 carbon atoms; and PUG is a photographic dye or reagent containing an oxygen or sulfur atom by which it is attached to the carbonyl group.

Claim 29

A photographic element comprising a support and at least one silver halide emulsion layer having associated therewith a photographic coupler represented by the structure: ##STR95## where: COUP is a coupler moiety; Z 1 is oxygen or sulfur and is attached to the coupling position of COUP; n is 2 or 3; R 3 is hydrogen, alkyl of 1 to 4 carbon atoms or aryl of 6 to 10 carbon atoms; and PUG is a photographic dye or reagent containing an oxygen or sulfur atom by which it is attached to the carbonyl group.

Claim 30

A photographic element of claim 23 wherein COUP is a ballasted yellow-dye-forming coupler.

Claim 31

A photographic element of claim 23 wherein COUP is a ballasted cyan dye forming coupler.

Claim 32

A photographic element of claim 23 wherein COUP is a ballasted magenta dye forming coupler.

Claim 33

A photographic element of claim 23 wherein COUP forms a colorless reaction product on reaction with oxidized color developing agent.

Claim 34

A photographic element of claim 23 wherein PUG is a mercaptotetrazole or benzotriazole development inhibitor.

Claim 35

A photographic element comprising a support having thereon a red-sensitive silver halide emulsion unit having associated therewith a cyan-dye-image-providing material, a green-sensitive silver halide emulsion unit having associated therewith a magenta-dye-image-providing material, and a blue-sensitive silver halide emulsion unit having associated therewith a yellow-dye-image-providing material, at least one of the silver halide emulsion units having associated therewith a photographic coupler containing a coupler moiety, a photographic dye or reagent, containing a hetero atom from Group VA or VIA of the periodic table having a negative valence of 2 or 3 and a timing group joining the coupler moiety and the photographic dye or reagent, the timing group comprising a nucleophilic group attached to the coupler moiety at a position from which it is capable of being displaced as a result of reaction of the coupler moiety with oxidized color developing agent, an electrophilic group attached to said hetero atom in the photographic dye or reagent and capable of being displaced therefrom by said nucleophilic group after said nucleophilic group is displaced from said coupler moiety, and a linking group spatially relating the nucleophilic group and the electrophilic group to undergo, after cleavage of the bond between the timing group and the coupler moiety, an intramolecular nucleophilic displacement reaction which cleaves the bond between the photographic dye or reagent and the timing group.

Claim 36

A photographic element comprising a support having thereon a red-sensitive silver halide emulsion unit having associated therewith a cyan-dye-image-providing material, a green-sensitive silver halide emulsion unit having associated therewith a magenta-dye-image-providing material, and a blue-sensitive silver halide emulsion unit having associated therewith a yellow-dye-image-providing material, at least one of the silver halide emulsion units having associated therewith a photographic coupler containing a coupler moiety, a photographic dye or reagent, containing a hetero atom from Group VA or VIA of the periodic table having a negative valence of 2 or 3 and a timing group joining the coupler moiety and the photographic dye or reagent, the timing group comprising a nucleophilic group attached to the coupler moiety at a position from which it is capable of being displaced as a result of reaction of the coupler moiety with oxidized color developing agent, an electrophilic group attached to said hetero atom in the photographic dye or reagent and capable of being displaced therefrom by said nucleophilic group after said nucleophilic group is displaced from said coupler moiety, and a linking group spatially relating the nucleophilic group and the electrophilic group to undergo, after cleavage of the bond between the timing group and the coupler moiety, an intramolecular nucleophilic displacement reaction which cleaves the bond between the photographic dye or reagent and the timing group.

Claim 37

A photographic element of claim 29 wherein the photographic coupler is represented by the structure ##STR96## where: COUP is a coupler moiety; PUG is a photographically useful group containing a hetero atom from Group VA or VIA of the periodic table having a negative valence of 2 or 3; Nu is a nucleophilic group containing an electron rich oxygen, sulfur or nitrogen atom, Nu being attached to a position on COUP from which it will be displaced upon reaction of COUP with oxidized color developing agent; E is an electrophilic group containing an electron deficient carbonyl, thiocarbonyl, phosphinyl or thiophosphinyl moiety, E being attached to said hetero atom in PUG and being displaceable therefrom by Nu after Nu is displaced from COUP; and X is a linking group for spatially relating Nu and E, upon displacement of Nu from COUP, to undergo an intramolecular nucleophilic displacement reaction with the formation of a three- to seven-membered ring and thereby release PUG.

Claim 38

A photographic element of claim 30, wherein PUG contains an oxygen, sulfur or heterocyclic nitrogen atom by which it is attached to E.

Claim 39

A photographic element of claim 30, wherein Nu contains an electron rich oxygen or sulfur atom; E contains an electron deficient carbonyl or thiocarbonyl group; and PUG contains an oxygen or sulfur atom by which it is attached to E.

Claim 40

A photographic element of claim 30, wherein X is alkylene or an arylene linking group.

Claim 41

A photographic element of claim 30, wherein said intramolecular nucleophilic displacement reaction involves the formation of a 5- or 6-membered ring.

Claim 42

A photographic element of claim 29 wherein the photographic coupler is represented by the structure ##STR97## where: COUP is a coupler moiety; Nu is a nucleophilic group attached to the coupling position of COUP, selected from the group consisting of ##STR98## where R is hydrogen, alkyl of 1 to 20 carbon atoms or aryl of 6 to 20 carbon atoms; Z represents the atoms necessary to complete a mono- or bicyclic aromatic or heterocyclic ring system containing 5 to 10 ring atoms; E is an electrophilic group selected from the group consisting of ##STR99## where each R is independently hydrogen, alkyl of 1 to 20 carbon atoms or aryl of 6 to 20 carbon atoms; n is an integer of 0 to 4 such that the ring formed upon reaction of the nucleophilic center of Nu with the electrophilic center of E contains 5 to 6 members; and PUG is a photographic dye or photographic reagent containing a hetero atom from Group VA or VIA of the periodic table having a negative valence of 2 or 3 through which it is attached to a position on E from which it will be displaced upon nucleophilic attack of Nu at the electrophilic center in E.

Claim 43

A photographic element of claim 35, wherein PUG contains an oxygen, sulfur or heterocyclic nitrogen atom by which it is attached to E.

Claim 44

A photographic element of claim 36 wherein PUG is a development inhibitor.

Claim 45

A photographic element of claim 36, wherein PUG is a dye or dye precursor.

Claim 46

A photographic element of claim 36, wherein PUG is a coupler.

Claim 47

A photographic element of claim 36, wherein PUG is a developing agent.

Claim 48

A photographic element of claim 36, wherein PUG is a bleach inhibitor.

Claim 49

A photographic element of claim 37, wherein PUG is a mercaptotetrazole or benzotriazole development inhibitor.

Claim 50

A photographic element of claim 37, wherein COUP is a coupler moiety which yields a colorless product on reaction with oxidized color developing agent.

Claim 51

A photographic element of claim 37, wherein COUP is a coupler moiety which yields a colored product on reaction with oxidized color developing agent.

Claim 52

A photographic element of claim 38, wherein PUG is a dye or dye precursor which on release from E in an alkaline photographic processing composition yields a dye of essentially the same color as the dye formed by reaction of COUP with oxidized color developing agent.

Claim 53

A photographic element of claim 29, wherein the photographic coupler is represented by the structure ##STR100## where: COUP is a coupler moiety; Z 2 is oxygen or sulfur and is attached to the coupling position of COUP; n is 0 or 1; R 3 is hydrogen, alkyl of 1 to 4 carbon atoms or aryl of 6 to 10 carbon atoms; PUG is a photographic dye or photographic reagent containing an oxygen or sulfur atom by which it is attached to the carbonyl group; and X 1 is hydrogen, halogen, cyano, nitro, alkyl of 1 to 20 carbon atoms, --OR 4 , --COOR 4 , --CONHR 4 , --NHCOR 4 , --NHSO 2 R 4 , --SO 2 NHR 4 or SO 2 R 4 where R 4 is hydrogen, alkyl of 1 to 20 carbon atoms or aryl of 6 to 20 carbon atoms.

Claim 54

A photographic element of claim 29 wherein the photographic coupler is represented by the structure ##STR101## where: COUP is a coupler moiety; Z 1 is oxygen or sulfur and is attached to the coupling position of COUP; n is 2 or 3; R 3 is hydrogen, alkyl of 1 to 4 carbon atoms or aryl of 6 to 10 carbon atoms; and PUG is a photographic dye or reagent containing an oxygen or sulfur atom by which it is attached to the carbonyl group.

Claim 55

A photographic element of claim 39 wherein the photographic coupler and the dye forming coupler yield dyes of essentially the same color on reaction with oxidized color developing agent.

Claim 56

A photographic element of claim 39 wherein the photographic coupler and the dye forming coupler yield dyes of different color on reaction with oxidized color developing agent.

Claim 57

A silver halide emulsion containing a photographic coupler having a coupler moiety, a photographic dye or reagent, containing a hetero atom from Group VA or VIA of the periodic table having a negative valence of 2 or 3 and a timing group joining the coupler moiety and the photographic dye or reagent, the timing group comprising a nucleophilic group attached to the coupler moiety at a position from which it is capable of being displaced as a result of reaction of the coupler moiety with oxidized color developing agent, an electrophilic group attached to said hetero atom in the photographic dye or reagent and capable of being displaced therefrom by said nucleophilic group after said nucleophilic group is displaced from said coupler moiety, and a linking group spatially relating the nucleophilic group and the electrophilic group to undergo, after cleavage of the bond between the timing group and the coupler moiety, an intramolecular nucleophilic displacement reaction which cleaves the bond between the photographic dye or reagent and the timing group.

Claim 58

A silver halide emulsion containing a photographic coupler having a coupler moiety, a photographic dye or reagent, containing a hetero atom from Group VA or VIA of the periodic table having a negative valence of 2 or 3 and a timing group joining the coupler moiety and the photographic dye or reagent, the timing group comprising a nucleophilic group attached to the coupler moiety at a position from which it is capable of being displaced as a result of reaction of the coupler moiety with oxidized color developing agent, an electrophilic group attached to said hetero atom in the photographic dye or reagent and capable of being displaced therefrom by said nucleophilic group after said nucleophilic group is displaced from said coupler moiety, and a linking group spatially relating the nucleophilic group and the electrophilic group to undergo, after cleavage of the bond between the timing group and the coupler moiety, an intramolecular nucleophilic displacement reaction which cleaves the bond between the photographic dye or reagent and the timing group.

Claim 59

A photograhic silver halide emulsion containing a photographic coupler represented by the structure: ##STR102## where: COUP is a coupler moiety; PUG is a photograhic dye or reagent containing a hetero atom from Group VA or VIA of the periodic table having a negative valence of 2 or 3; Nu is a nucleophilic group containing an electron rich oxygen, sulfur or nitrogen atom, Nu being attached to a position on COUP from which it will be displaced upon reaction of COUP with oxidized color developing agent; E is an electrophilic group containing an electron deficient carbonyl, thiocarbonyl, phosphinyl or thiophosphinyl moiety, E being attached to said hetero atom in PUG and being displacable therefrom by Nu after Nu is displaced from COUP; and X is a linking group for spatially relating Nu and E, upon displacement of Nu from COUP, to undergo an intramolecular nucleophilic displacement reaction with the formation of a three- to seven-membered ring and thereby release PUG.

Claim 60

A photograhic silver halide emulsion containing a photographic coupler represented by the structure: ##STR102## where: COUP is a coupler moiety; PUG is a photograhic dye or reagent containing a hetero atom from Group VA or VIA of the periodic table having a negative valence of 2 or 3; Nu is a nucleophilic group containing an electron rich oxygen, sulfur or nitrogen atom, Nu being attached to a position on COUP from which it will be displaced upon reaction of COUP with oxidized color developing agent; E is an electrophilic group containing an electron deficient carbonyl, thiocarbonyl, phosphinyl or thiophosphinyl moiety, E being attached to said hetero atom in PUG and being displacable therefrom by Nu after Nu is displaced from COUP; and X is a linking group for spatially relating Nu and E, upon displacement of Nu from COUP, to undergo an intramolecular nucleophilic displacement reaction with the formation of a three- to seven-membered ring and thereby release PUG.

Claim 61

A photographic silver halide emulsion containing a photographic coupler represented by the formula: ##STR103## where: COUP is a coupler moiety; Nu is a nucleophilic group attached to the coupling position of COUP, selected from the group consisting of ##STR104## where R is hydrogen, alkyl of 1 to 20 carbon atoms or aryl of 6 to 20 carbon atoms; Z represents the atoms necessary to complete a mono- or bicyclic aromatic or heterocyclic ring system containing 5 to 10 ring atoms; E is an electrophilic group selected from the group consisting of ##STR105## where each R is independently hydrogen, alkyl of 1 to 20 carbon atoms or aryl of 6 to 20 carbon atoms; n is an integer of 0 to 4 such that the ring formed upon reaction of the nucleophilic center of Nu with the electrophilic center of E contains 5 to 6 members; and PUG is a photograhic dye or reagent containing a hetero atom from Group VA or VIA of the periodic table having a negative valence of 2 or 3 through which it is attached to a position on E from which it will be displaced upon nucleophilic attack of Nu at the electrophilic center in E.

Claim 62

A photographic silver halide emulsion containing a photographic coupler represented by the formula: ##STR103## where: COUP is a coupler moiety; Nu is a nucleophilic group attached to the coupling position of COUP, selected from the group consisting of ##STR104## where R is hydrogen, alkyl of 1 to 20 carbon atoms or aryl of 6 to 20 carbon atoms; Z represents the atoms necessary to complete a mono- or bicyclic aromatic or heterocyclic ring system containing 5 to 10 ring atoms; E is an electrophilic group selected from the group consisting of ##STR105## where each R is independently hydrogen, alkyl of 1 to 20 carbon atoms or aryl of 6 to 20 carbon atoms; n is an integer of 0 to 4 such that the ring formed upon reaction of the nucleophilic center of Nu with the electrophilic center of E contains 5 to 6 members; and PUG is a photograhic dye or reagent containing a hetero atom from Group VA or VIA of the periodic table having a negative valence of 2 or 3 through which it is attached to a position on E from which it will be displaced upon nucleophilic attack of Nu at the electrophilic center in E.

Claim 63

A photographic silver halide emulsion containing a photographic coupler represented by the structure: ##STR106## where: COUP is a coupler moiety; Z 2 is oxygen, or sulfur and is attached to the coupling position of COUP; n is 0 or 1; R 3 is hydrogen, alkyl of 1 to 4 carbon atoms or aryl of 6 to 10 carbon atoms; PUG is a photographic dye or reagent containing an oxygen or sulfur atom by which it is attached to the carbonyl group; and X 1 is hydrogen, halogen, cyano, nitro, alkyl of 1 to 20 carbon atoms, --OR 4 , --COOR 4 , --CONHR 4 , --NHCOR 4 , --NHSO 2 R 4 , --SO 2 NHR 4 or SO 2 R 4 where R 4 is hydrogen, alkyl of 1 to 20 carbon atoms or aryl of 6 to 20 carbon atoms.

Claim 64

A photographic silver halide emulsion containing a photographic coupler represented by the structure: ##STR106## where: COUP is a coupler moiety; Z 2 is oxygen, or sulfur and is attached to the coupling position of COUP; n is 0 or 1; R 3 is hydrogen, alkyl of 1 to 4 carbon atoms or aryl of 6 to 10 carbon atoms; PUG is a photographic dye or reagent containing an oxygen or sulfur atom by which it is attached to the carbonyl group; and X 1 is hydrogen, halogen, cyano, nitro, alkyl of 1 to 20 carbon atoms, --OR 4 , --COOR 4 , --CONHR 4 , --NHCOR 4 , --NHSO 2 R 4 , --SO 2 NHR 4 or SO 2 R 4 where R 4 is hydrogen, alkyl of 1 to 20 carbon atoms or aryl of 6 to 20 carbon atoms.

Claim 65

A photographic silver halide emulsion containing a photographic coupler represented by the structure: ##STR107## where: COUP is a coupler moiety; Z 1 is oxygen or sulfur and is attached to the coupling position of COUP; n is 2 or 3; R 3 is hydrogen, alkyl of 1 to 4 carbon atoms or aryl of 6 to 10 carbon atoms; and PUG is a photographic dye or reagent containing an oxygen or sulfur atom by which it is attached to the carbonyl group.

Claim 66

A photographic silver halide emulsion containing a photographic coupler represented by the structure: ##STR107## where: COUP is a coupler moiety; Z 1 is oxygen or sulfur and is attached to the coupling position of COUP; n is 2 or 3; R 3 is hydrogen, alkyl of 1 to 4 carbon atoms or aryl of 6 to 10 carbon atoms; and PUG is a photographic dye or reagent containing an oxygen or sulfur atom by which it is attached to the carbonyl group.

Claim 67

A process of forming a photographic image which comprises developing an exposed silver halide emulsion layer with a color developing agent in the presence of a photographic coupler wherein the photographic coupler contains a coupler moiety, a photographic dye or reagent, containing a hetero atom from Group VA or VIA of the periodic table having a negative valence of 2 or 3 and a timing group joining the coupler moiety and the photographic dye or reagent, the timing group comprising a nucleophilic group attached to the coupler moiety at a position from which it is capable of being displaced as a result of reaction of the coupler moiety with oxidized color developing agent, an electrophilic group attached to said hetero atom in the photographic dye or reagent and capable of being displaced therefrom by said nucleophilic group after said nucleophilic group is displaced from said coupler moiety, and a linking group spatially relating the nucleophilic group and the electrophilic group to undergo, after cleavage of the bond between the timing group and the coupler moiety, an intramolecular nucleophilic displacement reaction which cleaves the bond between the photographic dye or reagent and the timing group.

Claim 68

A process of forming a photographic image which comprises developing an exposed silver halide emulsion layer with a color developing agent in the presence of a photographic coupler wherein the photographic coupler contains a coupler moiety, a photographic dye or reagent, containing a hetero atom from Group VA or VIA of the periodic table having a negative valence of 2 or 3 and a timing group joining the coupler moiety and the photographic dye or reagent, the timing group comprising a nucleophilic group attached to the coupler moiety at a position from which it is capable of being displaced as a result of reaction of the coupler moiety with oxidized color developing agent, an electrophilic group attached to said hetero atom in the photographic dye or reagent and capable of being displaced therefrom by said nucleophilic group after said nucleophilic group is displaced from said coupler moiety, and a linking group spatially relating the nucleophilic group and the electrophilic group to undergo, after cleavage of the bond between the timing group and the coupler moiety, an intramolecular nucleophilic displacement reaction which cleaves the bond between the photographic dye or reagent and the timing group.

Claim 69

A process of claim 55 wherein the photographic coupler is represented by the structure: ##STR108## where: COUP is a coupler moiety; PUG is a photographic dye or reagent containing a hetero atom from Group VA or VIA of the periodic table having a negative valence of 2 or 3; Nu is a nucleophilic group containing an electron rich oxygen, sulfur or nitrogen atom, Nu being attached to a position on COUP from which it will be displaced upon reaction of COUP with oxidized color developing agent; E is an electrophilic group containing an electron deficient carbonyl, thiocarbonyl, phosphinyl or thiophosphinyl moiety, E being attached to said hetero atom in PUG and being displaceable therefrom by Nu after Nu is displaced from COUP; and X is a linking group for spatially relating Nu and E, upon displacement of Nu from COUP, to undergo an intramolecular nucleophilic displacement reaction with the formation of a three- to seven-membered ring and thereby release PUG.

Claim 70

A process of claim 55 wherein the photographic coupler is represented by the formula ##STR109## where: COUP is a coupler moiety; Nu is a nucleophilic group attached to the coupling position of COUP, selected from the group consisting of ##STR110## where R is hydrogen, alkyl of 1 to 20 carbon atoms or aryl of 6 to 20 carbon atoms; Z represents the atoms necessary to complete a mono- or bicyclic aromatic or heterocyclic ring system containing 5 to 10 ring atoms; E is an electrophilic group selected from the group consisting of ##STR111## where each R is independently hydrogen or alkyl of 1 to 20 carbon atoms or aryl of 6 to 20 carbon atoms; n is an integer of 0 to 4 such that the ring formed upon reaction of the nucleophilic center of Nu with the electrophilic center of E contains 5 to 6 members; and PUG is a photographic dye or reagent containing a hetero atom from Group VA or VIA of the periodic table having a negative valence of 2 or 3 through which it is attached to a position on E from which it will be displaced upon nucleophilic attack of Nu at the electrophilic center in E.

Claim 71

A process of claim 57 wherein the photographic coupler is contained in the photographic element.

Claim 72

A process of claim 57 wherein the photographic coupler is contained in a processing solution with the color developing agent.

Claim 73

A photographic element comprising a support, at least one silver halide emulsion layer and a photographic coupler containing a coupler moiety, a photographic dye or reagent, containing a hetero atom from Group VA or VIA of the periodic table having a negative valence of 2 or 3 and a timing group joining the coupler moiety and the photographic dye or reagent, the timing group comprising a nucleophilic group attached to the coupler moiety at a position from which it is capable of being displaced as a result of reaction of the coupler moiety with oxidized color developing agent, an electrophilic group attached to said hetero atom in the photographic dye or reagent and capable of being displaced therefrom by said nucleophilic group after said nucleophilic group is displaced from said coupler moiety, and a linking group spatially relating the nucleophilic group and the electrophilic group to undergo, after cleavage of the bond between the timing group and the coupler moiety, an intramolecular nucleophilic displacement reaction, with the formation of a five- or six-membered ring, which cleaves the bond between the photographic dye or reagent and the timing group.

Claim 74

A photographic element comprising a support, at least one silver halide emulsion layer and a photographic coupler containing a coupler moiety, a photographic dye or reagent, containing a hetero atom from Group VA or VIA of the periodic table having a negative valence of 2 or 3 and a timing group joining the coupler moiety and the photographic dye or reagent, the timing group comprising a nucleophilic group attached to the coupler moiety at a position from which it is capable of being displaced as a result of reaction of the coupler moiety with oxidized color developing agent, an electrophilic group attached to said hetero atom in the photographic dye or reagent and capable of being displaced therefrom by said nucleophilic group after said nucleophilic group is displaced from said coupler moiety, and a linking group spatially relating the nucleophilic group and the electrophilic group to undergo, after cleavage of the bond between the timing group and the coupler moiety, an intramolecular nucleophilic displacement reaction, with the formation of a five- or six-membered ring, which cleaves the bond between the photographic dye or reagent and the timing group.

Claim 75

A photographic element comprising a support, at least one silver halide emulsion layer and a photographic coupler represented by the structure: ##STR112## where: COUP is a coupler moiety; PUG is a photographic dye or reagent containing a hetero atom from Group VA or VIA of the periodic table having a negative valence of 2 or 3; Nu is a nucleophilic group containing an electron rich oxygen, sulfur or nitrogen atom, Nu being attached to a position on COUP from which it will be displaced upon reaction of COUP with oxidized color developing agent; E is an electrophilic group containing an electron deficient carbonyl, thiocarbonyl, phosphinyl or thiophosphinyl moiety, E being attached to said hetero atom in PUG and being displaceable therefrom by Nu after Nu is displaced from COUP; and X is a linking group for spatially relating Nu and E, upon displacement of Nu from COUP, to undergo an intramolecular nucleophilic displacement reaction with the formation of a five- or six-membered ring and thereby release PUG.

Claim 76

A photographic element comprising a support, at least one silver halide emulsion layer and a photographic coupler represented by the structure: ##STR112## where: COUP is a coupler moiety; PUG is a photographic dye or reagent containing a hetero atom from Group VA or VIA of the periodic table having a negative valence of 2 or 3; Nu is a nucleophilic group containing an electron rich oxygen, sulfur or nitrogen atom, Nu being attached to a position on COUP from which it will be displaced upon reaction of COUP with oxidized color developing agent; E is an electrophilic group containing an electron deficient carbonyl, thiocarbonyl, phosphinyl or thiophosphinyl moiety, E being attached to said hetero atom in PUG and being displaceable therefrom by Nu after Nu is displaced from COUP; and X is a linking group for spatially relating Nu and E, upon displacement of Nu from COUP, to undergo an intramolecular nucleophilic displacement reaction with the formation of a five- or six-membered ring and thereby release PUG.

Claim 77

A photographic element comprising a support and at least one silver halide emulsion layer having associated therewith a photographic coupler represented by one of the structures: ##STR113## where: COUP is a coupler moiety; Z 2 is ##STR114## and is attached to the coupling position of COUP; n is 0 or 1; R 3 is hydrogen or alkyl of 1 to 20 carbon atoms or aryl of 6 to 20 carbon atoms; PUG is a photographic dye or reagent containing an oxygen or sulfur atom by which it is attached to the carbonyl group; and X 1 is hydrogen, halogen, cyano, nitro, alkyl of 1 to 20 carbon atoms, --OR 4 , --COOR 4 , --CONHR 4 , --NHCOR 4 , --NHSO 2 R 4 , --SO 2 NHR 4 or SO 2 R 4 where R 4 is hydrogen, alkyl of 1 to 20 carbon atoms or aryl of 6 to 20 carbon atoms.

Claim 78

A photographic element comprising a support and at least one silver halide emulsion layer having associated therewith a photographic coupler represented by one of the structures: ##STR113## where: COUP is a coupler moiety; Z 2 is ##STR114## and is attached to the coupling position of COUP; n is 0 or 1; R 3 is hydrogen or alkyl of 1 to 20 carbon atoms or aryl of 6 to 20 carbon atoms; PUG is a photographic dye or reagent containing an oxygen or sulfur atom by which it is attached to the carbonyl group; and X 1 is hydrogen, halogen, cyano, nitro, alkyl of 1 to 20 carbon atoms, --OR 4 , --COOR 4 , --CONHR 4 , --NHCOR 4 , --NHSO 2 R 4 , --SO 2 NHR 4 or SO 2 R 4 where R 4 is hydrogen, alkyl of 1 to 20 carbon atoms or aryl of 6 to 20 carbon atoms.

Claim 79

A photographic element comprising a support and at least one silver halide emulsion layer having associated therewith a photographic coupler represented by one of the structures: ##STR115## where: COUP is a coupler moiety; Y is ##STR116## or --NHSO 2 CH 2 SO 2 NH--; Z 2 is ##STR117## and is attached to the coupling position of COUP; n is 0 or 1; R 3 is hydrogen or alkyl of 1 to 20 carbon atoms or aryl of 6 to 20 carbon atoms; PUG is a photographic dye or reagent containing an oxygen or sulfur atom by which it is attached to the carbonyl group; and X 1 is hydrogen, halogen, cyano, nitro, alkyl of 1 to 20 carbon atoms, --OR 4 , --COOR 4 , --CONHR 4 , --NHCOR 4 , --NHSO 2 R 4 , --SO 2 NHR 4 or SO 2 R 4 where R 4 is hydrogen, alkyl of 1 to 20 carbon atoms or aryl of 6 to 20 carbon atoms.

Claim 80

A photographic element comprising a support and at least one silver halide emulsion layer having associated therewith a photographic coupler represented by one of the structures: ##STR115## where: COUP is a coupler moiety; Y is ##STR116## or --NHSO 2 CH 2 SO 2 NH--; Z 2 is ##STR117## and is attached to the coupling position of COUP; n is 0 or 1; R 3 is hydrogen or alkyl of 1 to 20 carbon atoms or aryl of 6 to 20 carbon atoms; PUG is a photographic dye or reagent containing an oxygen or sulfur atom by which it is attached to the carbonyl group; and X 1 is hydrogen, halogen, cyano, nitro, alkyl of 1 to 20 carbon atoms, --OR 4 , --COOR 4 , --CONHR 4 , --NHCOR 4 , --NHSO 2 R 4 , --SO 2 NHR 4 or SO 2 R 4 where R 4 is hydrogen, alkyl of 1 to 20 carbon atoms or aryl of 6 to 20 carbon atoms.