Pyrrolinone dyes

Claim 2

A photographic element containing a radiation-sensitive silver halide emulsion layer and a 3-pyrrolin-2-one dye, which dye has a 3 -position electron withdrawing group, and a moiety in conjugation with the 2-position oxygen which moiety is linked to the pyrrolinone ring 5-position through a substituted or unsubstituted methine bridge, and in which dye the pyrrolinone ring nitrogen has a substituent other than hydrogen.

Claim 3

A photographic element containing a radiation-sensitive silver halide emulsion layer and a dye of the formula: ##STR80## wherein; E 1 represents an electron withdrawing group; R 1 represents an aryl group of 6 to 14 carbon atoms or an alkyl group of 1 to 12 carbon atoms; R 2 represents an alkyl group of 1 to 20 carbon atoms, or an alkenyl group of 2 to 20 carbon atoms, or an aryl, aralkyl, heterocyclic or cycloalkyl group of 5 to 14 carbon atoms, or a hydroxy, cyano, chloro, nitro or hydrogen; each L represents a methine group; m is 0, 1, 2, or 3; and D is a moiety in conjugation with the oxygen of the pyrrolinone ring.

Claim 4

A photographic element containing a radiation-sensitive silver halide emulsion layer and a dye of the formula: ##STR80## wherein; E 1 represents an electron withdrawing group; R 1 represents an aryl group of 6 to 14 carbon atoms or an alkyl group of 1 to 12 carbon atoms; R 2 represents an alkyl group of 1 to 20 carbon atoms, or an alkenyl group of 2 to 20 carbon atoms, or an aryl, aralkyl, heterocyclic or cycloalkyl group of 5 to 14 carbon atoms, or a hydroxy, cyano, chloro, nitro or hydrogen; each L represents a methine group; m is 0, 1, 2, or 3; and D is a moiety in conjugation with the oxygen of the pyrrolinone ring.

Claim 5

A photographic element according to claim 2, wherein D contains an atom with an available electron pair positioned in conjugation with the oxygen of the pyrrolinone ring which atom si an O, N, Se or S, or is a C with at least one electron withdrawing group bonded thereto, or D is a group containing a benzene ring.

Claim 6

A photographic element according to claim 2 wherein D contains an O or N atom or --C(CN)2 position in conjugation with the oxygen of the pyrrolinone ring.

Claim 7

A photographic element according to claim 2 wherein D is any one of the following: ##STR81## and wherein: E 2 represents an electron withdrawing group; R 3 represents an aryl group of 6 to 14 carbon atoms or an alkyl group of from 1 to 12 carbon atoms; R 4 represents an alkyl or alkylthio group of 1 to 20 carbon atoms, or an alkenyl group of 2 to 20 carbon atoms, or an aryl, aralkyl, heterocyclic or cycloalkyl group of 5 to 14 carbon atoms or a hydroxy, cyano, chloro, nitro or hydrogen; R 5 represents an alkyl group o f1 to 20 carbon atoms or an alkenyl group of 2 to 20 carbon atoms, or an aryl, aralkyl or cycloalkyl group of 5 to 14 carbon atoms, and R 6 represents cyano, or an aryl, aminocarbonyl, or alkoxycarbonyl group of 2 to 20 carbon atoms, or an alkylsulfonyl, arylsulfonyl, or sulfamoyl group of 1 to 20 carbon atoms, or R 5 and R 6 may together represent the non-metallic atoms necessary to complete a substituted or unsubstituted ring containing at least one 5- or 6-membered heterocyclic or unsaturated alicyclic nucleus; R 7 , R 10 , R 11 , R 12 and R 13 each individually represents hydrogen, carboxy, carboxyalkyl, sulfonamido, sulfamoyl, or an alkyl, aralkyl, cycloalkyl, alkoxy, alkylamino, or alkylthio group of 1 to 10 carbon atoms; R 8 , R 9 , R 15 , and R 16 each individually represents an alkyl group of 1 to 20 carbon atoms or an alkenyl group of 2 to 8 carbon atoms, or an aryl, aralkyl or cycloalkyl group of 5 to 14 carbon atoms, or R 8 and R 9 , or R 15 and R 16 together represent the non-metallic atoms required to form a substituted or unsubstituted 5- or 6-membered ring with each other, or R 8 and R 9 individually represent the non-metallic atoms necessary to form a substituted or unsubstituted 5- or 6-membered fused ring with the phenyl ring to which the nitrogen is attached; R 14 represents an alkyl group of 1 to 20 carbon atoms, or an aralkyl or cycloalkyl group of 5 to 10 carbon atoms; G represents --O or --C(CN) 2; Y and Z each individually represents the non-metallic atoms necessary to complete a group containing at least one 5- or 6-membered heterocyclic ring; M + is a cation; L 1 through L 6 each individually represents a methine group; m is 0, 1, 2, or 3; n is 0 or 1; p is 0, 1, 2, 3, or 4; q is 0, 1, 2, or 3; r is 0, 1, 2, 3, 4, or 5; and s is 0, 1, or 2.

Claim 8

A photographic element according to claim 4 wherein (D4) is of the structure: ##STR82##

Claim 9

A photographic element according to claim 2 wherein the dye has at least one carboxy, sulfonamido, sulfamoyl, sulfato, or sulfo substituent.

Claim 10

A photographic element according to claim 2 wherein R 1 or D has at least one carboxy, sulfonamido, sulfamoyl, sulfato, or sulfo substituent.

Claim 11

A photographic element according to claim 2 wherein D2 is an active methylene moiety derived from the group consisting of benzoylacetonitrile, 2-pyrazolin-5-one, pyrazolidindione, barbituric acid, rhodanine, indandione, isoxazolinone, benzofuranone, chromandione, cyclohexanedione, dioxanedione, furanone, pyrazolopyridine, pyridone, isoxazolidinedione, pyrandione, and tricyanopropene.

Claim 12

A photographic element according to claim 4 wherein Y represents the atoms necessary to complete a pyrazole, indole, furan, or thiophene nucleus.

Claim 13

A photographic element according to claim 4 wherein Z represents the atoms necessary to complete a benzoxazole or a benzothiazole nucleus.

Claim 14

A photographic element according to claim 4 wherein E 1 or E 2 is cyano, acyl, phenacyl, aminocarbonyl, or alkoxycarbonyl.

Claim 15

A photographic element according to claim 2 wherein E 1 is cyano.

Claim 16

A photographic element according to claim 4 wherein E 1 and E 2 are cyano.

Claim 17

A photographic element according to claim 4 wherein L 1 through L 6 are CH.

Claim 18

A photographic element according to claim 2 wherein said dye is a filter dye which is in a hydrophilic layer different from said radiation-sensitive layer, said hydrophilic layer being located on the same side of the support as said radiation sensitive layer.

Claim 19

A photographic element according to claim 2 wherein said dye is a filter dye which is in a hydrophilic layer different from said radiation-sensitive layer, said hydrophilic layer being located on the side of the support opposite to said radiation-sensitive layer.

Claim 20

A photographic element according to claim 16 wherein said filter dye is in the form of a dispersion of solid particles.

Claim 21

A photographic element according to claim 18 wherein said particles have a mean diameter from 0.01 to 100 micrometers.

Claim 22

A photographic element according to claim 17 wherein said filter dye is in the form of a dispersion of solid particles.

Claim 23

A photographic element according to claim 20 wherein said particles have a mean diameter from 0.01 to 100 micrometers.

Claim 24

A photographic element according to claim 16 wherein said filter dye is dissolved in said hydrophilic layer.

Claim 25

A photographic element according to claim 17 wherein said filter dye is dissolved in said hydrophilic layer.

Claim 26

A photographic element containing a radiation-sensitive silver halide emulsion layer and a dye of the formula: ##STR83## in which D is selected from any of the following: ##STR84## wherein: E 1 and E 2 are independently cyano, acyl, phenacyl, aminocarbonyl or alkoxycarbonyl groups; R 1 and R 3 are independently aryl groups; R 2 and R 4 independently represent an alkyl or cycloalkyl group of 1 to 8 carbon atoms or a phenyl group; M + is a cation; each L represents a methine group; m is 0, 1, 2, or 3; D2 is an active methylene moiety derived from the group consisting of benzoylacetonitrile, 2-pyrazolin-5-one, pyrazolidindione, barbituric acid, rhodanine, indandione, isoxazolinone, benzofuranone, chromandione, cyclohexanedione, dioxanedione, furanone, pyrazolopyridine, pyridone, isoxazolidinedione, pyrandione, and tricyanopropene; R 7 , R 10 , R 11 , R 12 and R 13 each individually represents hydrogen, carboxy, carboxyalkyl, sulfonamido, sulfamoyl, or an alkyl, aralkyl, cycloalkyl, alkoxy, alkylamino, or alkylthio group of 1 to 10 carbon atoms; R 8 , R 9 , R 15 , and R 16 each individually represents an alkyl group of 1 to 20 carbon atoms or an alkenyl group of 2 to 8 carbon atoms, or an aryl, aralkyl or cycloalkyl group of 5 to 14 carbon atoms, or R 8 and R 9 , or R 15 and R 16 together represent the non-metallic atoms required to form a substituted or unsubstituted 5- or 6-membered ring with each other, or R 8 and R 9 individually represent the non-metallic atoms necessary to form a substituted or unsubstituted 5- or 6-membered fused ring with the phenyl ring to which the nitrogen is attached; R 14 represents an alkyl group of 1 to 8 carbon atoms, or an aralkyl or cycloalkyl group of 5 to 10 carbon atoms; Y represents the atoms necessary to complete a pyrazole, indole, furan, or thiophene nucleus; Z represents the atoms necessary to complete a benzoxazole or a benzothiazole nucleus.

Claim 27

A photographic element containing a radiation-sensitive silver halide emulsion layer and a dye of the formula: ##STR83## in which D is selected from any of the following: ##STR84## wherein: E 1 and E 2 are independently cyano, acyl, phenacyl, aminocarbonyl or alkoxycarbonyl groups; R 1 and R 3 are independently aryl groups; R 2 and R 4 independently represent an alkyl or cycloalkyl group of 1 to 8 carbon atoms or a phenyl group; M + is a cation; each L represents a methine group; m is 0, 1, 2, or 3; D2 is an active methylene moiety derived from the group consisting of benzoylacetonitrile, 2-pyrazolin-5-one, pyrazolidindione, barbituric acid, rhodanine, indandione, isoxazolinone, benzofuranone, chromandione, cyclohexanedione, dioxanedione, furanone, pyrazolopyridine, pyridone, isoxazolidinedione, pyrandione, and tricyanopropene; R 7 , R 10 , R 11 , R 12 and R 13 each individually represents hydrogen, carboxy, carboxyalkyl, sulfonamido, sulfamoyl, or an alkyl, aralkyl, cycloalkyl, alkoxy, alkylamino, or alkylthio group of 1 to 10 carbon atoms; R 8 , R 9 , R 15 , and R 16 each individually represents an alkyl group of 1 to 20 carbon atoms or an alkenyl group of 2 to 8 carbon atoms, or an aryl, aralkyl or cycloalkyl group of 5 to 14 carbon atoms, or R 8 and R 9 , or R 15 and R 16 together represent the non-metallic atoms required to form a substituted or unsubstituted 5- or 6-membered ring with each other, or R 8 and R 9 individually represent the non-metallic atoms necessary to form a substituted or unsubstituted 5- or 6-membered fused ring with the phenyl ring to which the nitrogen is attached; R 14 represents an alkyl group of 1 to 8 carbon atoms, or an aralkyl or cycloalkyl group of 5 to 10 carbon atoms; Y represents the atoms necessary to complete a pyrazole, indole, furan, or thiophene nucleus; Z represents the atoms necessary to complete a benzoxazole or a benzothiazole nucleus.

Claim 28

A photographic element according to claim 24 which has at least one carboxy, sulfonamido, sulfamoyl, sulfato, or sulfo substituent.

Claim 29

A photographic element according to claim 24 wherein R 1 or D has at least one carboxy, sulfonamido, sulfamoyl, sulfato, or sulfo substituent.