Photographic material containing sulphonic acid group containing disazo dyestuffs

Claim 2

Photographic material, characterized in that it contains, on a carrier, a layer with a symmetrical azo dyestuff of the formula ##STR511## wherein A 1 denotes hydrogen, methyl, hydroxyethyl, phenyl, lower alkyl phenyl, trifluoromethyl phenyl lower alkoxy phenyl, fluoro-, chloro- or bromophenyl, sulphophenyl, carboxyphenyl, lower alkyl sulphophenyl or lower alkyl carbonylphenyl, -- M 4 denotes carbonyl, isophthaloyl, nitroisophthaloyl, benzoylamino-isophthaloyl, terephthaloyl, nitroterephthaloyl, chloroterephthaloyl, naphthalenedicarbonyl, --OC-phenylene-methylene-phenylene-C0--, --OC-phenylene-carbonyl-phenylene-CO-- , --OC-phenylene-sulphonyl-phenylene-CO--, --OC-phenylene-azo-phenylene-CO--, --OC-phenylene-ureylene-phenylene-CO--, --OC-phenylene-ethylenedioxy-phenylene-CO-- --CO-phenylene-pentylenedioxy-phenylene-CO--, --OC-phenylene-CO-HN-phenylene-CO- or --OC-phenylene-CO-HN-(CH 2 ) p -HN-OC-phenylene-CO--, p being 2, 3 or 4, and D 1 denotes fluorine, chlorine or bromine, methyl, ethyl, methoxy, ethoxy, methylmercapto, ethylmercapto, hydroxyethylmercapto, trifluoromethyl, acetylamino or benzoylamino.

Claim 3

Photographic material according to claim 1 wherein the dyestuff, according to the formula of claim 1 is one wherein A 1 denotes hydrogen, methyl, 2,6-dimethylphenyl, 2,6-dimethoxyphenyl, 2-methyl-4-chlorophenyl, 3-acetylphenyl, 3-chlorophenyl, 4-chlorophenyl, 4-fluorophenyl or 4-bromophenyl.

Claim 4

Photographic material according to claim 1 wherein the azo dyestuff according to the formula of claim 1 is one wherein M 4 denotes isophthaloyl, 5-nitro-isophthaloyl, 5-benzoylamino-isophthaloyl, terephthaloyl, naphthalene-2,6-dicarbonyl, diphenylmethane-4,4' - or 3,4'-dicarbonyl, diphenylsulphone-4,4'- or -3,4'-dicarbonyl, benzophenone-4,4'- or 3,4'-dicarbonyl azobenzene-3,3'-dicarbonyl, N,n' -diphenylurea-4,4'-dicarbonyl, N-benzoylaniline-3,4'-dicarbonyl, N-benzoyl-2-chloroaniline-5,4'-dicarbonyl, N,n' -dibenzoylethylenediamine-4,4'-dicarbonyl, N,n' -dibenzoylbutylenediamine-4,4'-dicarbonyl,

Claim 5

2-diphenoxyethane-3',3"- or -4',4"-dicarbonyl or 1,5-diphenoxypentane-4',4"-dicarbonyl.

Claim 6

2-diphenoxyethane-3',3"- or -4',4"-dicarbonyl or 1,5-diphenoxypentane-4',4"-dicarbonyl.

Claim 7

Photographic material according to claim 1 wherein the azo dyestuff according to the formula of claim 1 is one wherein A 1 denotes hydrogen, methyl, 2,6-dimethylphenyl, 2,6-dimethoxyphenyl, 2-methyl-4-chlorophenyl, 3-acetylphenyl, 3-chlorophenyl, 4-chlorophenyl, 4-fluorophenyl or 4-bromophenyl and M 4 denotes isophthaloyl, 5-nitro-isophthaloyl, 5-benzoylamino-isophthaloyl, terephthaloyl, naphthalene-2,6-dicarbonyl, diphenylmethane-4,4'- or 3,4'-dicarbonyl, diphenylsulphone-4,4' - or -3,4'-dicarbonyl, benzophenone-4,4'- or 3,4'-dicarbonyl, azobenzene-3,3'-dicarbonyl, N,n' -diphenylurea-4,4'-dicarbonyl, N-benzoylaniline-3,4'-dicarbonyl, N-benzoyl-2-chloroaniline-5,4'-dicarbonyl, N,n' -dibenzoylethylenediamine-4,4'-dicarbonyl, N,n' -dibenzoylbutylenediamine-4,4'-dicarbonyl, 1,2-diphenoxyethane-3',3"- or -4',4"-dicarbonyl or 1,5-diphenoxypentane-4',4"-dicarbonyl.

Claim 8

Photographic material according to claim 1, wherein the azo dyestuff is one of the formula ##STR512## wherein D 4 denotes methyl or methoxy and M 6 denotes terephthaloyl, pyridine-2,5- or -2,4-dicarbonyl, benzophenone-4,4'-dicarbonyl, diphenylsulphone-4,4'-dicarbonyl, naphthalene-2,6-dicarbonyl, N-benzoylaniline-3,4'-dicarbonyl, N-benzoyl-2-chloroaniline-5,4'-dicarbonyl, 1,2-diphenoxyethane-3',3"- or -4',4"-dicarbonyl or N,N'-dibenzoylethylenediamine-4,4'-dicarbonyl.

Claim 9

Photographic material according to claim 1, wherein the azo dyestuff is one of the formula ##STR513##

Claim 10

Photographic material according to claim 1, wherein the azo dyestuff is one of the formula ##STR514##

Claim 11

Photographic material according to claim 1, wherein the azo dyestuff is one of the formula ##STR515##

Claim 12

Photographic material according to claim 1, wherein the azo dyestuff is one of the formula ##STR516## wherein D 5 denotes chlorine or methyl, methoxy or trifluoromethyl group and M 7 denotes the isophthaloyl, terephthaloyl, pyridine-2,5- or -2,6-dicarbonyl, benzophenone-4,4'-dicarbonyl, naphthalene-2,6-dicarbonyl, diphenylsulphone-4,4'-dicarbonyl, N-benzoylaniline-3,4'-dicarbonyl, N-benzoyl-2-chloroaniline-5,4'-dicarbonyl or 1,2-diphenoxyethane-3',3"- or -4',4"-dicarbonyl or N,N'-dibenzoylethylenediamine-4,4'-dicarbonyl.

Claim 13

Photographic material according to claim 1, wherein the azo dyestuff is one of the formula ##STR517##

Claim 14

Photographic material according to claim 1, wherein the azo dyestuf is one of the formula ##STR518##

Claim 15

Photographic material according to claim 1, wherein the azo dyestuff is one of the formula ##STR519##

Claim 16

Photographic material according to claim 1, wherein the azo dyestuff is one of the formula ##STR520## wherein A 3 denotes hydrogen or methyl-,2,6-dimethylphenyl or 2-methyl-4-chlorophenyl and B 7 denotes the radical ##STR521## wherein D 4 represents a methyl, methoxy or methylmercapto group and M 8 represents --OC--E.sub.2 --T.sub.5 --E.sub.2 --CO-- wherein E 2 denotes phenylene and T 5 denotes ##STR522##

Claim 17

Photographic material, characterized in that it contains, on a carrier, a layer with an azo dyestuff of the formula ##STR523## wherein A 1 denotes hydrogen, methyl, hydroxyethyl, phenyl, lower alkyl phenyl, Difluoromethyl phenyl, lower alkoxy phenyl, fluoro-, chloro- or bromophenyl, sulphophenyl, carboxyphenyl, lower alkyl sulphonyl phenyl or lower alkyl carbonyl phenyl D 1 denotes sulphophenylene or sulphonaphthylene E 1 and E' 1 denote phenylene, fluoro-, chloro- or bromophenylene, lower alkyl phenylene, lower alkoxy phenylene, nitro phenylene, acetylamino phenylene or nitrolophenylene, and __________________________________________________________________________ Z denotes CONH, ##STR524## SO.sub.2 NH, CONH(CH.sub.2).sub.n HNOC, ##STR525## O(CH.sub.2).sub.n O, SO.sub.2 NH(CH.sub.2).sub.n HNO.sub.2 S, S(CH.sub.2).sub.n S, ##STR526## SO.sub.2 (CH.sub.2).sub.n O.sub.2 S, ##STR527## ##STR528## NHCO(CH.sub.2).sub.n O __________________________________________________________________________ r representing hydrogen or alkyl with 1 to 4 carbon atoms, m representing an integer from 1 to 5 and n representing an integer from 1 to 12.

Claim 18

Photographic material, characterized in that it contains, on a carrier, a layer with an azo dyestuff of the formula ##STR523## wherein A 1 denotes hydrogen, methyl, hydroxyethyl, phenyl, lower alkyl phenyl, Difluoromethyl phenyl, lower alkoxy phenyl, fluoro-, chloro- or bromophenyl, sulphophenyl, carboxyphenyl, lower alkyl sulphonyl phenyl or lower alkyl carbonyl phenyl D 1 denotes sulphophenylene or sulphonaphthylene E 1 and E' 1 denote phenylene, fluoro-, chloro- or bromophenylene, lower alkyl phenylene, lower alkoxy phenylene, nitro phenylene, acetylamino phenylene or nitrolophenylene, and __________________________________________________________________________ Z denotes CONH, ##STR524## SO.sub.2 NH, CONH(CH.sub.2).sub.n HNOC, ##STR525## O(CH.sub.2).sub.n O, SO.sub.2 NH(CH.sub.2).sub.n HNO.sub.2 S, S(CH.sub.2).sub.n S, ##STR526## SO.sub.2 (CH.sub.2).sub.n O.sub.2 S, ##STR527## ##STR528## NHCO(CH.sub.2).sub.n O __________________________________________________________________________ r representing hydrogen or alkyl with 1 to 4 carbon atoms, m representing an integer from 1 to 5 and n representing an integer from 1 to 12.

Claim 19

Photographic material according to claim 14 wherein the azo dyestuff according to the formula of claim 14 is one wherein A 1 denotes hydrogen, methyl, 2,6-dimethylphenyl, 2,6-dimethoxyphenyl, 2-methyl-4-chlorophenyl, 3-acetylphenyl, 3-chlorophenyl, 4-chlorophenyl, 4-fluorophenyl or 4-bromophenyl.

Claim 20

Photographic material according to claim 14 wherein the azo dyestuff according to the formula of claim 14 is one wherein E 1 denotes phenylene, chlorophenylene, methylphenylene or methoxyphenylene.

Claim 21

Photographic material according to claim 14 wherein the azo dyestuff according to the formula of claim 14 is one wherein __________________________________________________________________________ Z denotes CONH, O(CH.sub.2).sub.p O, SO.sub.2 NH, COCON, ##STR529## or CONH(CH.sub.2).sub.p HNOC, ##STR530## __________________________________________________________________________ p representing an integer from 2 to 5.

Claim 22

Photographic material according to claim 14 wherein the azo dyestuff according to the formula of claim 14 is one wherein A 1 denotes hydrogen, methyl, 2,6-dimethylphenyl, 2,6-dimethoxyphenyl, 2-methyl-4-chlorophenyl, 3-acetylphenyl, 3-chlorophenyl, 4-chlorophenyl, 4-fluorophenyl or 4-bromophenyl. E 1 and E' 1 denote phenylene, chlorophenylene, methylphenylene or methoxyphenylene.

Claim 23

Photographic material according to claim 14 wherein the azo dyestuff according to the formula of claim 14 is one wherein A 1 denotes hydrogen, methyl, 2,6-dimethylphenyl, 2,6-dimethoxyphenyl, 2-methyl-4-chlorophenyl, 3-acetylphenyl, 3-chlorophenyl, 4-chlorophenyl, 4-fluorophenyl or 4-bromophenyl and __________________________________________________________________________ Z denotes CONH, O(CH.sub.2).sub.p O, SO.sub.2 NH, COCON, ##STR531## or CONH(CH.sub.2).sub.p HNOC, ##STR532## __________________________________________________________________________ p representing an integer from 2 to 5.

Claim 24

Photographic material according to claim 14 wherein the azo dyestuff according to the formula of claim 14 is one wherein E 1 and E' 1 denote phenylene, chlorophenylene, methylphenylene or methoxyphenylene and __________________________________________________________________________ Z denotes CONH, O(CH.sub.2).sub.p O, SO.sub.2 NH, COCON, ##STR533## or CONH(CH.sub.2).sub.p HNOC, ##STR534## __________________________________________________________________________ p representing an integer from 2 to 5.

Claim 25

Photographic material according to claim 14 wherein the azo dyestuff according to the formula of claim 14 is one wherein A 1 denotes hydrogen, methyl, 2,6-dimethylphenyl, 2,6-dimethoxyphenyl, 2-methyl-4-chlorophenyl, 3-acetylphenyl, 3-chlorophenyl, 4-chlorophenyl, 4-fluorophenyl or 4-bromophenyl, E 1 and E' 1 denotes phenylene, chlorophenylene, methylphenylene or methoxyphenylene and __________________________________________________________________________ Z denotes CONH, O(CH.sub.2).sub.p O, SO.sub.2 NH, COCON, ##STR535## or CONH(CH.sub.2).sub.p HNOC, ##STR536## __________________________________________________________________________ p representing an integer from 2 to 5.

Claim 26

Photographic material according to claim 14, especially for the silver dye bleach process, characterized in that it contains, on a carrier, at least one layer with an azo dyestuff of the formula ##STR537##

Claim 27

Photographic material according to claim 14, especially for the silver dye bleach process, characterized in that it contains, on a carrier, at least one layer with an azo dyestuff of the formula ##STR538##

Claim 28

Photographic material according to claim 14, especially for the silver dye bleach process, characterized in that it contains, on a carrier, at least one layer with an azo dyestuff of the formula ##STR539##

Claim 29

Photographic material according to claim 14, especially for the silver dye bleach process, characterized in that it contains, on a carrier, at least one layer with an azo dyestuff of the formula ##STR540##

Claim 30

Photographic material, characterized in that it contains, on a carrier, a layer with a symmetrical azo dyestuff of the formula ##STR541## wherein R' 1 denotes hydrogen or acetylamino R 12 denotes hydrogen, chlorine, methyl, methoxy or acetylamino, R 13 denotes hydrogen, methyl, methoxy or hydroxyethoxy X 3 denotes 1,4- or 1,3-phenylene Z 3 denotes 1,4- or 1,3-phenylene or 4-chloro-1,3-phenylene and Y 2 denotes --CONH-- --CO--HN--CH 2 CH 2 --NH--OC-- or --O--CH 2 --CH 2 --O--

Claim 31

Photographic material, characterized in that it contains, on a carrier, a layer with a symmetrical azo dyestuff of the formula ##STR541## wherein R' 1 denotes hydrogen or acetylamino R 12 denotes hydrogen, chlorine, methyl, methoxy or acetylamino, R 13 denotes hydrogen, methyl, methoxy or hydroxyethoxy X 3 denotes 1,4- or 1,3-phenylene Z 3 denotes 1,4- or 1,3-phenylene or 4-chloro-1,3-phenylene and Y 2 denotes --CONH-- --CO--HN--CH 2 CH 2 --NH--OC-- or --O--CH 2 --CH 2 --O--

Claim 32

Photographic material, characterized in that it contains, on a carrier, a layer with a symmetrical azo dyestuff of the formula ##STR542##

Claim 33

Photographic material, characterized in that it contains, on a carrier, a layer with a symmetrical azo dyestuff of the formula ##STR542##

Claim 34

Photographic material, characterized in that it contains, on a carrier, a layer with a symmetrical azo dyestuff of the formula ##STR543## wherein R' 3 denotes benzoyl, 4-methylsulphonyl-benzoyl, phenylsulphonyl or caproyl, R 21 denotes hydrogen, or methoxy X 3 denotes 1,4- or 1,3-phenylene, Z 3 4'1,4- or 1,3-phenylene or 4-chloro-1,3-phenylene and Y 2 denotes --CONH--, --CONH--CH 2 --CH 2 --HNOC-- and --O--CH 2 --O--

Claim 35

Photographic material, characterized in that it contains, on a carrier, a layer with a symmetrical azo dyestuff of the formula ##STR543## wherein R' 3 denotes benzoyl, 4-methylsulphonyl-benzoyl, phenylsulphonyl or caproyl, R 21 denotes hydrogen, or methoxy X 3 denotes 1,4- or 1,3-phenylene, Z 3 4'1,4- or 1,3-phenylene or 4-chloro-1,3-phenylene and Y 2 denotes --CONH--, --CONH--CH 2 --CH 2 --HNOC-- and --O--CH 2 --O--