Photographic materials and processes comprising color-forming sulfonamidodiphenylamine dye precursors and corresponding phenazine dyes

In a photographic element comprising a support having thereon a photographic silver salt and a dye precursor, the improvement comprising:

• as said dye precursor, a color-forming para-sulfonamidodiphenylamine represented by the formula:
• ##STR25## wherein:
• R is alkyl containing 1 to 20 carbon atoms, aryl containing 6 to 20 carbon atoms or alkaryl containing 7 to 20 carbon atoms;
• R.sup.1 and R.sup.2 are individually hydrogen, alkyl containing 1 to 4 carbon atoms or --NHSO.sub.2 R.sup.4 ;
• and at least one of R.sup.1 and R.sup.2 is --NHSO.sub.2 R.sup.4 ;
• R.sup.3 is alkoxy containing 1 to 20 carbon atoms, alkyl containing 1 to 20 carbon atoms or ##STR26## R.sup.4 is alkyl containing 1 to 20 carbon atoms, aryl containing 6 to 20 carbon atoms or alkaryl containing 7 to 20 carbon atoms;
• R.sup.5 is hydrogen or alkyl containing 1 to 20 carbon atoms;
• and
• R.sup.6 is alkyl containing 1 to 20 carbon atoms;
• and, wherein the para-sulfonamidodiphenylamine has one to two sulfonamido groups in positions ortho to the --NH-- moiety separating the two phenyl groups of the para-sulfonamidodiphenylamine, and,
• wherein the para-sulfonamidodiphenylamine, in oxidized form, intramolecularly reacts to produce a sulfonamido substituted phenazine dye.

In a photographic composition comprising a photographic silver salt and a dye precursor, the improvement comprising:

• as said dye precursor, a color-forming para-sulfonamidodiphenylamine represented by the formula:
• ##STR34## wherein:
• R is alkyl containing 1 to 20 carbon atoms, aryl containing 6 to 20 carbon atoms, or alkaryl containing 7 to 20 carbon atoms;
• R.sup.1 and R.sup.2 are individually hydrogen, alkyl containing 1 to 4 carbon atoms, or --NHSO.sub.2 R.sup.4 ;
• and at least one of R.sup.1 and R.sup.2 is --NHSO.sub.2 R.sup.4 ;
• R.sup.3 is alkoxy containing 1 to 20 carbon atoms, alkyl containing 1 to 20 carbon atoms, or ##STR35## R.sup.4 is alkyl containing 1 to 20 carbon atoms, aryl containing 6 to 20 carbon atoms, or alkaryl containing 7 to 20 carbon atoms;
• R.sup.5 is hydrogen or alkyl containing 1 to 20 carbon atoms;
• and
• R.sup.6 is alkyl containing 1 to 20 carbon atoms;
• and, wherein the para-sulfonamidodiphenylamine has one to two sulfonamido groups in positions ortho to the --NH-- moiety separating the two phenyl groups of the para-sulfonamidodiphenylamine;
• and,
• wherein the para-sulfonamidodiphenylamine, in oxidized form, intramolecularly reacts to produce a sulfonamido substituted phenazine dye.

A method of producing a phenazine dye enhanced silver image in an exposed photographic element comprising a support having thereon a photographic silver salt and a phenazine dye precursor consisting essentially of a color-forming para-sulfonamidodiphenylamine represented by the formula:

• ##STR43## wherein:
• R is alkyl containing 1 to 20 carbon atoms, aryl containing 6 to 20 carbon atoms, or alkaryl containing 7 to 20 carbon atoms;
• R.sup.1 and R.sup.2 are individually hydrogen, alkyl containing 1 to 4 carbon atoms or --NHSO.sub.2 R.sup.4 ;
• and at least one of R.sup.1 and R.sup.2 is --NHSO.sub.2 R.sup.4 ;
• R.sup.3 is alkoxy containing 1 to 20 carbon atoms, alkyl containing 1 to 20 carbon atoms, or ##STR44## R.sup.4 is alkyl containing 1 to 20 carbon atoms or aryl containing 6 to 20 carbon atoms;
• R.sup.5 is hydrogen or alkyl containing 1 to 20 carbon atoms;
• and
• R.sup.6 is alkyl containing 1 to 20 carbon atoms;
• and, wherein the para-sulfonamidodiphenylamine has one to two sulfonamido groups in positions ortho to the --NH-- moiety separating the two phenyl groups of the para-sulfonamidodiphenylamine;
• and, wherein the para-sulfonamidodiphenylamine, in oxidized form, intramolecularly reacts to produce a sulfonamido substituted phenazine dye;
• said process comprising the step of:
• developing said element by means of a 3-pyrazolidone cross-oxidizing silver halide developing agent.

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 para-sulfonamidodiphenylamine having one to two sulfonamido groups in positions ortho to the --NH-- moiety separating the two phenyl groups of the para-sulfonamidodiphenylamine and wherein the para-sulfonamidodiphenylamine, in oxidized form, intramolecularly reacts to produce a sulfonamido substituted phenazine dye.

An exposed and processed photographic element comprising a support having thereon a silver image and a phenazine dye image comprising a phenazine dye represented by the formula:

• ##STR47## wherein:
• R.sup.7 is alkyl containing 1 to 20 carbon atoms, aryl containing 6 to 20 carbon atoms, or alkaryl containing 7 to 20 carbon atoms;
• R.sup.8 is alkoxy containing 1 to 20 carbon atoms, alkyl containing 1 to 20 carbon atoms, or ##STR48## R.sup.9 is hydrogen, alkyl containing 1 to 4 carbon atoms or --NHSO.sub.2 R.sup.12 ;
• R.sup.10 is hydrogen or alkyl containing 1 to 20 carbon atoms;
• R.sup.11 is alkyl containing 1 to 20 carbon atoms;
• and
• R.sup.12 is alkyl containing 1 to 20 carbon atoms, aryl containing 6 to 20 carbon atoms or alkaryl containing 7 to 20 carbon atoms.

An exposed and processed photographic composition comprising, in binder, a silver image and a phenazine dye image comprising a phenazine dye represented by the formula:

• ##STR53## wherein:
• R.sup.7 is alkyl containing 1 to 20 carbon atoms, aryl containing 6 to 20 carbon atoms, or alkaryl containing 7 to 20 carbon atoms;
• R.sup.8 is alkoxy containing 1 to 20 carbon atoms, alkyl containing 1 to 20 carbon atoms, or ##STR54## R.sup.9 is hydrogen or alkyl containing 1 to 4 carbon atoms;
• R.sup.10 is hydrogen or alkyl containing 1 to 20 carbon atoms;
• R.sup.11 is alkyl containing 1 to 20 carbon atoms;
• and
• R.sup.12 is alkyl containing 1 to 20 carbon atoms, aryl containing 6 to 20 carbon atoms or alkaryl containing 7 to 20 carbon atoms.