Color-photographic recording material for the silver dye bleach process
AssigneeCiba-Geigy Corporation
InventorsJohn Lenoir, Gerald Jan, Mario Fryberg
Life of this patent
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AssigneeCiba-Geigy Corporation
InventorsJohn Lenoir, Gerald Jan, Mario Fryberg
Estimating the term…
A color-photographic recording material for the silver dye bleach process, which contains oil-soluble azo dyes of the formula ##STR1## in which R.sub.1 is hydrogen, alkyl, alkoxy, alkenyl, acyl, carbalkoxy, acylamino, carbamide, sulfonamide, alkylsulfone, arylsulfone, aryloxy, arylsulfonic acid ester, hydroxyl, cyano, nitro or halogen, R.sub.2 is hydrogen, alkyl, alkoxy, carbalkoxy, carbamide, sulfonamide, alkylsulfone, arylsulfone, aryloxy, cyano, nitro or halogen, R.sub.3 is hydrogen, alkyl, alkoxy, phenoxy, sulfonamide, alkylsulfone, sulfonic acid ester, cyano, nitro, halogen, carbalkoxy, carbamide or phosphoric acid diester, R.sub.4 is hydrogen, alkyl, alkoxy, carbalkoxy, carbamide, sulfonamide, acylamino, alkylsulfone, arylsulfone, hydroxyl, cyano, nitro or halogen, R.sub.5 is hydrogen, alkyl or carbalkoxy, X.sub.1 is hydrogen, alkyl, alkoxy, acylamino, alkylsulfonamide or hydroxyl, Y.sub.1 is hydrogen, alkyl, alkoxy, amino, carbalkoxy, arylsulfonamide, acylamino, halogen, hydroxyl or phosphamic acid ester, Z.sub.1 is hydrogen, alkyl, alkoxy, acylamino, acyl, carbalkoxy, alkylsulfonamide or halogen or forms a ring with Y.sub.1, and W.sub.1 is hydrogen, alkyl, alkoxy or halogen. The substituents mentioned can, where relevant, themselves be further substituted. The oil-soluble azo dyes are easily incorporated into silver halide gelatin emulsions and are very stable therein. Because of the good oil-solubility of the azo dyes, very thin layers can be cast in producing photographic materials, and this has an advantageous effect on, for example, the image sharpness.
A colour-photographic recording material for the silver dye bleach process which contains at least one diffusion-resistant, bleachable and oil-soluble monoazo dye dissolved in a high-boiling organic solvent in at least one silver halide emulsion layer or in a colloid layer adjoining the silver halide emulsion layer, and wherein the dye has the formula ##STR84## in which R.sub.1 is hydrogen, substituted or unsubstituted alkyl having 1 to 18 carbon atoms, substituted or unsubstituted alkoxy having 1 to 16 carbon atoms, substituted or unsubstituted alkenyl having 2 to 4 carbon atoms, substituted or unsubstituted aliphatic acyl having 2 to 5 carbon atoms, substituted or unsubstituted benzoyl, substituted or unsubstituted carbalkoxy having 2 to 20 carbon atoms or --NV.sub.1 COU.sub.1, in which V.sub.1 is hydrogen or alkyl having 1 to 4 carbon atoms and U.sub.1 is substituted or unsubstituted alkyl having 1 to 12 carbon atoms or substituted or unsubstituted alkenyl having 2 to 4 carbon atoms, or R.sub.1 is N-alkyl-substituted or N,N-dialkyl-substituted carboxamido or sulfonamido, in which each alkyl moiety has 1 to 12 carbon atoms and can be substituted further, or R.sub.1 is substituted or unsubstituted alkylsulfone having 1 to 12 carbon atoms, substituted or unsubstituted arylsulfone, substituted or unsubstituted aryloxy or substituted or unsubstituted arylsulfonic acid ester, or is hydroxyl, cyano, nitro or halogen, R.sub.2 is hydrogen, substituted or unsubstituted alkyl having 1 to 12 carbon atoms, substituted or unsubstituted alkoxy having 1 to 6 carbon atoms, substituted or unsubstituted carbalkoxy having 2 to 5 carbon atoms or N-alkyl-substituted or N,N-dialkyl-substituted sulfonamido or carboxamido, in which each alkyl moiety has 1 to 8 carbon atoms and can be substituted, or R.sub.2 is substituted or unsubstituted alkylsulfone having 1 to 6 carbon atoms, substituted or unsubstituted arylsulfone or substituted or unsubstituted aryloxy, or is cyano, nitro or halogen, R.sub.3 is hydrogen, substituted or unsubstituted alkyl or alkoxy having 1 to 4 carbon atoms, substituted or unsubstituted phenoxy, or N-alkyl-substituted or N,N-dialkyl-substituted sulfonamido or carboxamido, in which each alkyl moiety has 1 to 6 carbon atoms and can be substituted, or R.sub.3 is substituted or unsubstituted alkylsulfone having 1 to 4 carbon atoms, substituted or unsubstituted phenylsulfonic acid ester, cyano, nitro, halogen, substituted or unsubstituted carbalkoxy having 1 to 16 carbon atoms, or --P(O)(OT.sup.1).sub.2, in which T.sup.1 is alkyl having 1 to 4 carbon atoms, R.sub.4 is hydrogen, substituted or unsubstituted alkyl having 1 to 4 carbon atoms, substituted or unsubstituted alkoxy having 1 to 6 carbon atoms, substituted or unsubstituted carbalkoxy having 2 to 16 carbon atoms or N-alkyl-substituted or N,N-dialkyl-substituted sulfonamido or carboxamido, in which each alkyl moiety has 1 to 12 carbon atoms and can be substituted, or R.sub.4 is --NQ.sub.1 COT.sub.1, in which Q.sub.1 is hydrogen or alkyl having 1 or 2 carbon atoms and T.sub.1 is substituted or unsubstituted alkyl having 1 to 4 carbon atoms, or R.sub.4 is substituted or unsubstituted alkylsulfone having 1 to 12 carbon atoms, substituted or unsubstituted arylsulfone hydroxyl, cyano, nitro or halogen, R.sub.5 is hydrogen, substituted or unsubstituted alkyl having 1 to 4 carbon atoms or substituted or unsubstituted carbalkoxy having 2 to 13 carbon atoms, X.sub.1 is hydrogen, substituted or unsubstituted alkyl or alkoxy having 1 to 6 carbon atoms or --NL.sub.1 CO--M.sub.1, in which L.sub.1 is hydrogen or substituted or unsubstituted alkyl having 1 to 4 carbon atoms and M.sub.1 is substituted or unsubstituted alkyl or alkoxy having 1 to 24 carbon atoms, or X.sub.1 is substituted or unsubstituted alkylsulfonylamino having 1 to 25 carbon atoms or hydroxyl, Y.sub.1 is hydrogen, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted alkoxy having 1 to 12 carbon atoms, substituted or unsubstituted carbalkoxy having 2 to 5 carbon atoms or N-alkyl-substituted or N,N-dialkyl-substituted amino, in which each alkyl moiety has 1 to 6 carbon atoms and can be substituted, or Y.sub.1 is substituted or unsubstituted arylsulfonylamino or --NE.sub.1 COG.sub.1, in which E.sub.1 is hydrogen or substituted or unsubstituted alkyl having 1 to 8 carbon atoms and G.sub.1 is substituted or unsubstituted alkyl having 1 to 12 carbon atoms or substituted or unsubstituted alkoxy having 1 to 4 carbon atoms, or Y.sub.1 is --NE.sub.1 P(O)(OG.sup.1).sub.2, in which E.sub.1 is as defined above and G.sup.1 is alkyl having 1 to 12 carbon atoms, or Y.sub.1 is halogen or hydroxyl, Z.sub.1 is hydrogen, substituted or unsubstituted alkyl having 1 to 12 carbon atoms, substituted or unsubstituted alkoxy having 1 to 6 carbon atoms or --NA.sub.1 COD.sub.1, in which A.sub.1 is hydrogen or substituted or unsubstituted alkyl having 1 to 8 carbon atoms and D.sub.1 is substituted or unsubstituted alkyl having 1 to 18 carbon atoms, or Z.sub.1 is substituted or unsubstituted acyl having 2 to 9 carbon atoms, substituted or unsubstituted carbalkoxy having 2 to 19 carbon atoms, substituted or unsubstituted alkylsulfonylamino having 1 to 6 carbon atoms, halogen or the atoms which together with Y.sub.1 form a substituted or unsubstituted 5-membered or 6-membered, saturated or unsaturated ring which can contain 1 or 2 hetero-atoms, and W.sub.1 is hydrogen, substituted or unsubstituted alkyl or alkoxy, each having 1 to 4 carbon atoms, or halogen.
Dependencies are inferred from the claim text.