GB1109963A - Photographic materials containing hydrazone compounds - Google Patents

Abstract

Monoazo dyes of the formula (in the hydrazone form) <FORM:1109963/C4-C5/1> wherein X1 is alkyl or a mesomerizable group; X2 is a mesomerizable group; Y is -C(R2)2- or -CR2 = CR2-; R1 is h, alkyl, aryl, cycloalkyl, arylkyl, a heterocyclic group, -N = N-X2 or NR3(R4) in which R3 and R4 are H, alkyl, aryl, phenylalkyl, 5- or 6-membered heterocyclic rings, cycloaliphatic rings, or have the same meaning as R1; R2 is H, alkyl or aryl; and n is 0-3 are described. The mesomerizable groups may be olefinically unsaturated groups, or aromatic heterocyclic or carbocyclic rings. The azo dye hydrazones may be prepared by (a) reacting 1 mol of the a ,b -dicarbonyl compound with 0.5 mole of a hydrazine or ethyl a -methyl acetoacetate may be reacted with a diazonium salt of 4-(N-methyl - N - octadecylamino)aniline - 3 - sulphonic acid; (b) coupling a diazonium salt with an acetyl or benzoylacetic ester derivative and subjecting the dye to ketone-cleavage, e.g. diazotized aniline-4-sulphonic acid with stearyl acetic ester, and the product cleaved by refluxing in n-propanol and 2N-KOH; (c) coupling a diazonium salt with a monohydrazone of diacyl compound, e.g. diazotized 4-aminoanisole-2-sulphonic acid coupled with the product of (b) above; or (d) phenylglyoxyl acid amide aryl hydrazones may be prepared by, e.g. reacting a diazotized aniline with o -chloroacetophenone, and reacting the phenylglyoxyl-phenyl-hydrazone with morpholine in alcohol.ALSO:A photographic material contains a hydrazone of the formula <FORM:1109963/C2/1> wherein X1 is alkyl or a mesomerizable group; X2 is a mesomerizable group; Y is -C(R2)2- or -CR2=CR2-; R1 is H, alkyl, aryl, cycloalkyl, aralkyl, a heterocyclic group, or -NR3-(R4) in which R3 and R4 are H, alkyl, aryl, phenylalkyl, 5- or 6-membered heterocyclic rings, cycloaliphatic rings, or have the same meaning as R1; R2 is H, alkyl or aryl; and n is 0-3. The mesomerizable groups may be olefinically unsaturated groups, or aromatic heterocyclic or carbocyclic rings. A number of compounds are listed. The hydrazones may be prepared by (a) reacting 1 mol of the a ,b -dicarbonyl compound with 0.5 mole of a hydrazine or ethyl-a -methyl acetoacetate may be reacted with a diazonium salt of 4-(N-methyl-N-octadecyl-amino)aniline-3-sulphonic acid; (b) coupling a diazonium salt with an acetyl or benzoylacetic ester derivative and subjecting the dye to ketone-cleavage, e.g. diazotized aniline-4-sulphonic acid with stearyl acetic ester, and the product cleaved by refluxing in n-propanol and 2N-KOH; (c) coupling a diazonium salt with a monohydrazone of a diacyl compound, e.g. diazotized 4-amino-anisole-2-sulphonic acid coupled with the product of (b) above; or (d) phenylglyoxyl acid amide aryl hydrazones may be prepared by, e.g. reacting a diazotized aniline with o -chloroacetophenone, and reacting the phenylglyoxyl aryl hydrazone with morpholine in alcohol.