PHOTOGRAPHIC SILVER HALIDE MATERIAL CONTAINING DYE-RELEASING COMPOUND

摘要

1397964 Dyes containing hydroquinone sulphone radicals EASTMAN KODAK CO 6 July 1972 [6 July 1971] 31697/72 Heading C4P [Also in Divisions G2 and C2] 3 - [4 - (4 - Phenylazobenzamido)phenylsulphonyl] - 5 - pentadecylhydroquinone is prepared by reducing over palladium on carbon at 2 atmospheres hydrogen pressure in tetrahydrofuran 3 - (4 - nitrophenylsulphonyl) - 5 - pentadecylhydroquinone, removing the solvent in vacuo, dissolving the resulting gum in dry dioxane and adding 4-phenylazobenzoyl chloride and quinoline. 3-[4-(1-Hydroxy-4-isopropoxy-2- naphthylazo)phenylsulphonyl]- 5 - pentadecylhydroquinone diacetate is prepared by reducing in tetrahydrofuran over palladium on carbon 3 - (4 - nitrophenylsulphonyl) - 5 - pentadecylhydroquinone diacetate, filtering off the catalyst, removing the solvent in vacuo, dissolving the resulting gum in acetic acid, H 2 SO 4 and NaNO 2 and thus diazotizing and adding the solution to 4-isopropoxynaphthol in pyridine and methanol at 0‹ C. The corresponding hydroquinone is prepared by hydrolysing under nitrogen the hydroquinone diacetate in ethanol, water and 50% NaOH. 3 - [4 - (1 - Phenyl - 3 - methylcarbamyl- 4 - pyrazolin - 5 - onylazo)phenylsulphonyl] - 5- pentadecylhydroquinone is prepared by diazotizing 3 - (4 - aminophenylsulphonyl) - 5 - penta decylhydroquinone and adding the diazotized mixture to a solution of 1-phenyl-3-methylcarbamyl-5-pyrazolone in pyridine and methanol at 0‹C. 2 - Chloro - 3 - {4 - [4 - (1 - phenyl - 3 - methylcarbamyl - 4 - pyrazolin - 5 - onylazo)phenylsulphonamido]phenylsulphonyl} - 5 - pentadecylhydroquinone is prepared by mixing 2-chloro-3- (4 - aminophenylsulphonyl) - 5 - pentadecylhydroquinone, 4 - (1 - phenyl - 3 - methylcarbamyl - 4 - pyrazolin - 5 - onylazo)phenylsulphonyl chloride and pyridine, refluxing and pouring into cold water. 3-{3-[3-Oxo-4-benzamido-6- (4 - hydroxy - 3,5 - dichlorophenylimino)cyclohexadienylcarbamyl]- phenylsulphonyl} - 5- pentadecylhydroquinone benzylcarbonate is prepared by mixing 3-[3-(3-hydroxy-4-benzamidophenylcarbamyl)phenylsulphonyl]- 5 - pentadecylhydroquinone benzylcarbonate and 2,6- dichloro - 4 - N - chloroquinoneimine in tetrahydrofuran at room temperature.