Photographic materials containing aroylacetanilide type color couplers

• Main Authors: ROOSEN RAYMOND ALBERT, VERBRUGGHE MARCEL HENDRIK, CAT ARTHUR HENRI DE
• Format: Patent
• Language: English
• Published: 20.02.1968
• Subjects: ACYCLIC OR CARBOCYCLIC COMPOUNDS; AUXILIARY PROCESSES IN PHOTOGRAPHY; CHEMISTRY; CINEMATOGRAPHY; ELECTROGRAPHY; HOLOGRAPHY; METALLURGY; ORGANIC CHEMISTRY; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR,STEREO-PHOTOGRAPHIC PROCESSES; PHOTOGRAPHY; PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHYSICS

The invention comprises aroylacetarylamide colour couplers wherein the aroyl part contains a sulphonic acid group, the arylamide part may contain a hydrophobic group and either part contains a C5- 20 hydrophobic group inhibiting migration of the colour coupler. Exemplified compounds have the formula <FORM:1039965/C2/1> wherein (1)-(8), R2 = R4 = H, R1 = 3- or 4-SO3Na and R3 (Y is C16H33) is YO, YS, YSO2, YSO2NH, YNHCO or C15H31CONH; R4 = H and (9) R1,R2 = 3,5-di-SO3Na, R3 = 2-YS, (10) R1 = 3-SO3Na, R2 = 4-Cl, R3 = 3-YSO2, (11) R1 = 3-SO3Na, R2 = YO, R3 = H, (15) R1 = 3-SO3Na, R2 = 6-OMe, R3 = 4-Y; R2 = H and (12) R1 = 4-SO3Na, R3 = 2-OMe, R4 = 5-YNH SO2, (13) R1 = 3-SO3Na, R3 = 2-Cl, R4 = 5-YNH SO2, (14) R1 = 3-SO3Na, R3 = 2-YS, R4 = 5-F2CHSO2, (16) R1 = 3-SO3Na, R3R4 phenyl replaced by 2-YO-1-naphthyl; (17)-(19), R2 = R4 = H, R1 = 3-(3-SO3Na-C6H4-X) (X is -CONH-, -SO2-NH-or -NHCONH-), R3 = 2-YO. The compounds are prepared from an aroyl chloride substituted by FSO2, which is reacted with the Cu salt of ethyl acetoacetate, the acetyl group split off under acid conditions, the resulting ethyl aroylacetate reacted with the appropriate arylamine and the FSO2-group in the product hydrolyses to NaO3S-.