Multilayer silver halide elements containing thiazole color couplers for yellow

• Main Authors: ROOSEN RAYMOND ALBERT, VERBRUGGHE MARCEL HENDRIK, CAT ARTHUR HENRI DE
• Format: Patent
• Language: English
• Published: 16.07.1968
• Subjects: AUXILIARY PROCESSES IN PHOTOGRAPHY; CHEMISTRY; CINEMATOGRAPHY; ELECTROGRAPHY; HETEROCYCLIC COMPOUNDS; 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 compounds of the general formula <FORM:1075084/C2/1> wherein R1 represents a sulphonic acid group or a salt thereof, R2 represents a hydrogen atom, a halogen atom, an alkoxy group, a sulphonic acid group, a sulphonic acid salt group, or a group conferring fastness to diffusion comprising 5-20 carbon atoms, R3 represents a hydrogen atom, an alkyl group, an aryl group, or a group -X-R in which X is a direct bond, an oxygen atom or a sulphur atom and R is an acyclic aliphatic hydrocarbon group having 5-20 carbon atoms, and R4 represents a hydrogen atom, an alkyl group, a carboxyl substituted alkyl group, an aryl group, an aryl group substituted with an alkoxy group, a halogen atom, an alkylsulphonyl group, a group rendering fast to diffusion comprising 5-20 carbon atoms, such as an n-hexadecyloxy, n-hexadecylmercapto or pentadecyl group, or wherein R3 and R4 together represent the atoms necessary for completing an aromatic ring system. The compounds are prepared according to the reaction scheme <FORM:1075084/C2/2> wherein R2, R3 and R4 are as defined above 2 - Amino - 4 (41 - (n - hexadecyloxyphenyl))-thiazole is prepared by reacting p-n-hexadecyloxyphenacyl bromide with thiourea to give the aminothiazole hydrobromide and treating with conc. NH4OH to give the free base. 2 - Amino - 4 - methyl - 5 - tetradecylthiazole is prepared by reacting methyl pentadecyl ketone with bromine to give methyl 1-bromopentadecyl ketone which is then reacted with thiourea and neutralized with NH4OH. 2 - Amino - 4 - phenyl - 5 - tetradecylthiazole is prepared by reacting palmitoylbenzene with bromine to give a -bromopalmitoylbenzene which is then reacted with thiourea and neutralized with NH4OH. 2-Amino-4-(41-methoxyphenyl)-5 -tetradecylthiazole is prepared in a similar manner starting from 4-palmitoyl anisol via 4-(a -bromopalmitoyl)-anisol 4-Palmitoyl anisol is itself prepared by Friedel-Crafts acylation of anisol with palmitoyl chloride. Ethyl a -n-hexadecylacetoacetate is prepared from ethyl acetoacetate, n-hexadecyl bromide and sodium ethoxide and is then brominated to give, initially, ethyl a -bromo-a -n-hexadecylacetoacetate which is converted on standing to ethyl g - bromo - a - n - hexadecylacetoacetate. This compound is reacted with thiourea and neutralized with NH4OH to give 2-amino-4-(a -ethoxy-carbonylheptadecyl) -thiazole. 2 - Amino - 5 - n - hexadecylmercapto - thiazole is prepared from 2-amino-5-bromothiazole bromide, n-hexadecylmercaptan and potassium hydroxide. The following reactions are also described: <FORM:1075084/C2/3> wherein Z is -COCl or -NCO and W is -CO- or -NHCO-.