Patent GB-701545-A (GB)
Title: Developers for and method of producing phenazonium dyestuff photographic images with p-dialkylaminoaniline developing agents
IPC: G03C7/32
Filed: 1951-08-13
Abstract: 701,545. Photographic colour development. GENERAL ANILINE & FILM CORPORATION. Aug. 13, 1951 [Aug. 19, 1950], No. 19038/51. Class 98(2) Magenta phenazonium dye images are produced in an exposed gelatine silver halide emulsion layer by development with a a p-dialkylaminoaniline developing agent in the presence of a colour coupler of the general formulae wherein R is -COOH, -CONH 2 , or -CONHR 3  (R 3  being an alkyl radical of not more than 26' carbon atoms, a sulphonated alkyl radical of at least 10 carbon atoms, or a sulphonated aromatic radical substituted by an aliphatic radical of at least 5 carbon atoms), R, is H or a lower aliphatic radical, R 2  an aromatic or lower aliphatic radical, and X a halogen. Developing agents specified are 4-dimethylaminoaniline, 4-diethylaminoaniline, 4- dipropylaminoaniline, 4-(N-methyl: N-#-hydroxyethylamino)-aniline, 4-(N-ethyl: N-#-hydroxyethylamino),aniline, 4-(N: N-#: #-dihydroxyethylamino)- aniline, and the reaction products of 4-alkylaminoaniline and ethylene oxide. Numerous couplers are specified, including 2-phenyl-, 2-methyl-, 2-(3'- nitrophenyl)-, 2-(3<SP>1</SP>-aminophenyl)-, 2-(4<SP>1</SP>-chlorophenyl)-, and 2-(2<SP>1</SP>-sulphophenyl)-6-bromo-9-hydroxycinchoninic acid; 2-propyl-, 2-(#-naphthyl)-, 2-phenyl-3-carboxymethyl-, and 2-(3<SP>1</SP>-stearoylaminophenyl)-3-carboxymethyl-; 6-chloro-8-hydroxycinchoninic acid; 6-chloro-8-hydroxy-2- phenylcinchoninamide; 6-bromo-8-hydroxy-N- dodecyl-2(2<SP>1</SP>-sulphophenyl)-cinchoninamide; 6- caproylamino-2 -(2- phenyl- 6-bromo-8-hydroxycinchoninoyl)-aminotoluene-4-sulphonic acid; 2- phenyl-6- chloro - 8 hydroxycinchoninoyloctadecyltaurine; and 2-(4-(6-bromo-8-hydroxy-2-(2<SP>1</SP>-sulphophenyl)-cinchoninoyl)-aminophenyl)-1-octadecyl-jsulphobenzimidazole. The couplers may be incorporated in the silver halide emulsion or in the developing solution. The change from the cyan dye image produced on colour development to the magenta phenazonium dye image is hastened by treatment in an alkaline bath, which may be one of the processing baths or a separate alkaline bath. Dipotassium monosodium ferricyanide may be added to the alkaline bath to accelerate the change. The alkaline bath may also be an alkaline hypo or hardening bath. In example 1, colour development is effected using a developer containing 4-diethylaminoaniline and 2-phenyl-6-chloro-8-hydroxycinchoninic acid, and development is followed by treatment in a formaldehyde hardening bath containing sodium hydroxide. The coupler may, alternatively, be 6-bromo-8-hydroxy-2-(2<SP>1</SP>-sulphophenyl)-cinchoninic acid, 2-(4<SP>1</SP>-chlorophenyl)-6- bromo-8-hydroxycinchoninic acid, or 6-chloro-3- carboxymethyl-8-hydroxy-2-phenylcinchoninic acid. In example 2, the procedure is similar, using 2- propyl-6-bromo-8-hydroxycinchoninic acid, and in example 3 the procedure is similar to that of example 1, using a formaldehyde hardening bath containing sodium carbonate and sulphate and treating in a further bath containing sodium hydroxide. In example 4, a gelatino silver iodobromide emulsion containing 6-chloro-3-carboxymethyl-8-hydroxy-2-(3<SP>1</SP>-stearoylaminophenyl)-cinchoninic acid is exposed, developed with a p-dialkylaminoaniline developer, and hardened with the hardener of example 1. In example 5, the procedure is similar using the hardening and sodium hydroxide baths of example 3. In examples 6 and 8, the procedure is similar, using 6-bromo-8-hydroxy- 2 - (2<SP>1</SP>-sulphophenyl)-N-octadecylcinchoninamide and 2-(4-(6-bromo-8-hydroxy-2-(2<SP>1</SP>-sulphophenyl)-cinchoninoyl)-aminophenyl)-1-octadecyl-5- sulphobenzimidazole respectively, and in example 7, the procedure is similar to that of example 1, using 2-(#-naphthyl)-6-chloro-8-hydroxycinchoninic acid. In example 9, the exposed film is first developed in a black-and-white developer, and is then processed as in example 3. In example 10, a film carrying the emulsion of example 4 is processed similarly to the film of example 9. Specifications 644,863, 647,638, 659,479, and 701,531, [Group IV(b)], are referred to.