Patent GB-673091-A (GB)
Title: Improvements in or relating to colour photography
IPC: G03C7/333
Filed: 1949-07-15
Abstract: Para - o  : o 1 - dicyanodiethylaminobenzal - 3 - sulphoanil is prepared by adding a chloroform solution of o  : o 1-dihydroxydiethylaniline to a chloroform suspension of phosphorus pentabromide and boiling, distilling off the chloroform, dissolving in hot ethanol and isolating dibromodiethylaniline by adding caustic soda, and adding an ethanol solution of the dibromodiethylaniline to aqueous sodium cyanide and boiling, dissolving the o  : o 1-dicyanodiethylaniline obtained in benzene, cooling, and reacting with a cooled mixture of phosphorus oxychloride and N-methylformanilide, and adding a hot acetic acid solution of the p-o : o 1-dicyanodiethylaminobenzaldehyde obtained to a hot aqueous solution of metanilic acid.  p - di - (Ethylcarboxymethyl) - aminobenzaldehyde is prepared by reacting a dry benzene solution of diethyl phenyliminodiacetate with a mixture of phosphorus oxychloride and N-methylformanilide, adding a hot ethanol solution of the product to a hot aqueous solution of metanilic acid, and dissolving the precipitate in aqueous sodium carbonate solution.  p - di - (Ethylcarboxymethyl) - aminobenzal - 3 - sulphoanil is prepared by treating p-di-(ethylcarboxymethyl)-aminobenzaldehyde with metanilic acid in ethanol solution.  p - N - Methyl : N - cyanoethylaminobenzaldehyde is prepared by reacting a dry benzene solution of N-o -cyanoethyl : N-methylaniline with a mixture of phosphorus oxychloride and N-methylformanilide.  p - N - Methyl : N - carboxyethylaminobenzaldehyde is prepared by boiling p-N-methyl : N - o -cyanoethylaminobenzaldehyde with aqueous caustic soda.  p - N - Methyl : N - carboxyethylaminobenzaldehyde-anil is prepared by adding aniline to an aqueous solution of p-N-methyl : N-carboxyethylaminobenzaldehyde.  p - N - Methyl : N - o  - cyanoethylaminobenzaldehyde-3-sulphoanil is prepared by adding aqueous metanilic acid to a hot acetic acid solution of p-N-methyl : N-o -cyanoethylaminobenzaldehyde.ALSO:Yellow styryl dyes containing a sulphonic or carboxylic acid group, a substituent rendering the dyes fast to diffusion in gelatine, and the group <FORM:0673091/IV (c)/1> wherein the benzene nucleus may be substituted, the terminal carbon atom is the omega-carbon atom of a cyanacetyl radical or forms part of a heterocyclic nucleus, and at least one of the radicals R1 and R2 is an alkyl radical substituted with, for example, -CN, -COO-alkyl, -NO2, or a carboxylic or sulphonic acid group, and, when only one of the radicals R1 and R2 is an alkyl group so substituted, the other is a substituted or unsubstituted hydrocarbon radical, are prepared by condensing an anil of a p-substituted aminobenzaldehyde with a reactive methylene dye intermediate, e.g. a pyrazolone or cyanacetyl coupling component.  The p-substituted aminobenzaldehyde may be p - (N - methyl : N - b  - hydroxyethylamino) -, p - (N - ethyl : N - b - hydroxyethylamino) -, p - (b  : b 1 - dihydroxydiethylamino) -, p - (N - methyl : N - methoxyethylamino) -, p - (N - ethyl : N-methoxyethylamino)-, p-(N-butyl : N-b  - hydroxyethylamino) -, p - (N - methyl : N - b  - chloroethylamino) -, p - (N - ethyl : N - b  - chloroethylamino) -, p - (b  : b 1 - dichlorodiethylamino) -, 4 - (b : b 1 - dichlorodiethylamino) - 2 - methyl -, p - (N - methyl : N - b - cyanoethylamino) -, p - (b  : b 1 - dicyanodiethylamino) -, p - (N - methyl : N - b  - carboxyethylamino) -, p - (b  : b 1 - dicarboxydiethylamino) -, p - (N - methyl : N-b -sulphoethylamino)-, or 4-(b  : b 1-disulphodiethylamino) - 2 - methylbenzaldehyde, or p-[di-(carboxymethyl)-amino]-benzaldehyde or the corresponding diethyl ester.  The anil may be one obtained by reacting the aldehyde with aniline or a substituted aniline such as aniline sulphonic acid. The reactive methylene compound may be 1-(41-phenoxy-31 - sulphophenyl) - 3 - heptadecyl - 5 - pyrazolone, 1 - (phenyl - 31 - methanesulphonic acid) - 3 - heptadecyl - 5 - pyrazolone, or the compound obtained by acylating 4-cyanacetylaniline with octadecenylsuccinic anhydride. The reaction may be effected by mixing the dye-forming reagents together in weakly alkaline aqueous medium, or by heating in methanol with a catalyst such as piperidine or triethylamine.  1 - (41 - Phenoxy - 31 - sulphophenyl) - 3 - heptadecyl - 4 - p - o  : o 1 - dicyanodiethylaminobenzylidene)-4-pyrazolone (sodium salt) is prepared by reacting p - o  : o 1 - dicyanodiethylaminobenzal-3-sulphoanil in the presence of aqueous sodium carbonate with 1-(41-phenoxy-31-sulphophenyl)-3 - heptadecyl - 5 - pyrazolone.  1 - (41 - Phenoxy-31 - sulphophenyl) - 3 - heptadecyl - 4 - p - di-(ethylcarboxymethyl) - aminobenzylidene - 5 - pyrazolone (sodium salt), 1-(phenyl-31-methane sulphonic acid) - 3 - heptadecyl - 4 - p - N - methyl : N - carboxyethylaminobenzylidene - 5 - benzylidene-5-pyrazolone (sodium salt), and 1-b -octadecenylsuccinamido - 5 - (o  - cyano : o  - 41 - N - methyl : N - o 1 - cyanoethylaminobenzylidene)-acetobenzene are similarly prepared.