Patent GB-691989-A (GB)
Title: Photographic non-diffusing color formers
IPC: G03C7/32
Filed: 1951-01-01
Abstract: 61 - Carboxy - 21 - naphthyl - J - acid is prepared by adding the sodium salt of J-acid, neutral ammonium sulphite, and sodium metabisulphite to an aqueous ammonium hydroxide solution of 6-amino-2-naphthoic acid, refluxing, adding more of the sodium salt of J-acid, and further refluxing. 71-Carboxy-21-naphthyl-J-acid, 81-carboxymethoxy-21-naphthyl-J-acid, and 71 - carboxymethoxy - 21 - naphthyl - J - acid are similarly prepared.  4 - Carboxyphenyl - J - acid is prepared by adding p-aminobenzoic acid and sodium metabisulphite to an aqueous sodium hydroxide solution of J-acid, and refluxing.  The pyridine salt may be prepared by dissolving in hot water containing pyridine and strongly acidifying with hydrochloric acid. 41-Carboxymethylphenyl - J - acid, 31 - carboxymethylaminophenyl - J - acid, 2 - methyl - 4 - carboxy - 6-quinolino - J - acid, and 4 - carboxy - 6 - pyridino-J-acid are similarly prepared.  6 - [N - Acetyl - 4 - (3 - stearoylamino - 5-sulpho - o - tolylcarbamyl) - anilino] - 1 - naphthol-3-sulphonic acid is prepared by refluxing together 5-amino-3-stearoylamino-p-toluenesulphonic acid, p-carboxyphenyl-J-acid, pyridine, and benzene, adding a pyridine solution of PCl3 and further refluxing, removing the solvents at reduced pressure, dissolving in hot water, strongly acidifying with hydrochloric acid, and finally refluxing with acetic acid and acetic anhydride.  6-[N-Acetyl-3-(3-stearoylamino - 5 - sulpho - o - tolylcarbamylmethyl)-anilino]-1-naphthol-3-sulphonic acid, 6-[N-propionyl - 4 - (3 - stearoylamino - 5 - sulpho - o-tolylcarbamylmethyl) - anilino] - 1 - naphthol-3-sulphonic acid, the pyridine salt of 6-[N-acetyl - 4 - (2 - N - octadecyl - acetamido - 5-sulphophenylcarbamyl) - anilino] - 1 - naphthol-3-sulphonic acid (or of 6-p-[4-(1-octadecyl-5-sulpho - 2 - benzimidazolyl) - N - acetylanilino-1 - naphthol - 3 - sulphonic acid), and 6 - [N-acetyl - 3 - (2 - octadecylamino - 5 - sulphophenylcarbamyl) - anilino] - 1 - naphthol - 3 - sulphonic acid are similarly prepared.  6 - (N - Acetyl - 8 - octadecylcarbamylmethox-2 - naphthylamino) - 1 - naphthol - 3 - sulphonic acid is prepared by refluxing together potassium 6 - [81 - (carboxymethoxy) - 21 - naphthyl]-amino - 1 - naphthol - 3 - sulphonate and anhydous xylene under a water separator to remove water, and adding a solution prepared by adding an anhydrous toluene solution of phosphorus trichloride to an anhydrous toluene solution of octadecylamine and triethylamine, refluxing and filtering off precipitated triethylamine hydrochloride.  The mixture is heated, acetic acid is added and the mixture refluxed, a solution of potassium acetate in glacial acetic acid is added and the mixture further refluxed, and acetic anhydride added and the mixture again refluxed and then evaporated at reduced pressure.  6 - (N - Acetyl - 2 - methyl - 4 - octadecyl carbamyl - 6 - quinolinylamino) - 1 naphthol - 3 - sulphonic acid is similarly prepared.  5 - Amino - 3 - stearoylamino - p - toluenesulphonic acid is prepared by condensing potassium 3-amino-p-toluenesulphonate with octadecanoyl chloride in pyridine, nitrating the resulting stearamide, and reducing the product.  51 - Carboxy - 21 - pyridyl - J - acid is prepared by refluxing together 5-chloronicotinic acid and J-acid in water. Specifications 644,863 and 659,128 are referred to.