Patent GB-808276-A (GB)
Title: Improvements in or relating to colour couplers for colour photography
Inventor: CAT ARTHUR HENRI DE
IPC: G03C7/36
Filed: 1955-04-05
Abstract: o-, m- and p-Nitrobenzenesulphofluorides, p - chloro - m - nitrobenzenesulphofluoride, p - dimethylamino - m - nitrobenzenesulphofluoride, p - acetaminobenzenesulphofluoride, 2 - methoxy 5 - acetaminobenzenesulphofluoride, and 3 - acetamino - 4 - methoxybenzensulphofluoride, are prepared by reacting the corresponding sulphochlorides with potassium fluoride.  Reduction of the nitro compounds and of p-methyl-m-nitrobenzenesulphofluoride in ethyl alcohol with hydrogen in presence of Raney nickel yields the corresponding amino compounds.  m - Nitro - p - aminobenzenesulphofluoride is prepared by boiling with a methanol solution of HCl m - nitro - p - acetylaminobenzenesulphofluoride, itself prepared by nitrating p-acetylaminobenzenesulphofluoride.  p - Methoxy - m - aminobenzenesulphofluoride, 2 - methoxy - 5 - aminobenzenesulphofluoride, and 2 : 5 - dimethoxy - 3 - aminobenzenesulphofluoride are similarly prepared from the corresponding acetylamino compounds.  p - Myristoylamino - m - aminobenzenesulphofluoride is prepared by reducing with hydrogen in presence of Raney nickel the corresponding m-nitro compound, itself prepared by reacting with myristoyl chloride the corresponding p-amino-m-nitro compound.  m - (p - n - Hexadecyloxybenzoylacetamino) - benzenesulphofluoride is prepared by refluxing together m - aminobenzenesulphofluoride and ethyl p - n - hexadecyloxybenzoylacetate in toluene or xylene. p-(p-n-hexadecyloxybenzoylacetamino) - benzenesulphofluoride, o - (p - n - hexadecyloxybenzoylacetamino) - benzenesulphofluoride, p - methoxy - m - (p - n - hexadecyloxybenzoylacetamino) - benzenesulphofluoride, p - methyl - m - (p - n - hexadecyloxybenzoylacetamino) - benzenesulphowuoride, p - (p - dodecyloxybenzoylacetamino) - benzenesulphofluoride, m - [p - (p - iso-octylphenoxyethoxy) - benzoyl] - acetaminobenzenesulphofluoride, p - myristoylamino-m - benzoylacetaminobenzenesulphofluoride, 3 - (p - n - hexadecyloxybenzoylacetamino) - 6 - methoxybenzenesulphofluoride, 3 - (p - n - hexadecyloxybenzoylacetamino) - 4 - chlorobenzenesulphofluoride, 3 - (p - n - hexadecyloxybenzoylacetamino) - 4 - methylbenzenesulphofluoride, 3 - (p - n - hexadecyloxybenzoylacetamino) - 2 : 5 - dimethoxybenzenesulphofluoride, m - (4 - n - hexadecyloxynaphthoylacetamino) - benzenesulphofluoride, m - (4 - n - hexadecyloxy - 3 : 5 - dichlorobenzoylacetamino) - benzenesulphofluoride, m - (a  - n - hexadecyloxy - b  - naphthoylacetamino) - benzenesulphofluoride, m - (p - n - hexadecyloxy - m - methoxybenzoylacetamino) - benzenesulphofluoride, p - (n - hexadecyloxy - m - methoxybenzoylacetamino) - benzenesulphofluoride, and N - (p - hexadecylbenzoylacetyl) - metanilic acid fluoride are similarly prepared.  m - (m - Palmitoylaminobenzoylacetamino) - benzenesulphofluoride is prepared by condensing with palmitoyl chloride m-(m-aminobenzoylacetamino)-benzenesulphofluoride, prepared by reducing with hydrogen in presence of Raney nickel m - (m - nitrobenzoylacetamino) - benzenesulphofluoride, itself prepared by condensing m-aminobenzenesulphofluoride with ethyl m-nitrobenzoylacetate.  m - (m - a  - n - Hexadecylsuccinylaminobenzoylacetamino) - benzenesulphofluoride is similarly prepared.  p-n-Hexadecyloxybenzoic acid is prepared by adding n-hexadecyl bromide to a boiling solution of methyl p-hydroxybenzoate and sodium in ethylene glycol monomethyl ether and saponifying the methyl p-n-hexadecyloxybenzoate formed by refluxing with aqueous potassium hydroxide.  a  - n - Hexadecyloxy - b  - naphthoic acid is similarly prepared.  Methyl p - n - hexadecyloxybenzoylacetate is obtained by boiling p-n-hexadecyloxybenzoic acid and thionyl chloride together to obtain p - n - hexadecyloxybenzoyl chloride, reacting this with the sodium derivative of ethyl acetoacetate, adding a solution of sodium in methanol, and finally adding to boiling methanol. Methyl a  - n - hexadecyloxy - b  - naphthoylacetate, methyl 4 - n - hexadecyloxy - 3 - methoxybenzoylacetate and methyl p-hexadecylbenzoylacetate are similarly prepared.  Sodium m - (p - n - hexadecyloxybenzoylacetamino) - benzenesulphonate is prepared by adding aqueous sodium hydroxide to a refluxing acetone solution of m - (p - n - hexadecyloxybenzoylacetaminobenzenesulphofluoride and continuing boiling.  Sodium 3-(p-n-hexadecyloxybenzoylacetamino) - 4 - methoxybenzenesulphonate, sodium N - (a  - n - hexadecyloxy - b  - naphthoylacetyl) - metanilate, sodium N - (p - n - hexadecyloxybenzoylacetyl) - orthanilate, sodium N - (p - n - hexadecyloxy - m - methoxybenzoylacetyl) - metanilate, sodium p - myristoylamino-m - benzoylacetaminobenzenesulphonate, and sodium N - (p - hexadecylbenzoylacetyl) - metanilate are similarly prepared.  3 - Acetamino - 4 - methoxybenzenesulphochloride is prepared by reacting dry o-acetanisidide with chlorosulphonic acid.  3 - Methoxy - 4 - n - hexadecyloxybenzaldehyde is prepared by adding n-hexadecyl bromide dropwise to a heated mixture of sodium in ethylene glycol monomethyl ether, vanillin in ethylene glycol monomethyl ether, and potassium iodide.  3 - Methoxy - 4 - n - hexadecyloxybenzoic acid is prepared by oxidizing 3-methoxy-4-n-hexadecyloxybenzaldehyde in pyridine with warm potassium permanganate solution.  Hexadecylbenzene is prepared by reducing palmitoylbenzene with hydrogen in presence of copper barium chromite catalyst.  p-Hexadecylphenyl methyl ketone is prepared by reacting hexadecylbenzene with acetyl chloride. p-Hexadecylbenzoic acid is prepared by oxidizing p-hexadecylphenyl methyl ketone with sodium bromite.