Patent GB-1503798-A (GB)
Title: Photographic silver halide material containing a colour-providing o-sulphonamido naphthol
IPC: G03C8/10
Filed: 1975-09-03
Abstract: 1503798 Photographic and intermediate monoazo dyes containing ballasting groups EASTMAN KODAK CO 3 Sept 1975 [4 Sept 1974] 36308/75 Heading C4P [Also in Divisions G2 and C2] 3 - Hydroxy - 4 - [p - (1 - phenyl - 3 - methyl - 5 - pyrazolon - 4 - yl)azobenzenesulphonamido] - 2 - [4<SP>1</SP> - (2,4, - di - tert. - pentylphenoxy - n - butyl]naphthamide is prepared by adding 4 - (p - chlorosulphonylphenylazo) - 1 - phenyl - 3 - methyl - 5 - pyrazolone to 4 - amino - 3 - hydroxy - 2 - [4<SP>1</SP> - (2,4 - di - tert. -pentylphenoxy)n - butyl] - naphthamide in dry pyridine at 10 C. 3 - Octadecyloxy - I - [p - (I -phenyl - 3 - methyl - 5 - pyrazolon - 4 - yl)azobenzenesulphonamido] - 2 - naphthol, 1 - [4 - actamido - 5 - hydroxy - 6 - (o - methoxyphenylazo)- naphthalene - I - sulphonamido] - 3 - octadecyloxy -2 - naphthol, 3 - octadecanethio - 1 - [p - (1 - phenyl - 3 - methyl - 5 - pyrazolon - 4 - yl)azobenzenesulphonamido] - 2 - naphthol, 1 - [4 - acetamido - 5 -hydroxy - 6 - (o - methoxyphenylazo) - naphthalene -1 - sulphonamido] - 3 - octadecanethio - 2 - naphthol, 3 - octadecanesulphinyl - I - [p - (1 - phenyl - 3 -methyl -5 - pyrazolon - 4 - yl)azobenzenesulphonamido] - 2 - naphthol, 3 - octadecanesulphonyl - 1 - [p -(1 - phenyl - 3 - methyl - 5 - pyrazolon - 4 -yl)azobenzenesulphonamido]naphthol and 1 - [4 -acetamido - 5 - hydroxy - 6 - (o - methoxyphenylazo)naphthalene - 1 - sulphonamido] - 6 - (N - 4' - (2,4 - di - tert. - pentylphenoxy)butylsulphamyl] - 2 -naphthol are prepared similarly. 1 - (p - Methoxy -phenylazo) - 3 - octadecyloxy - 2 - naphthol is prepared by adding a diazonium salt solution prepared from p-anisidine in water containing concentrated HCl and aqueous sodium nitrite to 3-octadecyloxy-2-naphthol, NaOH, methanol and tetrahydrofuran at 0-5 C. I - (p - Methoxyphenylazo) - 3 - octadecane - thio - 2 - naphthol, I - (p -methoxyphenylazo) - 3 - octadecanesulphinyl - 2 -naphthol, 1 - (p - methoxyphenylazo) - 3 -octadecanesulphonyl - 2 - naphthol, 4 - (N,N -didodecylsulphamyl) - 2 - (p - methoxyphenylazo) - 1 - naphthol and 8 - hexadecanesulphonamido - 1 - (p -methoxyphenylazo) - 2 - naphthol are prepared similarly. 2 - [4 - Acetamido - 5 - hydroxy - 6 - (o -methoxyphenylazo)naphthalene - 1 - sulphonamido] - 4 - (N,N - didodecyl - sulphamyl) - I - naphthol is prepared by hydrogenating 4 - (N,N - didodecylsulphamyl) - 2 -(p - methoxyphenylazo) - 1 - naphthol in tetrahydrofuran containing palladium/carbon catalyst and adding 4-acetamido - 5 - hydroxy - 6 - (o -methoxyphenylazo)naphthalene - 1 - sulphonyl chloride to a cooled solution of the product in pyridine. 1 - (p - Methoxyphenylazo) - 6 - [N - (o -tetradecyloxyphenyl) - sulphamyl] - 2 - naphthol is prepared by refluxing 2 - benzenesulphonyloxy - 6 - [N - (o - tetradecyloxyphenyl)]naphthalene sulphonamide and NaOH in methanol, cooling to -10 C. and adding tetrahydrofuran, and adding a diazonium salt solution prepared from p-anisidine in water containing concentrated HCl and aqueous sodium nitrite. 1 - [p - (1 - Phenyl - 3 - methyl - 5 -pyrazolon - 4 - yl)azobenzenesulphonamido] - 6 - [N - (o - tetradecyloxyphenyl) sulphamyl] - 2 - naphthol is prepared by adding aqueous sodium dithionite to boiling 1 - (p - methoxy - phenylazo)- 6 - [N - (o -tetradecyloxyphenyl)sulphamyl] - 2 - naphthol in alcohol, and adding to the product in pyridine at 0 C. 4 - (p - chlorosulphonylphenylazo) - 1 - phenyl - 3 - methyl - 5 - pyrazolone. 1 - [4 - Acetamido - 5 - hydroxy - 6 - (o - methoxyphenylazo)naphthalene - 1 - sulphonamido] - 6 - [N - (o - tetradecyloxyphenyl) sulphamyl] - 2 - naphthol, 1 - [p - (1 - phenyl - 3 - methyl - 5 - pyrazolon - 4 - yl)azobenzenesulphonamido] - 6 - [N-4<SP>1</SP> - (2,4 - di - tert. - pentylphenoxy)butylsulphamyl] - 2 - naphthol, 1 - [4 - acetamido - 5 - hydroxy - 6 - (o - methoxyphenylazo) - naphthalene - 1 - sulphonamido] - 8 - hexadecanesulphonamido - 2 - naphthol and 1 - [4 - acetamido - 5 - hydroxy - 6 - (o - methoxyphenylazo)naphthalene - 1 - sulphonamido] - 6 - [N - # - (2,4 - di - tert. - pentylphenoxy)butylsulphamyl] - 2 - naphthol are prepared similarly. 1 - (p - Methoxy - phenylazo) - 6 - [N - 4' - (2,4 - di - tert. - pentylphenoxy)butylsulphamyl] - 2 - naphthol is prepared by adding 2 - benzenesulphonyloxy - 6 - naphthalene sulphonyl chloride to 4 - (2,4 - di - tert. - pentylphenoxy)butyl amine in pyridine at 0 C., refluxing the product in methanol containing NaOH, cooling and diluting with tetrahydrofuran and adding at 0 C. a diazonium salt solution prepared from p-anisidine in water containing concentrated HCl and aqueous sodium nitrite. 1 - (p - Methoxyphenylazo) - 6 - [N - # - (2,4 - di - tert. - pentylphenoxy)butylsulphamyl] - 2 - naphthol is prepared similarly. 3 - Hydroxy - 4 - (p - methoxyphenylazo) - 2 - [4' - (2,4 - di - t. - pentylphenoxy) - n - butyl] - naphthamide is prepared from diazotized p-anisidine and the appropriate 3-hydroxy-2-naphthamide.