Patent GB-554921-A (GB)
Title: Improvements in photographic light sensitive diazotype materials
IPC: G03C1/54
Filed: 1941-10-15
Abstract: 554,921. Naphthalene derivatives. KODAK, Ltd. Oct. 15, 1941, No. 13285. Convention date, Oct. 15, 1940. [Class 2 (iii)] [Also in Group XX] Methyl 1-naphthol-5-sulphonate is prepared by heating 1-acetoxynaphthalene-5-sulphonyl chloride with excess of methyl alcohol. 5-Benzylamino-1-naphthol is prepared by condensing 5-amino-1-naphthol with benzaldehyde and reducing the Schiff base catalytically or chemically. 5- Acylamino-1-naphthols are prepared (a) by condensing 2 moles of 5-amino-1-naphthol or 2 moles of a 5-alkylamino-1-naphthol with 1 mole of XC1 (where X represents an acyl group) or (b) by condensing 1 mole of the naphthol compound with 1 mole of XC1 in the presence of sodium acetate and acetic acid. The following compounds are prepared by method (a): 2 : 4 - dibromo - 5 - (N - benzyl - N - - naphthalene - # - sulphon) - amino - 1 naphthol, 2 : 4 - dichloro - 5 - (N - benzyl : N - α - naphthoyl) - amino 1 - naphthol, 2 : 4 - dichloro - 5 - (N - benzyl : N - # - naphthoyl) - amino - 1 - naphthol, 2 : 4 - dichloro - 5 - palmitylamino - 1 - naphthol, (halogenation being effected in these four examples by treatment with sulphuryl chloride or bromine), 5 - (N - benzyl - N - n - amylnaphthalene - α (or #) - sulphon) - amino - 1 - naphthol, 5 - (N - benzyl - N - naphthalene - x - sulphon) - amino - 1 - naphthol, 5 - (N - benzyl N - p - - tert. - amylbenzenesulphon) - amino - 1 - naphthol, 5 - (N - benzyl : N - n - valeryl) - amino - 1 - naphthol, and 5 - (p - sulphamylbenzamido) - 1 - naphthol. The following compounds are prepared by method (b) : 5 - (m : m<SP>1</SP> - dinitrobenzoylamino - 1 - naphthol, 5 - lauroylamino - 1 - naphthol, 5 - methylsulphonylamino - 1 - naphthol, and 5 -(p - - nitrobenzamido) - 1 - naphthol. 1 - - Hydroxy 2 - naphthamides are prepared by condensing 1 mole of 1-hydroxy-2-naphthoyl chloride with 2 moles of a compound of formula R-NH-R<SP>1</SP>, (where R and R<SP>1</SP> may be hydrogen, alkyl, or aryl). Examples are 1-hydroxy-2- (N - iso - amyl - N -, phenyl) - naphthamide, 1 - hydroxy - 2 - (N - ethyl : N - α - naphthyl) - naphthamide, 1 - hydroxy - 2 - (N - methyl) - naphthanilide and 1 - hydroxy - 2 - naphthanilide. 5 - (p - - Acylaminobenzamido) - 1 - - naphthols are prepared by condensing a 5-amino-1- naphthol with p-nitrobenzoyl chloride, reducing the nitro group, and then reacting with sodium acetate and XC1 (where X is an acyl group). Halogenation may be effected with sulphuryl chloride or bromine in a suitable solvent. Examples specified are 5 - [p - (p - acetaminobenzenesulphonamido) - benzamido] - 1 - naphthol, and 2 : 4 - dichloro - 5 - [p - - (p - benzamido) - benzamido] - 1 - naphthol. Dipiperidinomethyl - 1 : 5 - dihydroxynaphthalene is prepared by treating 1:5-dihydroxynaphthalene with formaldehyde and piperidine. 1-Naphthol - 3 : 6 di - (sulphon - N - methylanilide) is prepared by condensing 1- naphthol-3:6-disulphonic acid with sodium acetate and acetic anhydride, treating the product with PC1 5 , and the latter product with methylaniline and sodium acetate, and then hydrolysing with sodium hydroxide. 1 - - Naphthol 4 - - sulphon - ( N - ethyl - α- naphthalide) is prepared by condensing 4- propionyloxynaphthalenesulphonyl chloride with α-ethylnaphthylamine and sodium acetate and hydrolysing with sodium hydroxide. 2 - n valeryl - 1 - naphthol is prepared by heating α-naphthol with valeric anhydride and zinc chloride. 4 - n - valeryl - 1 - naphthol is prepared by condensing α-methoxynaphthalene with valeryl chloride and aluminium chloride.