GB807899A - New photographic developers - Google Patents

Abstract

The invention comprises compounds of the general formula <FORM:0807899/IV (b)/1> where R is C1-C4 alkyl or hydroxyalkyl, R1 is C1-C6 alkyl substituted in the omega position by an hydroxyl group, X is hydrogen or C1-C4 alkyl or alkoxy group, and n = 0 or 1, R may be e.g. methyl, ethyl, propyl, butyl, or the corresponding hydroxy radical, R1 may be hydroxymethyl, beta-hydroxyethyl, or delta hydroxybutyl, X may be e.g. methyl, methoxy, ethoxy or butoxy. The compounds of the invention may be prepared by reducing the corresponding 4 - nitroso - N:N - disubstituted aniline or 4-nitroso - N:N - disubstituted 3 - substituted aniline which in turn may be prepared by the action of nitrous acid on the corresponding N:N-disubstituted aniline or N:N-disubstituted 3-substituted aniline. The N:N-disubstituted aniline or N:N-disubstituted 3-substituted aniline is prepared from the corresponding 3-substituted aniline or aniline itself and the corresponding o -bromoalkyl acetate, or in the case of N-ethyl-N-(omega hydroxyhexy)-m-toluidine, from 6-bromohexan-1-ol and N-ethyl-m-toludine. The compounds of the invention may be isolated in the form of their salts, e.g. with sulphuric or naphthalene 1:5 disulphonic acid, or in the form of their substituted anils, e.g. by condensing with benzaldehyde-2-carboxylic acid, or 4-chlorobenzaldehyde-2-sulphonic acid and isolating the sodium salts therefrom. The invention further comprises a composition of the compounds of the invention in an aqueous alkaline solution. Examples are given of the preparation of the following compounds and their corresponding substituted aniline starting materials: (1) 4-amino-3-methyl - N - ethyl - N - (gamma - hydroxypropyl) aniline and the sodium salt of 3-methyl-4-(41-chloro - 21 - sulphobenzylidene - amino) - N-ethyl-N-(gamma-hydroxypropyl) aniline, and of the starting materials, viz. N-ethyl-N-(gamma-hydroxypropyl) m-toluidine and the corresponding nitroso compound; (2) 4-amino-3-methyl-N - ethyl - N - (delta - hydroxybutyl) aniline and the sodium salt of 3-methyl-4-(41-chloro-21-sulphobenzylideneamino) - N - ethyl - N - (delta-hydroxybutyl) aniline; (3) 4-amino-3-methyl-N-ethyl N-(omega-hydroxyl-hexyl) aniline and the corresponding sodium salt of its anil with 4-chlorobenzaldehyde-2-sulphonic acid; (4) 4-amino - 3 - methyl - N1N1 - di - (delta - hydroxybutyl) aniline; (5) 4 - amino - N1N1 - di-(gamma - hydroxypropyl) aniline; (6) 4-amino - N:N - di - (delta - hydroxybutyl) aniline; (7) 4 - amino - N:N - di - (epsilon-hydroxypentyl) aniline; (8) 4 - amino - 3-methoxy - N:N - di - (epsilon - hydroxypentyl) aniline. The preparation of the 1:5 naphthalenedisulphonate of the latter five compounds is also described. The epsilon-bromopentyl acetate used in the preparation of compound (7) above is prepared by reacting acetyl bromide and tetrahydropyran in the presence of anhydrous zinc chloride.