GB830306A - Salts of arylguanidines with aryldiazosulfonates or with aryltetrazodisulphonates - Google Patents

Abstract

The invention comprises aryl guanidine salts of diazosulphonates soluble in organic solvents, having the general formula <FORM:0830306/IV (b)/1> wherein Ar is an aromatic radical and R is hydrogen or an aromatic radical, at least two R's being an aromatic radical and at least one R being hydrogen. The invention also comprises aryl guanidine salts of tetra-azo-disulphonates. The salts are photo-sensitive and suitable for use in the manufacture of paper and metal lithographic plates. The salts are prepared by reacting an aqueous solution of an alkali-metal aryldiazosulphonate or aryltetrazodisulphonate with an arylguanidine acetate. In Example 1, a solution of 1,3-di-o-tolylguanidine in aqueous acetic acid is added, with stirring at 35-40 DEG C., to a solution of sodium p-ethoxybenzenediazosulphonate in water containing a low concentration of acetic acid. Yellow crystals having the probable structure <FORM:0830306/IV (b)/2> are precipitated. In Example 2, an acetic acid solution of 1,3-di-o-tolylguanidine is added to an aqueous solution of sodium 3-chloro-4,6-dimethoxybenzenediazosulphonate. A red oil is formed which is washed with water and allowed to stand. After 4 days the oil changes to yellow crystals of a salt having a chlorine atom and two methoxy groups in the benzene ring of the diazosulphonate part of the molecule. Example 5 describes the preparation of orange crystals having the structure <FORM:0830306/IV (b)/3> by treating an aqueous solution of sodium p-acetamidobenzenediazosulphonate with an aqueous solution of 1,3-di-o-tolylguanidine acetate. In Example (6), 2,21-methylenebis-(4-nitrophenol) is treated with ethyl sulphate and alkali; and the resulting methylenebis-(4-nitrophenetole) is reduced to 3,31-methylenebis-(p-phenetidine). The hydrochloride of this base is tetrazotized and converted to the corresponding methylenebis - (4 - ethoxybenzenediazosulphonate). An aqueous solution of the latter is then reacted with an aqueous solution of 1,3-di-o-tolylguanidine acetate whereupon there separates a yellowish-brown mass having the structure <FORM:0830306/IV (b)/4> In Example 7, a solution of N-benzyl-N-ethyl-p - aminobenzenediasonium chloride zinc chloride double salt is treated with sodium sulphite to give the diazosulphonate; and the latter is then reacted with 1,3-di-o-tolyl-guanidine acetate. There is obtained a yellow crystalline product having the structure <FORM:0830306/IV (b)/5> Example 8 describes the preparation of 1,2,3-triphenylguanidine - p - ethoxybenzene - diazosulphonate. A list of aryldiazosulphonates, which may be used for the salt formation, is given. There is also a list of suitable arylguanidines, which includes 1-(p-lauroylaminophenyl)-3-phenylguanidine and 1-(p-dodecyl-sulphamoylphenyl)-3-phenylguanidine.