Patent GB-829788-A (GB)
Title: Stilbene triazoles
IPC: C07D249/06
Filed: 1956-06-14
Abstract: Soap or detergent compositions contain as brightening agent a compound of the formula <FORM:0829788/III/1> where X1 and X2 are carboxylic acid or sulphonic acid, Y is halogen, acylamino, substituted triazinylamino, triazolyl attached via a nitrogen atom or arylo-triazolyl attached via a nitrogen atom, Z1 is H, alkyl, aryl, hydroxyalkyl or esterified carboxyl, and Z2 is H or the same as Z1. An example is given of a mixture of curd soap and the sodium salt of 4-[3-carboxynaphthotriazolyl - 21] - 41 - [triazolyl - 11]-stilbene-2 : 21-disulphonic acid.ALSO:The invention comprises compounds of the formula <FORM:0829788/IV (b)/1> where X1 and X2 are carboxylic acid or sulphonic acid, Y is halogen, nitro, acylamino, substituted triazinylamino, triazolyl (optionally substituted) attached via a nitrogen atom or arylo-triazolyl attached via a nitrogen atom, Z1 is H, alkyl, aryl, hydroxyalkyl or esterified carboxyl, and Z2 is H or the same as Z1.  These are made by reacting a compound of the formula <FORM:0829788/IV (b)/2> with acetylene (substituted by Z1 and Z2 if necessary), followed (if Y is nitro) by reduction to amino and conversion of this to the other groups by known methods; the other groups may, however, be present as such before reaction with the acetylene.  Products are described where Z1 is H, phenyl, methylol or carbomethoxy, Z2 is H or carbomethoxy, and Y is nitro, amino, acetylamino, chloro, phenylureido, 2 : 4-dimethoxybenzoylamino, triazolyl, naphthotriazolyl, 3 - carboxynaphthotriazolyl, 5 - sulphonaphthotriazolyl, 5 : 7 - disulphonaphthotriazolyl, and the following substituted triazinyl - 61 - amino groups: 21 - anilino - 41 chloro, 21 - anilino - 41 - diethanolamino, 21-anilino - 41 - morpholino, 21 - p - toluidino - 41-morpholino and 21 - anilino - 41 - ethanolamino.  Examples are given of the preparation of certain of these compounds, including (1) the preparation of Y=carboxy-naphthotriazolyl by coupling diazotised 4-amino-41-triazolyl-stilbene2 : 21-disulphonic acid with 2-naphthylamine-3-carboxylic acid to give an azo dye and oxidising this with hypochlorite, and (2) condensing in succession 4 - amino - 41 - triazolyl - stilbene - 2 : 21-disulphonic acid, cyanuric chloride, aniline and diethanolamine.  Stilbenes of the second general formula above are made from compounds of the formula <FORM:0829788/IV (b)/3> by diazotization and either treatment with an aromatic sulphonamide or reduction to the hydrazine and treatment of this with nitrous acid.  Examples are given of the former method where X1=X2=sulphonic acid and Y=nitro.ALSO:Compounds of the formula <FORM:0829788/IV(c)/1> are used as brightening agents as solutions in water or organic solvents, with or without detergents; X1 and X2 are carboxylic acid or sulphonic acid, Y is halogen, acylamino, substituted triazinylamino, triazolyl attached via a nitrogen atom or arylotriazolyl attached via a nitrogen atom, Z1 is H, alkyl, aryl, hydroxyalkyl or esterified carboxyl, and Z2 is H or the same as Z1. In examples: (1) an unbleached cotton fabric is warmed in a bath containing sodium chloride or sulphate and the sodium salt of 4-[21-anilino-41-diethanolamino-triazinyl-61 - amino] - 41 - [triazolyl - 11] - stilbene - 2 : 21 - disulphonic acid, and (2) white laundry goods are boiled with a detergent solution containing the sodium salt of 4-[5-sulphonaphthotriazolyl-21] - 41 - [triazolyl - 11] - stilbene - 2 : 21 - disulphonic acid.  Other products are mentioned.  A dye is made by coupling diazotized 4-amino-41 - [triazolyl - 11] - stilbene - 2 : 21 - disulphonic acid with 2-naphthylamine-3-carboxylic acid.