Patent GB-696296-A (GB)
Title: Manufacture of new derivatives of 4:4-diaminostilbene-disulphonic acid-(2:2)
Filed: 1950-10-19
Abstract: The invention comprises compounds of the formula <FORM:0696296/IV (b)/1> where w and z are amino groups in which at least one hydrogen atom is replaced by an unsubstituted alkyl group, a dialkylaminoalkyl group or a heterocyclic residue.  These are made by (1) reacting 2 mols. of cyanuric chloride in any order with one mol. of 4 : 41-diaminostilbene - 2 : 21 - disulphonic acid or salt thereof and 2 mols. (same or different) of an alkylamine, dialkylamine, N1 : N1 - dialkyl - alkylene diamine or heterocyclic amine, or (2) reacting 1 mol. of cyanuric chloride in any order with 1 mol. of 4-nitro-41-aminostilbene-2 : p  21-disulphonic acid and 1 mol. of an amine as above; the nitro group is then reduced to amino and a further mol. of cyanuric chloride reacted in any order with 1 mol. of the product and 1 mol. of an amine as above; instead of the nitro group there may be present another group convertible to amino, e.g. acylamino. The products form salts with alkali metals, ammonia and amines. Examples describe the preparation of sodium salts of compounds of the above formula where w and z are both methylamino or both ethylamino.  Preferably w and z represent alkylamino groups where the alkyl residue or residues contain 1-4 carbon atoms. Suitable groups are methylamino, ethylamino, propylamino, butylamino, dimethylamino, dipropylamino, dibutylamino, dimethylamino-ethylamino, isopropylamino, isobutylamino, di-isobutylamino, pipecolino, pyrrolidino, tetrahydroquinolino, morpholino, thiazolyl-2-amino and tetrazolyl-5-amino.  The process of Specification 645,413 is disclaimed.  Specification 624,052 also is referred to.ALSO:Stilbene derivatives of the formula <FORM:0696296/IV (c)/1> and salts thereof are used as fluorescent brightening agents; W and Z are amino groups in which at least one hydrogen atom is replaced by an unsubstituted alkyl group, a dialkyl-aminoalkyl group or a heterocyclic residue. The compounds may be applied in aqueous solution to vegetable or animal fibres, such materials being white, dyed or printed.  They are also applicable to fibres and films of synthetic condensation and polymerization products, e.g. polyamides and regenerated cellulose. They may be applied in conjunction with washing and bleaching agents, e.g. soaps, salts of sulphonated 2-higher-alkyl-benzimidazoles, salts of monocarboxylic esters of 4-sulphophthalic acid with higher fatty alcohols, fatty alcohol sulphonates, or condensation products of higher fatty acids with aliphatic hydroxy- or aminosulphonic acids. In examples: (1) cotton is treated with a solution of the disodium salt of 4 : 41 - bis - (2 - ethylamino - 4 - chloro - 6 - triazinyl-amino) - stilbene - 2 : 21 - disulphonic acid; (2) wool is treated with a solution of formic acid and the compound of (1); (3) textiles are washed with a soap-like mass obtained by mixing fused soap (60 per cent fatty acid) with the compound of (1).  Other suitable compounds are mentioned. Specifications 624,052 and 645,413 are referred to.ALSO:Stilene derivatives of the formula <FORM:0696296/III/1> and salts thereof are used as fluorescent brightening agents; w and z are amino groups in which at least one hydrogen atom is replaced by an unsubstituted alkyl group, a dialkyl-aminoalkyl group or a heterocyclic residue.  They may be incorporated in washing compositions for textile materials.  An example is given of a preparation obtained by adding to a fused soap mass (60 per cent fatty acid) a small amount of the disodium salt of 4 : 41-bis-(2-ethylamino-4 - chloro - 6 - triazinylamino) - stilbene - 2:21-disulphonic acid and allowing the mixture to cool.  The stilbene derivatives may be mixed with other synthetic washing agents such as salts of sulphonated 2-higher-alkyl benzimidazoles, salts of monocarboxylic esters of 4-sulphophthalic acid with higher fatty alcohols, fatty alcohol sulphonates, or condensation products of higher fatty acids with aliphatic hydroxy-or amino-sulphonic acids.