Patent GB-678291-A (GB)
Title: Fluorescent agents derived from bis [1,3,5-triazyl (6)] diaminostilbene 2,2-disulfonic acid
IPC: D06L3/12
Filed: 1949-08-18
Abstract: Fluorescent brightening agents of the formula <FORM:0678291/IV (b)/1> are made by reacting under substantially neutral conditions 2 mols. of cyanuric chloride with 1 mol. of 4 : 41-diaminostilbene-2 : 21-disulphonic acid and treating the product with 2 mols. of morpholine and 2 mols. of sulphoaniline or chloraniline or 2 additional mols. of morpholine; thus Z is sulphophenyl-amino, chlorophenyl-amino or morpholino.  Examples describe the preparation of compounds where Z is p-sulphophenylamino, o-chlorophenylamino and morpholino; these are obtained as sodium salts, from which the free acids are produced by acidification.  Specification 645,413 is referred to.  The Specification as open to inspection under Sect. 91 refers to similar compounds derived from 4 : 41-diaminostilbene sulphonic and carboxylic acids in general, e.g. the 3 : 31-disulphonic acid, 2 : 21 : 6 : 61-tetrasulphonic acid, 2 : 21-dicarboxylic acid and 3 : 31-dicarboxylic acid.  Z is a basic group -NXY where X and Y may vary widely.  If X is hydrogen, Y may be hydrogen, alkyl or substituted alkyl (e.g. methyl, ethyl, isopropyl, n-butyl, sec-butyl, dodecyl, ethylol, methylol), aryl (e.g. phenyl, tolyl, chlorophenyl, anisyl, sulphophenyl, xylyl, naphthyl, anthracyl), heterocyclic (e.g. pyrimidyl, thiazolyl, benzthiazolyl, tetrazolyl) or alicyclic (e.g. cyclohexyl, tetrahydronaphthyl). If X is alkyl or substituted alkyl (e.g. methyl, ethyl, propyl, ethylol, methylol), Y may be alkyl or substituted alkyl (e.g. methyl, ethyl, propyl, butyl, ethylol, methylol), aryl (e.g. phenyl, tolyl, chlorophenyl, anisyl, naphthyl) or heterocyclic (e.g. pyrimidyl, thiazolyl, benzthiazolyl).  Alternatively X and Y may form a ring, e.g. of pyrimidine, morpholine or thiomorpholine.  Such compounds are made by the above method using the appropriate reactants.  Further examples are given of the preparation of derivatives of 4 : 41-diaminostilbene-2 : 21-disulphonic acid of the above general formula where Z is anilino, o- and p-anisidino and m-and p-toluidino. Other specified reactants for introducing the Z groups are methylamine, dimethylamine, ethylamine, isopropylamine, n-and sec-butylamines, laurylamine, stearylamine, ethanolamine, naphthylamine, anthracene amine, pyrimidine and benzthiazole.  This subject-matter does not appear in the Specification as accepted.ALSO:Fluorescent brightening agents comprise compounds of the formula <FORM:0678291/IV (c)/1> where Z is sulphophenyl-amino, chlorophenylamino or morpholino. These are used (e.g. as sodium salts) for increasing the whiteness or brightening the colour of fabrics, e.g. by incorporating them in washing compositions, bleaching processes and discharge pastes. They may be applied to cellulosic fibres, wool or nylon. Specification 645,413 is referred to.  The Specification as open to inspection under Sect. 91 refers to similar compounds derived from 4 : 41-diaminostilbene sulphonic and carboxylic acids in general, e.g. 3 : 31-disulphonic, 2 : 21 : 6 : 61-tetrasulphonic and 2 : 21- and 3 : 31-dicarboxylic acids.  Z may be any group -NXY, where X is hydrogen or an aliphatic, aromatic, heterocyclic or alicyclic radical and Y is hydrogen or an aliphatic, aromatic or heterocyclic radical; alternatively, X and Y may together form a ring.  Many possible groups for X and Y are listed.  This subject-matter does not appear in the Specification as accepted.