Patent GB-990102-A (GB)
Title: Derivatives of 1,2,3-triazolyl-3-phenylcoumarin
Inventor: FLECK FRITZ
IPC: D06L4/60
Filed: 1963-06-04
Abstract: The invention comprises compounds of the formula <FORM:0990102/C2/1> wherein A represents the residue of a dihydroaryl group linked on two vicinal carbon atoms to two of the nitrogen atoms of the triazole ring, which residue may be substituted by a non-ionogenic group and R1 represents a hydrogen atom or a non-ionogenic group. Specific examples of non-ionogenic substituents are alkyl, alkoxy and cyano groups and halogen atoms.  The compounds are made by diazotizing an amine of the formula <FORM:0990102/C2/2> and reacting the resultant diazonium salt with a primary aromatic amine capable of coupling in the position orthoto the primary amine group, and oxidizing the resulting o-amino-azo dye to the corresponding 1,2,3-triazole derivative. Suitable coupling components are amino- and diamino-benzenes, aminonaphthalenes, aminoacenaphthenes, aminotriazoles, aminopyrazoles and aminoindazoles; when a polyamino is used as the coupling component it is necessary to acylate the amino groups remaining after triazolizing the azodye, or to remove or replace them by diazotization.  The preferred coupling components contain sulphonyl groups which are split off during coupling. Suitable agents for effecting the oxidation of the azo-dye are the alkali metal hypohalogenites, cupric salt complexes of inorganic or organic cupric salts and nitrogeneous bases.  The compounds of the invention are used as optical brighteners (see Divisions B5, C4 and D1).  In the invention is illustrated numerous examples.ALSO:o-Amino-azo dyes are obtained by diazotizing an amine of the formula <FORM:0990102/C4-C5/1> and coupling the resulting diazonium salt with a primary aromatic amine capable of coupling in vicinal relation to the primary amino group. Suitable coupling components are aminobenzenes, diaminobenzenes, aminonaphthalenes, aminoacenaphthenes, aminobenztriazoles, aminopyrazoles and aminoindazoles which may be further substituted by non-ionogenic groups, e.g. alkyl, alkoxy or cyano groups or halogen atoms, or by sulpho radicals which are split off on the formation of the dyestuff.ALSO:Woven materials are optically brightening by treatment with a compound of the formula <FORM:0990102/D1-D2/1> wherein A represents a dihydroaryl residue, which may be substituted by non-ionogenic groups, and R1 represents hydrogen or a non-ionogenic group.  The compounds are especially useful for treating fibres of, e.g. polyesters, polyamides, polyurethanes, polyacrylonitrile, polyvinylchloride and also acetate silk, cellulose triacetate and natural polyamides and particularly valuable for polyesters of the polyglycolterphthalate type.  The compounds may be used alone or with known brighteners and can be used in aqueous baths, preferably in the presence of dispersing agents or solvents, in washing baths and in chlorite bleaching baths.  They may also be applied according to the Foulardtherm process.  Examples (11), (12), (15) and (16) describe the treatment of a polyester, a cotton and polyester, an acetate silk and a second polyester woven material with 3-phenyl-7-naphthotriazolylcoumarin.  In Examples (14) a polyester fabric is treated with 3-phenyl-7-acenaphthotriazolylcoumarin.