Patent GB-1019785-A (GB)
Title: Improvements in or relating to 1,2,3-triazole derivatives
Inventor: FLECK FRITZ
IPC: C07D487/04
Filed: 1964-10-09
Abstract: O-amino-azo dyestuffs are obtained by diazotizing a primary amine of formula <FORM:1019785/C4-C5/1> where R1, R2 and R3 are each independently hydrogen or a non-ionogenic substituent, e.g. alkyl or alkoxy, and coupling the resulting diazonium salt with a primary aromatic amine or heterocyclic amine of aromatic character. 1,2,3-Triazole derivatives of 3-phenylcoumarin of formula <FORM:1019785/C4-C5/2> wherein A designates a substituent selected from dihydroaryl and dihydroheteroaryl radicals linked on 2 vicinal carbon atoms to the triazole ring as shown in said formula and such radicals substituted by non-ionogenic substituents are added to dry cleaning solvents (trichloro-ethylene /chlorobenzene in Example 13) as optical brightening agents for the articles cleaned.ALSO:1,2,3-Triazole derivatives of 3-phenylcoumarin of formula <FORM:1019785/C3/1> wherein A designates a substituent selected from dihydroaryl and dihydroheteroaryl radicals linked on 2 vicinal carbon atoms to the triazole ring as shown in said formula and such radicals substituted with a non-ionogenic substituent, and each of R1, R2 and R3 is selected from hydrogen atoms and non-ionogenic substituents, are incorporated into polymers as optical brightening or marking agents. Specified substrates include films, pressed articles, castings or fibres of polyesters, polyamides, polyurethanes, polyacrylonitrile, polyvinyl chloride, polyvinylidene chloride and polyolefines.  The triazoles may be incorporated in the plastic material before shaping, as such or in softeners, or may be added during the polymerization process (e.g. in polyester formation). Titanium dioxide may be present.ALSO:The invention comprises 1,2,3-triazole derivatives of 3-phenylcoumarin of formula <FORM:1019785/C2/1> wherein A designates a substituent selected from dihydroaryl and dihydroheteroaryl radicals linked on 2 vicinal carbon atoms to the triazole ring as shown in said formula and such radicals substituted with a non-ionogenic substituent, and each of R1, R2 and R3 is selected from hydrogen atoms and non-ionogenic substituents. Substituent groups include alkyl, alkylene, alkoxy, halogen, dimethylsulphonamide, cyano and acylamino.  The compounds are prepared by diazotizing a primary amine of formula <FORM:1019785/C2/2> coupling with a primary aromatic amine or heterocyclic amine of aromatic character capable of coupling in vicinal relation to a primary amino group and oxidizing the resulting o-amino-azo dyestuff to the corresponding 1,2,3-triazole, e.g. by means of a complex of a copper II salt of an organic or inorganic acid and a nitrogenous base or an alkali metal halogenite in an organic solvent.  The primary aromatic amine may contain a sulpho or sulphomethyl radical which is eliminated under the reaction conditions.  A polyamine may be used, but it is then necessary to acylate, remove or replace the amino radicals remaining after triazolizing the dyestuff.  The products are optical brightening agents.ALSO:1, 2, 3-Triazole derivatives of 3-phenylcoumarin of formula <FORM:1019785/D1-D2/1> wherein A designates a substituent selected from dihydroaryl and dihydroheteroaryl radicals linked on 2 vicinal carbon atoms to the triazole ring as shown in said formula and such radicals substituted with a non-ionogenic substituent, and each of R1, R2 and R3 is selected from hydrogen atoms and non-ionogenic substituents, are used as optical brightening or marking agents.  Specified materials treated include textiles and fibres of polyesters, polyamide, polyurethane, polyacrylonitrile, polyvinylchloride, polyvinylidene chloride, polyolefines, acetate silk, cellulose triacetate and cotton/polyester mixture.  The compounds may be applied from organic solutions, e.g. in drycleaning, from emulsions of organic solvents or carriers in which they are dissolved or from aqueous dispersion.  They may be added to chemical bleaching baths, e.g. of sodium chlorite/formic acid.  The sodium salt of dioctylphenylpolyglycol ether of hydroxyacetic acid may be present in aqueous dispersions.