GB1028923A - Naphthalene-substituted heterocyclic compounds - Google Patents

Abstract

Soaps or detergents are brightened by incorporating therein a compound of formula <FORM:1028923/C4-C5/1> where R and R1 are hydrogen, alkoxy, aralkoxy, aryloxy or acyloxy (not both being hydrogen), A is N, CH or CCl, and X and Y are halogen. amino, substituted amino, alkoxy, substituted alkoxy, aryloxy, mercapto or substituted mercapto (see Division C2).ALSO:The invention comprises the compounds of formula <FORM:1028923/C2/1> where R and R1 are hydrogen, alkoxy, aralkoxy, aryloxy or acyloxy (not both being hydrogen), A is N, CH or CCl, and X and Y are halogen, amino, substituted amino, alkoxy, substituted alkoxy, aryloxy, mercapto or substituted mercapto; the production of compounds in which X and Y are halogen by reacting a cyanuric halide or 2,4,6-trihalogenopyrimidine with an approximately equimolecular amount of a naphthalene having alkoxy, aralkoxy or aryloxy substituents in the 1 and/or 3 positions in the presence of a Friedel-Crafts catalyst; and the production of compounds in which X and/or Y is substituted amino, alkoxy, substituted alkoxy, aryloxy or substituted mercapto by reacting the compounds with X and Y as halogen with an amine, alcohol, phenol or mercaptan (or two in succession) in the presence of an acid binding agent. 2,4,5,6-Tetrachloropyrimidine may also be used as starting material. Other methods specified and/or exemplified are the alkylation or acylation of the products of Specification 1,028,922; heating the dichloro-compound with the sodium derivative of an alcohol; or with sodium phenate followed by heating the diphenoxy compound with excess of an alcohol and a catalytic amount of the corresponding sodium alkoxide; reacting the dichloro compound with NH3; acylating an amino compound; reacting the dichloro compound with H2S, and the product with dimethyl sulphate. Specified groups for R and R1 are methoxy, ethoxy, higher alkoxy, acetoxy, chloroacetoxy, higher acyloxy, benzyloxy and phenoxy; and for X and Y, chloro, bromo, amino, alkylamino, arylamino, dialkylamino, b -hydroxyethylamino, bis-(b -hydroxyethyl)-amino, alkoxy, b -hydroxyethoxy, aryloxy, 4-methoxyphenoxy, alkyl mercapto and arylmercapto. Water-soluble products are obtained by condensing the mono- or dichloro compound with an arylamine sulphonic acid such as sulphanilic, or with ethanolamine followed by sulphating or acetylating. The products of the invention are whitening agents (see Division D1).ALSO:Polymeric materials such as polyhexamethylene adipamide, polyethylene terephthalate, polyurethanes, polyacrylonitrile and hydrolysed polyacrylonitriles, polymethyl methacrylate, polystyrene, polyethylene, and polypropylene are brightened by incorporating into the molten or plasticized polymer a compound of formula <FORM:1028923/C3/1> where R and R1 are hydrogen, alkoxy, aralkoxy, aryloxy or acyloxy (not both being hydrogen), A is N, CH or CCl and X and Y are each halogen, amino, substituted amino, alkoxy, substituted alkoxy, aryloxy, mercapto or substituted mercapto (see Division C2).