Patent GB-981527-A (GB)
Title: New vat dyestuffs containing thioether, alkyl-sulphone or aryl-sulphone groups and process for their manufacture and use
IPC: C09B5/28
Filed: 1961-10-27
Abstract: The invention comprises vat dyes containing at least two anthraquinone residues or a vattable chromophore comprising at least four fused rings, which contain at least one acid group imparting solubility in water and at least one thioether, alkyl sulphone or aryl sulphone group. The dyes are prepared by introducing at least one thioether, alkyl sulphone or aryl sulphone group, by condensation or acylation, into a vat dye containing at least two anthraquinone residues or a vattable chromophore comprising at least four fused rings, with the simultaneous, prior or subsequent introduction of at least one water-solubilizing group.  The dyes may be prepared by a number of processes.  Thus a suitable vat dye containing an acylatable amino group and an alkyl- or aryl-sulphone or thioether group may be treated with an acylating agent containing a solubilizing group, e.g. a sulpho-benzoic acid halide.  An aminoanthraquinone containing at least one thioether or alkyl- or aryl-sulphone group may be reacted with a polyfunctional acylating agent, such as a halide of an aromatic, aliphatic or heterocyclic dicarboxylic acid or a poly-halo-triazine or -pyrimidine, and if the product has no water-solubilizing groups they may be introduced by sulphonation, acylation of a hydroxy group with a sulpho-carboxylic acid halide or sulphuric acid or reacting a labile halogen atom, e.g. in a triazine residue with an amine containing a carboxylic, sulphonic or sulphate group or with a carboxy- or sulpho-phenol. Suitable vat dyes containing replaceable halogen atoms may be reacted with thio-phenols or -naphthols and sulphonated if required.  A halo-acylamino- or alpha-halo-anthraquinone may be condensed with a dimercapto-benzene-sulphonic acid to give a di-anthraquinonyl derivative.  Vat dyes containing carbazole or oxodiazole rings may be obtained by ring-closing an arylmercaptoanthrimide or di-anthraquinone-carboxylic acid hydrazide, in the usual manner, if desired with simultaneous sulphonation.  The dyes may be used to colour cellulose ether and ester, polyester, polyamide, polyacrylonitrile and polyurethane fibres and particularly cellulose fibres, by the direct or exhaustion method.  They may also be applied to cellulose fibres by the vat dyeing process.  In examples the preparation of the following types of dyes is described:-2 anthraquinone residues linked by a triazine residue; 2 anthraquinone residues linked via an aliphatic, aromatic or heterocyclic dicarboxylic acid residue; 2 anthraquinone residues linked via a perylene tetracarboxylic acid imide residue; an anthraquinone and a phthaloylacridone residue linked via a triazine residue; 2-anthraquinone residues linked by a 4-mercapto-benzoylamino residue, a 1,3-dimercaptobenzene residue or an oxo-diazole ring; indanthrone; anthanthrone; pyrene-quinone; acedianthrone; 2 anthrapyridone residues linked via a thiophene dicarboxylic acid residue; phthaloyl-acridone; the product obtained by sulphonating and possibly carbazolizing a 2,8-di-(anthraquinonyl-(1)-amino)-chrysene or a trianthrimide; isothiazole - anthraquinoylamino-anthraquinone.