GB1027565A - New vat dyestuffs and process for their manufacture - Google Patents

Abstract

The invention comprises anthraquinone vat dyes having at least one stable sulphonic acid and/or carboxylic acid group, and free from carboxylic acid amide groups, that contain at least one 6-membered heterocyclic ring which contains two nitrogen atoms as the only hetero atoms, at least one of which is bound by a double bond, (which heterocyclic ring has) at most two halogen atoms attached to its carbon atoms. The stable acid groups are those which are not split off in the vatting process. The dyes may be prepared by the following processes: -(a) sulphonating a dye having the above characteristics other than the sulphonic acid group, (b) by hydrolysis of a vat dye containing a group hydrolysable to sulphonic or carboxylic acid groups, the dye having all the other required features as above, (c) by condensing a halogen derivative of a diazine with an amino-anthraquinone compound, either one of the reactants having the sulphonic or carboxylic acid group attached thereto, there being no carboxylic acid amide groups present and the final product having at most two halogen atoms on the heterocyclic ring, or (d) a vat dye having a diazine ring substituent with halogen is condensed with an aromatic aminosulphonic or aminocarboxylic acid until at most only two halogen atoms remain unsubstituted. The Specification particularly refers to derivatives of anthraquinone with pyrimidine and those compounds having more than one anthraquinone nucleus. Other dyes referred to in examples are, carbazole-anthraquinone-pyrimidine dyes, acedianthrone-pyrimidene dyes anthraquinone-acridone-quinoxaline dyes, dibenzanthrone-phthalazine dyes, anthraquinone-quinonaline dyes, dibenzanthrone-quinazoline dyes, benzthiazole-anthraquinone-quinazoline dyes, acedianthrone-pyridazone dyes, dianthrimide carbazole-quinazoline dyes, all of which are substituted by sulphonic or carboxylic acid groups.ALSO:2-diphenyl-4-chloroquinazoline is prepared by the following process. Diphenylcarboxylic acid chloride (4) is added to a suspension of anthronilic acid in a mixture of o-dichlorobenzene and pyridine, is heated and allowed to cool, the precipitate is washed with ethanol and water and in diphenoyl-anthronilic acid MP. 244-248 DEG C. which is pulverized and heated urea at 210 DEG C. the product 2-diphenylquinazoline (4) being recrystallized from acetic acid/dimethyl-formamide mixture MP. 282-284 DEG C. This compound is then boiled with a phosphorus pentachloride and oxychloride mixture in dimethylformamide, the solid residue is extracted with benzene filtered active carbon, the benzene evaporated and the product 2-diphenyl-4-chloroquinazoline recrystallized from ligroin, MP. 149-150 DEG C.