GB678983A - Process for the preparation of bright violet dyestuffs of the anthraquinone series - Google Patents

Abstract

The invention comprises bright violet dyes which are fast to fulling consisting of sulphonation products of compounds of formula <FORM:0678983/IV (c)/1> where A is H or Me, B is H or, when A is Me B may also be Me and R is a saturated aliphatic or cycloaliphatic hydrocarbon radical containing 4 to 8 C atoms. They are made by heating a compound of formula <FORM:0678983/IV (c)/2> where A and B are as above and X is Br or SO3H or an alkali metal salt of SO3H, with phenols which are substituted by a saturated aliphatic or cycloaliphatic hydrocarbon radical containing 4 to 8 C atoms, in the presence of acid binding agents, and sulphonating the ensuing dyestuff. Phenols specified are p-tert. butyl-, p-sec. amyl, p-tert. amyl, p-cyclohexyl and p-isooctyl phenol. Diluents such as nitrobenzene, di-p-tert.-butyl-p-cresol or methylhexaline may be present. Acid binding agents specified are hydroxides, carbonates and acetates of alkali metals advantageously those of sodium or potassium. Temperatures for completion of the condensation are about 200 DEG C. although lower temperatures, e.g. 140 DEG C. may be used. When 2-bromo compounds are reacted the formation of higher molecular weight compounds is obviated by an increased concentration of alkali. The dye bases are isolated on dilution with alcohol or on pouring into warm dilute caustic soda solution. Sulphonation is effected in sulphuric acid monohydrate at 20-50 DEG C. In examples the bases from the following condensations are sulphonated: (1) p-tert.-butyl phenol and the condensation product of 1-amino-2-sulpho-4-brom-anthraquinone with mesidine; (2) p-isooctyl phenol and 1-amino-2-brom-4-mesidino-anthraquinone; (3) p-isooctyl phenol and the sodium salt of 1-amino-2-sulpho-4-mesidinoanthraquinone; (4) p-tert.-amyl phenol and the condensation product of 1-amino-2-sulpho-4-brom-anthraquinone and vic.-m-xylidine; (5) p-sec. amyl phenol and the sodium salt of 1-amino - 2 - sulpho - 4 - vic. - m - xylidinoanthraquinone; (6) p-cyclohexyl phenol and the sodium salt of (5); (7) p-tert.-butyl phenol and the condensation product of 1-amino-2-sulpho-4-brom-anthraquinone with isoduridine; (8) p-tert.-amyl phenol and the sodium salt of 1-amino - 2 - sulpho - 4 - isoduridino - anthraquinone; (9) p-tert.-amyl phenol and 1-amino - 2 - brom - 4 - mesidino - anthraquinone; (10) p-tert.-butyl phenol and the sodium salt of 1 - amino - 2 - sulpho - 4 - vic. - m - xylidinoanthraquinone; (11) p(isooctyl phenol and the sodium salt of (10); (12) p-cyclohexyl phenol and the sodium salt of 1-amino-2-sulpho-4-mesidino-anthraquinone, and (13) p-sec.-amyl phenol and the sodium salt of (12). Specifications 26944/11, [Class 2 (iii)], 477,535 and 483,950 are referred to.