GB443776A - New anthraquinone dyestuffs - Google Patents

Abstract

Anthraquinone dyes carrying amino, substituted amino, hydroxy, ether or thioether residues in at least two a -positions are prepared by (1) reacting a nuclear long-chain alkyl (C8--20) benzene compound carrying a reactive nuclear amino, hydroxyl, or mercapto substituent with an appropriate anthraquinone derivative carrying at least one reactive halogen substituent, or (2) reacting a nuclear long-chain alkyl (C8--20) benzene compound which carries a nuclear amino substituent with an appropriate anthraquinone derivative which may be reduced to the leuco compound carrying at least one reactive a -hydroxy or -amino or -alkylamino substituent, and in either case sulphonating the compounds obtained, if they do not already contain a sulphonic acid group or enough sulphonic acid groups to make them sufficiently soluble for colouring purposes. Sulphonic acid groups may be introduced by direct sulphonation or replacement of a reactive halogen substituent. The products dye animal fibres in shades of improved fastness to washing and milling. In examples: (1) 1.3-dibromo-4-aminoanthraquinone is condensed with d-dodecylaniline and the product treated with sodium sulphite in phenol (dyes wool blue); the product may be further sulphonated with oleum; (2) 4-bromo-2-chloro-1-aminoanthraquinone is condensed with p-cetylaniline and sulphonated as in (1) (dyes blue shades); (3) 1.3-dibromo-4-aminoanthraquinone is condensed with p-octadecylaniline and treated with sodium sulphite (dyes blue shades); (4) leucoquinizarin is treated with p-dodecylaniline and the product sulphonated (green shades); (5) 1-bromo-4-methylaminoanthraquinone is condensed with p-dodecylphenol and the product sulphonated (blue-red shades); (6) 1-bromo-4-aminoanthraquinone - 3 - sulphonate is condensed with p - dodecylthiophenol (bluish - red shades. Samples have been furnished under Sect. 2 (5) of products prepared (a) by condensing leuco-1 . 4 - diaminoanthraquinone with p - dodecylaniline and sulphonating (b) by condensing 2 . 3 - dichloro - 1 . 4 - diaminoanthraquinone with p - dodecylphenol and sulphonated (red-violet shades). p-Cetylaniline and other long-chain alkyl-anilines specified above are prepared in a similar way to the p-octylaniline (cf. Berichte 18, 132). p-Dodecylphenol is prepared by treating p-dodecylbenzene diazonium sulphate with boiling aqueous sulphuric acid. p-Dodecylthiophenol is prepared by treating p-dodecylbenzene diazonium chloride with sodium ethylxanthate and hydrolyzing.