GB557456A - New anthraquinone dyestuffs useful for dyeing wool - Google Patents

Abstract

557,456. Dyes. TATUM, W. W., and IMPERIAL CHEMICAL INDUSTRIES, Ltd. May 11, 1942, No. 6327. [Class 2 (iii)] Dyestuffs, giving bright level shades, fast to light, on wool, are obtained by treating with an agent adapted to convert aminoalcohol derivatives into their acid sulphuric esters a 1-aminoanthraquinone carrying in 4-position a substituent of the general formula -NHÀCH#<SP>CH</SP>2<SP>R</SP> R 1 -OH wherein R represents H or alkyl and R<SP>1</SP> represents alkylene, and which may also 'carry in 2-position a substituent such as chlorine, bromine or methyl. Specified esterifying agents are sulphuric acid, chlorosulphonic acid and an alkali metal pyrosulphate in presence of a tertiary base, e.g. pyridine. Examples relate to the production of the acid sulphuric esters of (1) 1-amino-2-chloro-4-#- hydroxyisopropylamino - anthraquinone, by heating with sodium pyrosulphate in pyridine, (2) 1 - amino - 2 - methyl - 4 - # - hydroxyisopropylamino-anthraquinone, by a similar treatment, (3) 1 - amino - 2 - bromo - 4 - # - hydroxyisopropylamino-anthraquinone, by a similar treatment, (4) 1 - amino - 2 - methyl - 4 - (α : # - dimethyl y hydroxypropylamino) - anthraquinone, by a similar treatment, (5) 1-amino- 2 - bromo - 4 - # - hydroxyisopropylamino - anthraquinone by treatment with 96-100 per cent. sulphuric acid or fuming sulphuric acid at 20‹ C. 1 - Amino - 2 - chloro - 4 - # - hydroxyisopropylamino-anthraquinone is obtained by heating 1 - amino - 2 - chloro - 4 - bromo - anthraquinone with 2-aminopropanol for 16 hours at 100-120‹ C. in nitrobenzene containing potassium carbonate, potassium acetate and copper acetate. 1 - Amino - 2 - - methyl - 4 - # - hydroxyisopropylamino-anthraquinone is similarly obtained from 1 - amino - 2 - methyl - 4 - bromo - anthraquinone. 1 - Amino - 2 - bromo - 4 - - # - hydroxyisopropylamino-anthraquinone is obtained by heating 1 - amino - 2 : 4 - dibromo - anthraquinone with 2-aminopropanol in nitrobenzene containing potassium acetate and cuprous chloride. 1 - - Amino - 2 - methyl - 4 - (α : # - dimethyl - γ - hydroxypropylamino) - anthraquinone is obtained by heating 1-amino-2-methyl-4-bromoanthraquinone with 3-amino-2-methylbutanol for 20 hours at 90-100‹ C. in pyridine containing potassium acetate and cuprous chloride. Specification 285,641, [Class 2 (iii)], is referred to.