GB558330A - Manufacture of new monoazo dyestuffs - Google Patents

Abstract

558,330. Dyes. HEYWOOD, B. J., KNIGHT, A. H., LAPWORTH, M., and IMPERIAL CHEMICAL INDUSTRIES, Ltd. June 29, 1942, No. 8906. [Classes 2 (iii) and 15 (ii)] Monoazo dyes, soluble in water and suitable for dyeing or printing fibres of cellulose acetate, wool, silk, tin-weighted silk or synthetic polyamides, are obtained by coupling a diazotized p-aminophenyl-hydroxyalkyl ether sulphuric acid ester, which may carry substituents other than nuclear sulphonic, carboxylic or acidylamino groups, with a phenol substituted in 4- position by an alkyl, aralkyl, cycloalkyl, or aryl hydrocarbon residue containing from 2 to 8 carbon atoms. Alternatively, a dyestuff of the type, p-aminophenyl-hydroxyalkyl ether# a 4-substituted phenol as above, may be treated with a sulphating agent. Specified diazo components are p-aminophenyl-#-hydroxyethyl and γ-hydroxypropyl ethers, γ- and 8-(paminophenoxy-butanols, 4-amino 2-chlorophenyl-#-hydroxyethyl ether and 4-amino-2- or 3-methyl-phenyl-#-hydroxyethyl ethers and their sulphuric acid esters, and specified coupling components are the p-ethyl, p-npropyl-, p-n-butyl-, p-tert,-butyl-, p-tert.-amylp-n-hexyl-, p-cyclohexyl-, p-phenyl- and pbenzyl-phenols. The dyeings on cellulose acetate fibres are non-phototropic yellows, fast to light and dischargeable. Examples relate to the production of the following dyestuffs, (1) to (4), p-aminophenyl-#-hydroxyethyl ether sulphuric acid ester# (1) p-nbutylphenol, (2) p-cyclohexylphenol, (3) ptert.-butylphenol, (4) p-phenylphenol, (5) paminophenyl-γ-hydroxypropyl ether sulphuric acid ester# p-phenylphenol, (6) and (7), (6), p-aminophenyl-#-hydroxyethyl ether sulphuric acid ester, (7) the corresponding γ-hydroxypropyl compoundp-benzylphenol, (8) 4-amino- 2 - methyl - phenyl - # - hydroxyethyl ether sulphuric acid ester# p-benzyl- or p-phenylphenol, (9) and (10), (9) 4-amino-2-chlorophenyl-#-hydroxyethyl ether sulphuric acid ester, (10) p-aminophenyl-γ-hydroxypropyl ether sulphuric acid ester, # p-n-butylphenol, (11) p-aminophenyl-#-hydroxyethyl ether# p- -n-propylphenol, followed by sulphation with 90 per cent. sulphuric acid, (12) p-aminoohenyl- #-hydroxyethyl or γ-hydroxypropyl ether# pphenylphenol, followed by sulphation as in (11). p- Aminophenyl-hydroxyalkyl ether sulphuric esters are obtained by the action of sulphuric acid on the corresponding p-aminophenylhyroxyalkyl ethers. γ-(p-Aminophenoxy)-butanol is obtained by reducing the nitro group in the product of reaction of sodium p-nitrophenolate with γ- chlorobutanol. 8-(p- Aminophenoxy)-butanol is obtained by reducing the nitro group in the product obtained by condensation of sodium p-nitrophenolate with #-chlorobutyl acetate followed by hydrolysis with boiling water. p-n-Hexyl-phenol is obtained by reducing p-hydroxycaprophenone with zinc amalgam and hydrochloric acid. p- Hydroxycaprophenone is obtained by heating phenyl caproate with aluminium chloride in nitrobenzene at 60‹C., neutralizing with sodium hydroxide and removing by steam distillation the o-hydroxycaprophenone also formed. p-n-Butyl-phenol is obtained by diazotizing p-n-butyl-aniline and hydrolyzing the product.