GB1460860A - Production of 1-amino-4-hydroxyanthraquinone-2-alkyl ethers - Google Patents

Abstract

1460860 Preparing anthraquinone dyes BASF AG 29 March 1974 [31 March 1973] 14008/74 Heading C4P Compounds of the general formula wherein A is a chemical bond, a C 1 -C 11 alkylene or alkenylene radical which may contain the bridging member -O-, R is H, Cl, Br, OH, alkoxy, cyanoalkoxy or hydroxyalkoxy having 1-4 carbon atoms in the alkoxy radical, phenyl or phenoxy optionally substituted once or twice by Cl, Br, methyl, methoxy and/or ethoxy or is a -COOR<SP>1</SP>, -OCOR<SP>1</SP>, -CON(R<SP>2</SP>)- R<SP>3</SP> or group wherein R<SP>1</SP> is H or a C 1 -C 6 alkyl group, R<SP>2</SP> and R<SP>3</SP> are H or C 1 -C 4 alkyl optionally substituted by OH, methoxy or ethoxy or R<SP>2</SP> and R<SP>3</SP> together may complete a 5- or 6-membered heterocyclic ring which may also contain one or more oxygen, sulphur, or further nitrogen atoms, n is 1 or 2 and m is 3 or 4 are prepared by reacting 1-amino-2,4-dihydroxyanthraquinone with a compound wherein Hal is Cl or Br and A, R and n are as above in a polar solvent in presence of an agent having a basic reaction. In preferred embodiments, the reaction takes place at 40-180‹ C. using 1À0 to 1À5 moles of the haloalkyl compound per mole of 1-amino-2,4-dihydroxyanthraquinone and 1À0 to 1À2 equivalents of the agent having a basic reaction per mole of haloalkyl compound. The agents having basic reaction include alkali metal hydroxides, alcoholates, carbonates and hydrogen carbonates and mixtures thereof. The polar solvents include dimethylacetamide, dimethylformamide, dimethylsulphone, dimethylsulphoxide and N-methylpyrrolidone. The dyes dye or print secondary acetate rayon, polyamides and polyesters.