Patent GB-437598-A (GB)
Title: The manufacture of vat dyestuffs of the anthraquinone series
IPC: C09B5/36
Filed: 1934-04-25
Abstract: Vat dyes are prepared by reacting with entirely or practically anhydrous acid condensing agents in the absence of organic diluents upon anthraquinone-2.1(N)-benz- or naphthacridones, one hydrogen atom in the benzene or naphthalene nucleus of which is replaced by an a -aminoaroylaminoanthraquinone residue, and which have in the benzene or naphthalene nucleus one o-position to the 1-aminoaroylaminoanthraquinone residue and in the latter the o-position to the amino group unsubstituted, and if necessary subjecting any intermediate products formed to a subsequent oxidation process.  Suitable condensing agents are sulphuric acid monohydrate, fuming sulphuric acid, chlorsulphonic acid, aluminium chloride alone or with sodium chloride or with concentrated sulphuric acid.  The products are carbazoles which are particularly suitable for the sodium-formaldehyde sulphoxylatepotassium carbonate method of textile printing.  In examples: (1) anthraquinone-2.1(N) : 1<1>.2<1> (N) - 3<1>.6<1> - dichlorbenzeneacridone (prepared according to Specification 894/11 [Class 2 (iii)]) is condensed with 1-amino-5-benzoylaminoanthraquinone (dyes reddish-grey) and condensed with chlorsulphonic acid, or with sulphuric acid mono hydrate followed by oxidation with bromine, or with aluminium-sodium chloride followed by oxidation with sodium hypochlorite (reddish-brown shades); (2) anthraquinone-2.1 (N): 1<1>.2<1>(N) - 4<1>.6<1> - dichlorbenzene acridone (derived from 3.5-dichloraniline according to Specification 894/11), is condensed with 1 - amino - 5 - benzoylaminoanthraquinone (red shades) and with 1-amino-4-benzoylaminoanthraquinone (navy blue shades) followed by condensation with sulphuric acid monohydrate in each case (yellowish-brown and brownish red shades); (3) anthraquinone-2.1(N) : 1<1>.2<1>(N)-3<1>-methoxy-6<1>-chlorbenzene acridone (prepared by reacting 1-chloranthraquinone-2-carboxylic acid with 2-methoxy-5-chloraniline and condensing the product in benzoyl chloride at 130--160 DEG  C.) is condensed with 1-amino-5-benzoylaminoanthraquinone (olive - green shades) and the product condensed with sulphuric acid monohydrate at 70 DEG  C., or in the cold followed by oxidation with sodium hypochlorite, or with sulphuric acid followed by oxidation with nitrosylsulphuric acid (blackish-brown shades); using instead of 1-amino-5-benzoylaminoanthraquinone 1 - amino - 4 - benzoylamino - anthraquinone the resulting product (yellowish-green shades) is condensed with sulphuric acid monohydrate followed by oxidation with nitrosylsulphuric acid (reddish-violet shades); (4) p 3<1>-methyl-6<1>-chloro-2.1-anthraquinone benzacridone (prepared by reacting 1-chloranthraquinone-2-carboxylic acid with 5-chloro-2-toluidine and condensing the product with benzoyl chloride at 150 DEG  C.) is condensed with 1-amino - 5 - benzoylaminoanthraquinone (grey shades) and 1-amino-4-benzoylaminoanthraquinone (greenish shades), and the products condensed with sulphuric acid monohydrate (brown shades); (5) anthraquinone-2.1(N) : 1<1>.2<1>(N)-6<1>-bromonaphthalene acridone derived from 1 - chloranthraquinone - 2 - carboxylic acid and 6-bromo-2-naphthylamine) is condensed with 1-amino-5-benzoylaminoanthraquinone (red shades) and with 1-amino-4-benzoylaminoanthraquinone (olive shades) and the products condensed with sulphuric acid monohydrate (brown shades); (6) anthraquinone - 2.1(N) : 1<1>.2<1>(N) - 3<1> - ethoxy - 6<1> - chlorbenzacridone (prepared by condensing the product of 1-chloranthraquinone-2-carboxylic acid and 2-ethoxy-5-chloraniline with benzoylchloride in o-dichlorbenzene at 150 DEG  C.) is condensed with 1-amino-5-benzoylaminoanthraquinone (olive-green shades), and the product condensed with sulphuric acid monohydrate (black-brown shades); (7) 4<1>-chloro-2.1-anthraquinone benzacridone (prepared according to Specification 27637/10, [Class 2 (iii)]) is condensed with 1-amino-5-benzoylaminoanthraquinone (copper-red shades) and the product condensed with sodium-aluminium chloride followed by oxidation with sodium hypochlorite (reddish-brown shades); (8) 5<1>-bromanthraquinone - 2.1(N) - benzacridone (derived from p-bromaniline) is condensed with 1-amino-5-benzoylaminoanthraquinone (corinth shades) and the product condensed with sulphuric acid monohydrate (brown shades). For the final oxidation step where necessary nitrites, ferric chloride and manganese are also referred to as oxidizing agents. British Specification 361,423 and German Specification 258,808 also are referred to.