Patent GB-609585-A (GB)
Title: Anthraquinone dyestuffs
IPC: C09B1/30
Filed: 1946-03-18
Abstract: Dyes are made by reacting an amine of the formula NH2.CHR1R2, where R1 is an aryl or aralkyl group which carries a sulphonic acid group as substituent in the aryl nucleus and which may carry further substituents other than sulphonic acid groups in the aryl nucleus, R2 is a hydrocarbon radical which may carry substituents other than sulphonic acid groups and which may together with part of R1 form a cycloaliphatic ring, with an anthraquinone compound which is wholly or partly in the leuco form, which is substituted in the 1- and 4-positions by hydroxyl, amino, or alkylamino groups, and which may be further substituted by hydroxyl groups in one or both of the 5- and 8-positions or by halogen atoms in one or both of the 6- and 7-positions and oxidizing the resulting leuco derivative.  The reactants are stirred in aqueous alkaline medium, e.g. in presence of sodium hydrosulphite, and the leuco-derivative may be oxidized with sodium m-nitrobenzene sulphonate or with air or oxygen.  The products dye wool blue to violet shades.  Examples describe the reaction of leuco-quinizarin with (1) sodium a b -diphenylethylamine monosulphonate; (2) sodium 2-benzylcyclo-hexylamine monosulphonate; (3) sodium a  - phenyl - g  - aminobutane - monosulphonate; (4) potassium 4-chloro-a .a -diphenylmethylamine monosulphonate.  In example (2), leuco - 1,4,5 - tri- and 1,4,5,8 - tetra - hydroxyanthraquinone may be substituted for leuco-quinizarin.  The monosulphonates specified in the above examples are made by sulphonating the amine with sulphuric acid and oleum and neutralization with alkali.  Specifications 491,493, 497,016 and 564,859 are referred to.ALSO:Dyes are made by reacting an amine of the formula NH2CHR1R2, where R1 is an aryl or aralkyl group which carries a sulphonic acid group as substituent in the aryl nucleus and which may carry further substituents other than sulphonic acid groups in the aryl nucleus, R2 is a hydrocarbon radical which may carry substituents other than sulphonic acid groups and which may together with part of R1 form a cycloaliphatic ring, with an anthraquinone compound which is wholly or partly in the leuco form, which is substituted in the 1- and 4-positions by hydroxyl, amino, or alkylamino groups, and which may be further substituted by hydroxyl groups in one or both of the 5-and 8-positions or by halogen atoms in one or both of the 6- and 7-positions and oxidizing the resulting leuco derivative. The reactants are stirred in aqueous alkaline medium, e.g. in presence of sodium hydrosulphite, and the leuco-derivative may be oxidized with sodium m-nitrobenzene sulphonate or with air or oxygen.  The products dye wool blue to violet shades.  Examples describe the reaction of leuco-quinizarin with (1) sodium-a b -diphenylethylamine monosulphonate; (2) sodium 2-benzylcyclo-hexylamine monosulphonate; (3) sodium a  - phenyl - g - aminobutane - monosulphonate; (4) potassium 4-chloro-a a -diphenylmethylamine monosulphonate.  In (2), leuco-1 : 4 : 5 - tri- and 1 : 4 : 5 : 8 - tetra - hydroxy - anthraquinone may be substituted for leucoquinizarin.  The monosulphonates specified in the above examples are made by sulphonating the amine with sulphuric acid and oleum and neutralization with alkali.  Specifications 491,493, 497,016 and 564,859 are referred to.