Patent GB-190107541-A (GB)
Title: Manufacture of Dyestuffs and Intermediate Products of the Anthracene Series.
Inventor: IMRAY OLIVER
Filed: 1901-04-12
Granted: 1902-02-27
Abstract: 7541. Imray, O., [Farbwerke vorm. Meister, Lucius, & Br³ning]. April 12. Dyes, artificial, and anthraquinone derivatives.- Relates to the production of polyamidoanthraquinone sulphonic acids which contain two amido groups in one benzene nucleus and one, two, or no amido groups in the other benzene nucleus. These products dye unmordanted wool fast blue shades. Amidoanthraquinones, viz., alpha-monoamidoanthraquinone, 1 : 5 or 1 : 8-diamidoanthraquinone, or the mixture of amidoanthraquinones obtained by reducing the crude product of the nitration of anthraquinone, are the parent substances. The acidylated derivatives of these amidoanthraquinones, preferably the oxamic acids obtained by heating the amidoanthraquinones with oxalic acid, but also the acetylated or benzoylated derivatives, are nitrated, the nitrated acidylated products are reduced, and the acidylated polyamido products are simultaneously saponified and sulphonated by treatment with fuming sulphuric acid, or the acidyl groups may be eliminated before sulphonation is effected. The sulphonic acids are also produced by acting upon the acidylated polyamidoantbraquinones with alkali sulphites, or in this case also the acidyl groups may be first eliminated by means of acids or alkalies. An example is given in which tetramidoanthraquinone sulphonic acids are produced from erude dinitroanthraquinone as follows :-The diamido derivatives are heated with oxalic acid, the oxamic acids produced are purified, dried, and nitrated by slowly introducing them into a mixture of sulphuric and nitric acids at 5‹ C., and the oxamic acids of dinitrodiamidoanthraquinones thus produced are precipitated by ice water. They are reduced to the sodium salts of the oxamic acids of tetramidoanthraquinones by sodium sulphide, and these salts are precipitated by common salt and dye wool violet-blue shades. On boiling with mineral acids, these products yield salts of tetramidoanthraquinones which dye wool blue. The same products are obtained by acting with alkali sulphides on dinitrodiamidoanthraquinones which are obtained as brilliant red crystals by saponifying the acidylated dinitrodiamidoanthraquinones above mentioned. The tetramidoanthraquinones obtained by these processes are then sulphonated by treatment with fuming sulphuric acid, containing 20 per cent. of SO3, at 110‹-120‹ C., and the resulting mixture of sulphonic acids is precipitated by pouring the mixture into water. It may be used directly as a paste, or may be first purified by resolution and precipitation, and it dyes a greener tint than the base or its oxamic acids. In another example, dinitrodiamidoanthraquinone is converted into tetramidoanthraquinone sulpbonic acid by heating it with sodium-bisulphite solution. The diamidoanthraquinone sulphonic acids are bluishviolet dyes, and the triamido derivatives are intermediate in shade between the diamido and tetramido derivatives. The diamidoanthraquinone obtained by reducing mononitro-alpha-monoamidoanthraquinone is the 1 : 4-compound.