Patent GB-483325-A (GB)
Title: New anthraquinone dyestuffs
IPC: C09B5/14
Filed: 1936-10-16
Abstract: Sulphonic acids of arylaminoanthrapyridones and arylaminoanthrapyrimidones of the formula <FORM:0483325/IV/1> where A stands for nitrogen or for carbon combined with carbalkoxy, acetyl, or benzoyl, X stands for hydrogen, halogen, methyl or sulpho, Y stands for alkyl, alkoxy, or carbalkoxy wherein the alkyl residue has 8-18 carbon atoms and Z stands for hydrogen or sulpho, and at least one of X and Z stands for sulpho are made by (a) condensing at elevated temperatures urea, an alkylurea, urethane, a malonic alkyl ester or an acetylacetic or benzoylacetic acid ester with an anthraquinone compound of the formula <FORM:0483325/IV/2> in which X, Y, and Z are as above, or (b) introducing one or more sulpho groups into an anthraquinone compound of the formula <FORM:0483325/IV/3> in which A, X, Y, and Z are as above except that X and Z must not both be sulpho and neither may be sulpho.  The sulpho groups may be introduced by sulphonation with concentrated sulphuric acid, oleum, or chlorsulphonic acid, or by treatment of a compound in which X is halogen with a soluble sulphite or by both processes. The dyes may contain substituents such as methyl, chloro, or bromo in addition to those above-mentioned, and dye wool from a neutral or acid bath bluish-red to violet shades fast to washing, milling, and light.  In examples, sodium 1 - amino - 4 - p-dodecylsulphoanilinoanthraquinone - 2 - sulphonate is condensed with (1) urea, in presence of ammonium chloride and phenol, to give sodium 6 - p - dodecylsulphoanilinoanthrapyrimidone-4-sulphonate, or with (2) ethyl acetoacetate, in presence of sodium acetate and phenol to give sodium 1-acetyl-6-p-dodecylsulphoanilinoanthrapyridone-4-sulphonate; (3) sodium 1 - amino - 4 - m - carbododecoxyanilinoanthraquinone-2-sulphonate is condensed with ethyl acetoacetate as in (2) to give sodium 1 - acetyl - 6 - m - carbododecoxyanilinoanthrapyridone-4-sulphonate; 1 - amino - 4 - m - carbodecoxy- and 1 - amino - 4 - m - carbooctadecoxyanilinoanthraquinone-2-sulphonic acids may be similarly treated; (4) 4-bromo-1-acetyl-6-p-dodecylanilinoanthrapyridone (made from 2-bromo - 1 - amino - 4 - p - dodecylanilinoanthraquinone and ethyl acetoacetate) is heated with sodium sulphite, phenol, and water to give sodium 1 - acetyl - 6 - p - dodecylanilinoanthrapyridone - 4 - sulphonate; (5) 1-acetyl-6-p-dodecylanilinoanthrapyridone - 4 - sulphonate is sulphonated, using oleum and concentrated sulphuric acid; (6) 1-amino-4-p-decoxyanilinoanthraquinone-2-sulphonic acid is condensed with ethyl acetoacetate as in (2); 1-amino-4-p-dodecoxy- and p - octadecoxy - anilinoanthraquinone-2-sulphonic acids may be treated similarly; (7) 2-bromo-1-amino-4-p-dodecylsulphoanilinoanthraquinone is condensed with ethyl acetoacetate; (8) 1-amino-2-methyl-4-p-dodecylanilinoanthraquinone is condensed with ethyl acetoacetate, followed by sulphonation; (9) sodium sodium 1-amino-4-(p-dodecylsulphoanilino)anthraquinone is condensed with ethyl acetoacetate, followed by sulphonation; (10) 1 - amino - 2 - methyl - 4 - p - dodecylanilinoanthraquinone is condensed with diethyl malonate, followed by sulphonation. 1-Amino-2-methyl-4-p-dodecylanilinoanthraquinone is made by reacting 1-bromo-4-amino-3-methyl-anthraquinone with p-dodecylaniline. 1-Amino-4-(p-dodecylsulphoanilino)anthraquinone sodium salt is made by heating the aqueous solution of the corresponding sodium-2-sulphonate with caustic soda and glucose at 90-95 DEG  C. Specifications 377,419, 380,078, 393,331, 393,631, 393,632, 412,270, 443,776, and 469,449 are referred to.