Patent GB-533963-A (GB)
Abstract: 533,963. Dyes. SOC. OF CHEMICAL INDUSTRY IN BASLE. Aug. 23, 1939, Nos. 24264, 24265 and 24266. Convention dates, Aug. 27, 1938, Jan. 19, 1939, and Aug. 4, 1939. [Class 2 (iii)] Vat dyes of the fluoranthene series are made by causing fluoranthene carboxylic acids or their reactive derivatives, e.g., chlorides, to react with vattable compounds containing at least one reactive hydrogen atom attached to nitrogen. Examples of such compounds are aminoanthraquinones, aminopyranthrones, aminodibenzanthrones, aminoflavanthrones, aminobenzanthrones aminodianthrones, aminoanthranthrones, amino - N dihydroanthraquinoneazones, amino - 1 : 9 - anthrapyrimidines and - anthrapyridones, amino - 1 : 9 - isothiazolanthrones, amino-1 : 9-pyrozolanthrones, and 4- or 5-amino-1 :2-anthraquinoneacridones and their substitution products, e.g. those containing halogen, alkyl or sulphur-groups. In the case of fluoranthene carboxylic acids containing several carboxylic groups, more than one molecule of the same or different amino compounds may be caused to react simultaneously or successively with the fluoranthene polycarboxylic acid, and in this case only one of the amino compounds need be vattable. Where substituents which can give rise to the formation of a heterocyclic ring are present in ortho position to the amino group, ring-closing may occur in direct sequence to the condensation, or it may be effected in a separate operation. Thus oxazoles may be obtained from fluoranthene carboxylic acid chlorides and o-hydroxy-, nitro-and halogenaminoanthraquinones, thiazoles from o-mercaptoaminoanthraquinones, and imidazoles from o-diaminoanthraquinones, or from o-nitro - aminoanthraquinones with reduction of the nitro group, or from o-halogenaminoanthraquinones, after reaction with ammonia or a primary amine. In examples (1) fluoranthene- 4-carboxylic acid is converted into the chloride by treating with thionyl chloride and condensed with 1-aminoanthraquinone or 1-amirio-5-benzoylamino - anthraquinone, (2) fluoranthenedicarboxylic acid (Example 2 of Specification 533,962), is converted to the chloride by treating with phosphorus pentachloride or thronyl chloride and is condensed with (a) 1- amino-4-or 5-benzoylaminoanthraquinone (2 mols.), (b) 1-aminoanthraquinone (2 mols.), and the product brominated to yield a dibromo derivative, (c) 1-amino-4-methoxyanthraquinone (2 mols.), (d) 1-amino-4, 5 or 6-chloroanthraquinone (2 mols.), (e) 1-aminoanthraquinone (1 mol.) and 1-amino-4-phenylaminoanthraquinone (1 mol.) or with 1-amino-4- phenylaminoanthraquinone (2 mols.), (#) 1- amino-5-cinnamoyl, p-methoxy-benzoyl, pchlorbenzoyl, #-anthraquinonoyl or #-pyridoylaminoanthraquinone (2 mols.), (g) 4-or 5- aminoanthraquinone - 1 (N) - 2 - benzocridone (2 mols.), (h) aminopyranthrone, aminodibenzanthione or aminoanthranthrone (2 mols.), (i) 2-aminoanthraquinone or 1-methylamino-4- bromanthraquinone (2 mols.), (j) 4-amino-N- methyl-1 9-anthrapyridone or 4- or 5-amino- 1 : 9-anthrapyrimidine (2 mols.), (k) 1-amino-5- benzoylaminoanthraquinone (1 mol.), followed by further condensation with1-amino-5-benzoylaminoanthraquinone (1 mol.) or aniline ( 1 mol. ), (l) 1:2-diaminoanthraquinone (2 mols.); the product probably contains two imidazole rings, (m) 1-chlor-2-aminoanthraquinone (2 mols.), the product may be further condensed with aniline or 1-aminoanthraquinone and ring-closed to a product with two imidazole rings, (n) 1-mercapto-2-aminoanthraquinone (2 mols.) or ring-closing by boiling in ethylcarbazole, a product with two thiazole rings is obtained, (o) 1:3-dibrom-2-aminoanthraquinone (2 mols.) ; the product obtained on ring- closing probably has two oxazole rings, (3) dibromfluoranthene diacarboxylic acid (Example 3 of Specification 533,962) is converted to the chloride and condensed with 1-aminoanthraquinone (2 mols.) and (4) fluoranthene tricarboxylic acid (Example 4 of Specification 533,962) is converted to the chloride and condensed with 1-amino-5-benzoylaminoanthraquinone. Further examples are given of the dyeing of cotton in hydrosulphite vats with some of the dyestuffs.