Patent GB-1429261-A (GB)
Title: Vat dyestuffs derived from polycyclic quinones, their manufacture and use
IPC: C09B1/467
Filed: 1973-03-02
Abstract: 1429261 Dyestuffs derived from vattable polycyclic quinones CIBA-GEIGY AG 2 March 1973 [3 March 1972 22 Jan 1973] 10193/73 Heading C4P Novel vat dyestuffs of the formula wherein A is the radical of a vattable polycyclic quinone, X is O or S, B is the radical of a 6- membered heterocycle with 2 or 3 ring nitrogen atoms which optionally has one or more carbocyclic rings fused thereto, R is an aromatic radical with -X-B ortho or meta to the amide group, Z is H or -X-B ortho, meta or para to the amide group, and a is H or are prepared by condensing hydroxy or mercapto compounds of the formula wherein a<SP>1</SP> is H or -NHCO-R(Z<SP>1</SP>)-XH and Z<SP>1</SP> is H or -XH with BY 1  wherein Y 1  is an easily removable radical and optionally replacing one or more easily removable radicals in the product by -NH-Ar, -O-Ar, -S-Ar' -NH-A 1 , -X-A 1  or -CO-NH-A 1  wherein Ar is an aromatic radical and A 1  is the radical of a vattable polycyclic quinone. Preferred dyestuffs have the formula wherein K is -NH-aryl-NH-, -X-aryl-X-, -NH-aryl-N = N-aryl-NH-, -O-aryl-N = N-aryl-O-, -NH-aryl-CH = CH-aryl-NH-, -O-aryl-CH = CH-aryl-O- or -NH-anthraquinonyl-NH- and B 1  has the same meaning as B. Preferably B (or B 1 ) is a radical of the 1,3,5-triazine, pyrimidine, pyridazine, quinazoline, quinoxaline or phthalazine series which carries 1 or 2 substituents selected from halogen, alkyl, aryl, aryloxy, arylamino, -NH-aryl-N = N-aryl, -O-aryl-N = N-aryl, -NH-aryl-CH = CH-aryl, -O-aryl-CH = CH-aryl, -NH-A 1 , -X-A 1 , -CO-NH-A 1  and -NH-C 6 H 4 -CONH-A 1 , or if a is H, -X-R-CO-NH-A and -K-B 2 -(X-R-CONH-A) 2  where B 2  has the same meaning as B and A 1  is the radical of a vattable polycyclic quinone, A and A 1  being the same or different. Preferred values A and A 1  are optionally substituted anthraquinon-1-yl, anthraquinon-2-yl, 3,4-phthaloylacridon-2-yl and 3,4-phthaloylacridon-8-yl. R is preferably a benzene or naphthalene radical optionally alkyl-, aralkyl-, aryl-, acyl-, acylamino- or halogeno-substituted. In the process the heterocyclic ractive component containing at least 2 removable groups may be reacted, for example, with a compound and a compound H 2 N-A 1  or HX-A 1 . The starting material of the formula is prepared by heating equimolar amounts of 2 - phenyl - 4,6 - dichloro - 1,3,5 - triazine with 2 - amino - 3,4 - phthaloyl - acridone in N- methylpyrrolidone. 1 - Chloro - 3 - (3,4 - phthaloylacridon - 2 - ylamino) - 5 - (isothiazolanthron - 5 - yl - amino)- s-triazine is prepared from cyanuric chloride and the appropriate primary amines. The novel dyestuffs may be used (a) for dyeing and printing fibres of natural or regenerated cellulose in the presence of reducing agents; or (b) as pigments for dyeing rayon and viscose rayon, or cellulose ethers or esters, or superpolyamides or superpolyurethanes or polyesters in the melt, or for manufacturing pigmented lacquers or lake formers, solutions or products of acetyl cellulose, nitrocellulose, natural resins or synthetic resins, coloured pencils, cosmetic preparations or laminated sheets.