Patent GB-885547-A (GB)
Title: New dyestuffs containing triazinylamino and pyrimidylamino radicals
Inventor: RATTEE IAN DURHAM
IPC: C09B62/02
Filed: 1959-07-08
Abstract: The invention comprises dyestuffs which contain, attached to a carbon atom, at least one group of the formula <FORM:0885547/IV (c)/1> where R is hydrogen or a substituted or unsubstituted alkyl or cycloalkyl radical, T is a 1 : 3 : 5-triazine or pyrimidine ring which is attached to the nitrogen atom through a carbon atom of said ring and carries at least one group of the formula <FORM:0885547/IV (c)/2> each of which is attached to a carbon atom of the 1 : 3 : 5-triazine or pyrimidine ring, and wherein Z is the group of non-metallic atoms required to form a 5- or 6-membered heterocyclic ring, which may carry further substituents and may form part of a condensed ring system.  The dyestuffs may be of the mono-, dis- or poly-azo, nitro, anthraquinone or phthalocyanine series and may contain co-ordinatively bound metal.  Heterocyclic rings specified for the group of formula II are those derived from furane, pyran, thiophene, pyrrole, pyrrolidine, pyrazole, pyridine, pyridazine, pyrimidine, thiazole, selenazole, oxazole, benzoxazole, benzthiazole, benzselenazole, benziminazole, naphthothiazole, perinaphthoxazole, quinoline and quinoxaline. Besides the group of formula II the 1 : 3 : 5-triazine or pyrimidine ring may contain, attached to a carbon atom or atoms, hydrogen or halogen atoms or nitro, cyano, thiocyano, sulphonic acid, alkyl, aryl or dialkyldithiocarbamyl groups or substituted or unsubstituted mercapto, hydroxy or amino groups.  The dyestuffs are made by reacting a dyestuff containing attached to a carbon atom at least one group of the formula <FORM:0885547/IV (c)/3> where R is as above and T1 is a 1 : 3 : 5-triazine or pyrimidine ring carrying at least one halogen atom attached to carbon, with a compound of the formula <FORM:0885547/IV (c)/4> where W is hydrogen or a metal atom, or by reacting a dyestuff containing at least one -NHR group with a 1 : 3 : 5-triazine or pyrimidine having attached to carbon at least one halogen atom and at least one group of the formula II above.  Certain of the dyestuffs which contain other groups attached to the carbon atoms of the 1 : 3 : 5-triazine or pyrimidine ring in addition to groups of formula II may be made by reacting those dyestuffs containing halogen and a group of formula II attached to the 1 : 3 : 5-triazine or pyrimidine ring with a compound of the formula WQ, where W is hydrogen or a metal atom and Q is hydroxy, alkoxy, aryloxy, mercapto, alkyl- or aryl-substituted mercapto, substituted or unsubstituted amino or sulphonic acid.  Azo dyestuffs containing at least one group of formula I are made by diazotising a primary amine or the corresponding sulphamic acid and coupling it with a coupling component, the amine and/or the coupling component containing at least one group of formula I.  A very large number of examples is given.  The dyestuffs dye and print, in a wide variety of shades, cotton, regenerated cellulose, wool, silk, cellulose acetate, polyamides, polyacrylonitrile, modified polyacrylonitrile and aromatic polyester fibres from aqueous solution or dispersion, and may be applied to cellulose materials from aqueous solution in conjunction with a treatment with an acid-binding agent. The dyestuffs may also be applied to cellulose textile materials in conjunction with an acid catalyst and a resin-forming composition known to render textiles crease-resistant, and the textiles may then be subjected to a heat treatment, as illustrated in Examples 243 and 244.  The second Provisional Specification also describes dyestuffs of formula I above where R is hydrogen or a substituted or unsubstituted alkyl radical, T is a pyrimidine ring which is attached through a carbon atom and carries at least one group of the formula -S.Z where Z is a <FORM:0885547/IV (c)/5> -CSOY, -CSSY or -CH2COOH group, where R3 is alkyl, aralkyl or aryl, R1 is hydrogen or a substituted or unsubstituted hydrocarbon or heterocyclic radical, R2 is a substituted or unsubstituted hydrocarbon or heterocyclic radical, or R1 and R2 form with the nitrogen atom a 5- or 6-membered heterocyclic ring, and Y is an alkali-metal atom, alkyl, aryl or aralkyl.  The dyestuffs may be made by methods similar to those described above.  In an Example (3) an azo dyestuff is described in which group -S.Z is diethyldithiocarbamyl.  Specifications 209,723, 298,494, 467,815, 503,609, 772,030, 774,925, 775,308, 780,591, 781,930, 784,221, 785,120, 785,222, 802,935, 803,473, 805,562, 822,047, 822,948, 825,120, 825,377, 826,405, 828,353, 829,042, 832,400, 833,396, 834,304, 836,248, 836,647, 837,035, 837,124, 837,953, 837,985, 837,990, 838,311, 838,335, 847,635, 849,772, 851,537, 852,911, 863,754, 864,227, 869,279 and 870,985 are referred to.