Patent GB-937182-A (GB)
Title: New heterocyclic dyestuffs containing a quaternary ammonium group
Inventor: GAMLEN GEORGE ALBERT
IPC: C09B43/16
Filed: 1959-09-24
Abstract: The invention comprises dyestuffs which contain attached to a carbon atom at least one group of the formula -A-Z where A is -O- or-NY where Y is hydrogen or a substituted or unsubstituted alkyl radical or a cycloalkyl radical and Z is a heterocyclic ring containing in the ring only carbon and nitrogen atoms and at least one <FORM:0937182/IV(a)/1> group and which is attached to A through a carbon atom and which carries at least one group of the formula <FORM:0937182/IV(a)/2> where R1 and R2 are each methyl and R3 is substituted or unsubstituted aliphatic radical or at least two of R1, R2 and R3 are joined or fused together to form with the nitrogen atom a heterocyclic ring or rings, the nitrogen atom being linked to carbon atoms present in the said ring or rings by single bonds or through a single and a double bond.  The dyes may be of the mono- or polyazo, nitro, anthraquinone or phthalocyanine series and may or may not contain water-solubilizing groups.  Heterocyclic rings specified for Z are 1:3:5-triazine, pyrimidine, pyridine, quinoline, quinazoline and phthalazine rings.  For the heterocyclic rings formed by joining two of R1, R2 and R3 through a single bond there are specified pyrrolidine, pyrroline, piperidine, morpholine, piperazine and pyrrole, and through a single and a double bond pyridine and isoquinoline.  When R1, R2 and R3 are joined, polycyclic heterocyclic structures are formed wherein the nitrogen atom is common to two of the rings and those specified include 1:4-diazabicyclo-(2:2:2)-octane, 1-azabicyclo-(2:2:1)-heptane, quinuclidine, pyrro lisidine, 1-isogranatanine, conidine, julolidine and lilolidine.  The dyes may be made by treating a dye containing a group -A-Z1 where Z1 is a heterocyclic ring corresponding to Z but containing at least one labile halogen atom or a labile group with an amine of the formula NR1R2R3, while those of the azo series may be made by diazotization and coupling, at least one of the components containing an -A-Z group.  A large number of examples are given. The dyes dye, pad and print natural or regenerated cellulose materials in conjunction with a treatment with an acid-binding agent, and also wool, silk and polyamide, polyester and polyacrylonitrile fibres. The dyes may also be applied to cellulose textile materials by padding or printing with an aqueous solution containing the dye, a resin-forming composition and an acid catalyst and then heating to above 100 DEG C. Resin-formers include epoxy resins, polyisocyanates, formaldehyde/cresol or acrolein condensates and methylol derivatives or ethers thereof with ureas and thioureas, dicyandiamide, dicyandiamidine, biguanides, amides, carbamates, allophanates, aminotriazines, urons, ureins, ureides, imidazolidones, triazones and hydantoins and polyamides. Catalysts include ammonium nitrate, sulphate or chloride, zinc or magnesium chlorides and mineral salts of amines, some of which are specified.  The Provisional Specification further refers to dyes containing at least one group -A-Z where A may also be a sulphur atom and wherein the groups R1, R2 and R3 are substituted or unsubstituted hydrocarbon or heterocyclic radicals or may together form a heterocyclic ring or rings.  A list of specific radicals and heterocyclic rings is given for R1, R2 and R3 but no further dyes are specified and no further examples are given.  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, 825,377, 826,405, 829,042, 832,400, 833,396, 834.304, 836,248, 836,647, 837,035, 837,124, 837,953, 837,985, 838,311, 838,338, 838,340, 838,341, 838,342, 838,344, 838,345, 843,985, 846,765, 846,949, 847,635, 849,772, 852,911, 869,279, 870,985, 872,249, 874,544, 876,092, 876,923, 882,890, 883,550, 887,867, 889,833 and 927,772 are referred to.