Patent GB-996710-A (GB)
Title: New quaternary nitrogen derivatives, process for their preparation and process for dyeing and printing fibrous materials with the same
IPC: C07D251/42
Filed: 1962-12-05
Abstract: The invention comprises quaternary nitrogen compounds having no dyestuff character and having the formula <FORM:0996710/C2/1> wherein R represents (a) the residue of a halogen pyrimidine (including a ring condensed halogen pyrimidine, e.g. a trichloroquinazoline); (b) the residue of a halogen pyridazine, or (c) a triazine radical of the formula <FORM:0996710/C2/2> in which A1 and A2 each represent an NH2, OH or alkoxy group, or the residue of an aliphatic or aromatic amine; R1 represents the residue of a non-aromatic tertiary nitrogen compound containing a quaternated nitrogen atom directly linked to one of the hetero carbon atoms of R, such tertiaryamines being exemplified by amines of the formula <FORM:0996710/C2/3> or <FORM:0996710/C2/4> in which R1 and R2 represent alkyl, alkoxyalkyl or hydroxyalkyl radicals, R3 represents an alkylene or alkenylene radical, X1 represents a hydrogen atom, an optionally substituted hydroxyl group, a group -NR1R2, a group <FORM:0996710/C2/5> (where n is 1, 2, 3 or 4), or an optionally substituted aryl group, R4, R5 and R6 each represent an alkylene group, and Y1 represents a nitrogen atom or a CH group, or being exemplified by hydrazines of the formula <FORM:0996710/C2/6> or <FORM:0996710/C2/7> where R1 and R2 represent aliphatic hydrocarbon radicals, R3 represents an aliphatic hydrocarbon radical, a group HSSC-, a group HO3S-, a hydrogen atom or a group R1R2N-alkylene (where R1 and R2 may also complete a 5- or 6-membered ring), and r and s independently represent 3 or 4; and the anion may be an independent ion (e.g. Cl DEG ) or may be joined to R (e.g. -R-SO2-O DEG  or -R-O DEG ). The quaternary compounds may be prepared, for example, by reacting an appropriate non-aromatic tertiary nitrogen compound with a compound R-halogen.ALSO:Dyestuffs of the formulae <FORM:0996710/C4-C5/1> are obtained by condensing the appropriate aminoazo dyestuff or its copper complex with tetrachloropyrimidine or 2,4,6-trichloropyrimidine respectively in an aqueous medium having a pH ranging from 6 to 9.ALSO:Materials such as paper, leather, silk, linen, cotton and rayon are printed or dyed with water soluble or insoluble reactive dyestuffs or their intermediates in the presence of quaternary nitrogen compounds having no dyestuff character and having the formula <FORM:0996710/D1-D2/1> wherein R represents (a) the residue of a halogen pyrinidine (including a ring condensed halogen pyrinidine, e.g. trichloroquinozoline), (b) the residue of a halogen pyridazine, or (c) a triazine radical of the formula <FORM:0996710/D1-D2/2> in which A1 and A2 each represent an NH2, OH or alkoxy group, or the residue of an aliphatic or aromatic amine; R1 represents the residue of a non-aromatic tertiary nitrogen compound containing a quaternated nitrogen atom directly linked to one of the hetero carbon atoms of R, such tertiary amines being exemplified by amines of the formula <FORM:0996710/D1-D2/3> in which R1 and R2 represent alkyl, alkoxyalkyl or hydroxyalkyl radicals, by represents an alkylene or alkenylene radical, X1 represents a hydrogen atom, an optionally substituted hydroxyl group, a group -NR1R2, a group <FORM:0996710/D1-D2/4> (where n is 1, 2, 3 or 4), or an optionally substituted aryl group, R4, R5 and R6 each represent an alkylene group, and Y1 represents a nitrogen atom or a CH group, or being exemplified by hydrazines of the formula <FORM:0996710/D1-D2/5> where R1 and R2 represent aliphatic hydrocarbon radicals, R3 represents an aliphatic hydrocarbon radical, a group HSSC-, a group HO3S-, a hydrogen atom or a group R1R2N-alkylene-(where R1 and R2 may also complete a 5- or 6-membered ring, and r and s independently represent 3 or 4 and the anion may be an independent ion (e.g.cl.) or may be joined to R (e.g.-R-SO2-\yS or -R-O\yS).  The dyestuff and the quarternary compound may be applied together or separately using cold pad batch, exhaustion, pad steam pad dry, pad wet stream or printing methods.  Fixation may be achieved by means of steam, dry heat, liquid metal baths, high frequency electrical fields or storage in a plastic foil.