Patent GB-1121327-A (GB)
Title: New azole derivatives, process for their preparation and their use
IPC: D06L4/60
Filed: 1965-08-18
Abstract: Synthetic resins may have incorporated therein as optical brighteners azoles of the formula <FORM:1121327/C3/1> where A represents a benzene, naphthalene or tetrahydronaphthalene residue (which may be substituted) which is condensed with the azole ring in the manner indicated by the valency lines; B represents an aryl or aralkenyl radical or a heterocyclic residue which contains at least two conjugated double bonds which are in conjunction with the >C=N- bond of the azole ring; n stands for 1 or 2, and X represents -O- or -NQ-, where Q stands for a hydrogen atom or a cyanoalkyl group.  Examples describe (a) the incorporation of above azoles in polypropylene or high-pressure polyethylene rolled to and fro on a calender and then pressed to form panels, (b) incorporating azoles by mixing and melting with polyester granulate from polyterephthalic acid ethyleneglycol ester or by adding to the starting materials before or during polycondensation, and (c) melting compositions containing polyamide chips, titanium dioxide and azides of the above formula to produce a spinning melt; the polyamide may be prepared from hexamethylenediamine adipate or e -caprolactam.ALSO:Azoles of the formula <FORM:1121327/C2/1> where A represents a benzene, naphthalene or tetrahydronaphthalene residue, which may be substituted, which is condensed with the azole ring in the manner indicated by the valency lines, B represents an aryl or aralkenyl radical or a heterocyclic residue which contains at least two conjugated double bonds which are in conjunction with the > C = N- double bond of the azole ring; n stands for 1 or 2, and X represents -O- or -NQ- where Q stands for a hydrogen atom or a cyanoalkyl group, may be manufactured as follows. When n = 2 the process comprises the following steps: (a) an ortho-hydroxyamino compound of the formula <FORM:1121327/C2/2> is condensed with a carboxylic acid or halide of the formula <FORM:1121327/C2/3> (where R represents a hydroxyl group or a halogen atom) in equimolecular proportions, accompanied by elimination of HR, to form a condensate which is cyclized by heating to 150 DEG  to 350 DEG  C. with consequent elimination of water, if necessary in the presence of a dehydration catalyst, to the azole derivative <FORM:1121327/C2/4> (b) the alkyl ester group of the azole derivative is hydrolysed and optionally converted to a carboxylic acid halide group, and the resulting acid or the resulting acid halide, portion is condensed with an ortho-hydroxyamino compound of the formula <FORM:1121327/C2/5> in equimolar proportions with consequent elimination of water or hydrogen halide to form a condensate which is cyclized by heating to 150 DEG  to 350 DEG  C. with elimination of a mole of water, if necessary in the presence of a dehydration catalyst, to the further azole derivative <FORM:1121327/C2/6> and (c) the reaction sequence of the reaction step (b) is repeated in analogous manner on said further azole derivative with an ortho-substituted amino compound of the formula <FORM:1121327/C2/7> When n = 1 the step (b) is omitted and the product of (a) is reacted as in (c).  The Specification describes the preparation of many azole derivatives of the given formula and gives examples of their use as optical brighteners for organic materials.ALSO:Textile organic materials may have incorporated therein as optical brighteners azoles of the formula <FORM:1121327/D1-D2/1> where A represents a benzene, naphthalene or tetrahydronaphthalene residue (which may be substituted) which is condensed with the azole ring in the manner indicated by the valency lines, B represents an aryl or aralkenyl radical or a heterocyclic residue which contains at least two conjugated double bonds which are in conjunction with the >C=N- double bond of the azole ring, n stands for 1 or 2, and X represents -O- or -NQ- where Q stands for a hydrogen atom or a cyanoalkyl group. In an example a polyester fabric is padded with an aqueous dispersion containing an azole of the above formula and an adduct from about 8 mols of ethylene oxide with 1 mol of para-tertiary octylphenol, dried at about 100 DEG C and then exposed to dry heat at 150 to 220 DEG C for 2 minutes or less.