Patent GB-1073669-A (GB)
Title: 4-azolyl-4'-oxadiazolyl-stilbenes, their preparation and use
IPC: C07D413/10
Filed: 1965-09-03
Abstract: Optical brightening agents of the general Formula (I) <FORM:1073669/C4-C5/1> where A represents a naphtalene, tetrahydronaphthalene, or benzene residue condensed with the azole ring in the manner indicated; W represents a stilbene residue which is bound in the 4-position with the azole ring and in the 41-position with the oxadiazole ring; Z represents an aryl or aralkenyl residue or an aromatic heterocyclic residue; and X represents <FORM:1073669/C4-C5/2> where Q is a hydrogen atom, an alkyl,hydroxyalkyl, cyanoalkyl, alkenyl, aralkyl or aryl radical, are incorporated in adhesives and detergent compositions.  Specified detergents are soaps; cellulose sulphite waste liquor; salts of sulphonated benzimidazoles substituted on the carbon atom 2 by alkyl radicals of more than 4 carbon atoms; salts of monocarboxylic acid esters of 4-sulpho-phthalic acid with fatty alcohols of more than 4 carbon atoms; salts of fatty alcohol sulphonates; alkylarylsulphonic acids; condensation products of fatty acids of more than 4 carbon atoms with aliphatic hydroxysulphonic or aminosulphonic acids; condensation products of (possibly alkylated) naphthalene sulphonic acids and formaldehyde; and polyglycol ethers derived from ethylene oxide and fatty alcohols of more than 4 carbon atoms, alkylphenols or fatty amines.ALSO:The invention comprises 4-azolyl-41-oxadiazoly -stilbenes of the Formula I <FORM:1073669/C2/1> where A represents a naphthalene, tetrahydronaphthalene or benzene residue condensed with the azole ring as indicated; W represents a stilbene residue which is bound in the 4 position with the azole ring and in the 41 position with the oxadiazole ring; Z represents an aryl or aralkenyl residue or an aromatic heterocyclic residue; and X represents -O- or <FORM:1073669/C2/2> where Q is a hydrogen atom, an alkyl, hydroxyalkyl, cyanoalkyl, alkenyl, aralkyl or aryl radical.  These compounds may be prepared by (a) reacting an azolyl-stilbene monocarboxylic acid halide of the Formula II <FORM:1073669/C2/3> with a monoacylhydrazine of the Formula III <FORM:1073669/C2/4> in the presence of an organic solvent and treat-the diacylhydrazine of the Formula IV <FORM:1073669/C2/5> so formed with a dehydrating agent; (b) reacting an azolyl-stilbene monocarboxylic acid hydrazine of the formula <FORM:1073669/C2/6> with a monocarboxylic acid halide of the Formula VI <FORM:1073669/C2/7> in the presence of an organic solvent and dehydrating the diacylhydrazine of Formula IV so formed; or (c) reacting an oxadiazolylstilbene of the Formula VII <FORM:1073669/C2/8> where T represents an hydroxyl group or a halogen atom, with an ortho-amine compound of the Formula VIII <FORM:1073669/C2/9> and then dehydrating the resultant compound of the Formula IX <FORM:1073669/C2/100> or; (d) reaction of an existing compound of Formula I to introduce or replace groups therein by methods known per se.  The first step of process (c) above may be effected under such conditions that the compound of Formula IX may be dehydrated in statute nascendi.  The compounds of Formula VII may be prepared by either of the following reaction schemes <FORM:1073669/C2/111> or <FORM:1073669/C2/122> The compounds of Formulae II and V may be prepared by the reaction scheme <FORM:1073669/C2/133>ALSO:Optical brightening agents of the general Formula I <FORM:1073669/C3/1> where A represents a naphthalene, tetrahydronaphthalene or benzene residue condensed with the azole ring in the manner indicated, W represents a stilbene residue which is bound in the 4 position with the azole ring and in the 41 position with the oxadiazole ring; Z represents an aryl or aralkenyl residue or an aromatic heterocyclic residue; and X represents -O-or <FORM:1073669/C3/2> , where Q is a hydrogen atom, an alkyl, hydroxyalkyl, cyanoalkyl, alkenyl, aralkyl or aryl radical are incorporated with polycondensates, polymers or polyadducts before or during the polycondensation, polymerization or polyaddition respectively. Specified polycondensates are aniline resins, carbamide resins, furan resins, maleinate resins, melamine resins, phenolic resins, polyacetals, polyamides, polycarbonates, polyesters, polyethers, polythioethers, silicon resins and thioplasts and specified polyadducts are polyurethanes and epoxy resins.  Numerous types of polymer are specified.  In one embodiment of the invention 0.001 to 0.5% by weight of stilbenes of Formula I are homogeneously dispersed in a spinningmelt comprising an aromatic polyester, poly-a -olefine or synthetic polyamide which is then melt-spun.  Examples relate to such melt-spinning of polyterephthalic acid ethylene glycol ester (Example 15), a polyamide prepared from hexamethylenediamine adipate (Example 16), a polyamide prepared from e -caprolactam (Example 16) and polypropylene (Example 17).ALSO:Materials are optically brightened by applying thereto one or more compounds of the general formula: <FORM:1073669/D1-D2/1> where A represents a naphthalene, tetrahydronaphthalene or benzene residue condensed with the azole ring in the manner indicated; W represents a stilbene residue which is bound in the 4 position with the azole ring and in the 4\sv position with the oxadiazole ring; Z represents an aryl or aralkenyl residue or an aromatic heterocyclic residue; and X represents <FORM:1073669/D1-D2/2> or where Q is a hydrogen atom, an alkyl, hydroxyl alkyl, cyanoalkyl, alkenyl, aralkyl or aryl radical. The materials may be synthetic organic materials, semisynthetic organic materials or natural organic materials of animal or vegetable origin and may be in the form of continuous filaments, staple fibres, flocks, hanks, textile threads, yarns, doubled yarns, fibre fleeces, felts, cotton-wool, flocculated products, textile fabrics, textile laminates or knitwear.  Numerous materials are specified and an Example (Ex. 14) relates to padding a polyester fibre with an aqueous dispersion of a compound of formula 1 and an adduct of ethylene oxide with para.-tertiary octylphenol and then drying the padded fibre.ALSO:Optical brightening agents of the general formula I: <FORM:1073669/B1-B2/1> where A represents a naphthalene, tetrahydronaphthalene or benzene residue condensed with the azole ring in the manner indicated, W represents a stilbene residue which is bound in the 4 position with the azole ring and in the 41 position with the oxadiazole ring; Z represents an aryl or aralkenyl residue or an aromatic heterocyclic residue; and X represents <FORM:1073669/B1-B2/2> where Q is a hydrogen atom, an alkyl, hydroxyalkyl, cyanoalkyl, alkenyl, aralkyl or aryl radical, are incorporated in polymers, polycondensates or polyadducts which are employed for coating textile materials, fleeces, papers or leathers.