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total triazolyles derivatives (1) of the series of stilbene and bis styryl benzene, process of preparation and their use as azureursoptiques
total triazolyles derivatives (1) of the series of stilbene and bis styryl benzene, process of preparation and their use as azureursoptiques
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机译:二苯乙烯和双苯乙烯苯系列的总三唑衍生物(1),制备方法及其作为天青石衍生物的用途
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1307406 1,2,4-Triazolyl optical brighteners FARBWERKE HOECHST AG 16 April 1970 [16 April 1969 13 March 1970] Heading C2C [Also in Divisions C4 and D1] Novel 1,2,4-triazolyl optical brighteners of the general formula or the quaternary salts thereof, in which Z and Z 1 are hydrogen or a sulpho or carboxy group or a metal salt, ester or amide thereof, n is 1 or 2, and A is hydrogen or halogen or C 1-4 alkoxy, cyano, carboxy, or an ester thereof, an optionally substituted carbamoyl group, a group -NHCOR (where R is alkyl or an optionally substituted phenyl group or a group of the formulµ in which X and Y are chlorine, -NH 2 C 1-4 alkoxy or the residue of a primary or secondary aliphatic, aromatic or saturated heterocyclic amine, U 1 and U 4 are hydrogen or carboxy or a salt thereof, U 2 is hydrogen, C 14 alkyl or C 1-4 alkoxy, U 3 is C 1-4 alkyl or C 1-4 alkoxy, or U 2 and U 3 together represent a dioxamethylene group, or U 1 , U 2 , U 3 and U 4 together represent a fused benzene ring optionally substituted by one or more sulpho groups, or salts thereof, or a fused acenaphthene ring, are prepared (a) by tetrazotizing a diamino of the formula reducing the resulting tetrazonium salts to the bishydrazines of the formula and heating the dried bishydrazines at 150- 200‹ C. with a 3-10 fold amount by wt. of formamide to obtain those compounds in which A is triazolyl and, if required, obtaining those compounds in which Z and Z 1 are sulpho or carboxy esters or amides from the free acids via the acid chlorides, or (b) by diazotizing a nitroamine of the formula reducing the resulting diazonium to obtain an amino-hydrazine of the formula heating the dried amino-hydrazine at 150- 200‹ C. with 3-10 fold amount by wt. of formamide and hydrolysing by heating in an alkaline solution to obtain an intermediate in which A is an amino group and which is subsequently reacted (i) to obtain the diazonium salt which converted by known means to compounds in which A is hydrogen, halogen, C 1-4 alkoxy or cyano and, if required, transforming the latter into a carboxy group or an ester or amide thereof, (ii) to couple the diazonium salt with an aromatic amine of the formula to obtain the azo-dye of the formula which is cyclized by heating with an oxidizing agent at 50-100‹ C. to obtain compounds in which A is a fused-s-triazolyl group, (iii) by condensing with cyanuric halide to obtain the triazinyl compound which may, if required, be further reacted with a C 1-4 alcohol or a primary or secondary aliphatic, aromatic or saturated heterocyclic amine, or ammonia to obtain other values of X and Y or (iv) with carboxylic acid chlorides to obtain compounds in which A is -NHCOR, and, if required, quaternizing -any of the products, e.g. with a C 1-4 alkyl halide or sulphate or an aryl sulphonate. The 1,2,4-triazolylstilbenes are used as optical brighteners (see Division D1).
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