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filingDate 1975-06-10^^<http://www.w3.org/2001/XMLSchema#date>
publicationDate 1978-03-22^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber GB-1504764-A
titleOfInvention Benzotriazole-stilbene derivatives containing sulphonic groups and their use as optical brightening agents
abstract 1504764 Benzotriazolo-stilbene derivatives containing sulphonic groups CIBA-GEIGY AG 10 June 1975 [12 June 1974 (2)] 23829/75 Heading C2C [Also in Divisions C3 and G2] 2 - Stilbenzyl - 1,2,3 - triazoles of the formula wherein A denotes a benzene, naphthalene or acenaphthene ring which is optionally substituted by non-chromophoric substituents, the benzene nuclei B and C are optionally substituted by non-chromophoric substituents, and the molecule contains at least one sulpho group, are obtained by reacting a 2-tolyl-1,2,3-triazole of the formula in the presence of a strongly basic alkali metal compound in a strongly polar, neutral to basic, organic solvent or mixture thereof, with an acid of the formula wherein Ar denotes an optionally substituted aromatic radical. The 2-stilbenyl-1,2,3-triazoles of the formula wherein R denotes hydrogen, a salt-forming cation, C 1-4 alkyl optionally substituted by non- chromophoric substituents, or cyclohexyl, M denotes hydrogen or a salt forming cation, and n is 1 or 2, are claimed per se. Specified non- chromophoric substituents are C 1-4 alkyl halogen, C 1-4 alkoxy, phenoxy, C 1-4 alkylmercapto, phenylmercapto, carboxyl or sulpho or, in the case of two adjacent substituents, a methylene dioxy, trimethylene or tetramethylene group, and specified salt-forming cations are alkali and alkaline earth metal ions, NH 4 <SP>+</SP> and amine salt ions. The reaction is suitably effected at 10-150‹ C. and specified solvents are dialkylamides of formic or phosphoric acid and tetraalkyl ureas wherein the alkyl groups contain up to 4 carbon atoms; the strongly basic alkali metal compound is preferably an alkali metal alcoholate. The acid starting materials may be obtained by reacting an aldehyde with an appropriate aniline derivative, and the product may be reacted subsequently in situ. Amine salts may be obtained by converting an alkali metal salt of the sulphonic acid into the sulphochloride, followed by saponification in the presence of the desired amine. Carboxylic esters of the Formula IV may be manufactured by a known manner, e.g. by converting the carboxylic acids into the carboxylic acid chlorides and reacting the latter with alcohols; the sulphonic group, which may also be chlorinated, remains unchanged during the esterification step and may be converted to an appropriate salt in the subsequent saponification reaction. The triazole starting materials may be obtained by diazotizing a p-toluidine compound, reacting the product with an appropriate aminonaphthalene or aminobenzenesulphonic acid, followed by cyclization of the product. The products of Formula IV may be used to optically brighten a variety of organic materials, or they may be incorporated in cleansing compositions.
priorityDate 1974-06-12^^<http://www.w3.org/2001/XMLSchema#date>
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