Patent GB-917242-A (GB)
Title: Process for the optical brightening of acrylonitrile synthetic fibres, and fibres brightened thereby
IPC: C07D/
Filed: 1959-04-24
Abstract: 4 - (4.5 - Arylo-1.2.3-triazolyl-2)-stilbene sulphonic acid amide brightening agents of the general formula <FORM:0917242/IV (b)/1> in which A is an arylo radical of the benzene, naphthalene or acenaphthene series which is bound at vicinal aromatic carbon atoms with the nitrogen atoms of the triazole ring, B is a radical of the benzene series, X is a saturated organic radical, Y is an aliphatically substituted secondary, tertiary or quaternary amino group which, including the basic nitrogen atom and possibly oxygen, can form saturated heterocycles, D is a negative substituent which does not impart colour, including the group -SO2-NH-X-Y, and n is a whole number not greater than 4 unless D is a group -SO2-NH-X-Y, in which event, n may be zero, and in which the aromatic rings can contain non-ionogenic substituents with the exception of groups which impart colour, are prepared by converting the corresponding sulphonic acids into the sulphonic acid chlorides by reaction with phosphorus oxychloride in an inert organic solvent, e.g. chlorobenzene, and condensing the sulphonic acid chlorides obtained with compounds having the formula NH2-X-Y, in which X and Y have the meanings given above.  The aromatic rings may be substituted by halogen, alkyl, alkoxy, alkyl sulphonyl or aryl sulphonyl groups and the arylo radical A may be substituted by acylamino groups.  The benzene ring B may be substituted by a single alkoxy group or by two alkoxy groups provided that only one of them occupies either the o- or p-positions with regard to the vinylene group.  D may be the group Y-X-NH-SO2 or an alkyl, aralkyl, aryl sulphonyl, sulphonic acid aryl ester, tertiary sulphonic acid amide or cyano group and X-Y may be a mono- or di-alkylamino ethyl or -propyl group having N-alkyl substituents of 1-6 carbon atoms, a mono- or di-cyclohexylaminoethyl or -propyl group, a piperidino-N-ethyl or -propyl group or a 2-dialkylaminoethoxyalkyl-, 2-dialkylamino - 1 - cyclohexyl or dialkylaminoalkylaminoalkyl group.  Salts of the triazolyl stilbene sulphonic acid amides may be produced by reacting them with hydrochloric, sulphuric, phosphoric, formic, acetic, lactic, p-toluene sulphonic or tetrahydronaphthalene sulphonic acid.ALSO:Polymeric or copolymeric acrylonitrile fibres are brightened by treating them with aqueous solutions which contain (1) the salts of acids with 4-(4.5-arylo-1.2.3-triazolyl-2)-stilbene sulphonic acid amides of the formula <FORM:0917242/IV (b)/1> in which A is an arylo radical of the benzene, naphthalene or acenaphthene series which is bound at vicinal aromatic carbon atoms with the nitrogen atoms of the triazole ring, B is a radical of the benzene series, X is a saturated organic radical, Y is an aliphatically substituted secondary or tertiary amino group which, including the basic nitrogen atom and possibly oxygen, can form saturated heterocycles, D is a negative substituent which does not impart colour, including the group -SO2-NH-X-Y, and n is a whole number not greater than 4, unless D is a group -SO2-NH-X-Y, in which event n may be zero, and in which the aromatic rings can contain non-ionogenic substituents with the exception of groups which inpart colour, or (2) the quaternary ammonium salts derived therefrom which correspond to the formula given in which Y is an aliphatically substituted quaternary ammonium group.  The aromatic rings may be substituted by halogen, alkyl, alkoxy, alkyl sulphonyl or aryl sulphonyl groups and the arylo radical A may be substituted by acylamino groups.  The benzene ring B may be substituted by a single alkoxy group or by two alkoxy groups provided that only one of them occupies either of the o- or p-positions with regard to the vinylene group.  D may be the group -X-NH-SO2 or an alkyl, aralkyl, aryl sulphonyl, sulphonic acid aryl ester, tertiary sulphonic acid amide or cyano group and X-Y may be a mono- or di-alkyl amine ethyl or propyl group having N-alkyl substituents of 1-6 carbon atoms, a mono- or di-cyclohexylamine ethyl or propyl group, a piperidino-N-ethyl or -propyl group, a morphorlino-N-ethyl or -propyl group or a 2-dialkylaminoethoxyalkyl-, 2-dialkylamino-1-cyclohexyl or dialkylaminoalkylaminoalkyl group. Suitable acids for salt formation with the triazolyl stilbene sulphonic acid amides are hydrochloric, sulphuric, phospheric, formic, acetic, lactic, p-toluene sulphonic and tetrahydronaphthalene sulphonic acids. The fibres, which may be in the form of threads, yarns or fabrics, are preferably introduced into a previously warmed solution of the stilbene compounds and the temperature then raised to the boiling point.  From 0.025 to 0.1% of the stilbene compounds, calculated on the weight of the fibres, is preferably used.