GB1054436A - - Google Patents

Abstract

1,054,436. Naphthalimide derivatives. MITSUBISHI CHEMICAL INDUSTRIES Ltd. Oct. 18, 1963, No. 41336/63. Heading C2C. [Also in Divisions C3 and D1] The invention comprises naphthalimide derivatives of general formula where R 1 denotes an alkyl, aryl, aralkyl or cycloalkyl group which may be substituted, R 1 may also be an aryl group shown by the formula and R 2 denotes a hydrogen atom, alkyl, aryl, aralkyl or cycloalkyl group which may be substituted as in the case of R 1 . R 1 may be the same or different from R 2 . Compounds of the above general formula may be prepared by etherifying a 4-mercapto naphthalimide of the following formula where M denotes a hydrogen atom or alkali metal. Suitable etherifying agents are strong acid esters having no dyestuff character such as alkyl sulphates, organic compounds containing an active halogen atom. The etherification may be performed in the presence of alkaline substances at a temperature in the range from about 20‹ to 200‹ C. while preferably using inert diluents. 4 - Mercapto naphthalimides may be prepared from the corresponding 4-halogeno-naphthalmides of the following formula where X denotes a halogen atom by reacting with alkali metal sulphides of formula M<SP>1</SP> 2 .Sy, where M<SP>1</SP> denotes an alkali metal and y a number from 1 to 5, in the presence of an inert at a temperature from 30‹ to 100‹ C. 4-Halogenonaphthalimides may be obtained by the following routes. Another method of preparing naphthalimides of Formula I are condensing a compound of the formula or an anhydride thereof, with a compound R 2 -NH 2 . Specified naphthalimides which are prepared are: N - methyl - 4 - n - butylthionaphthalimide, N - methyl - 4 - methylthionaphthalimide, N - n - butyl - 4 - methylthionaphthalimide, N - (2<SP>1</SP> - hydroxy ethyl) - 4- methylthio - naphthalimide, 4 - methylthionaphthalimide, N - (N<SP>1</SP>,N<SP>1</SP> - dimethylaminopropyl) - 4 - methylthio - naphthalimide, N- phenyl - 4 - methylthio - naphthalimide, N- methyl - 4 - (2<SP>1</SP>- hydroxyethylthio) - naphthalimide, N - methyl - 4 - (N<SP>1</SP>,N<SP>1</SP> - dimethylaminoethylthio) - naphthalimide, N - methyl - 4- benzylthionaphthalimide, N - methyl - 4 - (4<SP>1</SP>- nitrophenyl) thionaphthalimide, bis [4 - N- methylnaphthalimide)] sulphide. The compounds are stated to exert a remarkable whitening effect on various materials, particularly on artificial or synthetic organic high molecular weight materials by fixing, penetrating, mingling, or adhering (see Divisions C3 and D1).