Patent GB-812726-A (GB)
Title: Ultra-violet absorbing filters
IPC: C07D215/16
Filed: 1956-08-21
Abstract: An ultra-violet filter layer consists of a lighttransmitting film-forming material which may be any of those specified in Specification 665,371, but particularly a polyvinyl butyral composition containing a compound having one of the general formul <FORM:0812726/IV (a)/1> wherein R1 is hydrogen, or an alkyl or aryl group, R2 is hydrogen or an alkyl, carboxylalkyl, alkylsulphonyl, acyl, aralkyl or aromatic group, R3 is an alkyl or aryl group, g  is hydroxyl or arylamino and Z completes a quinoline ring.  The ultra-violet absorbers may be added to the monomers before they are polymerized.  R1 or R2 may be methyl, ethyl, propyl, butyl, amyl, octyl, dodecyl, lauryl, octadecyl, phenyl or naphthyl, or R2 may be sulphophenyl, phenylsulphophenyl, methylphenylsulphophenyl, ethylphenylsulphophenyl, p - toluylsulphonyl, benzyl, methylnaphthyl, acetyl, propionyl, butyryl, stearoyl, carbamyl, benzoyl, carboxy-methyl, carboxyethyl, methylsulphonyl or ethyl-sulphony, R3 may be phenyl or naphthyl or any of the alkyl groups specified above for R1, and g  may be phenylamino or sulphophenylamino.  The quinoline nucleus completed by Z may be quinoline itself or 4-carboxy-6-sulpho-quinoline, 4 - carboxy - 6 - chloro - quinoline, 4 - carboxy-6 - chloro - 8 - bromo - quinoline or 4 - carboxy-6; 8-dihydroxy-quinoline.  Many compounds are specified. In Example (2) 4-acetyl-41-amino - biphenyl - phenylhydrazone is added to polyvinyl butyral in ethyl acetate, diacetone alcohol and methanol and cast as a filter foil.ALSO:4 - Amino - and 4 - acylamino - 41 - (2-quinolyl) biphenyls are prepared by refluxing isatin or a substituted isatin with an appropriate 4-amino-41-acyl-biphenyl, followed, if desired, by acylation of the 4-amino group, decarboxylation or conversion of quinolyl halogen substituents to hydroxy groups. Examples relate to the preparation of 4-amino-41-(411-carboxy-611 - sulpho - 211 - quinolyl) biphenyl (and the pyridine salt thereof) and the corresponding 4-acetylamino-, 4-myristoylamino-, 4-p-tolylsulphonamido -, 4 - methylsulphonamido - and 4-carbamylamido compounds, 4 - amino - 41 - (411-carboxy - 611 - chloro - 211 - quinolyl) biphenyl and the corresponding 411-carboxy-611-chloro-811-bromo- and 411-carboxy-611; 811-dihydroxy-211-quinolyl compounds, and 4-acetylamino-41-quinolyl-211-biphenyl.  4 - Acetylamino - 41 - acyl - biphenyls are prepared by condensing 4-acetylaminobiphenyl with an acyl chloride in the presence of aluminium chloride.  The preparation of 4-acetyl-amino-41-benzoylbiphenyl is exemplified. 4-Amino-41-acyl-biphenyls are prepared by hydrolysis of the corresponding 4-acetylamino compounds.  Examples relate to the preparation of 41 - benzoyl -, 41 - acetyl - and 41 - myristoyl-4 - aminobiphenyls.  4 - Alkylamino -, 4 - arylamino - and 4-aralkylamino - 41 - acyl - biphenyls are prepared by treating the corresponding 4-amino-compound with an alkyl, aryl or aralkyl halide in presence of an acid acceptor.  Examples relate to the preparation of 41-diethylamino-, 41 - benzylamino -, 41 - phenylamino - and 41-N - phenyl - N - methylamino - 4 - acetyl - biphenyls, N - (41 - benzoylbiphenyl) glycine and 4-propionyl-41-butylamino-biphenyl. Phenylhydrazenes of 4-amino-, 4-acylamino-, 4 - alkylamino -, 4 - arylamino - and 4 - aralkylamino - 41 - acyl - biphenyls are prepared by treating the 4-amino- or 4-substituted-amino-41-acyl-biphenyls with a phenylhydrazine in the presence of an acid acceptor.  Examples relate to the preparation of the phenylhydrazones of 41 - amino -, 41 - acetylamino - and 41 - benzoyl-amino - 4 - acetyl - biphenyls and of 4 - benzoyl - 41 - amino - biphenyl, and the p - sulphophenylhydrazones of 41-amino- and 41-acetyl-amino-4-acetyl-biphenyls.  4 - Amino - 41 - acyl - biphenyl oximes are prepared by treating the corresponding 4-amino-41-acyl-biphenyls with hydroxylamine hydrochloride in the presence of an acid acceptor. Examples relate to the preparation of the oximes of 4 - acetyl - 41 - aminobiphenyl and 4 - acetylamino - 41 - benzoyl - biphenyl.  Specification 665,371, [Group IV (a)], is referred to.