Patent GB-889292-A (GB)
Title: Triazine compounds and process for preparation
IPC: C07D251/50
Filed: 1960-06-01
Abstract: The invention comprises an improved cellulose in which at least 0,01% of the total free hydroxyl groups of the cellulose are esterified with triazinylamino benzophenones of the formula <PICT:0889292/IV (a)/1> in which D has the structure <PICT:0889292/IV (a)/2> where A represents a hydrogen atom or a hydroxyl group, B represents a hydrogen, chlorine or bromine atom or an alkyl or alkoxy group and is meta or para to the carbonyl group while para or meta, respectively, to the hydroxy group, and E represents a chlorine atom, the group NHD or a sulphoalkylamino or carboxyalkylamino group.  The cellulose, which may be natural or regenerated and in the form of fibre or sheet, may be esterified by treatment with the triazinylaminobenzophenone in an alkaline medium at elevated temperature to give a cellulose stabilized to the action of ultra-violet light.  Examples describe the treatment of cotton and "Cellophane" (Registered Trade Mark).ALSO:The invention comprises compounds of the general formula <FORM:0889292/IV (b)/1> in which D has the structure <FORM:0889292/IV (b)/2> where A represents a hydrogen atom or a hydroxyl group, B represents a hydrogen, chlorine or bromine atom or an alkyl or alkoxy group and is meta or para to the carbonyl group while para or meta, respectively, to the hydroxy group, and E represents a chlorine atom, the group NHD or a sulphoalkylamino or a carboxyalkylamino group; and a process for their preparation by condensing cyanuric chloride with 1 or 2 moles of an aminobenzophenone of the formula <FORM:0889292/IV (b)/3> and, if desired, when 1 mole of the aminobenzophenone is reacted, reacting the product with one mole of an aminoalkane sulphonic or carboxylic acid.  Examples describe the reaction of cyanuric chloride with one and two moles of the aminobenzophenone where alkyl and alkoxy are exemplified by methyl and methoxy and, where one mole only is reacted, the subsequent reaction with glycine and taurine.  The aminobenzophenones may be prepared by reacting a p-nitro-benzoyl or salicyloyl chloride with a p- or m-substituted anisole in the presence of aluminium chloride, demethylating the o-methoxy group in the resulting benzophenone by heating, and then reducing the nitro group or, when alkoxy groups other than methoxy are desired, by reacting a p-nitro-benzoic or salicyclic acid with, for example, resorcinol in the presence of boron trifluoride, alkylating the meta or para hydroxy group in the usual way and then reducing the nitro group.  Examples of these processes are given.ALSO:The invention comprises an improved cellulose in which at least 0.01% of the total free hydroxyl groups are esterified with compounds of the formula <FORM:0889292/IV (c)/1> in which D has the structure <FORM:0889292/IV (c)/2> where A represents a hydrogen atom or a hydroxyl group, B represents a hydrogen, chlorine or bromine atom or an alkyl or alkoxy group and is meta or para to the carbonyl group while para or meta, respectively, to the hydroxy group, and E represents a chlorine atom, the group NHD or a sulphoalkylamino or a carboxyalkylamino group. The cellulose may be esterified by treatment with the triazinylaminobenzophenone in an alkaline medium at elevated temperature to give a cellulose stabilised to the action of U.V. light.  In an example a cotton cloth is treated in a padding step with 2-chloro-4 - (2 - sulphoethylamino) - 6 - (4 - (2 - hydroxy 4 - methoxy-benzoyl)-anilino)-s-triazine in the presence of a wetting agent and in a fixing step with an alkaline sodium chloride solution.