Patent GB-1110806-A (GB)
Title: New 4,4'-bis-triazinylstilbenes,process for their preparation and their use
IPC: D06L3/12
Filed: 1965-09-15
Abstract: Optical brightening agents for addition and condensation polymers comprise compounds of the formula <FORM:1110806/C3/1> where R1- 4 may be the same or different and represent aryl, aralkenyl or aromatic heterocyclic radicals and W represents a stilbene residue bound in positions 4 and 41 to the triazine rings.  The brightening agents may be added before or after formation of the polymers and may be used in conjunction with conventional additives for polymer compositions. Examples describe optically brightened compositions containing (5) a terephthalic acid/ethyleneglycol polyester, (6) a hexamethylene-diamine adipate polyamide and titanium dioxide, (7) polyvinyl chloride, a Ba/Cd stabilizer and titanium dioxide and (8) polyethylene.ALSO:Optical brighteners which are used in combination with detergents comprise compounds of the formula <FORM:1110806/C4-C5/1> where R1- 4 may be the same or different and represent aryl, aralkenyl or aromatic hetero-cyclic radicals and W represents a stilbene residue bound in positions 4 and 41 to the triazine rings.  Specified detergents are soaps, e.g. salts of sulphonate washing agents such as sulphonated benzimidazoles substituted on the Z-carbon atom by C8- 18 alkyl groups, salts of monocarboxylic acid esters of 4-sulphophthalic acid and C8- 18 alcohols, salts of fatty alkyl sulphonates, alkylarylsulphonic acids or condensation products of fatty acids and aliphatic hydroxysulphonic or amino sulphonic acids; non-ionic detergents, e.g. polyglycol ethers derived from ethylene oxide and fatty alcohols, alkylphenols or fatty amines.ALSO:The invention comprises compounds of the formula <FORM:1110806/C2/1> where R1- 4 may be the same or different and represent aryl, aralkenyl or aromatic heterocyclic radicals and W represents a stilbene residue bound in positions 4 and 41 to the triazine rings.  Preferred compounds are those of the formula <FORM:1110806/C2/2> where R represents a substituted or unsubstituted benzene ring. Specified substituents for R are halogen, preferably chlorine, alkyl, alkoxy, phenyl, a free sulphonic acid group, or the ammonium, alkali metal, alkaline earth metal or amine salts thereof, sulphonamido groups, or a residue -(CH2CH2)n- 1Y, wher n is 1 or 2 and Y represents a carboxyl group, or a salt thereof, or a carbonamide group.  The compounds can be prepared (a) by heating above 250 DEG  C. a mixture of sulphur and an appropriately substituted 6-(p-methylphenyl)-1,3,5-triazine; or (b) by heating 1 mol. of a stilbene dicarboxylic acid dihalide with 4 mols. of a nitrile RCN at 70-130 DEG  C. in the presence of a Friedel-Crafts catalyst and heating the intermediate so formed with ammonium chloride at 70-130 DEG  C.  The stilbene derivatives are used as optical brighteners (see Divisions C3 and D1).  Examples relate to compounds in which each of R1- 4 are the same and are phenyl, p-toluyl, p-t-butylphenyl, p-methoxyphenyl, p-chlorophenyl and m-chlorophenyl radicals.ALSO:Optical brightening agents for fibrous materials comprise compounds of the formula <FORM:1110806/D1-D2/1> wherein R1-4 are the same or different and represent aryl, aralkenyl or aromatic heterocyclic groups and W represents a stilbene residue bound in positions 4 and 4\sv to the triazine rings.  The fibrous material may be in the form of continuous filaments, staple fibres, flocks, hanks, yarns, fleeces, felts, cottonwool, flocculated or laminate textiles or knitwear. Preferred substrates are polyamide and polyester fabrics. Treatment may be effected in an organic solvent bath, but it is preferred to operate in a neutral or slightly acid or alkaline aqueous bath, which may contain dispersants, at 50-100 DEG C.  The brightening may be combined with other treatments and the brightening agents may be used with, e.g. detergents or dressing agents.  Example 4 describes the treatment of a polyester fabric.