Patent GB-1100579-A (GB)
Title: Benzotriazolyl-coumarin derivatives
Inventor: WIRTH WOLF-DIETER
IPC: C08K5/3475
Filed: 1966-08-08
Abstract: Compositions containing an alkyd resin and/or a vinyl polymer or copolymer, particularly polyvinyl chloride and a compound of the formula <FORM:1100579/C3/1> wherein R1 is an alkoxy or alkoxyalkyleneoxy group containing 3 to 12 carbon atoms, and R2 is an alkyl group containing 1 to 4 carbon atoms, as brightening agent. Compositions comprising polyvinyl chloride, dioctyl phthalate, a tin stabilizer and rutile titanium dioxide; or comprising styrene, polyesters (e.g. derived from adipic acid and ethylene glycol), cyclohexanone peroxide, dibutyl phthalate and rutile titanium dioxide; together with 3-phenyl-7-(51-methyl61 - n - butoxy - benzotriazolyl - 21) - coumarin are formed into films and moulded articles in conventional manner.ALSO:o-Aminoazo-dyestuffs are prepared by coupling the diazonium salt derived from 3-phenyl-7-amino-coumarin to the ortho-position of a primary aromatic amine of the formula <FORM:1100579/C4-C5/1> wherein R1 is an alkoxy group containing 3 to 12 carbon atoms, the carbon chain of which is optionally interrupted by an oxygen atom, and R2 is an alkyl group containing 1 to 4 carbon atoms.  In particular, 4-amino-2-n-butoxy-1-methylbenzene is coupled with the above-mentioned diazonium salt to give an o-aminoazo-dye.ALSO:Compounds of the formula <FORM:1100579/C2/1> wherein R1 is an alkoxy group containing 3 to 12 carbon atoms the carbon chain of which is optionally interrupted by an oxygen atom and R2 is an alkyl group containing 1 to 4 carbon atoms and preparation thereof by condensing 4 - acetylamino - salicylaldehyde anilide with phenylacetic acid in the presence of sodium acetate and acetic anhydride, hydrolysing the acetylamino group in the product by means of hydrochloric acid, diazotizing the resultant 3 - phenyl - 7 - amino - coumarin hydrochloride, coupling the diazonium salt so obtained to the ortho position of a primary aromatic amine of the formula <FORM:1100579/C2/2> wherein R1 and R2 have the above significance and, finally, oxidizing the resultant o-amino-azo dye-stuff (e.g. with copper acetate) to give the desired product.  3 - Phenyl - 7 - (51 - methyl - 61 - n - butoxybenzotriazolyl-21-)-coumarin is prepared by oxidation of the corresponding o-aminoazo-dye-stuff as outlined above.  Related compounds substituted in the 61-position by isopropoxy, sec-butoxy, isoamyloxy, n-octoxy, n-dodecoxy and b -ethoxyethyloxy are also described.  3 - Phenyl - 7 - aminocoumarin hydrochloride is prepared as outlined above.ALSO:Synthetic materials are treated by applying a brightening agent of the formula: <FORM:1100579/D1-D2/1> wherein R1 is an alkoxy group containing 3 to 12 carbon atoms, the carbon chain of which is optionally interrupted by an oxygen atom, and R2 is an alkyl group containing 1 to 4 carbon atoms, by conventional means, optionally in the presence of a detergent, using an aqueous dispersion or a solution in an inert organic solvent.  In general 0.1 to 1% of the brightening agent referred to the weight of the synthetic material may be used.  The preferred synthetic materials are vinyl polymers and copolymers, e.g. polyvinyl chloride or polystyrene, or an alkyd resin and may be in the form of films, filaments, woven and knitted fabrics, or films, sheets or other shaped materials.