Patent GB-965908-A (GB)
Title: Use of 4-benzoyl-1-hydroxynaphthalene-2-carboxylic acid,its esters and amides as ultra-violet light absorbents
IPC: C08F2/00
Filed: 1960-08-26
Abstract: Compounds of formula: <FORM:0965908/C1/1> wherein R is a carboxylic acid ester or a substituted or unsubstituted carboxylic acid amide group are used as ultra-violet light absorbents (see Divisions C3 and D1).  They are prepared by reacting 4-benzoyl-1-naphthol-2-carboxylic acid or an alkali metal salt or halide thereof with ammonia or an amine, an alcohol or a phenol. In examples: (1) 4-benzoyl-1-naphthol-2-carboxylic acid sodium is reacted in an aqueous alkaline medium with dimethyl sulphate to yield the methyl ester; (2) 4-benzoyl-1-naphthol-2-carboxylic acid chloride dissolved in carbon tetrachloride is reacted with a solution of phenol in carbon tetrachloride and pyridine to give the phenyl ester; (3) a solution of 4-benzoyl-1-naphthol-2-carboxylic acid in toluene and o-anisidine is treated with phosphorus trichloride to give the 21-methoxy-phenylamide. Further compounds of the above formula are specified.ALSO:The invention comprises a synthetic plastic, a synthetic resin, a lacquer, a cellulose derivative, or a natural rubber-like material having incorporated therein an agent which absorbs ultra-violet rays and is of formula: <FORM:0965908/C3/1> wherein R is a carboxylic acid, carboxylic ester or substituted or unsubstituted carboxylic acid amide group (see Division C2).  The ultra-violet absorbent is incorporated in a proportion of 0.001 to 5% by weight e.g. by dissolving in a lacquer, adding to a synthetic resin before working up, mixing with a monomer before polymerization or polycondensation, spraying or mixing granules, powders, foils &c. with a solution of the absorbent in a solvent and drying or steeping a finished article in such a solution, possibly at elevated temperature and then drying. Specified substances which may be treated in this way include acetyl-cellulose, cellulose propionate, cellulose butyrate, nitrocellulose, polyvinyl acetate, polyvinyl alcohol, polyvinyl chloride, copolymers of vinyl chloride and vinylidene chloride, polyethylene, polypropylene, polyisobutylene, polyurethanes, polyamides, polyacrylonitriles, polyesters, polymethacrylates, epoxide resins, polystyrene, alkyd resins, melamine, urea and phenol-aldehyde resins and natural and synthetic rubbers, e.g. polychloroprene, polybutadiene or butadiene-styrene copolymers. In Examples: (4) a polyvinyl chloride foil containing 2% by weight of 4-benzoyl-1-naphthol-2-carboxylic acid 21-methoxy-phenylamide is specified; (5) a foil is obtained by mixing polyvinyl chloride, dibutyl phthalate and 4-benzoyl-1-naphthol-2-carboxylic acid 21-methylphenyl ester and working up the mass; (6) polyethylene powder is mixed with 0.05% of 4-benzoyl-1-naphthol-2-carboxylic acid or the corresponding methyl ester, rolled to form a sheet and then compressed to form plates; (7) a polyethyleneglycol terephthalate foil is immersed in a solution of 4-benzoyl-1-naphthol-2-carboxylic acid in acetone, rinsed with alcohol and dried; (8) a polyethylene foil is treated as in (7); (9) a lacquer is prepared from collodion cotton, butylacetate butyl alcohol, toluene, dibutyl phthalate a 4-benzoyl-1-naphthol-2-carboxylic acid methyl ester.ALSO:The invention comprises textile materials having incorporated therein an ultra-violet light absorbent of formula:-  <FORM:0965908/D1-D2/1> p wherein R is a carboxylic acid, carboxylic ester or substituted or unsubstituted carboxylic acid amide group.  Specified textile materials are fibres, yarns, filaments or fabrics of cotton, wool, silk, viscose rayon, acetate or cuprammonium rayon, regenerated cellulose, cellulose acetate, polyacrylonitrile, polyesters, polyamides, polyurethanes or polyvinyl alcohol.  The material may be sprayed with or steeped in a solution of the absorbent in a solvent and subsequently dried.