Patent GB-932154-A (GB)
Title: 2-phenyl-benzenetriazole-1-oxides and their use as agents absorbing ultra-violet rays
IPC: D06M13/35
Filed: 1959-10-05
Abstract: Ultra-violet light absorbents comprising 2phenyl-benzotriazole-1-oxides of formula, <FORM:0932154/IV(a)/1> in which X represents a hydroxyl, alkoxy, acyloxy, arylsulphoxy, amino, alkylamino, dialkylamino, arylamino, diarylamino, alkarylamino, acylamino, or arylsulphonylamino group; R1 a hydrogen or halogen atom or an alkyl, carboxylic acid, ester or amide group and R2 a hydrogen or halogen atom or an alkyl or sulphonic acid group, are incorporated in high molecular weight, plastics, synthetic resins or lacquers. The compounds, which are listed, may be mixed with granular resin or an aqueous solution or suspension thereof, or added to the monomer before polymerization, or the finished material may be added to a bath of a solution of the compound or the solution may be sprayed on the surface.  A proportion of from 0,001 to 5% by weight is used and examples describe the preparation of a film of polyvinyl chloride containing 2-(41-hydroxyphenyl)-benztriazole-1oxide, or 2-(41-methoxyphenyl)-benztriazole-1oxide and of polyethylene containing 2-(41methoxyphenyl)-benztriazole-1-oxide; the polymerization of styrene containing 2-(41-methoxyphenyl)-benztriazole-1-oxide; the preparation of films of a copolymer of vinylidene chloride and vinyl chloride with 2-(41-benzoylaminophenyl)-benztriazole-oxide, of acetyl cellulose with 2-(41-hydroxyphenyl)-benztriazole-1-oxide, of polyethylene glycol terephthalate with 2(41-methoxyphenyl)-benztriazole-1-oxide, of polypropylene with 2-(31-methyl-41-hydroxyphenyl) benztriazole-1-oxide, and of polyvinyl alcohol with 2-(41-methoxyphenyl)-benztriazole-1-oxide6-sulphonic acid; the polymerization of methacrylic acid methyl ester containing 2-(41-acetoxyphenyl)-benztriazole-1-oxide; and the preparation of a solution of colloidium wood in butyl alcohol and acetate, toluene and dibutyl phthalate with 2-(41-methoxyphenyl)-benztriazole-1oxide. Many polymers are listed including those derived from polyolefinically unsaturated compounds, chlorinated rubber, and polyesters, polyamides, polyisocyanates, phenolformaldehyde, melamine, urea, epoxide and alkyd resins; nitrocellulose lacquers and dispersion lacquers based on polyvinyl acetate or boiled linseed oil. The compounds absorb ultra-violet rays of 380 mm  and less and are permeable to visible radiation.ALSO:The invention comprises 2-phenyl-benztriazole-1-oxides of formula <FORM:0932154/IV(a)/1> in which X represents a hydroxyl, alkoxy, acyloxy, arylsulphoxy, amino, alkyl-amino, dialkylamino, arylamino, diarylamino, alkarylamino, acylamino, or arylsulphonylamino group; R1 a hydrogen or halogen atom, or an alkyl, carboxylic acid, ester or amide group and R2 a hydrogen or halogen atom or an alkyl or sulphonic acid group, which are used as absorbents for ultra-violet rays of wavelength 380 mm and less.  The compounds are prepared by coupling a diazotized o-nitraniline with a hydroxylbenzene or aminobenzene, and reducing the resultant o-nitrazobenzene with for example sodium dithionite, to give the correspondingly substituted derivative of 2-phenyl-benztriazole-1-oxide which may be further modified for example by alkylation or acylation.  The preparation of 2-(41-methoxyphenyl)-benztriazole-1-oxide is described and 2-(41-hydroxyphenyl)-, 2-(31-methyl-41-hydroxyphenyl)-, 2 - (31 - chloro-41-2-(41-aminophenyl)-, 2-(41-benzoylaminophenyl)-, 2 - (41 - phenylaminophenyl)-, 2-(41-dimethylaminophenyl)-, 2-(41-benzoylsulphoxyphenyl)-, 2-(41-acetoxyphenyl)-, 2 - (41-benzoyloxyphenyl)-benztriazole-1-oxides, 2 - (41 - hydroxyphenyl) - benztriazole-1-oxide-31-carboxylic acid, 2 - (41 - hydroxyphenyl)-benztriazole-1-oxide-31-carboxylic acid phenylamide, 2 - (41-hydroxyphenyl)-6-methylbenztriazole-1-oxide, 2-(41-hydroxyphenyl)-6-chlorobenztriazole - 1 - oxide, 2-(41-hydroxyphenyl)-benztriazole-1-oxide-6-sulphonic acid and 2-(41 - methoxyphenyl) - benztriazole-1-oxide-6-sulphonic acid are mentioned.  The products, colourless or slightly yellow crystalline compounds may be incorporated into plastics resins or lacquers which may in addition to making the base less sensitive to ultraviolet radiation be used as protective coatings of films.