Patent GB-660171-A (GB)
Title: Rosin ammonium phenoxides as fungicides
IPC: C09F1/00
Filed: 1949-05-27
Abstract: Rosin ammonium phenoxides are made by reacting a rosin amine (see Group IV (b) with a phenol. They may be made either by mixing the amine and the phenol, preferably in equimolecular amounts, in the presence or absence of solvents, or by mixing a salt of the amine and an acid with a metal salt of the phenol, e.g. a dimethylbenzyl rosin ammonium chloride with sodium phenoxide. Phenols specified are phenol, b -naphthol, cresol, xylol, menthol, chlorocresols, nitrocresols and menthyl-, monochloro-, dichloro-, trichloro-, tetrachloro-, pentachloro-, mononitro-, dinitro- and trinitro-phenols. The rosinamines specified are those made from wood or gum rosin, dehydrogenated rosin, hydrogenated rosin, polymerized rosin, and the corresponding pure acids: methyl-, ethyl-, dimethyl-, diethyl-, isopropyl-, butyl-, hydroxymethyl-, hydroxyethyl- and di-(hydroxy-ethyl)-dehydroabiethylamines and the corresponding amines of abietic-, dihydroabietic-, tetrahydroabietic- and polymerized abietic acids; trimethyl-, dimethylbenzyl-, dimethylallyl-, dimethylmethoxymethyl-, dimethyl b - hydroxyethyl - dihydroabietyl-(quaternary)-ammonium phenoxides and the corresponding abietyl, hydroabietyl and polyabietyl ammonium phenoxides.  Solvents specified are: kerosene, mineral oil, lubricating oil, naphtha, acetone and alcohol.  In examples: (1) dehydrogenated rosin amine is reacted with pentachlorophenol at 140 DEG  to 150 DEG  C.; (2) the same reaction is effected in benzene at 70 DEG  to 90 DEG  C; (3) dehydrogenated rosin amine and phenol are reacted at 100 DEG  C., and (4) in either at room temperature; (5) trimethylammonium hydroxide containing 20 per cent water is reacted with pentachlorophenol at 90 DEG  to 100 DEG  C., the water being removed by distillation with toluene.  The compounds may be used as fungicides for application in emulsions, protective coatings such as paints and for treating canvas and other textiles, wood, rope, leather, paper, etc.ALSO:Primary rosin amines are made by reacting the corresponding rosin acid with ammonia, e.g. by passing ammonia into the molten rosin material in the presence or absence of dehydration catalysts and vaporizing the water as fast as it is formed, and hydrogenating the resulting nitrile, which is preferably purified by neutralization or distillation before hydrogenation; the hydrogenation may be effected with or without a solvent using hydrogen under pressure with a hydrogenation catalyst such as nickel, cobalt, Raney nickel, Raney cobalt, active platinum, palladium, palladium on carbon or reduced platinum oxide. Thus abietic acid is converted to abietonitrile and thence to abietylamine, dehydroabietic acid to dehydroabietonitrile and dehydroabietylamine, etc; methyl-, ethyl-, dimethyl-, diethyl-, isopropyl-, butyl-, hydroxymethyl-, hydroxyethyl- and di-(hydroxyethyl)-dehydroabietyl amines and similar amines having the nucleus of abietic acid, dihydroabietic acid, tetrahydroabietic acid and polymerized abietic acid, may be made in this manner. Secondary and tertiary rosin amines may be made by reacting the corresponding primary amine with an alkyl halide or sulphate, by simultaneous condensation and reduction of the primary amine and an aldehyde or a ketone, or by reacting the amine with an epoxide such as ethylene oxide or with a chlorohydrin.  Quarternary rosin ammonium hydroxides, such as trimethyl-, dimethylbenzyl-, dimethylallyl-, dimethylmethoxymethyl- and dimethyl-b  - hydroxyethyl - dehydroabietyl ammonium hydroxides and the corresponding abietyl, hydroabietyl and polyabietyl ammonium hydroxides, may be made by adding an alkyl, alkenyl or aralkyl halide or a halohydrin, such as ethylene bromohydrin, to a tertiary rosin amine.