GB383493A - Process for the manufacture of aldehyde-phenol condensation products and the application thereof as moth-proofing or like agents - Google Patents

Abstract

Aliphatic and aromatic aldehydes or compounds yielding the same are condensed by means of acid condensing agents with o : o : p-substituted halogenated phenols having at least one free m-position, whereby di- and triarylmethanes, hydrols or anhydrides thereof or hydroxydibenzylethers are obtained. The products may be used for moth proofing or for bactericidal or fungicidal purposes. The material, e.g. wool may be impregnated with a solution in an organic solvent of the products, or the latter may be applied as in an acid dyeing process. In examples: (1) 3 : 3<1> dihydroxy-2 : 2<1> : 4 : 4<1> : 6 : 6 6<1>-hexachlortriphenylmethane-4<11>-sulphonic acid is obtained by condensing sodium benzaldehyde-p-sulphonate with 2 : 4 : 6-trichlorphenol by means of sulphuric acid; its barium, zinc, cupric and aluminium salts are referred to; 3 : 3<1>-dihydroxy-2 : 2<1> : 2<11>-4 : 4<1> : 6 : 6<1>-heptachlortriphenylmethane, 3 : 3<1>-dihydroxy - 2 : 2<1>-dimethyl-4 : 4<1> : 6 : 6<1>-tetrachlortriphenylmethane-4<11>-sulphonic acid and 3 : 3<1>-dihydroxy-5 : 5<1>-dimethyl-2 : 2<1> : 4 : - 4<1> : 6 : 6<1>-hexachlortriphenylmethane-4<11>-sulphonic acid are similarly prepared; cresols, e.g. a mixture of m- and p-cresols, after substitution by chlorine in all o- and p-positions may be condensed with the benzaldehyde-o-sulphonic acid; (2) sodium benzaldehyde-o-sulphonate is condensed with 2 : 4 : 6-trichlorphenol by means of oleum to give the hydrol anhydride, which may be converted into the hydrosulphonic acid by means of dilute acid, caustic soda or sodium carbonate; the latter is precipitated as a soluble resin by means of hydrochloric acid; (3) sodium benzaldehyde-p-sulphonate is condensed with 2 : 4 : 6-trichlorphenol, 2- (or 3-) methyl-4 : 6-dichlorphenol or 2 : 4 : 6-tribromphenol to give the corresponding hydrols; (4) the hydrol from benzaldehyde-p-sulphonic acid and 2 : 4 : 6-trichlorphenol is condensed with 2 : 4-dichlorphenol and with p-chlorphenol; (5) a hydrol prepared from m-nitrobenzaldehyde and 2 : 4 : 6-trichlorphenol is condensed with 2 : 4-dichlorphenol; the m-nitrobenzaldehyde may be replaced by p-nitrobenzaldehyde or nitrobenzalchlorides; (6) 3 : 3<1>-dihydroxy-2 : 2<1> : 4 : 4<1> : 6 : 6<1>-hexachlordiphenylmethane is prepared from paraformaldehyde and technical 2 : 4 : 6-trichlorphenol, after the latter has been freed from the small quantity of dichlorphenol by sulphonation; (7) paraformaldehyde is condensed with 2 : 4 : 6-trichlorphenol in the presence of chlorsulphonic acid and the product poured on to ice and washed with an ether-benzene mixture; both the insoluble portion and the residue obtained by evaporation of the ether-benzene solution are high molecular hydroxybenzylethers substituted to some extent by w-chlormethyl groups. Glacial acetic acid may be used as an acid condensing agent.