Patent GB-497214-A (GB)
Title: Improvements in or relating to a method of and means for protecting goods from pests
Filed: 1937-04-12
Abstract: Wool, textiles, fur, hair, feathers, leather, paper and natural or artificial fibres are rendered waterproof by treatment with a colourless aromatic hydroxy compound containing at least one aliphatic or cycloaliphatic residue containing at least 4 carbon atoms linked to the aromatic nucleus through oxygen, sulphur or nitrogen or esters or ethers thereof.  Suitable compounds include substituted phenols, cresols, xylenols, guaiacols, oxydiphenyls, oxydiphenylmethanes and naphthols.  Aliphatic residues include the hexyl, octyl, decyl, dodecyl, tetradecyl, hexadecyl, and octodecyl residues, and residues of higher fatty acids such as lauric acid, myristic acid, and palmitic acid.  Cycloaliphatic residues include the cyclo-hexyl, methyl-cyclohexyl, secondary butyl-cyclohexyl, secondary octyl-cyclohexyl, decylcyclohexyl, cyclohexyl-cyclohexyl, hexa-hydrobenzyl-cyclohexyl, decahydronaphthyl, and naphthenyl residues.  The linkages through oxygen, sulphur or nitrogen may be ether- or ester-like, sulphide-or sulphone-like, amine- or amide-like, the point of connection being not necessarily immediately at the nucleus.  The ethers may be methyl, ethyl, propyl, allyl, benzyl or phenyl ethers.  Suitable esters are those of acetic, chloro-acetic, propionic, lactic, butyric, benzoic, salicylic, and cinnamic acids.  The compounds may be substituted in the aromatic, aliphatic or cycloaliphatic residue by alkyl, aryl, mercapto, amino, ester, amide, sulphide, sulphone, carboxyl, sulphonic acid, sulphuric acid ester, quaternary ammonium, polyoxy, or polyether groups. Compounds specified are dodecyl-(2-oxy - 5 - chloro - benzyl) - ether, (41 - sec - octyl - 21-methyl - cyclohexyl) - 2 - oxy - 5 - chloro - benzylamine, decyl-(2-oxy-3, 5-dibromo-benzyl)-sulphide, lauric acid - (41 - oxy - diphenylyl) - ester, palmitic acid - (2 - oxy - 5 - chloro - benzyl) - amide, (2-oxy-5-chloro-phenyl acetic acid)-octyl ester, (2 - oxy - 5 - chloro - phenyl acetic acid) - undecylamide, (2 - oxy - 3, 5 - dichloro - benzoic acid)-dodecyl ester, (2-oxy-3, 5-dichloro-benzoic acid)-pentadecyl-amide, (2-oxy-3, 5-dichloro-benzene-sulphonic acid - 1) - dodecyl ester, (2 - oxy - 3, 5-dichloro - benzene - sulphonic acid - 1) - (41 - sec-octyl - 21 - methyl - cyclohexyl) - amide, (2 - oxy - 5 - chloro - benzene - disulphonic acid - 1,3) - dioctyl ester, lauric acid-(2-oxy-4, 5-dichloro-phenyl)-ester, 2,21 - dioxy - 5,51 - dichloro - diphenylmethane-3,31-dicarboxylic acid-dihexyl ester.  The ethers may be prepared by the double decomposition of alkyl halides with alkalialcoholates, or chlormethyl ethers may be allowed to act on phenols in the presence of acid catalysts such as zinc chloride or aluminium chloride.  The amines may be obtained by the double decomposition of primary or secondary aliphatic or cycloaliphatic amines with halogen methyl phenols. The sulphides may be obtained from alkali compounds of aliphatic or cycloaliphatic mercaptans and halogen methyl phenols.  The esters are obtained by the partial esterification of aromatic polyoxy compounds with fatty acids or by the esterification of aromatic or fatty-aromatic hydroxy carboxylic acids or hydroxy sulphonic acids with fatty alcohols or cycloaliphatic alcohols. The amides may be obtained by the double decomposition of fatty acids or fatty acid halides with fatty-aromatic oxyamines, or by the double decomposition of aromatic or fatty aromatic hydroxy carboxylic acids or hydroxy-sulphonic acids or acid halides with aliphatic or alicyclic amines.  The compounds may be applied as described in Specification 474,600.