Patent GB-495761-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 mothproof by treatment with one or more etherified or esterified aromatic oxy compounds containing at least one substituted or unsubstituted aliphatic residue containing at least 6 carbon atoms and having a straight chain of at least 4 carbon atoms, e.g. hexyl-, octyl-, decyl-, dodecyl-, tetradecyl-, hexadecyl-, and octadecyl residues. Examples of such compounds are substituted phenols, cresols, xylenols, guaiacols, hydroxydiphenyls, hydroxy-diphenylmethanes and naphthols in which the hydroxy-groups are etherified or esterified.  The compounds may be substituted in the aryl or alkyl residue, e.g. the corresponding alkyl aryl ketones may be used. The ethereal residues may be aliphatic, cycloaliphatic or aromatic, e.g. methyl-, ethyl-, propyl-, benzyl-, or phenyl-. Suitable esters are those of acetic, chloracetic, propionic, lactic, butyric, benzoic, salicylic and cinnamic acids.  The aromatic oxy compounds may be prepared as described in Specification 474,600. They may be substituted in the nucleus by halogen-, hydroxy-, alkoxy- or alkylgroups or by heterocyclic residues.  The alkyl groups and the ether and ester groups may be substituted by aryl-, hydroxyaryl-, hydroxyl,- mercapto-, amino-, ester, sulphide-, sulphonic-, carboxyl-, sulphonicacid-, sulphuric acid ester-, quaternary ammonium-, polyoxy- or polyether group.  Particular compounds specified are the ethers and esters of iso-octyliso-dodecyl and iso-tetradecylphenols, iso-decyl-thymol, a :b -dimethyl-propyl-phenols, di-iso-butyl phenols, capronoyl-, capryloyl-, caprinoyl-, lauroyl-and myristoyl-phenols; the alkyl-phenols obtained by reduction of the ketones, viz: octyl-, decyl-, tetradecyl-, hexadecyl-, and octadecyl - phenols and 5 - dodecyl - 2 - oxy-1 - methyl - benzene; ethers and esters of 4 - chloro - 2 - isohexyl - phenol, 4 - chloro-2-isoamyl - cresol, isooctyl - 4 - chloro - 3 - methyl phenol, 4 - chloro - 2 - isoheptyl - cresol, 4 - chloro - 2 - isodecyl - phenol, 4 - chloro-2 - caproyl - phenol, 4 - chloro - 2 - caprylylphenol, 4 - chloro - 2 - caprinyl - phenol, 4 - chloro - 2 - lauroyl - phenol, 4 - chloro - 2-myristoyl - phenol, 4 - chloro - 2 - palmitoyl-phenol, 4 - chloro - 2 - stearoyl - phenol, as well as the normal alkyl-phenols obtainable by reducing the ketones; 4-chloro-2-sec-dodecylanisole, a :o  - bis - (2 - oxy - 5 - methylphenyl) - hexane, b :g -bis - (2 - oxy - 5 - chlorophenyl) - decane, a :d  - bis - (2 - oxy - 5-chloro - phenyl) - a :d  - dioxo - butane, the condensation product of 2 mols of 4-chlorophenol with 1 mol of oleic alcohol, and condensation products of several mols of aromatic hydroxyl compounds of halogen-hydroxyl-compounds and octodecenediol or octodecanediol. These compounds may be prepared by esterifying dibasic acids with two molecular proportions of a phenol to give the corresponding phenol diester.  This is rearranged in the presence of aluminium chloride to give the corresponding diketone in which the keto-groups may then be reduced.  For example, the compound obtained from the diester of adipic acid and p-cresol is rearranged to give the diketone and the two keto groups are then reduced to give a :o -bis-(2-oxy-5-methylphenyl)-hexane.  The last (reduction) step may be omitted.  The last two compounds may be obtained for example by condensation of 2 mols 4-chlorophenol with 1 mol oleic alcohol in the presence of acid condensing agents, whereby one phenol radical enters the oleic alcohol molecule at the double bond and one phenol radical enters at the hydroxyl group.  The compounds may be applied as described in Specification 474,600.  The Specification as open to inspection under Sect. 91 comprises also the subject-matter of Specifications 495,639 and 497,214. This subject-matter does not appear in the Specification as accepted.