Patent GB-436726-A (GB)
Title: The manufacture of new quarternary ammonium compounds and disinfecting media containing the same
Filed: 1934-04-13
Abstract: Quaternary ammonium compounds containing attached to nitrogen at least one high-molecular aliphatic ether radicle of at least 8 carbon atoms in which the oxygen is separated from the nitrogen by at least two carbon atoms, the remaining organic radicles attached to nitrogen being saturated radicles, are prepared by (1) reacting upon a suitable amine with a reactive ester, e.g. a halide or benzene-sulphonyl ester, of the high-molecular aliphatic alcohol containing an oxygen atom in the chain, (2) treating an amine containing the high-molecular ether radicle with a reactive ester of a saturated alcohol, (3) reacting an appropriate alcohol with a saturated amine containing a radicle with a replaceable substituent such as chlorine, and (4) treating a saturated amine containing a hydroxyalkyl group with a reactive ester of a saturated alcohol; in each case the product is converted if necessary, into the quaternary form.  The compounds possess bactericidal and fungicidal properties and may be incorporated with inert dispersing agents.  According to the examples, (1) (y-dodecyloxy-b -hydroxypropyl)-trimethyl-ammonium chloride is prepared by allowing y-dodecyloxy-b -hydroxy-a -chloropropane to react with trimethylamine in cold benzene solution; the corresponding bromide is obtained by reacting with methyl bromide upon (y - dodecyloxy - b  - hydroxypropyl) - dimethylamine, which is prepared by treating y-dodecyloxy - b  - hydroxy - a  - chloropropane with dimethylamine; (2) cyclohexyl-ethylamine is heated with y-dodecyl-b -hydroxy-a -chloropropane and the product treated with methyl iodide to give methyl-cyclohexyl-ethyl-(y-dodecyloxy - b  - hydroxypropyl) - ammonium iodide.  Specification 369,614 is referred to.  The Specification as open to inspection under Sect. 91 describes the high-molecular aliphatic radicle as preferably containing p 8--20 carbon atoms and states that other substituents, such as alkoxy and amino groups may be present therein; octyloxyethyl, dodecyloxyethyl, octyloxypropyl, octadecyloxy - ethyl and decyloxy-hydroxypropyl radicles are mentioned.  It further states that the other saturated organic radicles are preferably lower alkyl groups, but may also comprise alkyl groups of 8--18 carbon atoms or cyclo-aliphatic groups, e.g. cyclopentyl and cyclohexyl groups.  The preparation of the following compounds is also described:--(1) tributyl-(y - dodecyloxy - b  - hydroxypropyl)-ammonium chloride from y-dodecyloxy-b -hydroxy-a -chlorpropane and tributylamine: (2) trimethyl-n - octyloxyethyl - ammonium bromide from trimethyl-amine and n-octyloxyethyl bromide obtained by reacting hydrogen bromide upon n-octyl-monoglycolether which results from the treatment of n-octyl alcohol with ethylene oxide; instead of trimethylamine, trihydroxyethylamine may be employed; (3) methyl-diethyl-decyloxyethyl-ammonium iodide from methyl iodide and diethylde cyloxyethylamine, the latter being obtained by treatment of sodium decylate with diethylaminoethylchloride Finally, it is stated that the quaternary ammonium products in the form of their hydrohalides may be converted into salts with nitric, sulphuric, alkyl- and phenyl-sulphonic, phosphoric, formic, acetic, lactic, citric, tartaric, benzoic and salicylic acids, or may be treated with caustic alkali to give the free bases.  This subject-matter does not appear in the Specification as accepted.