Patent GB-812180-A (GB)
Title: New quaternary ammonium compounds and process for their manufacture
IPC: C03C25/25
Filed: 1955-07-11
Abstract: Polymers and copolymers are obtained from acrylic esters of quaternated polyoxyamines which have only one quaternated nitrogen atom, there being attached thereto at least one hydrocarbon radical of 8-40 carbon atoms (directly or via a hetero atom) and a radical containing an epoxy group; any carbon atom attached to two nitrogen atoms carries only single bonds; all the groups joined to the quaternary nitrogen atom are aliphatic or cycloaliphatic.  The polyoxyamines are preferably those made by reacting long-chain aliphatic amines with ethylene oxide, and are then quaternated with epichlorhydrin.ALSO:the invention comprises quaternary ammonium compounds with only one quaternated nitrogen atom, the groups attached thereto being aliphatic or cycloaliphatic, of which at least one is a hydrocarbon radical of high molecular weight (8-40 carbon atoms, preferably 12-18) attached directly or via a bridge containing a hetero-atom, at least one is a hydroxyalkyl group (which may be etherified or esterified) and one is a radical containing an epoxy group; there is a further restriction that any carbon atom attached to two nitrogen atoms carries only single bonds, so that urea and triazine residues are excluded (but not carboxylic amide groups). Preferred compounds have an epoxypropyl group attached to the quaternary nitrogen atom and contain at least two hydroxyethyl groups.  The compounds are made by known quaternating reactions using reagents containing the prescribed groups, e.g. reacting an epihalohydrin with a tertiary aliphatic or cycloaliphatic amine containing a higher hydrocarbon residue and a hydroxy-alkyl group, or by quaternating an amine containing an epoxy group, e.g. a glycide ester group.  Primary amines can be initially alkylated or hydroxyalkylated to the tertiary stage. In examples: (1) a commercial mixture of octadecenylamine, hexadecylamine and octadecylamine is oxyalkylated with ethylene oxide and quaternated with epichlorhydrin; and (2) a commercial mixture of dodecyl-di-(hydroxy-ethyl)-amine and tetradecyl-di-(hydroxyethyl)-amine is treated with epichlorhydrin. Other amines that may be used as starting materials are abietylamine, triethanolamine mono-octadecyl ether, the mono-ester of ethyl-diethanolamine with coconut oil fatty acid, and acrylic esters of polyoxyamines.ALSO:Textile assistants comprise quaternary ammonium compounds with only one quaternated nitrogen atom, the groups attached thereto being aliphatic or cycloaliphatic, of which at least one is a hydrocarbon radical of high molecular weight (8-40 carbon atoms, preferably 12-18) attached directly or via a bridge containing a hetero-atom, at least one is a hydroxyalkyl group (which may be etherified or esterified) and one is a radical containing an epoxy group; there is a further restriction that any carbon atom attached to two nitrogen atoms carries only single bonds, so that urea and triazine residues are excluded (but not carboxylic amide groups). The compounds can be used for imparting a soft feel to cellulose, polyamide or polyacrylonitrile fibres, for deelectrifying fibres, for improving the wet fastness of dyeings with direct dyestuffs, and for cross-linking of assistants used in pigment dyeing and printing processes.  In an example, the surface conductivity of nylon fabric is improved by treating it with a mixture of triethylene tetramine and an alkyl-di-(hydroxyethyl) - epoxypropyl - ammonium chloride where the alkyl group is a mixture of hexadecyl, octadecyl and octadecenyl.