Patent GB-394196-A (GB)
Title: Improvements in or relating to the manufacture of new products suitable for use as washing, wetting-out, emulsifying, dispersing, peptising, foaming, cleansing and like agents
Filed: 1932-10-06
Abstract: Quaternary ammonium salts, which are stated to be wetting, washing, emulsifying, dispersing, peptising, foaming and cleansing agents, are obtained by condensing tertiary amines with a -halogen ethers, one or both of the reacting components containing at least one radicle of the aliphatic, alicyclic or fatty-aromatic series with at least eight carbon atoms.  The hydroxy compounds, from which the a -halogen ethers are derived by treatment with an aldehyde and hydrogenhalide, may be substituted, e.g by a carboxylic group.  The following hydroxy compounds are mentioned: methyl, ethyl, isopropyl, butyl, amyl, hexyl, lauryl, cetyl, stearyl, oleyl, furfuryl, benzyl and naphthenyl alcohols, cyclohexanol, tetra- and deca-hydro naphthols, castor oil and oxy acids such as lactic and ricinoleic acid; the following aldehydes are specified: formaldehyde, acetaldehyde, benzaldehyde, salicylicaldehyde, cinnamic aldehyde, piperonal, aenanthol, decanal, citronellal and furfural.  The tertiary amines may also be substituted, e.g. by hydroxy and carboxylic groups. Trimethyl-, triethyl- and tributyl amines, triethanolamine, dimethyl- and diethylanilines, pyridine, quinoline, naphthoquinoline, N-alkylpiperidines, dialkylcyclohexylamines, dicyclohexylalkylamines, benzylpiperidine and benzyldicyclohexylamine are mentioned.  In examples: (1) triethylamine is condensed with octadecylchlormethylether (prepared from octadecylalcohol, trioxymethylene and hydrogen chloride in benzene solution); (2) pyridine, and similarly quinoline, is condensed with the mixture of chlorethers derived from hydrogenchloride, trioxymethylene and the unsaturated alcohols obtained from sperm oil; (3) N-laurylpiperidine is condensed with chlorethers derived from paraldehyde, hydrogenchloride and lauryl or naphthenyl alcohol; (4) N-octadecylpiperidine is condensed with phenylchlormethylethylether; (5) diethylcetylamine is condensed with furyl-a -chlormethylcyclohexylether (from furfural, cyclohexanol and hydrogenchloride); (6) dicyclohexyllaurylamine is condensed in tetrahydronaphthalene with butylchlormethylether (from n-butyl alcohol, hydrogenchloride and trioxymethylene): the product yields an emulsion with water.  N-lauryl and N-octadecyl-piperidines are prepared by heating piperidine with lauryl and octadecyl-chlorides respectively, treating with alkali and distilling the liberated bases.  Dichlorohexyllaurylamine is prepared from lauryl chloride and excess dicyclohexylamine.ALSO:Quaternary ammonium salts which are stated to be emulsifying, dispersing and peptizing agents are obtained by condensing tertiary amines with a -halogen ethers, one or both of the reacting components containing at least one radicle of the aliphatic, alicyclic, or fatty-aromatic series with at least eight carbon atoms.  The hydroxy compounds from which the a -halogen ethers are derived by treatment with an aldehyde and hydrogenhalide, may be substituted, e.g. by a carboxylic group. The following hydroxy compounds are mentioned: methyl, ethyl, isopropyl, butyl, amyl, hexyl, lauryl, cetyl, stearyl. oleyl, furfuryl, benzyl and naphthenyl alcohols, cyclohexanol, tetra-and decahydronaphthols, castor oil and oxyacids such as lactic and ricinoleic acid; the following aldehydes are specified: formaldehyde, acetaldehyde, benzaldehyde, salicyclicaldehyde, cinnamic aldehyde, piperonal, oenanthol, decanal, citronellal and furfural.  The tertiary amines may also be substituted, e.g. by hydroxy and carboxylic groups.  Trimethyltriethyl- and tributylamines, triethanolamine, dimethyl- and diethylanilines, pyridine, quinoline, naphthoquinoline, N-alkyl piperidine, dialkylcyclohexylamine, dicyclohexylalkylamine are mentioned.  In examples: (1) triethylamine is condensed with octadecylchlormethylether; (2) pyridine, and similarly quinoline, is condensed with the mixture of chlorethers derived from hydrogenchloride, trioxymethylene and the unsaturated alcohols obtained from sperm oil; (3) N-laurylpiperidine is condensed with chlorethers derived from paraldehyde, hydrogenchloride and lauryl or naphthenyl alcohol; (4) N-octadecylpiperidine is condensed with phenylchlormethylethylether; (5) diethylcetylamine is condensed with furyl-a -chlormethylcyclohexylether; (6) dicyclohexyllaurylamine is condensed in tetrahydronaphthalene with butylchlormethylether; the product yields an emulsion with water.