Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Patent
1993-02-18
1994-09-20
O'Sullivan, Peter
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
564285, 564288, 564291, 564292, 564296, C07C20984
Patent
active
053491068
DESCRIPTION:
BRIEF SUMMARY
This invention relates to a process for reducing the residual content of free alkylating agent in aqueous solutions of cationic surfactants by aftertreatment of the solutions with an amine compound.
Cationic surfactants of the quaternary ammonium compound type are important products for the production of fabric softeners, hair conditioners, antistatic agents and disinfectants. They are generally synthesized from tertiary amines by reaction with an alkylating agent, for example methyl chloride, benzyl chloride or dimethyl sulfate (J. Falbe (ed.), "Surfactants in Consumer Products", Springer Verlag, Berlin, 1987, pages 107-114).
Since the alkylation is not quantitative, quaternary ammonium compounds produced by the methods mentioned above have a residual content of 0.1 to 3% by weight of the alkylating agent in the absence of an aftertreatment. Since it is necessary for obtaining toxicologically safe products to reduce the content of methyl chloride, benzyl chloride or dimethyl sulfate in the products to as low a level as possible, there has been no shortage of attempts in the past to achieve this goal by suitable working up. In this way, the content of free alkylating agent is normally reduced to a small amount by heat treatment for several hours. However, this procedure is highly time- and energy-consuming.
Accordingly, the problem addressed by the present invention was to provide a new process for the aftertreatment of cationic surfactants which would enable the content of free alkylating agent to be distinctly reduced and which would be free from the disadvantages mentioned above.
The present invention relates to a process for reducing the residual content of free alkylating agent in aqueous solutions of cationic surfactants, characterized in that the solutions are aftertreated with an amine compound selected from the group consisting of ##STR2## in which R.sup.1, R.sup.2 and R.sup.3 independently of one another represent linear or branched, optionally hydroxy-substituted alkyl radicals containing 1 to 18 carbon atoms or alkenyl radicals containing 8 to 18 carbon atoms,
It has surprisingly been found that this method of working up leads to lower residual contents of free alkylating agent in the cationic surfactant solutions in distinctly shorter times by comparison with the thermal aftertreatment. The invention is based on the observation that the amine compounds react off quickly and completely with the alkylating agent at elevated temperature.
Cationic surfactants in the context of the invention are known chemical substances and correspond to general formula (II) ##STR3## in which R.sup.4, R.sup.5 and R.sup.6 independently of one another represent linear or branched, optionally hydroxy-substituted alkyl radicals containing 1 to 18 carbon atoms or alkenyl radicals containing 8 to 18 carbon atoms, R.sup.7 is a linear or branched alkyl radical containing 1 to 4 carbon atoms or a phenyl radical and X is a halide ion, preferably chloride or bromide, or the anion of methyl sulfuric acid.
Alkylating agents in the context of the invention are benzyl chloride, dimethyl sulfate and, in particular, methyl chloride.
Suitable tertiary amines are linear or branched, but above all hydroxy-substituted trialkyl amines, such as for example triethanolamine, dimethyl ethanolamine or 3-dimethylaminopropanol.
Suitable C.sub.2-8 amino acids for the aftertreatment of the cationic surfactant solutions are alanine, arginine, asparagine, cystein, cystine, dibromotyrosine, diiodotyrosine, glutamine, glutamic acid, histidine, hydroxylysine, hydroxyproline, isoleucine, leucine, lysine, methionine, phenyl alanine, proline, serine, threonine, thyroxine, tryptophan, tyrosine and valine. The aftertreatment is preferably carried out with glycine.
The aftertreatment may also be carried out with oligopeptides which have a sufficiently low degree of oligomerization to be completely soluble in water under in-use conditions and in the in-use concentration, for example oligopeptides having an average molecular weight of 500 to 5000. Water-sol
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Behler Ansgar
Hensen Hermann
Ploog Uwe
Uphues Guenter
Henkel Kommanditgesellschaft auf Aktien
Jaeschke Wayne C.
Millson Jr. Henry E.
O'Sullivan Peter
Szoke Ernest G.
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