Process for making imidazolinium salts

DETAILED DESCRIPTION OF THE INVENTION In accordance with this invention, quaternary imidazolinium salts essentially free of amines, amine salts and alkoxylated forms of the imidazolinium salts are produced.
The reaction to form the desired imidazolinium salt involves the following steps: Formation of Imidazoline The imidazoline precursor for the desired imidazolinium salt is formed by reacting acylating or esterifying agents with alkylene or polyalkylene polyamines having two or three amino groups, one of which is a primary or secondary amino group in the 2 position to a primary amino group.
The reaction is conducted at a temperature of about 100.
degree.
C.
to about 250.
degree.
C.
for a period of about 3 to about 24 hours, at a molar ratio of acyl groups to primary amine and hydroxyl groups ranging from about 0.
33:1 to about 1.
5:1, preferably from about 1:1 to about 1.
5:1, and under reflux or at atmospheric pressure or slightly greater.
To facilitate the formation of the imidazoline ring structure the reaction mixture may subsequently be subjected to a vacuum of from about 0.
4 to about 10 mm of mercury for a period of from about 1 to about 8 hours.
The resulting mixture contains in addition to the desired imidazoline some of the original acylating material, some of the original polyamine, some of the noncyclized intermediate amide products and other mixed reaction products.
The acylating or esterifying agent may be any acid or other acyl containing compound having an aliphatic or cycloaliphatic hydrocarbon group of about 10-22 carbon atoms.
Examples of such materials include the fatty acids lauric, decanoic, undecanoic, dodecanoic, tridecanoic, myristic, pentadecanoic, hexadecanoic, palmitic and the like.
Preferred fatty acids are the mixtures thereof derived from tallow, soybean or coconut oils.
Particularly preferred are the soft or hardened tallow fatty acids.
Other acylating or esterifying agents include the alkyl esters of the fatty acids and the naturally occurring glyceride esters