Patent GB-834578-A (GB)
Title: Improvements in or relating to a polycarboxylic acid salt of an imidazoline and compositions employing the same
IPC: C10M173/02
Filed: 1956-07-26
Abstract: Motor and aviation gasoline, kerosene, mineral spirits, solvent naphthas, diesel oil, heater oil, furnace oil and power fuel are rust inhibited by the addition of or formation in situ of about 0.0001 to 0.01% by weight of one or more polycarboxylic acid salts of 1 : 2-disubstituted imidazolines corresponding to the formula <FORM:0834578/III/1> in which R is a hydrocarbon radical containing a chain of 10 to 30 carbon atoms attached at one end to the 2-position of the imidazoline nucleus, X is a C2 6 hydroxyalkyl, aminoalkyl or aminoalkylaminoalkyl radical, R1 is a hydrocarbon grouping derived from a C15-60 polycarboxylic acid and n is 1, 2 or 3.  R may be a saturated or unsaturated radical, an alkyl radical or a radical containing methyl branching or containing a phenylene radical.  The polycarboxylic acid component may be saturated or may contain one or more unsaturated linkages and one or more alicyclic residues, such as in dilinoleic and trilinoleic acids; other suitable acids are derived from lecithin or are provided by polymeric forms of lauric, stearic, oleic, oxo and synthol acids, e.g. a - distearic acid.  Suitable imidazolines are 1-hydroxyethyl-2-pentadecyl imidazoline, 1 - aminoethyl - 2 - heptadecyl imidazoline, 1 - hydroxyethyl - 2 - heptadecyl imidazoline, 1 - aminoethyl - 2 - heptadecenyl imidazoline, 1 - hydroxyethyl - 2 - heptadecenyl imidazoline and 1 - aminoethylaminoethyl - 2 - heptadecenyl imidazoline.  Salts of the latter three imidazolines with a mixture of dilinoleic and trilinoleic acids are preferred.  The imidazoline salts may be employed as 10 to 60% concentrates in organic solvents such as kerosene, solvent naphtha, toluene or xylene.  Subsequent to the addition of the imidazoline salts or concentrates containing such salts to the oil component, the latter may be treated with stabilizers such as N-alkylpropylene diamines (e.g. N - n - cetyl-, N -"coco-", N-"tallow-" and N-"soya"-propylene diamines) and salts thereof with hexanoic, nonanoic, lauric, stearic, oleic, linoleic, linolenic and palmitic acids, and also with detergents such as phosphosulphurized higher hydrocarbons (e.g. polymerized propylene, butylenes and amylenes) which have been neutralized by treatment with salts of K, Ca, Ba, Mg, Zn and Al.  Aqueous solutions of the imidazoline salts may be employed as rust-preventative compositions and are stated to have valuable lubricating properties.  To the aqueous solutions there may be added sodium hydroxide, triethanolamine, soaps such as sodium or ammonium mahogany sulphonates or alkyl aryl sulphonates and sodium naphthenate, watersoluble alcohols (e.g. isopropanol), ketones, aldehydes and esters, and/or benzoic acid.ALSO:The invention comprises polycarboxylic acid salts of 1:2-disubstituted imidazolines corresponding to the formula <FORM:0834578/IV (b)/1> in which R is a hydrocarbon radical containing a chain of 10 to 30 carbon atoms attached at one end to the 2-position of the imidazoline nucleus, X is a C2-6 hydroxyalkyl, aminoalkyl or aminoalkylaminoalkyl radical, R1 is a hydrocarbon grouping derived from a C15-60 polycarboxylic acid and n is 1, 2 or 3.  The salts are prepared by mixing equimolecular amounts of polycarboxylic acid and imidazoline, if desired in a hydrocarbon solvent.  R may be a saturated or unsaturated radical, an alkyl radical or a radical containing methyl branching or containing a phenylene radical.  The polycarboxylic acid component may be saturated or may contain one or more unsaturated linkages and one or more alicyclic residues, such as in dilinoleic and trilinoleic acids; other suitable acids are derived from lecithin or are provided by polymeric forms of lauric, stearic, oleic, isooctyl and synthol acids, e.g. a -distearic acid. Suitable imidazolines are 1-hydroxyethyl-2 - pentadecyl imidazoline, 1 - hydroxyethyl - 2 - heptadecenyl imidazoline, 1 - aminoethyl - 2 - heptadecenyl imidazoline, 1 - aminoethyl - 2 - heptadecyl imidazoline, 1 - hydroxyethyl - 2 - heptadecyl imidazoline and 1 - aminoethylaminoethyl - 2 - heptadecenyl imidazoline.  The examples describe the preparation of salts of 1 - hydroxyethyl - 2 - heptadecenyl imidazoline and 1 - aminoethyl - 2 - heptadecenyl imidazoline with a mixture of dilinoleic and trilinoleic acids. The salts may be water-solubilized by reacting the remaining free carboxylic groups with sodium hydroxide or triethanolamine to form the corresponding sodium and ethanolamine salts.  1 - Aminoethyl - 2 - heptadecenyl imidazoline is prepared by condensing oleic acid with diethylene triamine.