Patent GB-524847-A (GB)
Title: Improvements in or relating to oil compositions
IPC: C09K23/00
Filed: 1939-02-09
Abstract: 524,847. Disinfectants and vermin-destroying compositions. CARBIDE & CARBON CHEMICALS CORPORATION. Feb. 9, 1939, No. 4232. Convention date, Feb. 18, 1938. [Class 81 (i)] [Also in Groups III, IV and V] A water-dispersible composition is prepared by the admixture of a major proportion of an oil and a minor proportion of a 1 : 2-disubstituted glyoxalidine of the general formula where R is an alkyl or alkenyl group having from 9-19 carbon atoms ; R 1  is hydrogen or a lower alkyl group containing 1-4 carbon atoms ; R 2  is an alkylene group or a lower alkyl substituted alkylene group and X is a hydroxyl group or an W-amino-alkyl amino group. These compounds are prepared by heating a mixture substantially consisting of a hydroxyalkylene polyamine or an alkylene polyamine or a polyalkylene polyamine, said polyamines containing the atomic grouping R 2 X, and at least one free fatty acid containing from 10-20 carbon atoms or an amide or ester of such an acid and removing water during the time of heating, which is so correlated to the temperature as to cause the splitting off of water in excess of 1.5 mols. for each mol. of free fatty acid, or in excess of 0.5 mol. for each mol. of combined fatty acid involved in the reaction. Amines mentioned include diethylene triamine, hydroxyethyl ethylene diamine, dipropylene triamine, triethylene tetramine, and. tripropylene tetramine as well as other alkylene polyamines of similar nature. Fatty acid compounds used include the fatty acids themselves such as lauric, oleic,.linoleic, ricinoleic, stearic and palmitic acids as well as their salts and esters. Other such compounds which occur naturally in vegetable oils such as olive, cocoanut, linseed and cotton-seed oils which have from 10-20 carbon atoms in the molecule. The glyoxalidines prepared as above and having one free amino group may be reacted with acids to form neutral salts or soaps. If the acid used is a higher fatty acid, the salt so formed is in general soluble in hydrocarbons and may be used in substitution for the glyoxalidines themselves. Acids mentioned as suitable for this salt formation include mineral acids such as hydrochloric, sulphuric and phosphoric acids as well as organic acids such as acetic, lactic, oleic and stearic acids. If X in the general formula above stands for a hydroxy group this may be esterified by such acids as acetic, lactic, oleic, linoleic, stearic, and other similar aliphatic acids. Reaction temperatures for the process of the present invention vary between 140-300 C., the time of reaction being regulated by the temperature. Much lower temperatures may however be used when a water-entraining material is present. Agents of this type which are mentioned include toluene, xylene and dibutyl ether. The compounds of the present invention are chiefly intended for use in oil compositions to improve miscibility between oils and other oleaginous substances with water. They are also surface active agents capable of causing the dispersion, and emulsification of oils and water. They are effective as fibre or yarn lubricants, and are readily removed in the usual scouring process as applied to wool yarns. Other uses include applications when oil compositions compatible with water are necessary as in polishes, cleaning compositions, cutting oils, deodorants, machine lubricants and sizing preparations. In examples (1) 1- Aminoethyl-2-heptadecenyl glyoxalidine prepared by heating two mols. of diethylene triamine with one mol. of oleic acid for 16 hours to remove about 1.7 mols. of water and then distilling off the unreacted diethylene triamine under vacuum is added in an amount of 5 per cent. by weight to a mineral oil. The oil composition when present in an amount of 1 per cent. in an aqueous solution gave a stable emulsion even in the presence of 5 per cent. of hydrochloric acid. (2) 1-(Aminoethyl-ethylamino)-2-heptadecenyl glyoxalidine prepared by reacting oleic acid with triethylene tetramine as in example (1) is mixed in an amount of 1 per cent. with a mineral oil to produce a composition capable of dilution with water to any extent. (3) 1-Amino-ethyl-2-undecyl glyoxalidine prepared by heating diethylene triamine with commercial cocoanut fatty acids is made into a series of composition with a mineral oil in amounts of from 1 per cent.-10 per cent. The first two compositions possessed less stability than the others but all dispersed readily. (4) Compositions of a mineral oil and the following glyoxalidines were prepared and applied to skeins of worsted yarns:-1-aminoethyl-2-heptadecenyl-, 1-aminoethyl-2-heptadecyl -, 1 - hydroxyethyl - 2 - heptadecenyl -, 1 - aminoethyl - 2 -undecyl-, 1 - (aminoethyl ethylamino)-2-heptadecenyl-, 1-aminoisopropyl- 2 - heptadecenyl - 5 -methyl - glyoxalidine, and comparative tests were made to show the amount removed by a normal scouring operation. (5) 1-Hydroxyethyl-2-heptadecenyl glyoxalidine prepared by refluxing hydroxyethyl ethylene diamine with commercial oleic acid is used in oil compositions either in the free state or in the form of its esters with organic acids which are soluble. Specification 337,368, [Class 1 (i)], is referred to.