Patent GB-872106-A (GB)
Title: A process for the preparation of surface active compounds
IPC: D06M13/385
Filed: 1958-04-18
Abstract: Surface-active compounds are prepared by (1) forming a 3-halo-2-hydroxypropyl ether of a polyhydric alcohol by condensing one molar proportion of a polyhydric alcohol containing 3-6 hydroxyl groups with at least one molar proportion of an epihalohydrin other than epifluorohydrin, (2) separately forming an amide, imidazoline or tetrahydropyrimidine containing basic nitrogen which is the condensation product, open chain or cyclized, of one molar proportion of a polyalkylene polyamine containing 3-5 amino nitrogen atoms and 2 or 3 carbon atoms in each alkylene group with at least one molar proportion of a non-aromatic monocarboxylic acid containing 12-22 carbon atoms and, optionally, one or more molar proportions of an aliphatic monocarboxylic acid containing 2-6 carbon atoms, the total molar proportion of monocarboxylic acid being less, by at least one, than the number of amino nitrogens in the polyamine, and (3) condensing the ether of step (1) with the product of step (2) by reacting one halogen equivalent of the former with 1-3 amine equivalents of the latter at 75-150 DEG C.  The final products are of the formula:-  <FORM:0872106/IV (b)/1> where x is a number from 3-6, n is a number from 1 to x; R is the hydroxyl-free residue of the polyhydric alcohol; and each A is independently selected from the following:-  <FORM:0872106/IV (b)/2> <FORM:0872106/IV (b)/3> <FORM:0872106/IV (b)/4> <FORM:0872106/IV (b)/5> <FORM:0872106/IV (b)/6> <FORM:0872106/IV (b)/7> where a and b are integers (either of which may be zero) whose total is a number from 2 to 4; each c is an integer of from 0 to 4 whose total value in a given radical is 2-4; each d is an integer from 0 to 2, provided that their total in a given radical does not exceed 2; e is 1, 2 or 3; y is 2 or 3; each B is independently selected from hydrogen, hydroxyalkyl, acyl radicals of C12-22 fatty acids, and acyl radicals of C2-6 aliphatic acids; D is the hydrocarbon radical of an acyl variant of B; each E is hydrogen or hydroxyalkyl; each F is independently selected from hydroxyalkyl, acyl radicals of C12-22 fatty acids, and acyl radicals of C2-6 aliphatic acids; each G is independently hydroxyalkyl or amino hydrogen; and each J is independently selected from acyl radicals of C12-22 fatty acids, and acyl radicals of C2-6 aliphatic acids; provided that in a given radical at least one of B, F or J must contain from 12 to 22 carbon atoms.  The compounds form salts, e.g. nitrates, sulphates, alkyl sulphates, phosphates, formates, acetates, lactates, tartrates, benzene or toluene sulphonates, and citrates.  Suitable polyhydric alcohols are triols (e.g. glycerol), tetritols (e.g. erythritol), pentitols (e.g. xylitol, arabitol), hexitols (e.g. sorbitol, mannitol, dulcitol), pentaerythritol, trimethylolethane, trimethylolpropane, anhydro derivatives of polyhydric alcohol (e.g. 1,4-sorbitan), diglycerol, monosaccharides (e.g. sorbose, mannose, glucose, arabinose, xylose, methyl glucoside), and any of the above modified by the action of alkylene oxides.  In place of the monocarboxylic acids their esters may be used.ALSO:Surface-active agents useful as textile softeners are prepared by (1) forming a 3-halo-2-hydroxypropyl ether of a polyhydric alcohol by condensing one molar proportion of a polyhydric alcohol containing 3-6 hydroxyl groups with at least one molar proportion of an epihalohydrin other than epifluorohydrin, (2) separately forming an amide, an imidazoline or a tetrahydropyrimidine containing basic nitrogen which is the condensation product, open chain or cyclized, of one molar proportion of a polyalkylene polyamine containing 3-5 amino nitrogen atoms and 2-3 carbon atoms in each alkylene group with at least one molar proportion of a non-aromatic monocarboxylic acid containing 12-22 carbon atoms and, optionally, one or more molar proportions of an aliphatic monocarboxylic acid containing 2-6 carbon atoms, the total molar proportion of monocarboxylic acid being less, by at least one, than the number of amino nitrogens in the polyamine, and (3) condensing the ether of step (1) with the product of step (2) by reacting one halogen equivalent of the former with 1-3 amine equivalents of the latter at 75 DEG -150 DEG C.  In an example, samples of cotton, nylon, Vicara, Acrilan, Orlon, Dacron, cellulose acetate, Dynel, rayon and Darlan are treated with aqueous solutions of such products ("Acrilan," "Orlon," "Dacron," and "Dynel" are Registered Trade Marks).  The compounds may be applied as aqueous dispersions by the use of a dipping roll or padder, or by immersion of the material to be treated in a bath.ALSO:Hydrocarbon fuels of the low vapour pressure wide cut gasoline type contain as antistatic additives compounds prepared by (1) forming a 3-halo-2-hydroxypropyl ether of a polyhydric alcohol by condensing one molar proportion of a polyhydric alcohol containing from 3 to 6 hydroxyl groups with at least one molar proportion of an epihalohydrin other than epifluorohydrin, (2) separately forming an amide, an imidazoline or a tetrahydropyrimidine containing basic nitrogen which is the condensation product, open chain or cyclized, of one molar proportion of a polyalkylene polyamine containing 3-5 amino nitrogen atoms and 2-3 carbon atoms in each alkylene group with at least one molar proportion of a non-aromatic monocarboxylic acid containing 12-22 carbon atoms and, optionally, one or more molar proportions of an aliphatic monocarboxylic acid containing 2-6 carbon atoms, the total molar proportion of monocarboxylic acid being less, by at least one, than the number of amino nitrogens in the polyamine, and (3) condensing the ether of step (1) with the product of step (2) by reacting one halogen equivalent of the former with 1-3 amine equivalents of the latter at 75-150 DEG C.  The final products of the above process are also stated to be useful as additives for lubricating oils and corrosion inhibitors.