Patent GB-618767-A (GB)
Title: Manufacture of amido-amine soaps
IPC: C08K5/20
Filed: 1945-08-30
Abstract: Petroleum compositions comprise an amidoamine soap derived from a polyamine having 2-10 carbon atoms and at least two primary or secondary amino groups and a fatty acid containing 8 to 22 carbon atoms prepared in specified manner (see Group IV (b)). The soap may be mixed with crude oil, stripped crude oil or a mixture of asphalt or the like with crude oil or a high boiling fraction thereof.  There may be added an oil-soluble resin such as rosin, ester gum, dammar or a copal.  Examples describe a tall oil fatty acid amidoamine soap of ethylene diamine and a mixture of diethylene triamine, triethylene tetramine and tetraethylene pentamine.  Similar soaps may be derived from the fatty acids of linseed, cottonseed, corn and fish oils and the above amines, the corresponding propylene and butylene compounds, para-phenylene diamine, hydroxy-ethyl and hydroxy-propyl ethylene diamines and N-alkylated polyamines.  The compositions may be used as binders for road materials (see Group V).  The Specification as open to inspection under Sect. 91 relates to petroleum compositions comprising amine soaps and amido-amine soaps derived from any polyamine and a higher fatty acid.  This subject-matter does not appear in the Specification as accepted.ALSO:Amido-amine soaps are prepared by reacting a polyamine, containing 2-10 carbon atoms and at least two primary or secondary amino groups, with carbon dioxide in proportion at least equivalent theoretically to the amount required to neutralize one amino group in the polyamine, mixing the resultant product (an amine carbonate) with a fatty acid containing 8-22 carbon atoms and in proportion in excess of the amount of carbon dioxide utilized in neutralizing the said amino group, said proportion being at least 2 mols. of acid per mol. of polyamine, heating the mixture to the temperature of liberation of carbon dioxide and then to the temperature of decomposition of the resulting fatty acid soap, with the evolution of water of constitution and formation of an amide, continuing the heating at the latter temperature until the water of constitution evolved corresponds in amount to at least one mole. for each mole. of the polyamine used and discontinuing the heating before all the soap is converted to amide, so as to produce an amidoamine soap.  Specified amines for the process comprise ethylene diamine, diethylene triamine, tetraethylene pentamine, the corresponding propylene and butylene compounds, paraphenylene diamine, hydroxy ethyl ethylene diamine, hydroxypropyl ethylene diamine and polyamines N-alkyl substituted by, for example, the methyl ethyl or propyl radicals.  The preferred fatty acids are the C12 to C18 acids and they may be used pure or as mixtures as, for example, tall oil and fatty acids from linseed, cottonseed, corn and fish oils.  The products are surface-active agents which may be used with bituminous material in road compositions and with petroleum oils as binders for road materials (see Groups III and V).  In examples: (1) a 30 per cent aqueous solution of ethylene diamine is saturated with carbon dioxide and then mixed with dehydrated tall oil fatty acids and the mixture heated to expel the carbon dioxide, free water and sufficient of the water of constitution to produce an amido-amine soap; (2) the procedure of (1) is repeated using a mixture of diethylene triamine, triethylene tetramine and tetraethylene pentamine If too much water of constitution is removed and the amido-amine soap is converted to the polyamide, then the latter is converted back to the amine soap by heating with excess water and then the dehydration step is repeated. Specification 607,604 is referred to.  The Specification as open to inspection under Sect. 91 relates to the preparation of a surface-active agent comprising treating any polyamine with a volatile weak acidic substance such as carbon dioxide, sulphur dioxide, hydrogen sulphide and acetic, propionic and butyric acids, mixing the product with a higher fatty acid and heating to expel the volatile acidic substance and form a soap with the higher fatty acid; heating may be continued to remove water of constitution and form an amido-amine soap.  According to an additional example, the procedure of examples (1) or (2) may be followed, substituting sulphur dioxide for carbon dioxide.  This subject-matter does not appear in the Specification as accepted.ALSO:Amido-amine soaps having surface-active properties are prepared by reacting a polyamine containing 2-10 carbon atoms and at least two primary or secondary amino groups with carbon dioxide in proportion at least equivalent theoretically to the amount required to neutralize one amino group in the polyamine, mixing the resultant product (an amine carbonate) with a fatty acid containing 8-22 carbon atoms and in proportion in excess of the amount of carbon dioxide utilized in neutralizing the said amino group, said proportion being at least 2 mols. of acid per mol. of polyamine, heating the mixture to the temperature of liberation of carbon dioxide and then to the temperature of decomposition of the resulting fatty acid soap, with the evolution of water of constitution and formation of an amide, continuing the heating at the latter temperature until the water of constitution evolved corresponds in amount to at least 1 mol. for each mol. of the polyamine used and discontinuing the heating before all the soap is converted to amide, so as to produce an amidoamine soap (see Group IV (b)).  Examples are given.  The products may be used with bituminous material in road compositions and with petroleum oils as binders for road materials (see Groups III and V). Specification 607,604, [Group IV (b)], is referred to.  The Specification as open to inspection under Sect. 91 relates to the preparation of a surface-active agent comprising treating any polyamine with a volatile weak acidic substance such as carbon dioxide, sulphur dioxide, hydrogen sulphide and acetic, propionic and butyric acids, mixing the product with a higher fatty acid and heating to expel the volatile acidic substance and form a soap with the higher fatty acid; heating may be continued to remove water of constitution and form an amido-amine soap.  This subject-matter does not appear in the Specification as accepted.ALSO:A surface active agent for use in road compositions comprises an amido-amine soap derived from a polyamine containing 2 to 10 carbon atoms and having at least two primary or secondary amino groups and a fatty acid containing 8 to 22 carbon atoms prepared in specified manner (see Group IV).  The agent may be mixed with a petroleum oil and used as a binder for sand or dirt roads; an oil-soluble resin such as rosin, ester-gum or copal may be added. It may be incorporated into asphalt or other bituminous paving material and then applied to wet or dry aggregate.  Alternatively, the agent may be dissolved in naphtha, benzine, gasoline or other inert volatile solvent, the solution stirred with the aggregate and then mixed with asphalt or tar.  Examples describe tall oil fatty acid amide-amine soaps of ethylene diamine and a mixture of diethylene triamine, triethylene tetramine and tetraethylene pentamine.  Other amido-amine soaps may be derived from linseed, cottonseed, corn and fish oil acids and the above amines, the corresponding propylene and butylene compounds, para-phenylene diamine, hydroxyethyl-ethylene diamine, hydroxy propyl ethylene diamine and N-alkylated polyamines. Specification 607,604 is referred to.  The Specification as open to inspection under Sect. 91 relates to surface active agents having the same application but comprising amine soaps and amido-amine soaps derived from any polyamine and higher fatty acids.  This subject-matter does not appear in the Specification as accepted.