Patent GB-1018302-A (GB)
Title: Novel alkylolamine derivatives of undecylenic acid
IPC: A61Q15/00
Filed: 1962-06-12
Abstract: Washing preparation or hair shampoos contain as an active ingredient an alkolamine undecylenic derivative of general formula <FORM:1018302/C4-C5/1> in which R represents a hydrogen atom, a hydroxyl substituted alkyl group having 1-4 carbon atoms, or a partial ether chain of 1-30 carbon atoms, m is an integer of 1-3, n is an integer of 1-4 and Y is zero or an integer of 1-30, R1 and R2, which may be the same or different, each represents a hydrogen atom, a sulphonic acid group or a sulphuric acid halfester SO3X or R1 and R2 together represent a double bond, X and Y which may be the same or different represent a hydrogen atom, an alkali metal, ammonium, an organic amine or an alkylolamine (see Division C2).  The compounds exhibit bactericidal and fungicial activity; and may be added to solid soap or to an aqueous solution of soap or synthetic detergent. An example describes the use of a compound prepared by the reaction of maleic anhydride with undecylenic acid monoethanolamide followed by reaction with sodium sulphite, in an aqueous solution with triethanolamine lauryl sulphate and lauric acid diethanolamide. The resulting composition is a shampoo which combats dandruff.ALSO:The invention comprises alkylolamine undecylenic derivatives of formula <FORM:1018302/C2/1> in which R represents a hydrogen atom, a hydroxyl-substituted alkyl group with 1-4 carbon atoms or a partial ether chain having from 1 to 30 carbon atoms; m is an integer of 1 to 3, n is an integer of 1-4 and y is zero or an integer of 1 to 30; R1 and R2 which may be the same or different, each represents a hydrogen atom, a sulphonic acid group, or a sulphuric acid half ester SO3X (where X represents a hydrogen atom, an alkali metal, ammonium, an organic amine or an alkylolamine, or together they represent a double bond; and Y may be selected from the same class as X and may be the same or different.  The derivative may be used, together with an acceptable vehicle as pharmaceutical and/or cosmetic compositions. The compounds are prepared by reacting an anhydride of a dibasic acid, e.g. maleic or succinic anhydride with an alkylol-amide, e.g. undecylenic acid monoethanolamide or mono-isopropanolamide or these reacted with 1-6 mols. of ethylene oxide, and neutralizing, e.g. with caustic soda, an alkylolamine or ammonia, or reacted with a sulphite or bisulphite, e.g. sodium sulphite and which may be followed by neutralization.  Examples describe the reaction of succinic anhydride or maleic anhydride with undecylenic acid monoethanolamide followed by neutralization.  The products may be formulated with carriers, extenders and diluents for pharmaceutical purposes (see Division A5), or as hair shampoos (see Division C5).ALSO:Pharmaceutical and/or cosmetic compositions comprise alkylolamine undecylenic derivatives of general formula <FORM:1018302/A5-A6/1> in which R represents a hydrogen atom, a hydroxyl-substituted alkyl group (1-4c), or a partial ether chain (1-30C); m is an integer of from 1-3, n is an integer of from 1-4, and y is zero or an integer of 1-30; R1 and R2, which may be the same or different, each represents a hydrogen atom a sulphonic acid group or a sulphuric acid half ester SO3X, or R1 and R2 together represent a double bond; and X and Y which may p  be the same or different each represents a hydrogen atom, an alkali metal, ammonium, an organic amine or an alkylolamine, (see Division C2), together with an acceptable vehicle.  An aqueous or non-aqueous solvent base or a solid fine powder, may be used and the solvent base may include an emulsifying agent, oils, fats, or waxes, and may be a solid base of a pessary, suppository, lipstick or soap or the oily base of hair oil or grease.  The compounds have bactericidal and fungicidal activity.  Examples describe the use of a compound prepared by the reaction of maleic anhydride with undecylenic acid monoethanolamide followed by reaction with sodium sulphite, in a cream made from olive oil mixed with propylene glycol monostearate and stearic acid, and containing triethanolamine and propylane glycol in addition to the undecylenic acid derivative, to treat fungal conditions; and an undecylenic acid monoethanolamide succinate in aqueous ethyl alcohol as a hair tincture.