Patent GB-583031-A (GB)
Title: Surface-active compounds
IPC: D06M15/423
Filed: 1943-03-08
Abstract: Emulsifying agents comprise the products obtained by reacting a methylol-amide of the formula R-CO-NR1-CH2-OH or R-O-CO-NR1-CH2-OH, where R is an alkyl radical of 8 to 22 carbon atoms and R1 is hydrogen or an alkyl radical having less than 8 carbon atoms, with an alcohol or a glycol or a hydroxy-alkanecarboxylic or sulphonic acid, [see Group IV], In examples, the following products are described: stearamido-methyl ether of glycollic acid, stearamido-methyl ether of lactic acid, mono-stearamido-methyl ether of ethylene glycol, stearamidomethyl diethylene glycol mono-ether, glycollic acid ether of methyloloctadecyl-carbamate, stearamidomethyl-methyl ether, the reaction product of hydroxy-ethane sulphonic acid and methylol stearamide, and the octyl ether of methylol stearamide; reference is made to the reaction of the methylol compounds of a fatty acid amide containing 20 and 22 carbon atoms and of the amide of the coconut oil acids with glycollic acid yielding corresponding glycollic acid ether.  Isopropyl alcohol and ethyl alcohol are also specified as starting materials for reacting with the above defined methylolamides.  Reference has been directed by the Comptroller to Specification 523,396.ALSO:Compounds useful as textile-treating agents are prepared by reacting a methylol-amide of the formula R-CO-NR1-CH2OH or R-O-CO-NR1-CH2OH, where R is an alkyl radical of 8 to 22 carbon atoms and R1 is hydrogen or a lower alkyl radical (i.e. less than 8 carbon atoms), with an alcohol, or a glycol, or a hydroxy-alkane-carboxylic or -sulphonic acid in presence of an acid condensing agent.  As typical starting materials there are mentioned methylol-stearamide and octadecylcarbamido - methanol and as hydroxy compounds, methanol, ethanol, isopropyl alcohol, octyl alcohol, glycollic acid, lactic acid and hydroxyethane-sulphonic acid.  The compounds are reacted together in presence of a condensing agent which may be one of the reagents itself; thus, glycollic acid may be reacted without any additional acid condensing agent, whereas ethylene glycol needs a small amount of an anhydrous acid-reacting agent such as PCl3, maleic anhydride or anhydrous hydrogen chloride. The reaction may be carried out at a temperature between 0 DEG  C. to 100 DEG  C., and if desired, in the presence of an inert diluent such as acetone, ethyl acetate or dioxane.  Preferably, an excess of the hydroxy compound is employed.  The products may be employed as wetting agents, scouring agents, softening agents and emulsifying agents (see Group III) and as dye-fixing, starch fixing and water-proofing agents (see Group VIII).  Examples: (1) glycollic acid in acetone is reacted with methylol-stearamide to yield the stearamidomethyl ether of glycollic acid, the ammonium salt of which is prepared by passing ammonia into an acetone solution of the free acid; the methylol stearamide may be replaced by the methylol compound of a fatty acid amide containing 20-22 carbon atoms or of the amide of the coconut oil acids; (2) methylolstearamide is reacted with lactic acid yielding a product believed to have the formula C17H35CONH.CH2O.CH(CH3)COOH; (3) ethylene glycol and methylol-stearamide are reacted in the presence of maleic anhydride yielding the mono-stearamido-methyl ether of ethylene glycol; (4) diethylene glycol and methylolstearamide in ethyl acetate are reacted in the presence of PCl3 to yield stearamidomethyl diethylene glycol mono-ether; (5) glycollic acid in acetone is reacted with methylol-octadecylcarbamate (prepared by reacting paraformaldehyde and octadecyl carbamate in alcohol containing potassium carbonate) yielding the glycollic acid ether of the methylol-carbamate; (6) methyl alcohol and methylol stearamide are reacted in the presence of concentrated sulphuric acid, added in methanol solution, to yield stearamidomethyl-methyl ether; (7) hydroxy-ethane sulphonic acid suspended in acetone is reacted with methylol stearamide and the sulphonic acid derivative precipitated from the reaction product by pouring it on to ice and filtering; (8) octyl alcohol and methylol stearamide are reacted by passing a slow stream of hydrogen chloride through the mixture at 30 DEG  to 40 DEG  C. yielding the octyl ether of methylol stearamide.  Reference has been directed by the Comptroller to Specification 523,396.