Patent GB-716128-A (GB)
Title: Ethenoxy n-monoethanolamides of abietic acid
IPC: C07C233/12
Filed: 1951-08-03
Abstract: New ethenoxy N-mono ethanol amides of abietic acid containing 8 to 50 ethenoxy units per mol. of ethanolamide may be prepared by heating abietic acid, including wood and gum rosins or mixtures of fatty acids containing abietic acid such as tall oil, with mono-ethanolamine and condensing the resulting ethanolamide with 8 to 50 mols. of ethylene oxide.  The amide is preferably made by heating the acid with a slight excess of the amine at about 140 DEG -200 DEG C., the water of reaction being removed as it is formed and thereafter distilling off the unreacted amine under reduced pressure. The resulting amide is, desirably, condensed with the ethylene oxide at about 100 DEG -150 DEG C. in the presence of an alkaline catalyst such as sodium alcoholate, sodium or potassium hydroxide, a C2 to C4 aliphatic amine, e.g. mono- or di-ethylamine, propylamine or butylamine or an excess of the mono-ethanolamine.  Preferably, the ethanolamide and catalyst are heated to, say, 120 DEG C. and then the calculated amount of ethylene oxide is passed in at a rate to maintain a slow reflux; atmospheric or antogenic pressure may be used.  A volatile polar solvent, e.g. isopropanol or sec. butanol, may be present.  The ethenoxy compounds have wetting and detergent properties; the preferred compounds are derived from mixtures of acids containing 20 to 99 per cent. abietic acid and 80 to 1 per cent. C16 to C18 fatty acids.  Many examples are given describing products derived from abietic acid, wood and gum rosins, various grades of tall oil and synthetic mixtures of abietic acid and fatty acids, and containing numbers of ethenoxy groups over the whole range of from 8 to 50.ALSO:The invention relates to ethenoxy N-monoethanolamides of abietic acid containing 8 to 50 ethenoxy units per mol. of ethanolamide.  They may be prepared by heating abietic acid including wood and gum rosins or mixtures of fatty acids containing abietic acid such as tall oil with monoethanolamine and condensing the resulting ethanolamide with 8 to 50 mols. of ethylene oxide.  The amide is preferably made by heating the acid with a slight excess of the amine at about 140-200 DEG  C., the water of reaction being removed as it is formed and thereafter distilling off the unreacted amine under reduced pressure.  The condensation of the resulting amide with ethylene oxide is desirably carried out at about 100-150 DEG  C. in the presence of an alkaline catalyst such as sodium alcoholate, sodium or potassium hydroxide, a C2 to C4 aliphatic amine, e.g. mono- or di-ethylamine, propylamine or butylamine, or an excess of the mono-ethanolamine.  Preferably, the ethanolamide and catalyst are heated to, say, 120 DEG  C. and then the calculated amount of ethylene oxide is passed in at a rate to maintain a slow reflux; condensation may be effected under autogenic or atmospheric pressure.  A volatile polar solvent may be present, e.g. isopropanol or sec.-butanol during the condensation.  The ethenoxy compounds have wetting and detergent properties and vary from liquids of low solubility to waxes giving clear aqueous solutions. The preferred products are derived from mixed acids containing 20 to 99 per cent abietic acid and 80 to 1 per cent C16-C18 fatty acids.  Many examples are given describing products derived from abietic acid, wood and gum rosins, various grades of tall oil and synthetic mixtures of abietic acid and fatty acids, and containing numbers of ethenoxy groups over the whole range of from 8 to 50.ALSO:New ethenoxy N-monoethanolamides of abietic acid containing 8 to 50 ethenoxy units per mol of ethanolamide which may be prepared by heating abietic acid, including wood and gum rosins, or mixtures of fatty acids containing abietic acid with mono-ethanolamine and condensing the resulting amide with 8 to 50 mols of ethylene oxide (see Group IV(b)) have wetting and detergent properties.