Patent GB-613835-A (GB)
Title: Fatty acid esters having amphoteric properties
IPC: C11C3/00
Filed: 1945-09-13
Abstract: Mono-esters obtained by heating a fatty acid containing at least six carbon atoms with an aliphatic amino alcohol having the formula H2N.C(R1)(R2)CH(R3)(OH) in which R1, R2 and R3 may be H, alkyl or alkylol and the sum of the carbon atoms in R1 and R2 is at least one (see Group IV) may be used as self-emulsifying oils and waxes and for emulsification of oils and waxes or as synthetic waxes to replace natural waxes in polishes, creams or cosmetics.  A solution of the mono-ester obtained from palmitic acid and 2-amino 1-butanol in a low-viscosity mineral oil sets to a thick vaseline-like grease.  When the ester products contain a free hydroxyl group or a double bond they may be sulphated, preferably by treatment with concentrated sulphuric acid to yield sulphated esters which may be used in insecticide emulsions, paints and cosmetics.  Reference has been directed by the Comptroller to Specifications 414,403 and 538,859.ALSO:Mono-esters containing an unsubstituted primary amino group are prepared by heating a fatty acid containing at least six carbon atoms with an aliphatic amino alcohol having the formula H2N.C(R1)R2).CH(R3)(OH) in which R1, R2 and R3 may be H, alkyl or alkylol and the sum of the carbon atoms in R1 and R2 is at least one, at dehydrating temperatures until substantially one molecular proportion of water is removed.  Specified fatty acids are caproic, caprylic, capric, lauric, myristic, palmitic, oleic, stearic, ricinoleic, linoleic, arachidic, behenic, lignoceric, palmitoleic, linolenic, elaeostearic and clupandonic acids or mixtures thereof, coconut fatty acids and the acids obtained from cotton seed, corn, peanut and sunflower.  Specified amino alcohols are 2-amino-2-methyl (or 2-ethyl) 1,3-propanediol and the propyl and isopropyl compounds, tris-(hydroxy-methyl)-amino methane, 2-amino-2-methyl-1-propanol and the ethyl, propyl and isopropyl substituted compounds, 2-amino-1-propanol, -isopropanol and -1-butanol, 2-amino-1,3-propanediol, 3-amino-3-methyl-2-butanol, 4-amino-5-methyl-3-hexanol and 5-amino-4-octanol.  Catalysts such as acids, acid salts, e.g. sodium bisulphate, or powdered metals such as tin and copper may be used.  The composition of the reaction mixture is gauged by the reduction of its acid number. When the ester products contain a free hydroxyl group or a double bond derived from an unsaturated fatty acid radical, they may be sulphated, preferably by treatment with concentrated sulphuric acid under mild sulphation conditions to yield a sulphated ester. Boric acid may be added to the sulphation mass to yield boro-sulphates or acetic acid to produce sulphoacetic compounds. The sulphated esters are amphoteric and have combined cation and anion activity.  Examples describe the production of mono-esters from coconut fatty acids, stearic acid, oleic acid, ricinoleic acid, palmitic acid, myristic acid, caproic acid and lauric acid and 2-amino-2-methyl-1,3-propanediol, 2-amino-2-ethyl-1,3-propanediol, 2-amino-2-methyl - 1 - propanol, 2 - amino - 1 - butanol and tris-(hydroxy-methyl)-amino methane. The products are variously light coloured oils and waxes.  The mono-ester of coconut fatty acid with 2 - amino - 2 - methyl - 1,3 - propanediol, of stearic acid with tris-(hydroxy-methyl)-amino methane, and of oleic acid with 2-amino-2-ethyl-1,3-propanediol are added, respectively, to 100 per cent sulphuric acid at about 35 DEG C., and after cooling a solution of sodium hydroxide is added until neutral.  The products are useful as dispersing and wetting agents, for softening textiles, for level dyeing with basic dyes and to increase the fastness of direct dyeing.  The mono-esters may also be used for flocculating acidic compounds, emulsification of oils and waxes or as synthetic waxes in polishes and creams, and the sulphated esters may also be used in insecticide emulsions, paints and cosmetics.  The amino alcohols used as starting materials may be prepared by condensing a nitro-paraffin with an aldehyde to form a nitrohydroxy compound and then reducing the latter, thus 2-amino-2-methyl-1-propanol may be obtained by reacting 2-nitropropane with formaldehyde to give 2-nitro-2-methyl-1-propanol and reducing the latter.  Reference has been directed by the Comptroller to Specifications 414,403 and 538,859.ALSO:Mono-esters containing an unsubstituted primary amino group are prepated by heating a fatty acid containing at least six carbon atoms with an aliphatic amino alcohol having the formula: H2N.C.(R1)(R2).CH(R3)(OH) in which R1, R2 and R3 may be H, alkyl or alkylol and the sum of the carbon atoms in R1 and R2 is at least one, at dehydrating temperatures until substantially one molecular proportion of water is removed.  Specified fatty acids are caproic, caprylic, capric, lauric, myristic, palmitic, oleic, stearic, ricinoleic, linoleic, arachidic, behenic, lignoceric, palmitoleic, linolenic, elaeostearic and clupandonic acids or mixtures thereof, cocoanut fatty acids and the acids obtained from cotton seed, corn, peanut and sun flower. Specified amino alcohols are 2 - amino - 2 - methyl (or 2-ethyl) 1,3-propanediol and the propyl and isopropyl compounds, Tris(hydroxy-methyl) amino methane, 2-amino 2-methyl 1-propanol and the ethyl, propyl and isopropyl substituted compounds, 2-amino-1-propanol, -isopropanol and -1-butanol, 2-amino-1-3-propanediol, 3-amino 3-methyl 2-butanol, 4-amino 5-methyl 3-hexanol and 5-amino-4-octanol. Catalysts such as acids, acid salts, e.g. sodium bisulphate, or powdered metals such as tin and copper may be used.  The composition of the reaction mixture is gauged by the reduction of its acid number.  When the ester products contain a free hydroxyl group or a double bond derived from an unsaturated fatty acid radical they may be sulphated, preferably by treatment with concentrated sulphuric acid under mild sulphation conditions to yield a sulphated ester. Boric acid may be added to the sulphation mass to yield boro sulphates or acetic acid to produce sulphoacetic compounds.  The sulphated esters are amphoteric and have combined cation and anion activity.  Examples describe the production of mono-esters from cocoanut fatty acids, stearic acid, oleic acid ricinoleic acid, palmitic acid, myristic acid, caproic acid and lauric acid and 2-amino 2-methyl 1-3-propanediol, 2-amino 2-ethyl 1-3-propanediol, 2-amino 2-methyl 1-propanol, 2-amino 1-butanol and Tris (hydroxy-methyl) amino methane.  The products are variously light coloured oils and waxes.  The mono-ester of cocoanut fatty acid with 2-amino 2-methyl 1,3-propanediol, of stearic acid with Tris (hydroxy methyl) amino methane, and of oleic acid with 2-amino 2-ethyl 1-3-propanediol are added, respectively, to 100 per cent sulphuric acid at about 35 DEG  C. and after cooling a solution of sodium hydroxide is added until neutral.  The products are useful as dispersing and wetting agents, for softening textiles, for level dying with basic dyes and to increase the fastness of direct dyeing. The mono esters may also be used for flocculating acidic compounds, emulsification of oils and waxes or as synthetic waxes in polishes and creams, and the sulphated esters may also be used in insecticide emulsions, paints and cosmetics.  The amino alcohols used as starting materials may be prepared by condensing a nitro paraffin with an aldehyde to form a nitro hydroxy compound and then reducing the latter, thus 2-amino, 2-methyl 1-propanol may be obtained by reacting 2-nitro propane with formaldehyde to give 2-nitro-2-methyl-1-propanol and reducing the latter.  Reference has been directed by the Comptroller to Specifications 414,403 and 538,859.