Patent GB-680688-A (GB)
Title: Production of trihydroxyalkyl-dialkylene triamines, their hydrohalide salts and condensation products thereof
IPC: D06M13/332
Filed: 1950-12-06
Abstract: Trihydroxyalkyl - dialkylene - triamines of general formula <FORM:0680688/IV (b)/1> (in which R and R1 represent alkylene radicals containing 2-6 carbon atoms) or their hydrohalide salts are obtained by reacting primary hydroxyalkylamines containing 2 to 6 carbon atoms with dihalides of aliphatic hydrocarbons containing 2 to 6 carbon atoms, at elevated temperatures, in amounts of about 2 mols. of the hydroxyalkylamine to each mol. of dihalide and, if desired, treating the resulting hydrohalide salts with alkaline reacting substances to produce the free trihydroxyalkyl-dialkylenetriamines. The reaction may be represented as follows: <FORM:0680688/IV (b)/2> in which R and R1 are alkylene radicals with 2 to 6 carbon atoms and X is halogen.  The reaction is carried out at temperatures between 90 DEG  and 200 DEG  C., preferably between 100 DEG  and 120 DEG  C. The free hydroxy alkylamine bases are obtained from the hydrohalide salts by the addition of alkaline-reacting substances such as caustic soda solution, potassium hydroxide or calcium oxide.  Suitable primary hydroxyalkylamines are, for example, monoethanolamine, monoisopropanolamine and 1-amino-3-hydroxbutane.  Suitable dihalides are 1,2-dichlormethane, 1,2-dibromethane, 1,3-dibrompropane, 1,2-dichlorobutane and 1,4-dichlorobutane.  Condensation products which are readily soluble or dispersible in water are obtained by reacting the trihydroxyalkyldi-alkylene-triamines of the formula <FORM:0680688/IV (b)/3> obtained in the manner described above, with fatty acids of high molecular weight or their anhydrides, esters or acid halides. Particularly useful compounds are obtained by condensing the trihydroxyalkyl-dialkylene-triamines with fatty acid alkanolamides at temperatures in the range 160-240 DEG  C.  The products are useful as softening and preparing agents for the textile and leather industries.  In the form of their water-soluble salts they are suitable as binding agents for tar and bitumen.  In the examples: (a) monomethanolamine is reacted with dichlorethane and the product is treated with caustic soda to give trihydroxyethyl-diethylene-triamine which is condensed with (i) stearic acid to give a product which is suitable as a preparing or reviving agent for viscose artificial silk and staple fibre; (ii) oleic acid, the product being treated with acetic acid to give a salt which increases the adhesive properties of tar, asphalt and bitumen; (iii) stearic acid monoethanolamide and (iv) oleic acid monopropanolamide.ALSO:Condensation products obtained by reacting trihydroxyalkyl-dialkylene triamines of formula <FORM:0680688/IV (c)/1> (in which R and R1 are alkylene radicals with 2 to 6 carbon atoms) with fatty acids of high molecular weight or their functional derivatives, are readily dispersible in water and may be used for imparting a smooth soft feel to textiles.  In an example trihydroxyethyldiethylene triamine is condensed with stearic acid to give a product suitable as a preparing or reviving agent for viscose artificial silk and staple fibre.ALSO:The water-soluble salts of the condensation products of trihydroxyalkyl-dialkyl triamines and high fatty acids or their functional derivatives are suitable as binding agents for tar or bitumen.  In an example trihydroxyethyl-diethylene triamine of formula <FORM:0680688/V/1> is condensed with oleic acid and then treated with acetic acid; the addition of 1 to 2 per cent of the resulting acetic acid salt to tar asphalt or bitumen imparts to these materials an increased adhesion to stone or concrete.