Patent GB-420883-A (GB)
Title: Process for the manufacture of new reaction products of acid amides
IPC: C07C233/16
Filed: 1933-03-02
Abstract: Materials useful as auxiliary agents in the textile and other industries are prepared by reacting glycide with organic compounds containing one or more carboxylic acid amide and/or sulphonic acid amide groups, at least two molecular proportions of glycide being present for each of the amide groups.  The products may subsequently be etherified or esterified, e.g. with inorganic or organic acids or their acid chlorides or anhydrides, chlorethane sulphonic acid, benzyl chloride sulphonic acid, ethylene sulphonic acid, alkylene oxides and epichlorhydrin.  The products are useful as emulsifying, cleansing, wetting, dispersing, impregnating and softening agents in the textile, leather, caoutchouc, lacquer and paper industries, as protective colloids in the dye industry, and in the cosmetic and pharmaceutical industries for preparing creams and salves.  An example is given of the treatment of coconut oil fatty acid hydroxyethylamide with glycide to give a wetting and dispersing agent.  Other starting materials mentioned are butyric acid ethylamide, lactic acid hydroxyethylamide, oleylamide, palmitic acid hydroxyethylamide, linoleic acid anilide, ricinoleic acid dihydroxypropylamide, benzoic acid butylamide, salicyclic acid naphthylamide, phthalimide, phthalamic acid, p-toluenesulphonic acid cyclohexylamide and laurylethylenediamine.  The samples are prepared by (1) reacting benzylsulphonamide with glycide; (2) treating the reaction product of p-toluenesulphonic acid cyclohexylamide and glycide with concentrated sulphuric acid at 30--35 DEG  C., or ethylene oxide at 180--185 DEG  C.; (3) heating the reaction product of coconut oil fatty acid ethanolamide and glycide with concentrated sulphuric acid at 35 DEG  C.  The Specification as open to inspection under Sect. 91 is not restricted to the above proportions of the reactants and states that the amount of the glycide used may be such as to lead to an incomplete conversion of the amide starting material.  The formul  of the products given therein contain only one glycide residue.  This subject-matter does not appear in the Specification as accepted.ALSO:Materials prepared by reacting glycide with organic compounds containing one or more carboxylic acid amide and/or sulphonic acid amide groups, at least two molecular proportions of glycide being present for each of the amide groups, are stated to be useful as emulsifying and dispersing agents in the textile, leather, caoutchouc, lacquer and paper industries, and as protective colloids in the dye industry.  The products may subsequently be etherified or esterified, e.g. with inorganic or organic acids or their acid chlorides or anhydrides, chlorethane sulphonic acid, benzyl chloride sulphonic acid, ethylene sulphonic acid, alkylene oxides and epichlorhydrin.  An example is given of the treatment of coconut oil fatty acid hydroxyethylamide with glycide to give a dispersing agent.  Other starting materials mentioned are butyric acid ethylamide, lactic acid hydroxyethylamide, oleylamide, palmitic acid hydroxyethylamide, linoleic acid anilide, ricinoleic acid dihydroxypropylamide, benzoic acid butylamide, salicylic acid naphthylamide, phthalimide, phthalamic acid, p-toluenesulphonic acid cyclohexylamide and laurylethylene-diamine.  The samples are prepared by (1) reacting benzylsulphonamide with glycide; (2) treating the reaction product of p-toluene sulphonic acid cyclohexylamide and glycide with concentrated sulphuric acid at 30--35 DEG  C., or ethylene oxide at 180--185 DEG  C., (3) heating the reaction product of coconut oil fatty acid ethanolamide and glycide with concentrated sulphuric acid at 35 DEG  C.  The Specification as open to inspection under Sect. 91 is not restricted to the above proportions of the reactants and states that the amount of the glycide used may be such as to lead to an incomplete conversion of the amide starting material.  The formulae of the products given therein contain only one glycide residue.  This subject-matter does not appear in the Specification as accepted.ALSO:Materials useful in the preparation of salves are prepared by reacting glycide with organic compounds containing one or more carboxylic acid amide and/or sulphonic acid amide groups, at least two molecular proportions of glycide being present for each of the amide groups.  The products may subsequently be etherified or esterified, e.g. with inorganic or organic acids or their acid chlorides or anhydrides, chlorethane sulphonic acid, benzyl chloride sulphonic acid, ethylene sulphonic acid, alkylene oxides and epichlorhydrin.  An example is given of the treatment of coconut oil fatty acid hydroxyethylamide with glycide.  Other starting materials mentioned are butyric acid ethylamide, lactic acid hydroxyethylamide, oleylamide, palmitic acid hydroxyethylamide, linoleic acid anilide, ricinoleic acid dihydroxypropylamide, benzoic acid butylamide, salicylic acid naphthylamide, phthalimide, phthalamic acid, p-toluenesulphonic acid cyclohexylamide and laurylethylenediamine.  The samples are prepared by (1) reacting benzylsulphonamide with glycide; (2) treating the reaction product of p-toluenesulphonic acid cyclohexylamide and glycide with concentrated sulphuric acid at 30-35 DEG  C., or ethylene oxide at 180-185 DEG C., (3) heating the reaction product of coconut oil fatty acid ethanolamide and glycide with concentrated sulphuric acid at 35 DEG C.  The Specification as open to inspection under Sect. 91 is not restricted to the above proportions of the reactants and states that the amount of the glycide used may be such as to lead to an incomplete conversion of the amide starting material.  The formul  of the products given therein contain only one glycide residue.  This subject-matter does not appear in the Specification as accepted.