Patent GB-621324-A (GB)
Title: Manufacture of new semi-esters of dicarboxylic acids
IPC: D06M13/402
Filed: 1947-02-18
Abstract: Semi-esters of dicarboxylic acids which contain no C-C double bonds, except such as may be present in an aromatic ring, are prepared by reacting the acids or their functional derivatives with an N-hydroxyalkyl amide of an unsaturated fatty acid, in the proportion of one mol. of acid or derivative for each alcoholic hydroxy group in the hydroxy-alkylamide, the latter reagent containing at least twelve carbon atoms but not more than one ether group.  Specified dicarboxylic acids are malonic, succinic, adipic, phthalic, terephthalic and naphthalic acids, and specified amides are the N-(b -hydroxyethyl) amides of oleic and ricinoleic acids and oleic acid N-(2-hydroxypropyl) amide.  The alkali salts of the products are useful as textile assistants or as foaming or cleansing agents or for softening cellulose fibres.  Examples are given in which N-(b -hydroxyethyl) oleic acid amide is heated to 95-100 DEG  C. with phthalic anhydride and to 130-140 DEG  C. with succinic anhydride, and the products are converted into their sodium salts.  The Specification as open to inspection under Sect. 91 refers to the manufacture of semi-esters from the acids specified above and aliphatic compounds having at least twelve carbon atoms, at least one alcoholic hydroxy group, at least one double bond, and at least one hetero-atom interrupting the carbon chain, but no basic nitrogen atom.  Specified aliphatic compounds of this kind are hydroxyalkyl esters of unsaturated higher fatty acids, such as b -hydroxyethyl oleate, and hydroxyalkyl ethers of unsaturated fatty alcohols, such as oleyl alcohol b -hydroxyethyl ether.  An example is given in which b -hydroxyethyl oleate is heated to 95 100 DEG  C. with phthalic anhydride and the product is converted into its sodium salt.  This subject-matter does not appear in the Specification as accepted.ALSO:Semi-esters of dicarboxylic acids which contain no C-C double bonds, except such as may be present in an aromatic ring, are prepared by reacting the acids or their functional derivatives with an N-hydroxyalkyl amide of an unsaturated fatty acid in the proportion of one mol. of acid or derivative for each alcoholic hydroxy group in the hydroxyalkylamide, the latter reagent containing at least twelve carbon atoms, but not more than one ether group. Specified dicarboxylic acids are malonic, succinic, adipic, phthalic, terephthalic and naphthalic acids, and specified amides are the N-(b -hydroxyethyl) amides of oleic and ricinoleic acids and oleic acid N-(2-hydroxypropyl) amide.  The alkali salts of the products are useful as textile assistants or as foaming or cleansing agents or for softening cellulose fibres; they are useful also as softening additions to anticreasing baths for textiles.  They may be used alone or with other textile assistants, e.g. dispersing agents stable to lime.  Examples are given in which N-(b -hydroxyethyl) oleic acid amide is heated to 95-100 DEG  C. with phthalic anhydride and to 130-140 DEG  C. with succinic anhydride, and the products are converted into their sodium salts; a mixture of the product of the first example with the disodium salt of N - benzyl - m  - heptadecylbenzimidazole disulphonic acid may be used for softening cellulosic fibres.  In examples of the treatment of textiles, (3) viscose artificial silk yarn is softened by treatment in an aqueous bath containing the mixture referred to in example (1), and (4) for imparting anti-crease properties and a soft feel to viscose crepe, the latter is soaked in a bath containing dimethylolurea, ammonia, ammonium chloride and the mixture referred to in example (1), whereafter the material is squeezed, dried at 70 DEG  C. and heated for five minutes at 140 DEG  C.  The Specification as open to inspection under Sect. 91 refers to the manufacture of semiesters from the acids specified above and aliphatic compounds having at least twelve carbon atoms, at least one alcoholic hydroxy group, at least one double bond, and at least one hetero-atom interrupting the carbon chain, but no basic nitrogen atom.  Specified aliphatic compounds of this kind are hydroxyalkyl esters of unsaturated higher fatty acids, such as b -hydroxyethyl oleate, and hydroxyalkyl ethers of unsaturated fatty alcohols, such as oleic alcohol b -hydroxyethyl ether.  An example is given in which b -hydroxyethyl oleate is heated to 95-100 DEG  C. with phthalic anhydride and the product is converted into its sodium salt.  This subject-matter does not appear in the Specification as accepted.