Patent GB-615665-A (GB)
Title: Manufacture of new semi-esters of unsaturated dicarboxylic acids
IPC: C07C69/52
Filed: 1946-04-09
Abstract: Semi-esters of unsaturated aliphatic or cycloaliphatic dicarboxylic acids are prepared by reacting the acids or their functional derivatives with an N-hydroxyalkylamide of a fatty acid in the proportion of one mol. of acid or derivative for each alcoholic hydroxy group in one mol. of the hydroxyalkylamide, the latter reagent containing at least twelve carbon atoms but not more than one ether group.  Specified dicarboxylic acids are fumaric acid, maleic acid, and cyclohexene dicarboxylic acids such as tetrahydrophthalic acid (from maleic acid and butadiene) and addition products of maleic acid with homologues of butadiene. Specified hydroxyalkylamides are the N-(b -hydroxyethyl) amides of palmitic, stearic and oleic acids and stearic acid N-(2-hydroxypropyl) amide.  Examples are given in which (1) stearic acid N-(b -hydroxyethyl) amide and maleic anhydride are heated to 95-100 DEG  C. and the product is converted into its sodium salt; (2) maleic anhydride and N-(b -hydroxyethyl) oleic acid amide are heated to 95-100 DEG  C. and the product is converted into its 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 containing at least twelve carbon atoms, at least one alcoholic hydroxy group 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 higher fatty acids, such as b -hydroxyethyl stearate, hydroxyalkyl ethers of higher fatty alcohols, such as octodecyl alcohol b -hydroxyethyl ether, and thioethers of high molecular weight containing hydroxyalkyl groups, such as octadecyl-b -hydroxyethyl thioether.  An example is given in which maleic anhydride and b -hydroxyethyl stearate are heated to 95-100 DEG  C. and the product is converted into its sodium salt. This subject-matter does not appear in the Specification as accepted.ALSO:Semi-esters of unsaturated aliphatic or cycloaliphatic dicarboxylic acids are prepared by reacting the acids or their functional derivatives with an N-hydroxyalkylamide of a fatty acid in the proportion of one mol. of acid or derivative for each alcoholic hydroxy group in one mol. of the hydroxy alkylamide, the latter reagent containing at least twelve carbon atoms, but not more than one ether group.  Specified dicarboxylic acids are fumaric acid, maleic acid, and cyclohexene dicarboxylic acids such as tetrahydrophthalic acid (from maleic acid and butadiene) and addition products of maleic acid with homologues of butadiene. Specified hydroxy alkylamides are the N-(b -hydroxyethyl) amides of palmitic, stearic and oleic acids and stearic 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 cellulosic fibres. They may be used alone or with other textile assistants, e.g. salts or dispersing agents stable to lime.  Examples are given in which (1) stearic acid N-(b -hydroxyethyl) amide and maleic anhydride are heated to 95-100 DEG  C. and the product is converted into its sodium salt; a mixture of the latter with the disodium salt of N-benzyl-m -heptadecyl benzimidazole disulphonic acid may be used for softening cellulosic fibres; (2) maleic anhydride and N-(b -hydroxyethyl) oleic acid amide are heated to 95-100 DEG  C. and the product is converted into its sodium salt; (3) viscose artificial silk yarn is softened by treatment in an aqueous bath containing the mixture referred to in example (1).  The Specification as open to inspection under Sect. 91 refers to the manufacture of semi-esters from the acids specified above and aliphatic compounds containing at least twelve carbon atoms, at least one alcoholic hydroxy group 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 higher fatty acids, such as b -hydroxyethyl stearate, hydroxyalkyl ethers of higher fatty alcohols, such as octadecyl alcohol b -hydroxyethyl ether, and thioethers of high molecular weight containing hydroxyalkyl groups, such as octadecyl-b -hydroxyethyl thioether.  An example is given in which maleic anhydride and b -hydroxyethyl stearate are heated to 95-100 DEG  C. and the product is converted into its sodium salt. This subject-matter does not appear in the Specification as accepted.