GB1195087A - Method for the Production of Salts of Amino Triazine Carboxylic Acids Soluble in Water - Google Patents

Abstract

1,195,087. Production of water-soluble salts of aminotriazine carboxylic acids. REICHHOLD-ALBERT-CHEMIE A.G. 4 Oct., 1967 [6 Oct., 1966; 4 Feb., 1967 (3); 25 April, 1967], No. 45122/67. Heading C2C. [Also in Division C7] Water-dilutable salts of amino-triazine carboxylic acids are obtained by (a) reacting an etherified amino-triazine formaldehyde condensation product, which contains at least one mole of volatile alcohol groups as a component of the ether structure, with an acyclic aliphatic monohydroxycarboxylic acid ester by heating, and (b) saponifying the reaction product in an alkaline medium. The saponification product may subsequently be (c) subjected to an azeotropic distillation for separation of the water, with the help of an azeotropic entraining agent under vacuum and with heating, (d) the distillation residue, by the addition of an acid which is preferably organic and which may be dissolved in an organic solvent, may be converted into the free resin carboxylic acid, wherein the added acid is of such amount that it neutralizes most of the alkali but without any remaining surplus of acid, (e) the resulting salt separated, and (f) the resin carboxylic acid converted into watersoluble products by the addition of ammonia and/or a strong organic base which, in 50% by wt. aq. solution, has a pH of at least 9. Reaction step (a) above is suitably carried out in the presence of a catalyst at 100-180‹ C. The etherified amino-triazine formaldehyde condensation products employed as starting materials are the etherified reaction products of amino-triazines of the formulµ wherein R is an alkyl, allyl, cycloalkyl or aryl group, with formaldehyde, preferably those which contain 4-6 moles formaldehyde per mole of melamine and at least 60% of the methylol groups are etherified with monovalent alcohols including at least one mole of a volatile alcohol; other preferred starting materials are the benzoguanamino-methylol ethers of monovalent alcohols which include 3-4 moles of formaldehyde groups. The ester starting materials are preferably hydroxycarboxylic acid esters of mono-, di- and tri-hydric alcohols with 1-6 carbon atoms where the hydroxycarboxylic acids have 2 to 18 carbon atoms and the hydroxyl groups are in primary or secondary positions. The molecular weights of the products may be increased, e.g. by heating in an acid medium during or after the re-etherification with the hydroxycarboxylic acid ester until the product has an acid number between 30 and 160. The preparation of the starting materials is described by methylolating and subsequently etherifying an appropriate amino-triazine derivative.