Resinous salts, their preparation, and their use in coatings

Abstract

Carboxylate salts, prepared by a Mannich reaction and useful in the preparation of water-borne coatings, have the general formula ##STR1## where R.sup.1 represents an aliphatic, aromatic, or araliphatic divalent group which may contain a further --COO.sup.- M.sup.+ ; R.sup.2 represents --H, --CH(R.sup.3)N(R.sup.10)R.sup.1 COO.sup.- M.sup.+, or alkyl which may be substituted by --COO.sup.- M.sup.+, --CH(R.sup.3)OH, or --CH(R.sup.3)OR.sup.8, R.sup.1 and R.sup.2 containing together not more than one --COO.sup.- M.sup.+ ; R.sup.3 represents --H or alkyl; each R.sup.4 represents --H, halogen, alkyl, or alkenyl; R.sup.5 represents --H, halogen, alkyl, alkenyl, or a group --CH(R.sup.3)OH, --CH(R.sup.3)OR.sup.8, or --CHR.sup.3 --NR.sup.2 --R.sup.1 --COO.sup.- M.sup.+ ; either R.sup.6 represents --H and R.sup.7 represents the residue of a polyepoxide, preferably of average mol. wt. 1000-5000, or R.sup.6 represents a covalent bond linked to the group R.sup.7, and R.sup.7, together with the indicated hydroxyethylene group, forms a cycloaliphatic ring; R.sup.8 represents alkyl or alkoxyalkyl; R.sup.9 denotes the residue of an optional terminating group; R.sup.10 denotes --H, --COO.sup.- M.sup.+, or an alkyl group which may be substituted by --COO.sup.- M.sup.+, --CH(R.sup.3)OH, or --OCH(R.sup.3)OR.sup.8 ; m represents 1, 2, 3, or 4; n and p represent zero or 1, X represents alkylene, carbonyl, sulfonyl, oxygen, sulfur, or a valence bond; and M.sup.+ represents a hydrogen ion or a monovalent cation derived from an alkali metal, ammonia, or an amine, at least 25% of the ions being a said monovalent cation. Compositions comprising these salts and, if required, a phenoplast, an aminoplast, or blocked polyisocyanate, are stable when dispersed in water, usually with the aid of a minor amount of an organic solvent, and may be used to form protective films, especially for metal containers.