Verfahren zur Herstellung von N-alkoxymethyl-substituierten ungesättigten Amiden

Compounds of the formula R1CONHCH2OR, where R is alkyl or alkenyl or up to 8 carbon atoms or alkoxyethyl, alkyl portions having 1-8 carbon atoms, and R1 is an aliphatic radical containing a single polymerizable double bond, are prepared by reacting R1CONH2 with formaldehyde in the presence of from 25 to 100 grams per mole of amide of a polar solvent (which may be the alcohol ROH) while maintaining the pH between 7.5 and 11 until substantially all of the amide has reacted with the formaldehyde, then adding at least 100 grams (per mole of amide) of ROH, readjusting the pH to 2.5-7, and heating in the presence of a polymerization inhibitor until substantially all of the methylol groups have been esterified. Suitable solvents include dioxan, tetrahydrofuran, dimethylformamide, dimethylacetamide, 1,2-dimethoxyethane, dibutyl ether and methylene chloride. Specified amides R1CONH2 are acrylamide, methacrylamide, a -cyanoacrylamide, a -chloroacrylamide, crotonamide and the mono- and diamides of itaconic and fumaric acids. Specified alcohols ROH are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, amyl, octyl and allyl alcohols and their monoethers with ethylene glycol. Reference has been directed by the Comptroller to Specification 780,284.