Methylolamides containing amino acid groups: Their use as wash‐wear finishing agents for cotton

The acid‐catalyzed etherification of cellulose with methylolamides containing a tertiary amino group is often inhibited by the presence of this basic group. In the production of wash‐wear fabrics an incomplete reaction generally produces a low degree of wrinkle resistance and/or leaves the treated fabric susceptible to deterioration during use. In this work it is postulated that the insertion of a carboxylic acid group into such a crosslinking agent neutralizes the basic group by the formation of an inner salt (zwitterion). Such agents were prepared by methylolation of the products of a Michael addition of the sodium salt of selected amino acids to acrylamide. All the compounds synthesized are thought to be new. Those which were isolated and characterized include sodium N ‐2‐carbamoylethylglycinate, sodium N , N ‐bis(2‐carbamoylethyl)glycinate, N , N ‐bis(2‐carbamoylethyl)glycine, sodium N , N ‐bis(2‐carbamoylethyl)α‐alaninate, and N , N ‐bis(2‐carbamoylethyl)‐α‐alanine. Similar adducts from β‐alanine, lysine, and aspartic acid were prepared; however, the adducts obtained were oils, and this complicated their isolation and characterization. For textile treatments isolation of the intermediates is unnecessary. The N ‐methylol crosslinking agents derived from these Michael adducts are highly reactive to cotton, as indicated by high add‐ons at relatively mild conditions. The treated fabrics are highly wrinkle resistant and possess other desirable properties. The data obtained from the use of these agents indicate that further study is desirable, based on the concept developed in this work.