The Fate of a Monofunctional N-Methylol Reagent on Pad-Dry-Cure Reaction with Cotton

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Abstract
Chemically modified cottons resulting from reactions of hydroxymethylmethylethyleneurea (HMEU) and methoxymeihylmethyletbyleneurea (MMEU) with cotton fabric at 160°C by zinc nitrate catalysis were studied. From these cottons modified with the monofunctional analog of dimethylolethyleneurea (DMEU) positive evidence was found for the presence of trapped dimer of HMEU and for oxymethylene linkages in addition to the expected methyleneethyleneurea substituents. The estimate is: for approximately 1% of bound nitrogen or 4% add-on of HMEU, half of the nitrogen is present as the methyleneethyleneurea substituents; the remaining nitrogen is primarily dimer of HMEU; and 0.1% formaldehyde (on weight of fabric) is present as oxymethylene linkages. This estimate corresponds to 0.2 mol of oxymethylene linkages and 1 mol of trapped ethyleneurea units per mole of covalently attached methyleneethyleneurea substituents. The results are discussed relative to structures developed when cotton is treated with DMEU.