SYNTHESIS, CHARACTERIZATION, AND EVALUATION OF METHYLATED DERIVATIVES OF DMDHEU (DURABLE PRESS)
Abstract
Methylated dimethyloldihydroxyethyleneurea (DMDHEU) durable press agents that reduce formaldehyde release from finished cotton fabrics were investigated. Six derivatives of DMDHEU, methylated at various positions and levels were isolated and characterized by HPLC, $\sp{13}$C-NMR, and mass spectrometry. Four methylated derivatives appeared as cis/trans -isomers with respect to the 4,5-dihydroxy groups. In all four cases the cis -isomer exhibited a longer HPLC retention time than the trans -isomer and the cis ring carbons appeared 6-10 ppm upfield from the corresponding trans ring carbons. HPLC and $\sp{13}$C-NMR data was obtained on over twenty substituted urea and substituted 2-imidazolidinone compounds. HPLC and $\sp{13}$C-NMR suggest themselves to be important analytical tools for identification of linear and cyclic N-methylol and methylated N-methylol durable press reagents. DMDHEU, six methylated DMDHEU compounds, and three commercial DMDHEU durable press finishes were applied to 100% cotton printcloth using the pad-dry-cure process. Eight performance properties were analyzed using standard AATCC and ASTM test methods: wrinkle recovery, breaking strength and elongation, flex abrasion resistance, tear resistance, nitrogen content, total formaldehyde, formaldehyde release, and color difference. The usual decrease in breaking strength, percent elongation, and flex abrasion with increasing wrinkle resistance was evident. All ten treatments resulted in some degree of yellowing. Giving the finished fabrics an afterwash resulted in a decrease in formaldehyde release. As the level of methylation increased, the amount of formaldehyde released from the finished fabrics decreased. The difference in the level of methylation resulted in statistically significant differences in performance properties between the ten finishes. Overall, the 4,5-dimethylated DMDHEU compound gave the best combination of formaldehyde release and performance properties.
Degree
Ph.D.
Subject Area
Textile research
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