Crosslinking of cotton cellulose in the presence of serine and glycine. I. Physical properties and reaction kinetics

Abstract

Serine and glycine were used to combine with dimethyloldihydroxyethyleneurea (DMDHEU) as crosslinking agents to study the physical properties of the crosslinked fabrics and the reaction kinetics, and find that the bound nitrogen is in the series of DMDHEU Ͼ Ͼ DMD-HEU-serine Ͼ DMDHEU-glycine at the same resin concentration. The results also show that the wet crease recovery angle (WCRA) value of the treated fabrics for the three crosslinking agent systems is in the series of DMDHEUserine Ͼ DMDHEU-glycine Ͼ DMDHEU alone at a given dry crease recovery angle (DCRA). The DCRA values of the treated fabrics for DMDHEU alone are higher than those for DMDHEU-␣-amino acids for a given value of tensile strength retention (TSR). WCRA values for the various treated fabrics is in the rank of DMDHEU-serine Ͼ DMD-HEU alone Ͼ DMDHEU-glycine at the same TSR. Rate constants for the various crosslinking agents are in the series of DMDHEU-glycine Ͼ DMDHEU-serine Ͼ DMDHEU alone at the given heated temperatures. Energies needed to crosslink and the values of enthalpies and entropies of activation are all DMDHEU-glycine Ͼ DMDHEU-serine Ͼ DM-DHEU alone. Infrared ray (IR) spectra strongly suggest the reaction between DMDHEU and serine and the reaction between the hydroxyl group (cellulose) and serine can occur in the pad-dry-cure process, but only a little for the latter. The reaction between the functional groups of serine and the aluminum ion to form a complex also confirm with IR spectrum.

Release behavior and kinetic evaluation of formaldehyde from cotton clothing fabrics finished with DMDHEU-based durable press agents in water and synthetic sweat solution

“…28,29 This will provide an additional N-CH 2 OH group, which can hydrolyze, thus resulting in a slow formaldehyde release (equation (7)). It was reported that the methylated DMDHEU is more resistant to both acid and alkaline hydrolysis than those from DMDHEU.…”

“…The fourth source is the formaldehyde released from the breaking of the crosslinks between DMDHEU and cellulose molecules, which was revealed by the gradual disappearing of ether group (1108 cm À1 ) as well as the formations of absorbing bands of -CH 2 OH (1027 cm À1 and 1077 cm À1 ) for DMDHEU and absorption peak of -OH for cotton fiber in their IR spectra. 28,29 This will provide an additional N-CH 2 OH group, which can hydrolyze, thus resulting in a slow formaldehyde release (equation ( 7)). It was reported that the methylated DMDHEU is more resistant to both acid and alkaline hydrolysis than those from DMDHEU.…”

Cellulose hydrogels physically crosslinked by glycine: Synthesis, characterization, thermal and mechanical properties

“…Yao et al have investigated crosslinking of cotton cellulose in the presence of serine, glycine, and dimethyloldihydroxyethyleneurea and the physical properties of the crosslinked fabrics. 35 Remadevi et al described glycine-treated cotton fibers at different pH values and studied their tensile, physical, and microstructure properties. 36 However, hydrogel preparation with crosslinking of microcrystalline cellulose by glycine has not been at the primary focus of any research groups to the best of our knowledge.…”

“…Yao et al . have investigated crosslinking of cotton cellulose in the presence of serine, glycine, and dimethyloldihydroxyethyleneurea and the physical properties of the crosslinked fabrics . Remadevi et al .…”

Reaction Mechanism of Dimethyloldihydroxyethyleneurea/ Alpha-amino Acids Co-reactants on the Crosslinking of Cotton Cellulose in the Presence of Aluminum Sulfate Catalyst

“…studies [3,7] pointed out that the carboxylic acid of tartaric acid could interact with aluminum ion to release hydrogen ions to improve the catalytic effect, the crease recovery angles and the reaction rate constants. Our previous studies [8,9] showed that the physical properties of the treated fabrics with DMDHEU/alpha-amino acids were changed with the kinds of alpha-amino acids used.…”