The investigation of triethylammonium carboxylates influence on the kinetics of urethane formation processing during waterborne polyurethane synthesis

Abstract

Kinetic features of the catalytic reaction of isophorone diisocyanate with triethylammonium salt of 2,2‐bis(hydroxymethyl)propionic acid, a hydrophilic agent for obtaining waterborne polyurethane, also with the model 1,1‐bis(hydroxymethyl)ethane and with physical mixture 1,1‐bis(hydroxymethyl)ethane‐triethylamine were studied using IR spectroscopy. The observed rate constant ratios of isophorone diisocyanate aliphatic and cycloaliphatic isocyanate groups interaction with the studied compounds were established, and the catalysis efficiency was evaluated. It was shown that a synergic effect is observed in catalytic systems based on dibutyltin dilaurate and triethylammonium carboxylates with regard to the reactivity of isophorone diisocyanate aliphatic group alone in the urethane formation reaction.

Nanocellulose-Based Thermoplastic Polyurethane Biocomposites with Shape Memory Effect

“…Materials based on MDI retain good cytocompatibility and can be used in the medical industry [111,112]. Hard segments based on cycloaliphatic IPDI with different isocyanate group reactivity [113,114] show a weak hydrogen bonding network, which leads to a high proportion of mixing of soft and hard segments, violating the phase-separated morphology [14]. This results in low strength and relaxation characteristics of the material, though, in combination with biodegradable polyols, it gives good biocompatibility and no cytotoxicity, permitting use in medical applications [108,[115][116][117].…”

“…In the aliphatic IPDI molecule of asymmetric structure, the secondary isocyanate group (-NCO substituent directly linked to the ring) has a higher reactivity than the primary isocyanate group due to steric hindrance of the adjacent methyl group [152]. The reaction selectivity of the secondary isocyanate group can be increased by using dibutyltin dilaurate (DBTDL) as the main catalyst for the urethane formation reaction, while the primary isocyanate groups can be selectively inverted with 1,4-diazabicyclo[2.2.2]octane (DABCO) [113]. This enables the optimization of the selective addition of isocyanate groups to nanocellulose surfaces using two types of catalysts, DBTDL and DABCO [142], the effectiveness of which has been practically demonstrated.…”

Synthesis and Characterization of Waterborne Sulfonate Polyesters

“…That is, the carboxyl group is introduced into polyesters, and amine or alkali is used as a neutralizer to make polyesters become salt and hydrophilic. [16][17][18] However, carboxylate is a weak acid and polyester prepared by this method is less stable. WSP does not need to add solvent, and has no amine neutralizers, [19] is safe and nonirritating, can be dissolved in warm water by selfemulsification, has good dispersion and has the advantages of low film-forming temperature, and is an ideal choice as a joining material.…”

Synthesis and Study of Properties of Waterborne Polyurethanes Based on β-Cyclodextrin Partial Nitrate as Potential Systems for Delivery of Bioactive Compounds

“…The choice of IPDI is stipulated by high hydrolysis resistance and the possibility of controlling urethane formation reactions due to different reactivity of isocyanate groups [ 17 , 18 ]. To enhance environmental safety, it is recommended to use biodegradable polycaprolactone diol (PCL) as oligo diol [ 8 ], and 2,2-bis(hydroxymethyl)propionic acid (DMPA) should be used to provide the hydrophilicity of a polyurethane matrix and the possibility of preparing stable aqueous dispersions [ 19 ].…”