Effects of Poly(propylene glycol)‐Based Triamine on the Sol/Gel Curing and Properties of Hybrid Non‐Isocyanate Polyurethanes

Abstract

Non-isocyanate polyurethanes (NIPUs) synthesized from biodiesel-derived diglycerol dicarbonate (DGC) and triamine functional poly(propylene glycol) (Jeffamine) are investigated to improve upon poor water resistance and slow curing kinetics observed in (DGC/diamine functional Jeffamine) NIPUs. The structural, thermal, and rheological properties of the prepolymer formulations match those of their diamine-prepared analog previously reported. The NIPU prepolymers (number average molecular weight, M N between 4200 and 6400 g mol −1 ) are subsequently functionalized with trimethoxy silane end-cappers to yield moisture-curable hybrid NIPUs. The prepolymers are both successfully end-capped and subsequently cured under ambient conditions. The sol/gel curing kinetics of the prepolymers are extensively studied, and the effects of the capping methodology, moisture, and the amount of catalyst are quantified so that gel times are observed in as little as 1.4 h at room temperature. The developed curing methods are effective leading to final hybrid films with high gel contents (>86%). The tensile properties of the final films resulting are considerably better compared to previously reported DGC/Jeffamine-based NIPUs, which are too soft to undergo mechanical testing. Also, the films are found to exhibit a tenfold decrease in water absorption compared to the latter (5% vs 70%, respectively).

Polyhydroxyurethanes from Biobased Monomers and CO2: A Bridge between Sustainable Chemistry and CO2 Utilization†

“…[ 215 ] DGC recently served to prepare PHU‐poly(ε‐caprolactone) polymer brushes produced by ring‐opening polymerization of ε‐caprolactone initiated by the ‐OH groups of a DGC ‐based PHU. [ 216 ] Other recently reported PHU hybrid systems involving DGC are PHU prepolymers capped with different end‐groups such as trimethoxy silanes [ 217 ] or other moisture‐curable moieties, [ 218 ] employed for the preparation of water resistant films. [ 219 ]…”

Sugar-Based Thermoplastic Polyhydroxyurethanes: Effects of Sorbitol and Mannitol Diastereomers on Polymer Properties and Applications in Melt Blending

“…Diglycerol dicarbonate (DGC) is derived from glycerol, which is a byproduct obtained from the hydrolysis of biomass wastes, the methanolysis of triglycerides, and the production of biodiesel, whereas sorbitol and mannitol biscarbonates (SBC and MBC, respectively) are acquired from sugars obtained from glucose processing . While DGC was extensively explored in the literature for different PHU formulations, − SBC and MBC were not, − and that could be related to the low melting point of DGC (65 °C), , which allows it to react with diamines in bulk and at moderate conditions, compared to the high melting points of SBC and MBC (214–216 °C and 181–183 °C, respectively) …”

Tuning the Catalytic Activity of Recyclable Heterogeneous Catalysts for the Direct Etherification Reaction of Glycerol Using Antagonistic Additives

“…Polyglycerol, a product of the conversion of glycerol by etherification, has tremendous potential in a variety of fields including polymers, cosmetics, food, dispersants, pharmaceutical industry, lubricants, biomedical, or pharmaceutical delivery systems [1][2][3][4]. In particular, diglycerol (DG) and triglycerol (TG) are converted into derivatives such as fatty acid esters, which can be used as multifunctional additives for pharmaceuticals, cosmetics, foods, and polyurethans [1,2,[5][6][7][8][9][10]. DG and TG can also be used as water-soluble plasticizers and emulsions.…”