Development of hydrophobically modified ethoxylated urethane
(HEUR)
rheology modifiers enabled the widespread application of waterborne
paints and coatings, replacing their environmentally burdening solvent-based
predecessors. However, the diisocyanates, required for the conventional
synthesis of HEURs, pose severe eco-sustainability threats. In this
paper, we demonstrate an innovative approach to avoiding toxic components
in the preparation of rheology modifiers by obtaining a new class
of water-soluble isocyanate-free hydrophobically modified ethoxylated
poly(hydroxy-urethane)s (IFHEURs). The first step in the synthetic
pathway was the preparation of CO
2
-based five-membered
poly(ethylene glycol) bis(cyclic carbonate) and its subsequent aminolysis
using 4,7,10-trioxa-1,13-tridecanediamine, yielding poly(hydroxy-urethane)
(PHU) prepolymers terminated with cyclic carbonate groups. The PHU
prepolymers were further extended in a reactive extrusion (REX) synthesis
using biobased hydrophobic diamine PRIAMINE 1075. The REX technique
made it possible to overcome the typical limitations of the aminolysis
reaction and to reach the desired conversion within a moderate reaction
time. IFHEURs have been structurally elucidated using FT-IR and NMR
spectroscopy techniques, MALDI-ToF mass spectrometry, and SEC analysis
and applied as rheology modifiers. The study of their associative
behavior in aqueous solutions confirmed that the architectural flexibility
of the obtained IFHEURs, containing terminal and pendant hydrophobic
groups, opens a perspective for tuneable thickening performance.
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