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Hydrogen bonding in polyurethane (PU) is imposed by molecular parameters. In this study, the effect of structural isomerism of certain monomers on hydrogen bonding of waterborne polyurethane (WBPU) was studied theoretically and experimentally. Two dihydroxybenzene (DHB)-based structural isomers such as catechol (CC) and hydroquinone (HQ), with different OH positions on the inner benzene core, had been used. Two series of WBPU dispersions were prepared using CC and HQ with defined contents. The binding energies between the catechol (CC)/hydroquinone (HQ) (respective OH group) and urethane/urea were calculated theoretically. By using a density functional theory (DFT) method, it was found that the largest binding energy between the urea and CC was higher than that of urea and HQ. The FT-IR analysis of synthesized polymer was also carried out to compare the results with the theoretical values. The CC-based polymers showed a stronger hydrogen bond both theoretically and experimentally than those for HQ-based polymers. The higher level of hydrogen bond was reflected in their properties of CC-based polymers. The adhesive strength, thermal stability, and hydrophobicity were higher for CC-based materials than those for HQ-based materials. The adhesive strength was increased 25% with the addition of 2.0 wt% CC content. This adhesive strength slightly deviated at a moderately high temperature of 80 °C.

Theoretical and Experimental Studies of Hydrogen Bonded Dihydroxybenzene Isomers Polyurethane Adhesive Material