A sulfur-quinone diol monomer, 2,5-bis-(2-hydroxyethylthio)-1,4-benzoquinone (SQM-2), was prepared by the reaction of 2-mercaptoethanol with 1,4-benzoquinone.SQM-2 and polycaprolactone diol (M n = 1250) were condensed with toluene diisocyanate to give a sulfur-quinone polyurethanes, SQPU-1, containing 7 mole percent SQM-2. SQPU-1 was coated onto an iron square and exposed to either 0.1 M sodium chloride electrolyte or substitute ocean water. Electrochemical impedance spectroscopy monitored any degradation of the coatings and showed that the sulfur-quinone polyurethane protected the iron against corrosion. Reflectance absorption infrared spectroscopy showed that the chemisorbed sulfur-quinone functional group lies parallel to the iron surface.For more than a decade polymers containing the 2,5-diamino-1,4-benzoquinone functional group have been of interest, since Erhan's observation that this class polymers have a strong affinity for the surface of iron. 1 They found that the amine-quinone polymers could displace moisture from the surface of iron, making it hydrophobic. If the amine-quinone polymers would prevent moisture from adsorbing onto the iron surface, then they would inhibit corrosion. Indeed, they reported salt-spray testing data showing that aminequinone polymers prevent corrosion. 2 We have synthesized amine-quinone polyurethanes by condensing the amine-quinone monomer, 2,5-bis(N-2-hydroxyethyl-N-methylamino)-1,4-benzoquinone, and an oligomeric diol monomer (e.g., polycaprolactone diol, 168
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