Amine-quinone polyurethanes: Preparation of polyurethane segmented block copolymers containing 2,5-bis(N-2-hydroxyethyl-N-methylamino)-1,4-benzoquinone,toluene diisocyanate,and an oligomeric polyether diol

The amine-quinone diol monomer 2,5-bis(N-2-hydroxyethyl-N-methylamino)-1,4-benzoquinone (AQM-1) was prepared by the condensation of 2-(N-methylamino)ethanol with hydroquinone in the presence of oxygen and copper(II) chloride. This crystalline monomer was used to prepare a series of amine-quinone polyurethanes by condensation polymerization, either in the melt or in DMF solution, with toluene diisocyante and an oligomeric diol either poly(1,2-butylene glycol) or polytetrahydrofuran. The amine-quinone functional group was incorporated into the polymer mainchain, giving red-brown polyurethanes that had molecular weights in the range of 20,000–80,000 and were soluble in THF, MEK, DMF, and DMSO. The thermal properties were consistent with a two-phase morphology with an amorphous soft segment, containing the oligomeric diol, and a microcrystalline hard segment, containing AQM-1. These polymers had a high affinity for the surface of commercial iron particles used in state of the art magnetic tape and prevented the corrosion of the particles. © 1999 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 37: 2339–2345, 1999