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

摘要

The amine-quinone diol monomer 2,5-bis (N-2-hydroxyethyl-N-mehtyl-amino)1,4-benzoquinone (AQM-1) was prepared by the comdensation of 2-(N-methyl-amino) ethanol with hydroquinone in the presence of oxygen and copper (II) chloride. This crystalline monomer was used to preapre 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 main-chain, giving red-brwon polyurethanes that had moleular 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 uded in state of the art magnetic tape and prevented the corrosion of the particles.