2,5,-Dimethoxy-and 2,5-di-n-butoxy-,4-benzoquinone Reactions and Polymerization with 1,6-hexanediamine
Polymers and High Performance Materials
The serendipitous formation of 2,5-dimethoxy-1,4-benzoquinone is reported from the reaction of 1,4-benzoquinone with methanol, DABCO, and paraformaldehyde. This monomer, and its di-n-butoxy analog, are also available from 2,5-dihydroxy-1,4-benzoquinone. These materials are capable of novel polycondensation reactions with diamines such as 1,6-hexanediamine. Use of m-cresol as polymerization solvent gave a dark, insoluble product while various amide solvents lead to orange or pink polymers that had average degrees of polymerization from 5 up to > 30. These polymers, plus model compounds obtained from 1-aminopropane and N,N'-dimethyl-1,6-hexanediamine, were characterized by FTIR, solution, and solid-state NMR.
Journal of Polymer Science Part A: Polymer Chemistry
Colletti, R. F.,
Stewart, M. J.,
Taylor, A. E.,
MacNeill, N. J.,
Mathias, L. J.
(1991). 2,5,-Dimethoxy-and 2,5-di-n-butoxy-,4-benzoquinone Reactions and Polymerization with 1,6-hexanediamine. Journal of Polymer Science Part A: Polymer Chemistry, 29(11), 1633-1638.
Available at: https://aquila.usm.edu/fac_pubs/7080