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Mechanistic and catalytic studies of β‐nitroalcohol crosslinking with polyamine
Author(s) -
Li Xia,
Li Yongjun,
Rao Yi,
Solomon Marissa R.,
Paik David C.,
Turro Nicholas J.
Publication year - 2012
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.38604
Subject(s) - catalysis , formaldehyde , fourier transform infrared spectroscopy , chemistry , amine gas treating , reaction mechanism , sodium bicarbonate , polymer , polyamine , combinatorial chemistry , polymer chemistry , organic chemistry , chemical engineering , biochemistry , engineering
Abstract β‐Nitroalcohols (βNAs) are promising corneoscleral crosslinking agents for the treatment of diseases such as keratoconus and myopia. Although it is believed that formaldehyde is released from the crosslinking reactions of βNAs, the mechanism by which βNAs react with amine‐functionalized polymers has yet to be known. In this study, we present the reaction mechanism of the βNA crosslinking. Fourier transform infrared (FTIR) and nuclear magnetic resonance (NMR) data provide strong evidence that formaldehyde is released during the reaction. Catalytic studies show that sodium bicarbonate (NaHCO 3 ) and salmon testes DNA accelerate the reaction while hydroxynitrile lyase from Arabidopsis thaliana decelerates the crosslinking reaction. These results suggest that βNAs are potential self‐administered crosslinking agents for future clinical use. © 2012 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2013