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β‐Nitrostyrene Derivatives as Inhibitors of the Free Radical Polymerization
Author(s) -
Encinas M. Victoria,
Lissi Eduardo A.,
Jimenez Sergio,
Norambuena Ester
Publication year - 2001
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/1521-3935(20010301)202:5<689::aid-macp689>3.0.co;2-1
Subject(s) - chemistry , polymerization , monomer , double bond , polymer chemistry , nitro , radical polymerization , reactivity (psychology) , radical , photochemistry , organic chemistry , polymer , medicine , alkyl , alternative medicine , pathology
Abstract The free radical polymerization of vinyl monomers is efficiently inhibited by β‐nitrostyrene derivatives. The high reactivity of the growing radicals towards the β‐nitro compounds is controlled by the electron‐donor character of the macroradical and the electron deficiency of the double bond of the β‐nitro derivative. Electron withdrawing substituents at the 4‐position of β‐nitrostyrene increase markedly the inhibition rate. The inhibition efficiency of β‐nitrostyrenes towards electron deficient monomer double bonds is strongly reduced. Polymerization rates and 1 H NMR results show that the β‐nitrostyrene derivatives act as strong inhibitors of the polymerization through a mechanism that involves the release of NO 2 .