Polymerization of butyl acrylate and butyl methacrylate in the presence of o-quinone methacrylate

Abstract

The reactivity of o-quinone methacrylate (2-(2,5-di-tert-butyl-3,4-dioxocyclohexa-1,5-dienyloxy)ethyl methacrylate) in the radical copolymerization with butyl acrylate and butyl methacrylate and in the polymerization of these monomers in the presence of the nonpolymerizable analog of o-benzoquinone methacrylate, 4-methoxy-3,6-di-tert-butylbenzoquinone-1,2, have been investigated. It has been shown that o-quinone methacrylate, with methacrylate and quinone structural fragments, behaves as both a monomer and an inhibitor. The polydispersity coefficients of the polymers decrease to 1.19 as the quinone concentration increases. With the example of the model reaction of AIBN with 4-methoxy-3,6-di-tert-butylbenzoquinone-1,2, it has been shown that the main reaction product is phenol ether. A mechanism of the “pseudoliving” polymerization of butyl acrylate and butyl methacrylate in the presence of o-quinone methacrylate or its analog through the two-step inhibition of polymerization by a quinone molecule, macromonomer formation, and polymerization via the addition-fragmentation mechanism has been proposed. It has been found that the resulting polymers initiate postpolymerization.