Synthesis of novel polymeric HALS stabilizers and chain transfer effect of hindered amine norbornene derivatives on ring-opening metathesis polymerization

Abstract

Cyclooctadiene (COD) was polymerized via ring-opening metathesis polymerization (ROMP) in the presence of 5-norbornene-exo, endo-2-carboxylic acid 2,2,6,6-tetramethyl-4-piperidinyl ester (PN) or 5-norbornene-2-exo-3-endo-dicarboxylic acid bis(2,2,6,6-tetramethyl-4-piperidinyl) ester (2,3-PN) to prepare a new kind of polymeric hindered amine (HALS) stabilizers. Unexpectedly, hindered amine norbornene derivatives PN and 2,3-PN did not act as comonomer but acted as chain transfer agent (CTA). The resulting polymers were characterized by gel permeation chromatography (GPC) and 1H-NMR. Investigation of polymerization behavior showed that hindered amine groups were introduced into polymer chain by virtue of chain degradation resulted from chain transfer. The molecular weight (Mn) and HALS content of the resulting polymeric HALS stabilizer could be regulated by varying molar ratio of initial monomer to catalyst.