Synthesis and metathesis polymerization of substituted cyclododecadienes

Abstract

The present work involves the syntheses of butadiene based sequence-controlled copolymers which are composed of commercial monomeric units such as styrene, propylene, ethylene, vinylacetate, and methylacrylate. Structure analysis of the resulting polymers and their thermal properties are also investigated. In the synthetic work new substituted cyclododecadiene derivatives, 9-phenyl-1,5-cyclododecadiene, 9-methyl-1,5-cyclododecadiene, 9-acetyl-1,5-cyclododecadiene, methyl-4,8-cyclododecadienecarboxylate, and 1,5-cyclododecadiene were synthesized. The polymers of 9-phenyl-1,5-cyclododecadiene were rubbery with glass transition at $-33.6^\circ C$. The analysis of the $^1H$-NMR spectra and $^{13}C$-NMR spectra confirmed the structure of 2:1:1 alternating copolymer of butadiene, ethylene and styrene. The polymers of 9-methyl-1,5-cyclododecadiene gave alternating copolymer of butadiene, ethylene and propylene. The polymer of 9-acetyl-1,5-cyclododecadiene and the polymer of methyl-4,8-cyclododecadienecarboxylate was the 2:1:1 copolymer of butadiene, ethylene and vinylacetate, and the 2:1:1 copolymer of butadiene, ethylene and methylacrylate. And the polymer of 1,5-cyclododecadiene gave 2:2 alternating copolymer of butadiene and ethylene.