The Unsaturated Polyester Via Ring-Opening Metathesis Polymerization (ROMP) of ω-6-Hexadecenlactone

Title:The Unsaturated Polyester Via Ring-Opening Metathesis Polymerization (ROMP) of ω-6-Hexadecenlactone

Volume: 15 Issue: 4

Author(s): Araceli Martinez*, Mikhail A. Tlenkopatchev*Selena Gutierrez

Affiliation:

• Unidad Profesional Interdisciplinaria en Ingenieria y Tecnologias Avanzadas, Instituto Politecnico Nacional, Av. I.P.N. 2580, Col. Barrio La Laguna Ticoman, 07340 Gustavo A. Madero, Ciudad de Mexico,Mexico

• Instituto de Investigaciones en Materiales, Universidad Nacional Autonoma de Mexico, Apartado Postal 70-360, CU, Coyoacan, 04510, Ciudad de Mexico,Mexico

Keywords: Unsaturated polyester, ring opening metathesis polymerization, poly(ω-6-hexadecenlactone), crystallinity, ruthenium-alkylidene catalysts, ruthenium-vinylidene catalyst.

Abstract: Background: Ring opening metathesis polymerization of lactones using alkylidene catalysts is an alternative to obtain unsaturated linear polyesters with remarkable thermal and mechanical properties. Also, these polyesters have properties of biodegradability which opens up a wide range of applications as environmentally friendly thermoplastics and biomaterials.

Objective: This research aims to present one route to obtain an unsaturated linear polyester poly(ω-6- hexadecenlactone) via ring opening-metathesis polymerization of ω-6-hexadecenlactone using the rutheniumalkylidene [Ru(Cl)2(=CHPh)(PCy3)2] (I), [Ru(Cl2)(=CHPh)(1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene)( PCy3)] (II) and [Ru(Cl2)(=CH(o-isopropoxyphenylmethylene))(1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene)] (III) and the ruthenium-vinylidene [RuCl2(=C=CH(p-C6H4CF3))(PCy3)2] (IV) catalysts.

Conclusion: The high number-average molecular weights of the poly(ω-6-hexadecenlactone) between Mn = 114,800-155,400 g/mol and yields ranging from 96 to 98 % can be achieved by II and III catalysts. The catalysts II and III with the N-heterocyclic carbene ligand showed superior activity and stability upon catalysts I and IV bearing PCy3 ligands. The hydrogenation of poly(ω-6-hexadecenlactone) using Wilkinson catalyst [RhCl(PPh3)3] was studied. The percent crystallinity of the unsaturated poly(ω-6-hexadecenlactone) was 31% with a melting temperature 47.60ºC. Stress-strain measurements of several poly(ω-6-hexadecenlactone) were determined.

Cite this article as:

Martinez Araceli *, Tlenkopatchev A. Mikhail *, Gutierrez Selena , The Unsaturated Polyester Via Ring-Opening Metathesis Polymerization (ROMP) of ω-6-Hexadecenlactone, Current Organic Synthesis 2018; 15 (4) . https://dx.doi.org/10.2174/1570179414666171011155831