Enzymatic syntheses of unsaturated polyesters based on isosorbide and isomannide

Author(s)

Naves, Alliny F. ^[1] ; Fernandes, Henrique T. C. ^[1] ; Immich, Ana P. S. ^[1] ; Catalani, Luiz H. ^[1]

Affiliation

^[1] Univ Sao Paulo, Inst Quim, Dept Quim Fundamental, BR-05513970 Sao Paulo - Brazil

• Document type: Journal article
• Source: JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY; v. 51, n. 18, p. 3881-3891, SEP 15 2013.
• Web of Science Citations: 23

Abstract

The search for materials produced from renewable sources aiming at the substitution of petroleum-based derivates is an area of intense investigation. In this work, the enzymatic copolymerization of isosorbide or isomannide with diethyl adipate and fractions of different unsaturated diesters (diethyl itaconate, diethyl fumarate, diethyl glutaconate, and diethyl hydromuconate) were examined using CAL-B as catalyst. The polyesters prepared using one-step syntheses were characterized by SEC, NMR, and MALDI-TOF MS. In addition, syntheses with linear diols were carried out in bulk to evaluate the reactivity of cyclic diols in producing unsaturated polyesters using enzymatic catalysis, as well as to evaluate the occurrence of addition side reactions on the double bonds. Isosorbide and isomannide yielded unsaturated polymers with M-w values in the order of 4,000-16,000 when fumarate or glutaconate esters were added in 5 mol % ratio against adipate. In all cases MALDI-TOF confirmed the presence of unsaturated units. Although these polyesters have unreacted double bonds they are prone to crosslinking and ready to further functionalization, like anchoring bioactive molecules. (C) 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 3881-3891 (AU)

• FAPESP's process: 08/06445-6 - New Biodegradable Polyesters by Enzymatic Synthesis: Use of Monomers Based on Renewable Sources.
• Grantee: Alliny Ferreira Naves
• Support type: Scholarships in Brazil - Post-Doctorate
• FAPESP's process: 05/02855-7 - Synthetic polymers applied to biomaterials
• Grantee: Luiz Henrique Catalani
• Support type: Research Projects - Thematic Grants
• FAPESP's process: 11/18017-1 - DEVELOPMENT OF ELECTROSPUN POLYMERIC MATRICES FOR THE REGENERATION OF TYMPANIC MEMBRANE PERFORATIONS.
• Grantee: Ana Paula Serafini Immich Boemo
• Support type: Scholarships in Brazil - Post-Doctorate
• FAPESP's process: 11/21442-6 - Synthetic and natural polymers applied to tissue engineering
• Grantee: Luiz Henrique Catalani
• Support type: Research Projects - Thematic Grants