Carbohydrate-Based Polycarbonates. Synthesis, Structure, and Biodegradation Studies

Abstract

Linear homo- and co-polycarbonates have been prepared from the sugar-based diols 2,3,4-tri-O-methyl-l-arabinitol and 2,3,4-tri-O-methylxylitol. Statistical co-polycarbonates were obtained from molar feed ratios of sugar:bisphenol A of 1:1 and 2:1. The polycarbonates were stable up to ∼280 °C with maximum decomposition rate above 345 °C. The arabinitol-based homopolymer was found to be semicrystalline whereas the xylitol-based one was amorphous. All the copolymers were amorphous with T g ranging between 60 and 80 °C. Both homo- and co-polycarbonates showed high resistance to chemical hydrolysis; however, they were enzymatically degraded in different degree. The xylitol-based polycarbonates were the more easily degraded by lipase B from Candida antarctica in acetonitrile at 70 °Cthis enzyme showing a high selectivity toward the configuration of the sugar-based moiety.

Synthetic Polymers from Sugar-Based Monomers

“…In another study, both methods mentioned above were tested in the synthesis of a sugar-based [AB]-polyurethane (Scheme 30). The aminoalcohol 1-amino-1-deoxy 2,3,4,5-tri-O-methyl-D-glucitol (80) was the precursor for the synthesis of α,ω-hydroxyl isocyanate monomer, which polymerized in the presence of a catalyst [Zr(acac) 4 , Sn(oct) 2 , or TEA]. An alternative method was proposed: the free hydroxyl group of 80 was activated, preparing the α-amino-ω-phenylcarbonate monomer, and further self-polycondensation was conducted in THF and in the presence of diisopropylethylamine (DIPEA).…”

Sweet polymers: Synthesis and characterization of xylitol-based epoxidized linseed oil resins

“…Xylitol is related to the reduction of tooth decay because it inhibits the growth of cariogenic bacteria Streptococcus mutans, and it is known to provide fewer calories and to decrease blood sugar levels, among other properties [22]. Xylitol with protected secondary hydroxyls is also an important monomer in the linear polyesters and polyamides industries [23][24][25][26][27], improving properties such as hydrophilicity, biocompatibility and biodegradability. Some of the most desirable characteristics within industrial polyols are low viscosity and high hydroxyl number, which may be interesting for the polyurethanes industry as well [28][29][30][31].…”

A high-molecular-weight and high-Tg poly(ester carbonate) partially based on isosorbide: synthesis and structure–property relationships

“…[1][2][3][4][5][6] Among the wide diversity of the bio-based monomers, isosorbide (Is) is regarded as a promising feedstock for polycondensation due to its attractive rigidity, chirality and non-toxicity. [16][17][18] As far as polycarbonates are concerned, the bicyclic structure of Is is able to provide polycondensates with a high glass transition temperature (T g ), which is comparable to commonly used bisphenol A polycarbonate. It is the only bicyclic carbohydrate-based monomer industrially available today.…”