Renewable Sugar-Based Diols with Different Rigid Structure: Comparable Investigation on Improving Poly(butylene succinate) Performance

Abstract

In order to improve the mechanical and oxygen barrier properties of poly­(butylene succinate) (PBS), two series of sugar-containing PBS copolyesters with different molecular stiffness were synthesized and comparatively investigated, in which a cyclic alditol, isosorbide (Is) or 2,3-O-isopropylidene-l-threitol (ITh) was, respectively, used as a comonomer. Both cyclic alditols were easily available from biomass feedstock, such that Is is a bicyclic compound derived from d-glucose, and ITh is a monocyclic acetalized compound coming from naturally occurring l-tartaric acid. All these copolyesters containing up to 30 mol % of sugar-based units had satisfactory number-average molecular weights in the 16 000–83 000 g mol–1 range, and presented a random microstructure together with excellent thermal stability. The sugar-containing copolyesters were all semicrystalline and still possessed the monoclinic crystal structure of PBS. The incorporation of either Is or ITh units with rigid cyclic structure into PBS chain decreased the crystallinity and crystallization rate of PBS, while it enhanced its glass transition temperature. In addition, the partial replacement of 1,4-butanediol by sugar-based units endowed PBS with steadily enhanced hydrophilicity. Depending on the type and content of sugar units, the copolyesters show different oxygen barriers and mechanical properties. It was found that copolyester with bicyclic Is sugar units exhibited a better oxygen barrier and mechanical property than that with monocyclic ITh units.

Ecofriendly Preparation and Characterization of a Cassava Starch/Polybutylene Adipate Terephthalate Film

“…The application of biodegradable packaging has gradually become a trend. In addition, researchers have used low-cost natural degradable materials for blending with biodegradable polymers to prepare composite materials and achieve certain results [1][2][3][4].…”

Rational design of sustainable polyurethanes from castor oil: towards simultaneous reinforcement and toughening

“…Isosorbide [33][34][35], a commercially available compound with double aliphatic rings, may be the good modifier for castor oilbased polyurethane. Besides the stiff nature, the hydroxyl of isosorbide is also secondary hydroxyl group, and thus has comparable activity with castor oil when reacting with diisocyanate.…”

Isosorbide‐based polysebacates as polymeric components for development of in situ forming implants

“…The molecular and thermal characteristics of the (co)polysebacates are listed in Table and shown in the Supporting Information. It is known that IS has rigid molecular structure due to the fused five‐membered rings, and this is the reason for improved thermal stability and elevated glass transition temperatures of IS‐based polyesters . In order to alternate some properties of pure PISEB, 10 or 25 mol% of IS was replaced in the feed by other nontoxic diol—1,2‐propanediol (PG).…”

“…It is known that IS has rigid molecular structure due to the fused five-membered rings, and this is the reason for improved thermal stability and elevated glass transition temperatures of IS-based polyesters. [26][27][28][29] In order to alternate some properties of pure PISEB, 10 or 25 mol% of IS was replaced in the feed by other nontoxic diol -1,2-propanediol (PG). Thermal properties of obtained polymers were determined by a DSC.…”