Hydroxyl-functionalized amphiphilic triblock copolyesters made of tartaric and lactic acids: Synthesis and nanoparticle formation

Abstract

Bio-based triblock copolyesters were synthesized by ring-opening polymerization of Llactide in solution using a hydroxyl-ended polytartrate as di-functional macroinitiator. This telechelic polyester with a M n about 3000 g•mol-1 was obtained by non-stoichiometric melt polycondensation of dimethyl 2,3-di-O-isopropylidene-L-tartrate and 1,4-butanediol. Two symmetrical triblock copolyesters with M n in the 5,000-7,000 g•mol-1 range and differing in the length of the polylactide blocks were prepared. The protecting isopropylidene group was removed in trifluoracetic acid to generate amphiphilic triblock copolyesters bearing free hydroxyl groups in the central block. All copolyesters started to decompose approximately at 260-280 ºC, were semicrystalline, and readily degraded by hydrolysis of the main chain under both acid and basic conditions. The acetalized copolyesters had a single T g , whereas free-hydroxyl bearing copolyesters showed two T g indicative of blocks phase separation. All copolyesters were able to form nanoparticles with average diameters within the ~200-450 nm range. The influence of the block lengths and protection/deprotection of the hydroxyl groups on size and ζ-potential of the nanoparticles was evaluated.

Biodegradable Block Poly(ester amine)s with Pendant Hydroxyl Groups for Biomedical Applications

“…Unfortunately, the masses of the obtained copolymers were low, amounting to only a few thousand g/mol. These copolymers did not have antibacterial properties; on the contrary, they were a suitable medium for them [ 35 ]. After the protection of methoxy groups, the tartaric acid derivative was used in the reaction with diamines to obtain a series of polyesteramides.…”

Fully biobased biodegradable poly(l‐lactide)‐b‐poly(ethylene brassylate)‐b‐poly(l‐lactide) triblock copolymers: synthesis and investigation of relationship between crystallization morphology and thermal properties

“…Diacids and diols or hydroxyl acids derived from plants or animals or available from the chemical industry are employed to synthesize polyesters by condensation polymerization. A large number of polyesters have been reported acting as the mid‐block of triblock copolymers, such as poly(ricinoleic acid), poly(1,4‐butylene adipate), poly(butylene succinate), poly(propylene‐ co ‐neopentyl glycol succinate), poly(glucitol succinate), poly(butylene carbonate) and poly(1,4‐butylene tartrate), and these polyesters improve the toughness of PLLA effectively. However, the relatively low molecular weight and the lack of control of the polymers are still the main limitations to utilizing this approach.…”

ROP and crystallization behaviour of partially renewable triblock aromatic-aliphatic copolymers derived from L-lactide

“…In this work, the triblock copolymers were synthesized using TBD as catalyst, due to the effectiveness shown by this catalyst to copolymerize LA with other monomers maintaining low transesterification. 26,27 Due to the above, it is expected that the TBD has a catalytic activity that promotes the formation of triblock copolymers (PLA-b-PHTb-PLA and PLA-b-PHF-b-PLA).…”