Copolyesters of ε-caprolactone and l-lactide catalyzed by a tetrabutylammonium phthalimide-N-oxyl organocatalyst

Abstract

By utilizing tetrabutylammonium phthalimide-N-oxyl organocatalyst, copolymer PCLA with Mn over 20 000 g mol−1 was synthesized by sequential ring-opening polymerization of ε-caprolactone and l-lactide under bulk conditions.

A wide range of poly(glycolic acid)‐based di‐ and tri‐block polyesters by a single organocatalyst: Synthesis and characterization

“…Considering the thermal degradation of PGA and TBACB at high temperatures, 105, 120, and 135 °C were selected as the reaction temperatures. Different from the polymerization of LA or ε‐CL, 53 TBACB had higher catalytic activity for GA, and no extra initiator was needed in the reaction system. The ratio of GA and TBACB was 200:1.…”

“…All monomers were used after further purification. 13,53,54 All solvents were purified using the MIKROUNA solvent purification system. All deuterated reagents were used as received.…”

“…All materials were stored in the glovebox. The TBACB was synthesized 53 and confirmed by proton nuclear magnetic resonance ( 1 H NMR) (Figure S1) and Fourier transform infrared (Figure S2). In Figure S3, TBACB began to lose weight rapidly and underwent degradation from about 180 C. In Figure S4, the melting point of TBACB was around 165 C, which accessed the polymerization in a wide temperature range.…”

“…41 Recently, we developed the tetrabutylammonium 2-(carbamyl)benzoate (TBACB) catalyst (as shown in Figure S1) for the aliphatic lactone ROP. 52,53 TBACB with cheap raw materials and simple preparation was stable in air with low toxicity and could produce PLA or even PCL under solution or bulk polymerization within hours. What is more, TBACB displayed high catalytic activity toward ε-CL, and the reactivity for the ROP of LA and ε-CL was comparable.…”

Guaiacolate derivatives‐containing sodium complexes as catalysts for l‐lactide polymerization

“…[23][24][25] However, for the biological applications of PLA-based biomaterials, problems such as residual toxic components resulting from the use of toxic metal catalyst in PLA production must be resolved. Suitable alternatives to toxic metal catalysts are organic catalysts [26][27][28][29][30][31][32] or nontoxic metal catalysts, such as group I, [33][34][35][36][37][38][39][40] group II, [41][42][43][44] group IV, [45][46][47][48][49] zinc, [50][51][52][53][54][55][56] and aluminum [57][58][59][60][61][62] catalysts.…”