Biobased copolyesters from renewable resources: synthesis and crystallization kinetics of poly(propylene sebacate-co-isosorbide sebacate)

Abstract

In this work, a series of novel biobased copolymers, poly(propylene sebacate-co-isosorbide sebacate) (P(PSe-co-IS)), were synthesized by melt-polycondensation from sebacic acid (SA) and isosorbide (IS) with 1,3-propanediol (PD). In order to analyze the effects of isosorbide on the relative properties of poly(propylene sebacate) (PPSe), the composition, crystal structure, crystallization behavior, multiple melting behavior, and spherulitic morphology of these copolymers were investigated by 1 H-NMR, WAXD, DSC, TMDSC and POM, respectively. Results of 1 H-NMR indicated that IS have been successfully introduced into the PPSe main chains with the designed molar ratio. DSC data showed that crystallization ability of P(PSe-co-IS) copolymers was retarded with the introduction of IS. With the increment of IS, the overall crystallization rate decreased gradually. Furthermore, crystallization temperature (T c ), crystallization enthalpy (DH c ), melting temperature (T m ), and equilibrium melting temperature (T o m ) of P(PSe-co-IS) copolymers also decreased apparently with the increase of IS content. WAXD suggested that crystal structure of PPSe was not affected by IS, and POM revealed that all spherulites possess the typical "Maltese Cross" image. Furthermore, no obvious ring-banded spherulites could be detected for P(PSe-co-IS) copolymers in the wide temperature range except neat PPSe due to the hindrance of IS. With the increment of IS and crystallization temperature, the number of spherulites decreased rapidly and the size of spherulites increased, respectively.

Biobased copolyesters: synthesis, crystallization behavior, thermal and mechanical properties of poly(ethylene glycol sebacate-co-ethylene glycol 2,5-furan dicarboxylate)

“…As proposed by Wei et al, by analogy with poly(propylene sebacate), peak I can be attributed to the melting of secondary crystals (small and imperfects crystals) formed during the isothermal crystallization process. 29 The same observations were reported in the case of poly(ethylene-2,5-furanoate) and poly(ethylene terephthalate). 30,31 Fig .…”

Synthesis and Characterization of Renewable Polyester Coil Coatings from Biomass-Derived Isosorbide, FDCA, 1,5-Pentanediol, Succinic Acid, and 1,3-Propanediol

“…The use of isosorbide in polyesters can be motivated by several features: rigidity, chirality, non-toxicity [8], and recently, its use as a monomer for the preparation of UV-cured coatings has been highlighted [11]. Isosorbide has a relatively high thermostability and low segmental mobility, and can be used to improve the glass transition temperatures of polyesters [12]. However, the hydroxyl group in endo position easily forms intra-molecular hydrogen bonds with the oxygen in the other ring, which leads to the poor reactivity of the secondary hydroxyl group and the low number average molecular weights of copolyesters [13].…”

“…The polyesters had T g from −28 °C to −11 °C, which increased by increasing the mol % isosorbide, while the esterification yield decreased. Zhou et al [12,13,20] studied the properties and crystallization kinetics of copolyesters based on isosorbide, sebacic acid, and either 1,10-decanediol [20] or 1,3-propanediol [12]. The authors varied the mol % isosorbide from 5.3 mol % to 66.2%, reporting T g ranging from −26 °C to −5 °C, although no glass transition was observed when the mol % isosorbide was below 30%.…”

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

“…Unsaturated derivatives of IS have also been proposed as polymerizable compounds of injectable, biodegradable or stable in physiological environment, biomaterials intended for bone surgery . The synthesis by melt or azeotropic polycondensation and properties of various IS‐based polyesters were investigated and described by many authors during several last years . It was proved by Catalani et al that efficient method for synthesis of IS‐derived polyesters is polytransesterification catalyzed by lipase B .…”

“…12,13 The synthesis by melt or azeotropic polycondensation and properties of various IS-based polyesters were investigated and described by many authors during several last years. [14][15][16][17][18][19] It was proved by Catalani et al that efficient method for synthesis of ISderived polyesters is polytransesterification catalyzed by lipase B. 18,19 Such enzymatic polymerization route is recognized nowadays as very effective and preferable alternative to conventional chemically catalyzed processes.…”