Synthesis of Star-Shaped e-Caprolactone Oligomers for use as Plasticizers of Poly(L-Lactide) Bioplastic Films

Imsombut, Thanonchat; Srisa-ard, Mangkorn; Baimark, Yodthong

doi:10.13005/ojc/330213

Cited by 7 publications

(5 citation statements)

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“…The toughness of the blended PCL and PLA was not significantly improved, and the strength and modulus decreased, which was mainly attributed to the poor interface compatibility. To improve the compatibility, various methods, such as adding block or random polymer compatibilizers, − adding inorganic compatibilizers, , and interfacial crystallite cross-linking, have been studied.…”

Section: Introductionmentioning

confidence: 99%

Toughening of Poly(l-Lactide) with Branched Polycaprolactone: Effect of Chain Length

Yang

Liu

et al. 2020

ACS Omega

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In this work, a series of branched polycaprolactone (BPCL) samples with different ε-caprolactone (CL) chain lengths were synthesized and used to toughen poly (lactic acid) (PLA). The spherical structure increased the free volume, facilitating the free movement of the PLA chain segment and increasing the ductility. In addition, the hydrogen bonds between the multiterminal hydroxyl group of BPCL x and PLA improved the interaction between them. The glass-transition temperatures (T g ) and crystallization temperatures (T c ) of the blends were significantly lower than those of PLA, and these temperatures increased with the chain length of polycaprolactone. BPCL x increased the crystallization rate of PLA through heterogeneous nucleation. A longer chain length of CL increased the mutual entanglement in the blends, reduced the hydrogen bonding between BPCL x and PLA, and increased the entanglement of BPCL x chains. When the chain length of CL was 6, the impact strength and elongation at break of the PLA/BPCL blends exhibited an increase of 151.72 and 465.8%, respectively, as compared with PLA.

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Section: Introductionmentioning

confidence: 99%

Toughening of Poly(l-Lactide) with Branched Polycaprolactone: Effect of Chain Length

Yang

Liu

et al. 2020

ACS Omega

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“…It has been proven that in the case of using the HPA-2 heteropolyacid (H 5 [PMo 12 −2V 2 O 40 ]•aq/MeOH) linear oligomers are obtained [85]. The synthesis of ε-caprolactone copolymers with various compounds, e.g., other lactones (ω-pentadecalactone, γ-butyrolactone or γ-valerolactone), carboxylic acids, methyl esters, glucopyranosides and carbonates was studied [90][91][92][93][94][95][96][97][98][99][100]. Popular comonomers with caprolactone also include LA and ethylene glycol.…”

Section: Methods For the Synthesis Of Lactones Derivativesmentioning

confidence: 99%

“…The methods of preparing polymer or oligomer blends with an additional component are relatively simple and are based on mixing both components in a solvent and then applying this solution onto a desired material or simply a plain surface. After the evaporating of the solvent, a blend-covered product or a thin film is obtained [98]. Diols of OCL, and also triols and tetraols, are suitable for the production of two-dimensional structures.…”

Section: Methods For the Synthesis Of Lactones Derivativesmentioning

confidence: 99%

Recent Developments in Lactone Monomers and Polymer Synthesis and Application

2021

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Lactones are a group of compounds that have been known for several decades. The commercial importance of lactones results from the possibility of manufacturing of a broad scope of derivatives and polymers with a wide spectrum of applications. In this work the synthesis and characterization of simple lactones are described, which due to the easy methods of the synthesis are of high importance for the industry. The chemical as well as biochemical methods are included with special attention paid to the methods that avoid metal catalysts, initiators or toxic solvents, allowing the use of the final products for the medical applications, e.g., for controlled drug-release systems, resorbable surgical threads, implants, tissue scaffolds or for the production of drugs. Lactone-based derivatives, such as polymers, copolymers, composites or three-dimensional structures are also presented. The work is focused on the methods for the synthesis of lactones and lactones derivates, as well as on the special properties and application of the studied compounds.

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“…The terminal hydroxyl groups in OCL can also be transformed in order to give the oligomer special characteristics, e.g., a product with a so-called shape memory [ 7 ]. On the other hand, the use of a special initiator with a multi-arm structure allows for obtaining an OCL with a star-like structure, which can be used as a plasticizer of a modern bioplastic-poly(L-lactide) ( Scheme 2 ) [ 8 , 9 ].…”

Section: Introductionmentioning

confidence: 99%

Oxidation of Cyclohexanone with Peracids—A Straight Path to the Synthesis of ε-Caprolactone Oligomers

et al. 2022

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During Baeyer–Villiger (BV) oxidation of cyclohexanone with peracids, oligo(ε-caprolactone) (OCL) may be formed. In this work, a two-step one-pot method for the synthesis of OCL involving the BV oxidation of cyclohexanone with peracids and then oligomerization of the resulting ε-caprolactone has been developed. The process was carried out in two solvents: toluene and cyclohexane. Based on the studies, it was determined that the increased temperature (45–55 °C) and the longer reaction time (4 h) favor the formation of OCls. Among the tested peracids (perC8-C12), perC10 turned out to be the most effective oxidant. Moreover, the obtained oligomers were characterized by means of NMR, MS MALDI TOF, and TGA analyses, which made it possible to determine the structure of oligomers (length and terminal groups of the chains). Additionally, the oligomers obtained after the distillation of the reaction mixture were analyzed.

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Synthesis of Star-Shaped e-Caprolactone Oligomers for use as Plasticizers of Poly(L-Lactide) Bioplastic Films

Cited by 7 publications

References 0 publications

Toughening of Poly(l-Lactide) with Branched Polycaprolactone: Effect of Chain Length

Toughening of Poly(l-Lactide) with Branched Polycaprolactone: Effect of Chain Length

Recent Developments in Lactone Monomers and Polymer Synthesis and Application

Oxidation of Cyclohexanone with Peracids—A Straight Path to the Synthesis of ε-Caprolactone Oligomers

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