Synthesis and degradability of a star-shaped polylactide based on l-lactide and xylitol

Teng, Lijing; Xu, Xianglan; Nie, Wangyan; Zhou, Yifeng; Song, Linyong; Chen, Pengpeng

doi:10.1007/s10965-015-0719-1

Cited by 21 publications

(13 citation statements)

References 35 publications

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“…[11][12][13][14][15][16][17][18] In several reviews, researchers have comprehensively surveyed the literature in this area. 19,20 Star-shaped polymers are characterized by a low melt viscosity and a lower T g and are less crystalline and more compact in size compared to linear polymers of similar molecular weights.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of well‐defined random and block copolymers of ε‐caprolactone with l‐lactide as an additive for toughening polylactide: Influence of the molecular architecture

Deokar

Idage

et al. 2015

J of Applied Polymer Sci

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Well-defined multiarmed star random and block copolymers of e-caprolactone with L-lactide with controlled molecular weights, low polydispersities, and precise numbers of arms were synthesized by the ring-opening polymerization of respective cyclic ester monomers. The polymers were characterized by 1 H-NMR and 13 C-NMR to determine their chemical composition, molecular structure, degree of randomness, and proof of block copolymer formation. Gel permeation chromatography was used to establish the degree of branching. Star-branched random copolymers exhibited lower glass-transition temperatures (T g 's) compared to a linear random copolymer. When the star random copolymers were melt-blended with poly(L-lactic acid) (PLA), we observed that the elongation of the blend increased with the number of arms of the copolymer. Six-armed block copolymers, which exhibited higher T g 's, caused the maximum improvement in elongation. In all cases, improvements in the elongation were achieved with no loss of stiffness in the PLA blends.

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Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of well‐defined random and block copolymers of ε‐caprolactone with l‐lactide as an additive for toughening polylactide: Influence of the molecular architecture

Deokar

Idage

et al. 2015

J of Applied Polymer Sci

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“…All the peaks are assigned to the protons of the polymers. The degree of polymerization (DP) of PBnLA was calculated by comparing the integration of the signals at 4.35 ppm for terminal C H OH and 3.86–4.07 ppm for C H 2  of PBnLA . The calculated DP is 45, thus the molecular weight of PBnLA is 8000.…”

Section: Resultsmentioning

confidence: 99%

A Functionalized Cyclic Lactide Monomer for Synthesis of Water‐Soluble Poly(Lactic Acid) and Amphiphilic Diblock Poly(Lactic Acid)

Zhang

Dai

2016

Macromol. Rapid Commun.

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Biodegradable and bioabsorbable poly(lactic acid)s are one of the most important biomedical materials. However, it is difficult to introduce the functional groups into poly(lactic acid)s in order to improve their hydrophilicity and degradation rate. Here the authors describe the synthesis of functionalized cyclic lactide monomer 3,6-bis(benzyloxymethyl)-1,4-dioxane-2,5-dione (BnLA) using an advanced synthetic route. Water-soluble hydroxyl-functionalized homopoly(lactic acid) (P(OH)LA) is synthesized via ring-opening polymerization (ROP) of BnLA, followed by a hydrogenolytic deprotection reaction. Amphiphilic diblock poly(lactic acid) (P(OH)LA-PLA) is synthesized via ROP of DL-lactide using PBnLA as an initiator, followed by a hydrogenolytic deprotection reaction. P(OH)LA-PLA is able to form polymeric micelles with the diameter of sub-100 nm.

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“…However, since these initiators used as cores of the star-shaped biodegradable polyesters are not favorable natural products, there is a possibility that these residual core compounds are not bioresorbed after the complete biodegradation of the polyester arms [ 18 ]. Thus, active research on star-shaped biodegradable polyesters possessing sugar alcohols (H m SAs) such as glycerol (GC), erythritol (ET), xylitol (XL) and sorbitol (SB) as the core molecules has been carried out in recent years ( Scheme 1 ) [ 18 , 19 , 20 , 21 , 22 , 23 ]. GC is mainly produced as a by-product in the conversion of naturally occurring fats and oils to fatty acids or fatty acid methyl esters for biodiesel [ 24 , 25 ].…”

Section: Introductionmentioning

confidence: 99%

Stereocomplexation, Thermal and Mechanical Properties of Conetworks Composed of Star-Shaped l-Lactide, d-Lactide and ε-Caprolactone Oligomers Utilizing Sugar Alcohols as Core Molecules

et al. 2017

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Abstract:It is important to develop tailor-made biodegradable/biocompatible polymer networks usable for biomaterials whose thermal and mechanical properties are easily controlled by changing the composition. We synthesized sugar-alcohol-based polymer networks (SPN-mscLAO/3CLO, m = 4, 5 or 6) by the crosslinking reactions of erythritol, xylitol or sorbitol-based m-armed star-shaped L-lactide and D-lactide oligomers (HmSLLAO and HmSDLAO), a glycerol-based 3-armed star-shaped ε-caprolactone oligomer (H3SCLO) and hexamethylene diisocyanate (HDI) at the weight ratios of HmSLLAO/HmSDLAO = 1/1 and (HmSLLAO + HmSDLAO)/H3CLO = 100/0, 75/25, 50/50, 25/75 or 0/100). The influence of the arm number on the crystallization behavior, thermal and mechanical properties of SPN-mscLAO/3CLOs were systematically investigated by comparing with those of sugar-alcohol-based homochiral polymer network (SPN-mLLAO, m = 4, 5 or 6) prepared by the reaction of HmSLLAO and HDI. Stereocomplex (sc) crystallites are dominantly formed for SPN-mscLAO/3CLOs 100/0-25/75, whereas SPN-mLLAOs were amorphous. The higher order of melting temperature of sc-crystals for SPN-mscLAO/3CLOs 100/0-25/75 was m = 5 > m = 6 > m = 4. The sc-crystallinities of SPN-4scLAO/3CLOs 100/0-50/50 were significantly lower than those of SPN-mscLAO/3CLOs 100/0-50/50 (m = 5 and 6). The larger order of the sc-spherulite size at crystallization temperature of 110 • C was m = 5 > m = 6 > m = 4 for SPN-mscLAO/3CLO 100/0. The size and number of sc-spherulites decreased with increasing crystallization temperature over the range of 110-140 • C and with increasing CLO fraction. Among all the networks, SPN-5scLAO/3CLOs 75/25 and 50/50 exhibited the highest and second highest tensile toughnesses (21.4 and 20.3 MJ·m −3 ), respectively.

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Synthesis and degradability of a star-shaped polylactide based on l-lactide and xylitol

Cited by 21 publications

References 35 publications

Synthesis and characterization of well‐defined random and block copolymers of ε‐caprolactone with l‐lactide as an additive for toughening polylactide: Influence of the molecular architecture

Synthesis and characterization of well‐defined random and block copolymers of ε‐caprolactone with l‐lactide as an additive for toughening polylactide: Influence of the molecular architecture

A Functionalized Cyclic Lactide Monomer for Synthesis of Water‐Soluble Poly(Lactic Acid) and Amphiphilic Diblock Poly(Lactic Acid)

Stereocomplexation, Thermal and Mechanical Properties of Conetworks Composed of Star-Shaped l-Lactide, d-Lactide and ε-Caprolactone Oligomers Utilizing Sugar Alcohols as Core Molecules

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