Triblock Copolymers Based on 1,3‐Trimethylene Carbonate and Lactide as Biodegradable Thermoplastic Elastomers

Zhang, Zheng; Grijpma, Dirk W.; Feijén, Jan

doi:10.1002/macp.200300184

Cited by 143 publications

(143 citation statements)

References 40 publications

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“…Thus, physical properties should be improved by copolymerizations of lactide with other monomers in order to generate softer and tougher materials. For this purpose, cyclic carbonates are of great interest as comonomers because of the soft property of the resulting copolymers [11][12][13][14][15][16][17]. In our previous works, we studied synthesis and biodegradabilities of random copolymers of L-LA with (R)-, (S)-, or rac -1-methyltrimethylene carbonate polymerized by using a samarium initiator (C 5 Me 5 ) 2 SmMe(THF) (Sm1) [18][19][20][21][22][23].…”

Section: Introductionmentioning

confidence: 99%

Comparison of Sm complexes with Sn compounds for syntheses of copolymers composed of lactide and cyclic carbonates and their biodegradabilities

Nakayama

Yasuda

Yamamoto

et al. 2005

Reactive and Functional Polymers

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The comparison of organolanthanide complexes, (C 5 Me 5 ) 2 SmMe(THF) (Sm1) and [(C 5 Me 5 ) 2 Sm] 2 (PhC=C=C= CPh) (Sm2), with tin compounds, Bu 2 Sn(OMe) 2 (Sn1) and Bu 2 Sn(OCH 2 CH 2 CH 2 O) (Sn2), in the preparation of random, diblock, and triblock copolymers composed of L-lactide (L-LA) or D,L-LA and cyclic carbonates, trimethylene carbonate (TMC) or 2,2-dimethyltrimethylene carbonate (DTC) is reported. The biodegradabilities of the resulting copolymers with proteinase K and a compost were examined. The copolymerization of L-LA with cyclic carbonates by Sm1 or Sm2 afforded copolymers with relatively low melting points (<160 °C) due to the accompanying epimerization in comparison with those obtained with Sn1 or Sn2. In the degradation of the polymers with a compost, the copolymers based on D,L-LA were more degradable than those based on L-LA. On the other hand, the effect of the incorporated cyclic carbonate on its degradability was more drastic in the copolymers based on L-LA than those in the copolymers based on D,L-LA. The introduction of only a small amount of the cyclic carbonates into PLLA significantly enhanced the degradability of PLLA with a compost or proteinase K. In the enzymatic degradation of L-LA-containing polymers, the copolymerization of L-LA with TMC was also quite effective to improve the degradability of PLLA. Triblock copolymerization tends to be effective to enhance the degradability of PLLA.

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Section: Introductionmentioning

confidence: 99%

Comparison of Sm complexes with Sn compounds for syntheses of copolymers composed of lactide and cyclic carbonates and their biodegradabilities

Nakayama

Yasuda

Yamamoto

et al. 2005

Reactive and Functional Polymers

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“…Feijen et al [22] has reported the blends of biodegradable triblock copolymers based on 1,3-trimethylene carbonate (TMC) and different lactides (i.e. L-lactide (LLA), D-lactide (DLA).…”

Section: Compound Modificationsmentioning

confidence: 99%

Advances in chemical modifications of polylactide biodegradable materials

Li¹,

Chen²

2018

Proceedings of the 2017 3rd International Forum on Energy, Environment Science and Materials (IFEESM 2017)

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Abstract. Biodegradable materials have been actively studied in applications of food packaging, agricultural film, and biomedical materials. As one of the most important biodegradable materials, polylactide (PLA) has attracted great attention due to its excellent biodegradable property. Despite favorable performance, PLA has some drawbacks to limit its applications. Various modifications have been applied to improve on the overall properties of PLA. In this paper, a summary on literature review of chemical modifications of PLA-based materials is addressed.

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“…Polymer micelles are aggregates formed from polymers containing hydrophilic and hydrophobic segments, where various functions can be imparted to the structure by the polymer design. For the hydrophobic polymer segment we have focused on PTMC, which has an amorphous structure and is an attractive material in terms of degradability in vivo [1][2]. For the hydrophilic block, PNIPAAm and PMPC are attractive, and they are broadly used in the biomedical field, where PNIPAAm shows thermo-responsive behavior and PMPC polymer shows high water solubility and high compatibility in vivo.…”

Section: Introductionmentioning

confidence: 99%

Thermo-Responsive Polymer Colloids Prepared Using a Hybrid Polymer Synthesis Technique

Tsunematsu

Miyake

Watanabe

et al. 2012

Trans. Mat. Res. Soc. Japan

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In the present study, we have designed a polymer colloid from a multi-block polymer chain composed of a hydrophobic and a hydrophilic segment. The hydrophobic segment consisted of the amorphous polymer poly(trimethylene carbonate) (PTMC) and was synthesized by ring-opening polymerization (ROP) of trimethylene carbonate. The hydroxyl terminal on the PTMC was functionalized for subsequent living radical polymerization of two functional vinyl monomers: N-isopropylacrylamide (NIPAAm) and 2-methacryloyloxyethyl phosphorylcholine (MPC), where poly-NIPAAm (PNIPAAm) shows thermo-responsive behavior, and poly-MPC (PMPC) is highly biocompatible. In this way, functional polymers were obtained via a hybrid polymer synthesis technique. The chemical structure of the resulting polymer was determined by 1 H-NMR and IR, and its solution properties were evaluated by UV spectroscopy, fluorescence spectroscopy, and dynamic light scattering (DLS). It was confirmed that the resulting polymers spontaneously self-aggregated in water by the Tyndall phenomenon, where the hydrophilic PNIPAAm and PMPC presumably covered the hydrophobic and amorphous PTMC domain. From DLS, we found that the diameter of the aggregation was changeable in terms of polymer sequence. Aggregates of the tri-block copolymer in water showed a diameter of 460 nm at 25°C, while at 35°C, the particle size decreased to 370 nm as a result of the increased hydrophobicity of the NIPAAm unit on the polymer. The polymer colloid could encapsulate a fluorescent probe proving the existence of a hydrophobic domain in the aggregate.

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Triblock Copolymers Based on 1,3‐Trimethylene Carbonate and Lactide as Biodegradable Thermoplastic Elastomers

Cited by 143 publications

References 40 publications

Comparison of Sm complexes with Sn compounds for syntheses of copolymers composed of lactide and cyclic carbonates and their biodegradabilities

Comparison of Sm complexes with Sn compounds for syntheses of copolymers composed of lactide and cyclic carbonates and their biodegradabilities

Advances in chemical modifications of polylactide biodegradable materials

Thermo-Responsive Polymer Colloids Prepared Using a Hybrid Polymer Synthesis Technique

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