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Mechanochemical synthesis of poly(trimethylene carbonate)s: an example of rate acceleration.

ABSTRACT: Mechanochemical polymerization is a rapidly growing area and a number of polymeric materials can now be obtained through green mechanochemical synthesis. In addition to the general merits of mechanochemistry, such as being solvent-free and resulting in high conversions, we herein explore rate acceleration under ball-milling conditions while the conventional solution-state synthesis suffer from low reactivity. The solvent-free mechanochemical polymerization of trimethylene carbonate using the organocatalysts 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) are examined herein. The polymerizations under ball-milling conditions exhibited significant rate enhancements compared to polymerizations in solution. A number of milling parameters were evaluated for the ball-milling polymerization. Temperature increases due to ball collisions and exothermic energy output did not affect the polymerization rate significantly and the initial mixing speed was important for chain-length control. Liquid-assisted grinding was applied for the synthesis of high molecular weight polymers, but it failed to protect the polymer chain from mechanical degradation.

SUBMITTER: Park S

PROVIDER: S-EPMC6541340 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature

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Poly(trimethylene carbonate-co-ε-caprolactone) promotes axonal growth.

Project description:Mammalian central nervous system (CNS) neurons do not regenerate after injury due to the inhibitory environment formed by the glial scar, largely constituted by myelin debris. The use of biomaterials to bridge the lesion area and the creation of an environment favoring axonal regeneration is an appealing approach, currently under investigation. This work aimed at assessing the suitability of three candidate polymers - poly(ε-caprolactone), poly(trimethylene carbonate-co-ε-caprolactone) (P(TMC-CL)) (11∶89 mol%) and poly(trimethylene carbonate) - with the final goal of using these materials in the development of conduits to promote spinal cord regeneration. Poly(L-lysine) (PLL) coated polymeric films were tested for neuronal cell adhesion and neurite outgrowth. At similar PLL film area coverage conditions, neuronal polarization and axonal elongation was significantly higher on P(TMC-CL) films. Furthermore, cortical neurons cultured on P(TMC-CL) were able to extend neurites even when seeded onto myelin. This effect was found to be mediated by the glycogen synthase kinase 3β (GSK3β) signaling pathway with impact on the collapsin response mediator protein 4 (CRMP4), suggesting that besides surface topography, nanomechanical properties were implicated in this process. The obtained results indicate P(TMC-CL) as a promising material for CNS regenerative applications as it promotes axonal growth, overcoming myelin inhibition.

| S-EPMC3937290 | biostudies-literature

Synthesis of Poly(Trimethylene Carbonate) from Amine Group Initiation: Role of Urethane Bonds in the Crystallinity.

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| S-EPMC7829917 | biostudies-literature

Hybrid Networks of Hyaluronic Acid and Poly(trimethylene carbonate) for Tissue Regeneration.

Project description:To improve the mechanical performance of hyaluronic acid (HA)-based hydrogels, we prepared novel hybrid hydrogels consisting of hydrophilic HA and hydrophobic poly(trimethylene carbonate) (PTMC). Both polymers were functionalized with methacrylic anhydride, yielding HAMA and PTMC-tMA. Hybrid networks with different ratios of PTMC-tMA:HAMA were prepared by photo-cross-linking, using DMSO pH 2.7 as a common solvent for both macromers. The hybrid networks had high gel contents. The hydrophilicity of the networks increased with increasing HAMA content. The networks consisted of the intended amounts of both macromers. The suture retention strength and compression modulus of the networks increased with increasing PTMC-tMA content. While the 100% HAMA network could not be sutured, the 50:50 PTMC-tMA:HAMA network had a suture retention strength of 5.3 N/mm. This is comparable to that of natural vascular tissues. Also the compression modulus (867 kPa) was significantly higher than that of the 100% HAMA network (13 kPa). Moreover, the networks were compatible with human mesenchymal stem cells. In conclusion, these resilient PTMC-tMA:HAMA networks are promising new biomaterials for tissue regeneration.

| S-EPMC10565833 | biostudies-literature

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| S-EPMC7962012 | biostudies-literature

A drug eluting poly(trimethylene carbonate)/poly(lactic acid)-reinforced nanocomposite for the functional delivery of osteogenic molecules.

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Membranes for Modelling Cardiac Tissue Stiffness In Vitro Based on Poly(trimethylene carbonate) and Poly(ethylene glycol) Polymers.

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Poly(ethylene glycol)-b-poly(1,3-trimethylene carbonate) Copolymers for the Formulation of In Situ Forming Depot Long-Acting Injectables.

Project description:This article describes the utilization of (methoxy)poly(ethylene glycol)-b-poly(1,3-trimethylene carbonate) ((m)PEG-PTMC) diblock and triblock copolymers for the formulation of in situ forming depot long-acting injectables by solvent exchange. The results shown in this manuscript demonstrate that it is possible to achieve long-term drug deliveries from suspension formulations prepared with these copolymers, with release durations up to several months in vitro. The utilization of copolymers with different PEG and PTMC molecular weights affords to modulate the release profile and duration. A pharmacokinetic study in rats with meloxicam confirmed the feasibility of achieving at least 28 days of sustained delivery by using this technology while showing good local tolerability in the subcutaneous environment. The characterization of the depots at the end of the in vivo study suggests that the rapid phase exchange upon administration and the surface erosion of the resulting depots are driving the delivery kinetics from suspension formulations. Due to the widely accepted utilization of meloxicam as an analgesic drug for animal care, the results shown in this article are of special interest for the development of veterinary products aiming at a very long-term sustained delivery of this therapeutic molecule.

| S-EPMC8146374 | biostudies-literature

Biodegradable 3D Printed Scaffolds of Modified Poly (Trimethylene Carbonate) Composite Materials with Poly (L-Lactic Acid) and Hydroxyapatite for Bone Regeneration.

Project description:Biodegradable scaffolds based on biomedical polymeric materials have attracted wide interest in bone transplantation for clinical treatment for bone defects without a second operation. The composite materials of poly(trimethylene carbonate), poly(L-lactic acid), and hydroxyapatite (PTMC/PLA/HA and PTMC/HA) were prepared by the modification and blending of PTMC with PLA and HA, respectively. The PTMC/PLA/HA and PTMC/HA scaffolds were further prepared by additive manufacturing using the biological 3D printing method using the PTMC/PLA/HA and PTMC/HA composite materials, respectively. These scaffolds were also characterized by Fourier transform infrared spectroscopy (FT-IR), gel permeation chromatography (GPC), automatic contact-angle, scanning electronic micrographs (SEM), diffraction of X-rays (XRD), differential scanning calorimetry (DSC), and thermogravimetry (TG). Subsequently, their properties, such as mechanical, biodegradation, cell cytotoxicity, cell compatibility in vitro, and proliferation/differentiation assay in vivo, were also investigated. Experiment results indicated that PTMC/PLA/HA and PTMC/HA scaffolds possessed low toxicity, good biodegradability, and good biocompatibility and then enhanced the cell multiplication ability of osteoblast cells (MC3T3-E1). Moreover, PTMC/PLA/HA and PTMC/HA scaffolds enhanced the adhesion and proliferation of MC3T3-E1 cells and enabled the bone cell proliferation and induction of bone tissue formation. Therefore, these composite materials can be used as potential biomaterials for bone repatriation and tissue engineering.

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Poly(trimethylene carbonate-<i>co</i>-valerolactone) copolymers are materials with tailorable properties: from soft to thermoplastic elastomers.

Project description:Aliphatic poly(ester-carbonates) are receiving extensive research attention as tailorable materials suitable for multiple applications from tissue engineering and 3D scaffold printing to drug delivery. Thus, simple reliable procedures for producing easily tailorable poly(ester-carbonates) without metal residues are continuously sought after. In this work, we report on one-pot synthesis of random copolymers of TMC and δ-VL using metal-free biocompatible 1,5,7-triazabicyclo[4.4.0]dec-5-ene as a catalyst and benzyl alcohol and poly(ethylene oxide) as initiators. Random poly(ester-carbonates) with TMC : VL unit ratios ranging from 80 : 20 to 20 : 80 were synthesized via ring-opening polymerization while displaying excellent agreement of comonomers' ratios in the feed and copolymer chains. The copolymers' supramolecular structure, thermal and mechanical properties were thoroughly analyzed by various methods. The obtained results clearly indicated that the physicochemical properties can be controlled simply by varying the ratio of comonomers and the length of segments in the copolymer chain. Several copolymers exhibited behavior of thermoplastic elastomers with the most promising one exhibiting a 2200% increase in elongation at break compared to the poly(valerolactone) homopolymer while retaining tensile strength and Young's modulus suitable for biomedical applications. Overall, our work contributed to widening the portfolio of tailorable copolymers for specialized bioapplications and possibly paving a way for the use of more sustainable polymers in the biomedical field.

| S-EPMC9059556 | biostudies-literature

In vitro and in vivo degradation behavior of poly(trimethylene carbonate-co-d,l-lactic acid) copolymer.

Project description:We present P(TMC-co-DLLA) copolymer with the molar ratio of TMC: DLLA = 15: 85 was used to systematic study of in vivo and in vitro degradation behaviors. Dense homogeneous copolymer specimens were prepared by compression molding method. The in vitro and in vivo degradation were, respectively, performed at simulative body condition and implanted into rat's subcutaneous condition. Investigations were followed via physicochemical and histological analysis such as SEM, GPC, DSC, FTIR and H&E stain. The results demonstrate that copolymeric material can degrade in phosphate buffer solution (PBS) and in rat's body, and the in vivo degradation rate is faster. Obvious decline of molecule weight and mass loss has been observed, which led to the attenuation of mechanical strength. Furthermore, apart from the hydrolysis, macrophagocytes took part in the phagocytosis in vivo, indicating that degradation rate could be regulated by the combinational mechanism. It is concluded that P(TMC-co-DLLA) copolymer is a promising candidate for tissue repair.

| S-EPMC5544909 | biostudies-other

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