Synthesis and cellular compatibility of multi-block biodegradable poly(ε-caprolactone)-based polyurethanes

Khan, Ferdous; Valere, Simon; Fuhrmann, Steven; Arrighi, Valeria; Bradley, Mark

doi:10.1039/c3tb00358b

Cited by 23 publications

(12 citation statements)

References 42 publications

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“…For the HDI‐based polyurethane, an increase was reported in the tear strength and thermal stability due to the presence of a crystalline phase, which acted as a physical crosslinking. The effect of diisocyanate structure on polyurethane properties was also reported by Khan and co‐workers . They verified the effect of using methylenediphenyl diisocyanate, 1,4‐phenylene diisocyanate, 1,1′‐methylenebis(4‐isocyanatocyclohexane) or 2,4‐TDI and the chain extenders ethylene glycol and BDO on the mechanical and thermal properties of PCL‐based polyurethanes.…”

Section: Introductionsupporting

confidence: 68%

“…Among the diisocyanates, 2,4‐TDI is one of the most widely used due to its high reactivity . While some polyurethanes designed for biomedical applications are based on 2,4‐TDI, their final application must be well defined as the degradation of such polyurethanes leads to toxic products, such as aromatic diamines and other aromatic moieties . The replacement of toxic or pro‐toxic precursors is necessary when aiming for the development of new biomedical materials.…”

Section: Introductionmentioning

confidence: 99%

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Effect of diisocyanates and chain extenders on the physicochemical properties and morphology of multicomponent segmented polyurethanes based on poly(l‐lactide), poly(ethylene glycol) and poly(trimethylene carbonate)

Trinca

Felisberti

2015

Polymer International

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Multicomponent segmented polyurethanes (SPUs) based on poly(ethylene glycol), poly(l‐lactide) and poly(trimethylene carbonate) as macrodiols, 2,4‐toluene diisocyanate (2,4‐TDI) or 1,6‐hexane diisocyanate (HDI) as diisocyanate, and 1,4‐butanediol (BDO) or 2,2‐bis(hydroxymethyl)propionic acid (DMPA) as chain extenders were synthesized. The molecular, thermal, dynamic mechanical and morphological features of this set of uncrosslinked polyurethanes are characterized using 1H NMR, gel permeation chromatography, differential scanning calorimetry, dynamic mechanical thermal analysis (DMTA) and atomic force microscopy techniques. The lower reaction rate of HDI in comparison with 2,4‐TDI allows for better control of the SPU compositions, so that the intrinsic properties of each block can be better combined and modulated. HDI‐based SPUs are semi‐crystalline, while those based on 2,4‐TDI are amorphous, affecting the mechanical properties of these polyurethanes. All SPUs are heterogeneous, presenting morphologies of a disperse phase in a matrix which varies with the macrodiol ratios as well as with the nature of the diisocyanate and chain extender (a finer dispersion of the disperse phase is observed for SPUs of HDI and BDO). DMTA results indicate that the phases are complex mixtures of the different blocks with at least one rich in PLLA. The PEG content is shown to be the most important factor influencing the water sorption capability, while the incorporation of hindering carboxylic acid groups by the use of DMPA allows the water uptake of SPUs to be controlled by the solution pH. All SPUs show a significant loss of molar mass in hydrolytic degradation experiments and, in general, the PLLA‐rich SPUs are more susceptible to degradation. © 2015 Society of Chemical Industry

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Section: Introductionsupporting

confidence: 68%

Section: Introductionmentioning

confidence: 99%

Effect of diisocyanates and chain extenders on the physicochemical properties and morphology of multicomponent segmented polyurethanes based on poly(l‐lactide), poly(ethylene glycol) and poly(trimethylene carbonate)

Trinca

Felisberti

2015

Polymer International

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“…PCL is known for slow resorption due to its hydrophobicity and highly crystalline structure (Khan et al, 2013). In this study, the uncoated 3DP structures disintegrated within a week, while only 10% mass loss was recorded for PCL-coated samples following 7 day immersion in buffer solution.…”

Section: Discussionmentioning

confidence: 80%

Effects of poly (ε-caprolactone) coating on the properties of three-dimensional printed porous structures

Zhou

Cunningham

Lennon

et al. 2017

Journal of the Mechanical Behavior of Biomedical Materials

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Powder-based inkjet three-dimensional printing (3DP) to fabricate pre-designed 3D structures has drawn increasing attention. However there are intrinsic limitations associated with 3DP technology due to the weak bonding within the printed structure, which significantly compromises its mechanical integrity. In this study, calcium sulphate ceramic structures demonstrating a porous architecture were manufactured using 3DP technology and subsequently post-processed with a poly (ε-caprolactone) (PCL) coating. PCL concentration, immersion time, and number of coating layers were the principal parameters investigated and improvement in compressive properties was the measure of success. Interparticle spacing within the 3DP structures were successfully filled with PCL material. Consequently the compressive properties, wettability, morphology, and in vitro resorption behaviour of 3DP components were significantly augmented. The average compressive strength, Young's modulus, and toughness increased 217%, 250%, and 315%, following PCL coating. Addition of a PCL surface coating provided long-term structural support to the host ceramic material, extending the resorption period from less than 7 days to a minimum of 56 days. This study has demonstrated that application of a PCL coating onto a ceramic 3DP structure was a highly effective approach to addressing some of the limitations of 3DP manufacturing and allows this advanced technology to be potentially used in a wider range of applications.

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“…Although proteins are highly biocompatible, their very fast degradation and low mechanical strength result in a lack of structural support during tissue development. Polymeric biomaterials are also developed by polymerizing one or more monomers either by homopolymer reaction or copolymer reaction to form non-biodegradable [ 6 , 7 ] and biodegradable materials [ 8 , 9 ]. The structure, molecular chain length, and stereochemistry can be tailored by varying chemical and physical parameters during synthesis.…”

Section: Introductionmentioning

confidence: 99%

Designing Smart Biomaterials for Tissue Engineering

Khan

Tanaka

2017

IJMS

Self Cite

221

129

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The engineering of human tissues to cure diseases is an interdisciplinary and a very attractive field of research both in academia and the biotechnology industrial sector. Three-dimensional (3D) biomaterial scaffolds can play a critical role in the development of new tissue morphogenesis via interacting with human cells. Although simple polymeric biomaterials can provide mechanical and physical properties required for tissue development, insufficient biomimetic property and lack of interactions with human progenitor cells remain problematic for the promotion of functional tissue formation. Therefore, the developments of advanced functional biomaterials that respond to stimulus could be the next choice to generate smart 3D biomimetic scaffolds, actively interacting with human stem cells and progenitors along with structural integrity to form functional tissue within a short period. To date, smart biomaterials are designed to interact with biological systems for a wide range of biomedical applications, from the delivery of bioactive molecules and cell adhesion mediators to cellular functioning for the engineering of functional tissues to treat diseases.

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Synthesis and cellular compatibility of multi-block biodegradable poly(ε-caprolactone)-based polyurethanes

Cited by 23 publications

References 42 publications

Effect of diisocyanates and chain extenders on the physicochemical properties and morphology of multicomponent segmented polyurethanes based on poly(l‐lactide), poly(ethylene glycol) and poly(trimethylene carbonate)

Effect of diisocyanates and chain extenders on the physicochemical properties and morphology of multicomponent segmented polyurethanes based on poly(l‐lactide), poly(ethylene glycol) and poly(trimethylene carbonate)

Effects of poly (ε-caprolactone) coating on the properties of three-dimensional printed porous structures

Designing Smart Biomaterials for Tissue Engineering

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