Synthesis and characterization of biodegradable polyurethanes made from cholic acid and l-lysine diisocyanate ethyl ester

Açık, Gökhan; Karabulut, Ferhat; Altınkök, Çağatay; Karatavuk, Ali Osman

doi:10.1016/j.polymdegradstab.2019.04.015

Cited by 45 publications

(36 citation statements)

References 44 publications

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“…On the other hand, in the same period, the total residual weight for the F-PCL 24 h sample was 52%, which was lower compared to that found for F-PCL 48 h (65%) in the presence of lipase. The overall higher degradation rate of the F-PCL 24 h sample was attributed to the presence of hydrophobic polymer segments possessing higher fluorine groups, which impede lipase diffusion within the material [3].…”

Section: Resultsmentioning

confidence: 99%

“…The main reason for this sharp increase is the rapid development of agriculture, medicine, and food and packaging industries. In recent years, biodegradable materials offered in different areas have been an increasing research interest due to environmental concerns that are important to every living creature in the world [2][3][4]. Thus, it is crucial to increase the biodegradability of polymeric materials to make a significant contribution to environmental sustainability.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, properties and enzymatic biodegradation behavior of fluorinated poly(ε-caprolactone)s

Açık¹

2020

Express Polym. Lett.

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This study reports on the synthesis of new fluoro functionalized poly(ε-caprolactone)s (F-PCLs) via ring-opening polymerization (ROP) of ε-caprolactone (ε-CL) for different time intervals (24 and 48 h.) by using 2,2,3,3,4,4,5,5-octafluoro-1-pentanol (OFP) as an initiator. The structure and properties of F-PCLs are investigated by Fourier-transform infrared (FT-IR), proton and fluorine 19 nuclear magnetic resonance (1 H-NMR and 19 F-NMR) spectroscopies, gel permeation chromatography (GPC), energy dispersive scanning electron microscopy (SEM-EDS), atomic force microscopy (AFM), water contact angle (WCA) measurements, thermogravimetric analysis (TGA), and differential scanning calorimetry (DSC). Enzymatic degradation experiments are also conducted to study the biodegradation behavior of terminal F-PCLs. Experimental observations obtained by 1 H-NMR, 19 F-NMR and GPC indicate that higher reaction time leads to the formation of higher fluorinated repeating units in F-PCLs. This observation is confirmed by results of SEM-EDS, AFM, WCA, DSC and TGA analyses, respectively. Based on the biodegradability study of F-PCLs in degradation solutions in the presence and absence of porcine pancreatic lipase, it can observed that utilization of more extended time in the ROP reaction medium decreases the biodegradation of resulting polymer. With the obtained features, biodegradable F-PCLs might have potential applications, particularly in the fields of drug delivery and tissue engineering, requiring improved thermal but lower wettability properties.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis, properties and enzymatic biodegradation behavior of fluorinated poly(ε-caprolactone)s

Açık¹

2020

Express Polym. Lett.

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“…However, the obtained results did not confirm this. Also, the expected increase in water contact, due to the increased cross-links, was not found [23]. An increase in the amount of PCL t in the structure of soft segments (at the same time reduction in M c ) from 5 wt % to 15 wt % increased the contact angle, whereas a further increase in the amount of triol reduced it ( Figure 6 and Table S4).…”

Section: Pur (Phb/pcl T )mentioning

confidence: 89%

Predicted Studies of Branched and Cross-Linked Polyurethanes Based on Polyhydroxybutyrate with Polycaprolactone Triol in Soft Segments

et al. 2020

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The number of cross-links in the non-linear polyurethane structure is the basic factor affecting its properties. Selected properties of aliphatic polyurethanes with soft segments made of different amounts of polycaprolactonetriol, polycaprolactonediol and synthetic, telechelic poly([R,S]-3-hydroxybutyrate) were determined. On the basis of changes in polyurethane properties, the correlation between these properties and the construction of soft segments was found. The structure of polyurethanes, their morphology, hydrophilicity, thermal and mechanical properties were examined. These properties were changed linearly up to 15% content of polycaprolactonetriol in soft segments. A further increase in the amount of triol causes that these properties are mainly determined by the high number of cross-links.

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“…Increased interest in biodegradable polyurethanes is arising for their use as tissue scaffolds. Cholic acid facilitated the formation of polyurethane scaffolds with improved biocompatibility, wettability and biodegradability (Acik, Karabulut, Altinkok, & Karatavuk, 2019). Dental composite materials made from polymers have been known to leach cytotoxic unreacted monomers.…”

Section: Biomineralization Phenomenamentioning

confidence: 99%

Application of bile acids for biomedical devices and sensors

2020

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Bile acids (BAs) are physiologically important biosurfactants (Singh, Metrani, Shivanagoudra, Jayaprakasha, & Patil, 2019), which solubilize cholesterol, lipids, proteins, fatty acids, monoglycerides and vitamins in a human body. The strong solubilization power of BAs is related to their amphiphilic chemical structure, which is fundamentally different from the structures of other surfactants. As a general feature, natural BAs molecules have a steroid nucleus with concave hydrophilic and convex hydrophobic sides, containing OH and methyl groups, respectively (Figure 1a and Table 1). The chemical structures of BAs contain a short hydrocarbon chain with COOH or SO 3 H end groups. As a result, dissociated BAs molecules exhibit anionic properties in solutions. Properties of BAs are influenced by the number of OH groups bonded to a steroid core and nature of anionic groups. Modifying the hydroxyl or carboxyl groups of BAs creates a diverse set of BA-based compounds, maintaining some original properties and introducing novel properties as well. The unique distribution of hydrophilic and hydrophobic domains allows these molecules to self-organize into supramolecular assemblies in water. BAs salts form mixed micelles (Figure 1b) with various water-insoluble molecules and facilitate their dissolution. Moreover, BAs allow dispersion of hydrophobic materials, such as carbon nanotubes (Ata, Poon, Syed, Milne, & Zhitomirsky, 2018). The bifacial amphipathic BAs molecules act as compatibilizing agents between the water-insoluble

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Synthesis and characterization of biodegradable polyurethanes made from cholic acid and l-lysine diisocyanate ethyl ester

Cited by 45 publications

References 44 publications

Synthesis, properties and enzymatic biodegradation behavior of fluorinated poly(ε-caprolactone)s

Synthesis, properties and enzymatic biodegradation behavior of fluorinated poly(ε-caprolactone)s

Predicted Studies of Branched and Cross-Linked Polyurethanes Based on Polyhydroxybutyrate with Polycaprolactone Triol in Soft Segments

Application of bile acids for biomedical devices and sensors

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