Synthesis and Characterization of Isosorbide-Based Polyurethanes Exhibiting Low Cytotoxicity Towards HaCaT Human Skin Cells
Abstract
:1. Introduction
2. Experimental Section
2.1. Materials
2.2. Polymer Synthesis
2.2.1. Synthesis of Quasi-Prepolymers
2.2.2. Syntheses of Polyurethanes PU1–PU4
2.3. FTIR Characterization
2.4. NMR Spectroscopy Characterization
2.5. Measurement of the Diffusion Coefficients by NMR Spectroscopy
2.6. Gel Permeation Chromatography/Size-Exclusion Chromatography (GPC/SEC) Characterization
2.7. Thermal Behavior Characterization by Differential Scanning Calorimetry (DSC)
2.8. In Vitro Cytotoxicity Assay
3. Results and Discussion
3.1. Syntheses of the PUs
3.2. FTIR of the PUs
3.3. NMR of the PUs
3.4. Determination of Hydrodynamic Radii of the PUs
3.5. Determination of the Molecular Weights of the PUs
3.5.1. Determination by GPC/SEC
3.5.2. Determination by 13C NMR Spectroscopy
3.6. Thermal Properties of the PUs
3.7. Cytotoxicity Assay
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Monomers | Pre-1 | Pre-2 | Pre-3 |
---|---|---|---|
IPDI | 6 | 6 | - |
HMDI | - | - | 6 |
PPG | 1 | 2 | 1 |
Monomers | Polymers | |||
---|---|---|---|---|
PU1 n (mol)/m (g) | PU2 n (mol)/m (g) | PU3 n (mol)/m (g) | PU4 n (mol)/m (g) | |
IPDI | 0.06/13.33 | 0.06/13.33 | 0.06/13.33 | - |
HMDI | - | - | - | 0.06/15.74 |
PPG | 0.01/10.00 | 0.02/20.00 | 0.01/10.00 | 0.01/10.00 |
D-isosorbide | 0.05/7.30 | 0.05/7.30 | 0.06/8.76 | 0.05/7.30 |
Hard segment content (wt %) a | 67.4 | 50.8 | 68.8 | 69.7 |
Polyurethane | D0 × 1011 (m2/s−1) | rh (nm) |
---|---|---|
PU1 | 7.04 | 1.62 ± 0.04 |
PU2 | 4.49 | 2.65 ± 0.15 |
PU3 | 6.74 | 1.69 ± 0.04 |
PU4 | 4.51 | 2.52 ± 0.19 |
Polyurethane No. | Mwa (Dalton) | Mna (Dalton) | Ð (Mw/Mn) |
---|---|---|---|
PU1 | 15,600 | 10,300 | 1.50 |
PU2 | 19,200 | 12,800 | 1.48 |
PU3 | 9200 | 7200 | 1.27 |
PU4 | 23,500 | 15,100 | 1.55 |
Polyurethane No. | Number of Isosorbide Units a | Number of IPDI Units a | Number of HDMI Units a | Number of PPG Segments | Mn b (Dalton) |
---|---|---|---|---|---|
PU1 | 5 (t) | 6 (t) | - | 1 | 3040 |
PU2 | 5 (t) | 7 (t,b) | - | 2 | 4270 |
PU3 | 6 (t) | 6 | - | 1 | 3210 |
PU4 | 5 (t) | - | 6 (t) | 1 | 3380 |
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Gregorí Valdés, B.S.; Gomes, C.S.B.; Gomes, P.T.; Ascenso, J.R.; Diogo, H.P.; Gonçalves, L.M.; Galhano dos Santos, R.; Ribeiro, H.M.; Bordado, J.C. Synthesis and Characterization of Isosorbide-Based Polyurethanes Exhibiting Low Cytotoxicity Towards HaCaT Human Skin Cells. Polymers 2018, 10, 1170. https://doi.org/10.3390/polym10101170
Gregorí Valdés BS, Gomes CSB, Gomes PT, Ascenso JR, Diogo HP, Gonçalves LM, Galhano dos Santos R, Ribeiro HM, Bordado JC. Synthesis and Characterization of Isosorbide-Based Polyurethanes Exhibiting Low Cytotoxicity Towards HaCaT Human Skin Cells. Polymers. 2018; 10(10):1170. https://doi.org/10.3390/polym10101170
Chicago/Turabian StyleGregorí Valdés, Barbara S., Clara S. B. Gomes, Pedro T. Gomes, José R. Ascenso, Hermínio P. Diogo, Lídia M. Gonçalves, Rui Galhano dos Santos, Helena M. Ribeiro, and João C. Bordado. 2018. "Synthesis and Characterization of Isosorbide-Based Polyurethanes Exhibiting Low Cytotoxicity Towards HaCaT Human Skin Cells" Polymers 10, no. 10: 1170. https://doi.org/10.3390/polym10101170