Influence of e-Beam Irradiation on the Physicochemical Properties of Poly(polyol Succinate-co-Butylene Succinate) Ester Elastomers
Abstract
:1. Introduction
2. Materials and Methods
2.1. Synthesis of Elastomers and Sample Preparation
2.2. Irradiation
2.3. Experimental Methods
2.3.1. Nuclear Magnetic Resonance Spectroscopy (NMR)
2.3.2. Fourier Transform Infrared Spectroscopy (FTIR)
2.3.3. Differential Scanning Calorimetry (DSC)
2.3.4. Dynamic Thermomechanical Analysis (DMTA)
2.3.5. Mechanical Properties
2.3.6. Water Contact Angle
2.3.7. Cross-Linking Density
2.3.8. Hardness
2.3.9. Gel Permeation Chromatography
3. Results and Discussion
3.1. Nuclear Magnetic Resonance Spectroscopy (NMR)
3.2. Fourier Transform Infrared Spectroscopy (FTIR)
3.3. Thermal Properties: Differential Scanning Calorimetry (DSC)
3.4. Dynamic Thermomechanical Analysis (DMTA)
3.5. Mechanical Properties
3.6. Cross-Linking Density
3.7. Water Contact Angle
4. Conclusions
Author Contributions
Funding
Conflicts of Interest
References
- Rouif, S. Radiation cross-linked polymers: Recent developments and new applications. Nucl. Instrum. Methods Phys. Res. Sect. B Beam Interact. Mater. Atoms 2005, 236, 68–72. [Google Scholar] [CrossRef]
- Drobny, J.G. Ionizing Radiation and Polymers: Principles, Technology, and Applications; William Andrew: Norwich, NY, USA, 2012. [Google Scholar]
- Zhu, G.; Xu, Q.; Qin, R.; Yan, H.; Liang, G. Effect of γ-radiation on crystallization of polycaprolactone. Radiat. Phys. Chem. 2005, 74, 42–50. [Google Scholar] [CrossRef]
- Changyu, H.; Xianghai, R.; Kunyu, Z.; Yugang, Z.; Lisong, D. Thermal and Mechanical Properties of Poly(e-caprolactone) Crosslinked with g Radiation in the Presence of Triallyl Isocyanurate. J. Appl. Polym. Sci. 2006, 103, 2676–2681. [Google Scholar]
- Zhu, G.; Liang, G.; Xu, Q.; Yu, Q. Shape-memory effects of radiation crosslinked Poly(ε-caprolactone). J. Appl. Polym. Sci. 2003, 90, 1589–1595. [Google Scholar] [CrossRef]
- Huang, Y.; Gohs, U.; Müller, M.T.; Zschech, C.; Wiessner, S. Electron beam treatment of polylactide at elevated temperature in nitrogen atmosphere. Radiat. Phys. Chem. 2019, 159, 166–173. [Google Scholar] [CrossRef]
- Quynh, T.M.; Mai, H.H.; Lan, P.N. Properties of Radiation-Induced Crosslinking Stereocomplexes Derived From Poly(L-Lactide) and Different Poly(D-Lactide). Radiat. Phys. Chem. 2013, 83, 105–110. [Google Scholar] [CrossRef]
- Nagasawa, N.; Kasai, N.; Yagi, T.; Yoshii, F.; Tamada, M. Radiation-induced crosslinking and post-processing of poly(l-lactic acid) composite. Radiat. Phys. Chem. 2011, 80, 145–148. [Google Scholar] [CrossRef]
- Jung, C.H.; Hwang, I.T.; Jung, C.H.; Choi, J.H. Preparation of flexible PLA/PEG-POSS nanocomposites by melt blending and radiation crosslinking. Radiat. Phys. Chem. 2014, 102, 23–28. [Google Scholar] [CrossRef]
- Suhartini, M.; Mitomo, H.; Nagasawa, N.; Yoshii, F.; Kume, T. Radiation crosslinking of poly(butylene succinate) in the presence of low concentrations of trimethallyl isocyanurate and its properties. J. Appl. Polym. Sci. 2003, 88, 2238–2246. [Google Scholar] [CrossRef]
- Manas, D.; Mizera, A.; Navratil, M.; Manas, M.; Ovsik, M.; Sehnalek, S.; Stoklasek, P. The electrical, mechanical and surface properties of thermoplastic polyester elastomer modified by electron beta radiation. Polymers 2018, 10, 1057. [Google Scholar] [CrossRef] [Green Version]
- Mizera, A.; Manas, M.; Manas, D.; Stoklasek, P.; Bednarik, M.; Hylova, L. Mechanical properties change of thermoplastic elastomer after using of different dosage of irradiation by beta rays. MATEC Web Conf. 2016, 76, 8–11. [Google Scholar] [CrossRef] [Green Version]
- Zhu, S.; Shi, M.; Tian, M.; Qu, L.; Chen, G. Effects of irradiation on polyethyleneterephthalate(PET) fibers impregnated with sensitizer. J. Text. Inst. 2018, 109, 294–299. [Google Scholar] [CrossRef]
- Zhu, S.; Shi, M.; Tian, M.; Xiaoqingguo, L. Burning behavior of irradiated PET flame-retardant fabrics impregnated with sensitizer. Mater. Lett. 2015, 160, 58–60. [Google Scholar] [CrossRef]
- Malinowski, R. Application of the electron radiation and triallyl isocyanurate for production of aliphatic-aromatic co-polyester of modified properties. Int. J. Adv. Manuf. Technol. 2016, 87, 3307–3314. [Google Scholar] [CrossRef]
- Hooshangi, Z.; Feghhi, S.A.H.; Sheikh, N. The effect of electron-beam irradiation and halogen-free flame retardants on properties of poly butylene terephthalate. Radiat. Phys. Chem. 2015, 108, 54–59. [Google Scholar] [CrossRef]
- Mizera, A.; Manas, M.; Manas, D.; Holik, Z.; Stanek, M.; Navratil, J.; Bednarik, M. Temperature stability of Modified PBT by Radiation Cross-Linking. In Advanced Materials Research; Trans Tech Publications Ltd: Stafa-Zurich, Switzerland, 2014; Volume 1025, pp. 256–260. [Google Scholar]
- Ashby, R.D.; Cromwick, A.M.; Foglia, T.A. Radiation crosslinking of a bacterial medium-chain-length poly(hydroxyalkanoate) elastomer from tallow. Int. J. Biol. Macromol. 1998, 23, 61–72. [Google Scholar] [CrossRef]
- Bergmann, A.; Teßmar, J.; Owen, A. Influence of electron irradiation on the crystallisation, molecular weight and mechanical properties of poly-(R)-3-hydroxybutyrate. J. Mater. Sci. 2007, 42, 3732–3738. [Google Scholar] [CrossRef]
- Rai, R.; Tallawi, M.; Roether, J.A.; Detsch, R.; Barbani, N.; Rosellini, E.; Kaschta, J.; Schubert, D.W.; Boccaccini, A.R. Sterilization effects on the physical properties and cytotoxicity of poly(glycerol sebacate). Mater. Lett. 2013, 105, 32–35. [Google Scholar] [CrossRef]
- Bruggeman, J.P.; Bettinger, C.J.; Nijst, C.L.E.; Kohane, D.S.; Langer, R. Biodegradable xylitol-based polymers. Adv. Mater. 2008, 20, 1922–1927. [Google Scholar] [CrossRef]
- Bruggeman, J.P.; Bettinger, C.J.; Langer, R. Biodegradable xylitol-based elastomers: In vivo behavior and biocompatibility. J. Biomed. Mater. Res. Part A 2010, 95, 92–104. [Google Scholar] [CrossRef] [Green Version]
- Dasgupta, Q.; Chatterjee, K.; Madras, G. Combinatorial approach to develop tailored biodegradable poly(xylitol dicarboxylate) polyesters. Biomacromolecules 2014, 15, 4302–4313. [Google Scholar] [CrossRef] [PubMed]
- Bruggeman, J.P.; De Bruin, B.J.; Bettinger, C.J.; Langer, R. Biodegradable poly(polyol sebacate) polymers. Biomaterials 2008, 29, 4726–4735. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Ning, Z.Y.; Zhang, Q.S.; Wu, Q.P.; Li, Y.Z.; Ma, D.X.; Chen, J.Z. Efficient synthesis of hydroxyl functioned polyesters from natural polyols and sebacic acid. Chinese Chem. Lett. 2011, 22, 635–638. [Google Scholar] [CrossRef]
- Kavimani, V.; Jaisankar, V. Synthesis and Characterisation of Sorbitol Based Copolyesters for Biomedical Applications. J. Phys. Sci. Appl. 2014, 4, 507–515. [Google Scholar]
- Hu, J.; Gao, W.; Kulshrestha, A.; Gross, R.A. “Sweet polyesters”: Lipase-catalyzed condensation-polymerizations of alditols. ACS Symp. Ser. 2006, 999, 275–284. [Google Scholar]
- Kumar, A.; Kulshrestha, A.S.; Gao, W.; Gross, R.A. Versatile route to polyol polyesters by lipase catalysis. Macromolecules 2003, 36, 8219–8221. [Google Scholar] [CrossRef]
- Piątek-Hnat, M.; Bomba, K.; Pęksiński, J. Synthesis and selected properties of ester elastomer containing sorbitol. Appl. Sci. 2020, 10, 1628. [Google Scholar] [CrossRef] [Green Version]
- Piątek-Hnat, M.; Bomba, K. The influence of of cross-linking process on the physicochemical properties of new copolyesters containing xylitol. Mater. Today Commun. 2020, 22, 100734. [Google Scholar] [CrossRef]
- Piatek-Hnat, M.; Bomba, K.; Pęksiński, J. Structure and Properties of Biodegradable Poly (Xylitol Sebacate-Co-Butylene Sebacate) Copolyester. Molecules 2020, 25, 1541. [Google Scholar] [CrossRef] [Green Version]
- Piątek-Hnat, M.; Bomba, K.; Pęksiński, J.; Kozłowska, A.; Sośnicki, J.G.; Idzik, T.J. Effect of E-Beam Irradiation on Thermal and Mechanical Properties of Ester Elastomers Containing Multifunctional Alcohols. Polymers 2020, 12, 1043. [Google Scholar] [CrossRef]
- ISO 111 37 1:2006 Sterilization of health care products—Radiation—Part 1: Requirements for development, validation and routine control of a sterilization process for medical devices; American National Standards Institute (ANSI): Washington, DC, USA, 2007.
- PN EN ISO 527:2019 Plastics—Determination of tensile properties; Polish Committee for Standardization: Warsaw, Poland, 2019.
- Flory, P.J. Principles of Polymer Chemistry; Cornell University Press: Ithaca, NY, USA, 1953. [Google Scholar]
- Chen, Q.Z.; Bismarck, A.; Hansen, U.; Junaid, S.; Tran, M.Q.; Harding, S.E.; Ali, N.N.; Boccaccini, A.R. Characterisation of a soft elastomer poly(glycerol sebacate) designed to match the mechanical properties of myocardial tissue. Biomaterials 2008, 29, 47–57. [Google Scholar] [CrossRef] [PubMed]
Material/Dose | Molar Composition (mol) | H ShA | CA | Prepolymer | Molar Composition by 1H NMR (mol) | Mw (g/mol) | PDI | |||
---|---|---|---|---|---|---|---|---|---|---|
- | SuA | GL | BG | - | - | GL | BG | - | ||
PGBSu_0 kGy | 2 | 1 | 1 | 38.8 +/− 4.95 | 68.1 +/− 2.04 | PGBSu | 0.32 | 1.00 | 35,000 | 1.3 |
PGBSu_50 kGy | 45.8 +/− 4.84 | 74.1 +/− 1.35 | ||||||||
PGBSu_100 kGy | 37.7 +/− 3.34 | 84.6 +/− 1.15 | ||||||||
PGBSu_150 kGy | 38.9 +/− 2.50 | 111.3 +/− 1.16 | ||||||||
- | SuA | ER | BG | ER | BG | - | ||||
PEBSu_0 kGy | 2 | 1 | 1 | 32.7 +/− 2.77 | 64 +/− 10.15 | PEBSu | 0.20 | 1.00 | 32,000 | 1.6 |
PEBSu _50 kGy | 43.08 +/− 4.01 | 76.7 +/− 8.33 | ||||||||
PEBSu_100 kGy | 42.8 +/− 5.27 | 86.4 +/− 9.15 | ||||||||
PEBSu_150 kGy | 37.08 +/− 3.45 | 100.8 +/− 4.20 | ||||||||
- | SuA | XL | BG | - | XL | BG | - | |||
PXBSu_0 kGy | 2 | 1 | 1 | 30.2 +/− 6.77 | 49.9 +/− 3.05 | PXBSu | 0.25 | 1.00 | 28,000 | 2.0 |
PXBSu_50 kGy | 41.33 +/− 3.73 | 88.8 +/− 2.05 | ||||||||
PXBSu_100 kGy | 48.25 +/− 2.42 | 96.8 +/− 2.14 | ||||||||
PXBSu_150 kGy | 41.25 +/− 3.08 | 112.9 +/− 5.12 | ||||||||
- | SuA | SB | BG | - | - | SB | BG | - | ||
PSBSu_0 kGy | 2 | 1 | 1 | 66.8 +/− 2.25 | 48.7 +/− 2.43 | PSBSu | 0.22 | 1.00 | 24,000 | 2.3 |
PSBSu_50 kGy | 59.27 +/− 6.38 | 71.1 +/− 3.24 | ||||||||
PSBSu_100 kGy | 71.08 +/− 6.10 | 89.7 +/− 5.11 | ||||||||
PSBSu _150 kGy | 65.83 +/− 1.34 | 105.4 +/− 4.23 |
Material/Dose | Molar Composition (mol) | E_50% (MPa) | E_100% (MPa) | σr (MPa) | εr (%) | n (mol/m3) | ||
---|---|---|---|---|---|---|---|---|
- | SuA | GL | BG | - | ||||
PGBSu_0 kGy | 2 | 1 | 1 | 0.07 +/− 0.01 | 0.06 +/− 0.02 | 0.40 +/− 0.03 | 501 +/− 35.09 | 19.36 +/− 8.66 |
PGBSu_50 kGy | 0.12 +/− 0.1 | 0.10 +/− 0.01 | 0.21+/− 0.03 | 414 +/− 12.01 | 16.20 +/− 12.32 | |||
PGBSu_100 kGy | 0.18 +/− 0.03 | 0.16 +/− 0.03 | 0.31 +/− 0.05 | 357 +/− 33.09 | 12.34 +/− 17.21 | |||
PGBSu_150 kGy | 0.19 +/− 0.02 | 0.17 +/− 0.12 | 0.38 +/− 0.06 | 312 +/− 32.58 | 13.20 +/− 21.81 | |||
- | SuA | ER | BG | - | ||||
PEBSu_0 kGy | 2 | 1 | 1 | 0.204 +/−0.04 | 0.190+/−0.04 | 0.509+/−0.12 | 239 +/− 55.44 | 66.34 +/−25.22 |
PEBSu_50 kGy | 0.272 +/− 0.11 | 0.278 +/− 0.11 | 0.733 +/− 0.19 | 324 +/− 17.81 | 165.21 +/− 53.71 | |||
PEBSu_100 kGy | 0.267 +/− 0.06 | 0.279 +/− 0.06 | 0.663 +/− 0.09 | 215 +/− 68.17 | 124.93 +/− 33.59 | |||
PEBSu_150 kGy | 0.248 +/− 0.05 | 0.261 +/− 0.06 | 0.669 +/− 0.07 | 234 +/− 79.12 | 71.29 +/− 16.88 | |||
- | SuA | XL | BG | - | ||||
PXBSu_0 kGy | 2 | 1 | 1 | 0.215 +/− 0.06 | 0.175 +/− 0.05 | 0.545+/− 0.06 | 259 +/− 31.64 | 251.78 +/− 37.32 |
PXBSu_50 kGy | 0.220 +/− 0.05 | 0.184 +/− 0.05 | 0.66+/− 0.10 | 263 +/− 27.75 | 254.83 +/− 35.24 | |||
PXBSu_100 kGy | 0.212 +/− 0.03 | 0.177 +/− 0.03 | 0.641 +/− 0.06 | 275 +/− 21.91 | 287.44 +/− 31.54 | |||
PXBSu_150 kGy | 0.196 +/− 0.07 | 0.155 +/− 0.07 | 0.694 +/− 0.12 | 301 +/− 66.80 | 287.51 +/− 36.77 | |||
- | SuA | SB | BG | - | ||||
PSBSu_0 kGy | 2 | 1 | 1 | 0.503 +/− 0.06 | 0.396 +/− 0.05 | 0.93 +/− 0.41 | 205 +/− 13.03 | 450.04 +/− 42.19 |
PSBSu_50 kGy | 0.428 +/− 0.11 | 0.357 +/− 0.10 | 0.90 +/− 0.09 | 208 +/− 30.34 | 414.22 +/− 36.68 | |||
PSBSu_100 kGy | 0.385 +/− 0.05 | 0.322 +/− 0.05 | 0.88 +/− 0.10 | 215 +/− 13.22 | 432.16 +/− 47.28 | |||
PSBSu _150 kGy | 0.426 +/− 0.07 | 0.355 +/− 0.05 | 0.95 +/− 0.12 | 209 +/− 13.70 | 399.48 +/− 40.82 |
Material/Dose | Tg | ΔCp | Tm | ΔHm |
---|---|---|---|---|
(°C) | (J/g°C) | (°C) | (J/g) | |
PGBSu | ||||
PGBSu_0 kGy | −25.5 | 0.749 | 48.9 | 2.83 |
PGBSu_50 kGy | −21.9 | 0.626 | 51.3 | 12.14 |
PGBSu_100 kGy | −22.1 | 0.635 | 51.2 | 11.79 |
PGBSu_150 kGy | −22.9 | 0.719 | 50.9 | 12.85 |
PEBSu | ||||
PEBSu_0 kGy | −18.9 | 0.731 | 53.8 | 3.19 |
PEBSu_50 kGy | −14.7 | 0.708 | 55.4 | 5.24 |
PEBSu_100 kGy | −14.8 | 0.701 | 55.8 | 4.87 |
PEBSu_150 kGy | −15.1 | 0.734 | 55.1 | 5.52 |
PXBSu | ||||
PXBSu_0 kGy | −13.7 | 0.763 | - | - |
PXBSu_50 kGy | −8.2 | 0.799 | - | - |
PXBSu_100 kGy | −7.4 | 0.759 | - | - |
PXBSu_150 kGy | −4.5 | 0.729 | - | - |
PSBSu | ||||
PSBSu_0 kGy | −2.6 | 0.686 | - | - |
PSBSu_50 kGy | −0.4 | 0.764 | - | - |
PSBSu_100 kGy | 1.9 | 0.729 | - | - |
PSBSu_150 kGy | −0.3 | 0.769 | - | - |
© 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
Share and Cite
Piątek-Hnat, M.; Bomba, K.; Pęksiński, J.; Kozłowska, A.; Sośnicki, J.G.; Idzik, T.J.; Piwowarska, D.; Janik, J. Influence of e-Beam Irradiation on the Physicochemical Properties of Poly(polyol Succinate-co-Butylene Succinate) Ester Elastomers. Materials 2020, 13, 3196. https://doi.org/10.3390/ma13143196
Piątek-Hnat M, Bomba K, Pęksiński J, Kozłowska A, Sośnicki JG, Idzik TJ, Piwowarska D, Janik J. Influence of e-Beam Irradiation on the Physicochemical Properties of Poly(polyol Succinate-co-Butylene Succinate) Ester Elastomers. Materials. 2020; 13(14):3196. https://doi.org/10.3390/ma13143196
Chicago/Turabian StylePiątek-Hnat, Marta, Kuba Bomba, Jakub Pęksiński, Agnieszka Kozłowska, Jacek G. Sośnicki, Tomasz J. Idzik, Danuta Piwowarska, and Jolanta Janik. 2020. "Influence of e-Beam Irradiation on the Physicochemical Properties of Poly(polyol Succinate-co-Butylene Succinate) Ester Elastomers" Materials 13, no. 14: 3196. https://doi.org/10.3390/ma13143196