Sustainable production of polyurethane from castor oil, functionalized with epoxy- and hydroxyl-terminated poly(dimethyl siloxane) for biomedical applications
Source abstract
Abstract
A sustainable method has been employed for the production of a biomedical material in an economical way. Among biomedical polymers, two mostly used polymers are silicones (PDMS) and polyurethanes (PU). PDMS can outperform other polymers due to its biocompatibility and flexibility, but its high cost became a major roadblock for many applications. PU can be produced from a variety of sustainable resources in a cost effective manner. In this work, vegetable oil-based PU is blended with PDMS to produce a biomedical material which can contribute to the economy and environment. In this method, siliconized epoxy-terminated polyurethanes (EPDMS) were prepared from castor oil, 4,4’ methylene-bis-(cyclohexyl isocyanate), glycidol, and hydroxy-terminated poly-(dimethyl siloxane) (HTPDMS). The properties of the resulting products were compared with virgin PU with a NCO/OH ratio of 1.2:1 and epoxy-terminated PU (EPU) with a polyol/diisocyanate/glycidol ratio of 1:3:3. The structural elucidation of PU, EPU, and EPDMS were carried out by FTIR and 1HNMR spectroscopic techniques. The effect of incorporation of siloxane and glycidol on the thermal properties of PU was analyzed by thermogravimetric analysis and differential scanning calorimetry analysis. The improved hydrophobicity of the EPDMS was observed from water contact angle measurements. The surface morphology was examined using atomic force microscopy analysis. In vitro cytotoxicity analysis revealed the cytocompatibility of the EPDMS which makes them suitable for biomedical applications.
Source: openaire · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Polymer composites and self-healing · Carbon dioxide utilization in catalysis · Epoxy Resin Curing Processes
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (26)
Show source-provided references
1. Huang J, Zhang L (2002) Effects of NCO/OH molar ratio on structure and properties of graft-interpenetrating polymer networks from polyurethane and nitrolignin. Polymer 43(8):2287–229410.1016/S0032-3861(02)00028-9 ↗
2. Husić S, Javni I, Petrović ZS (2005) Thermal and mechanical properties of glass reinforced soy-based polyurethane composites. Compos Sci Technol 65(1):19–2510.1016/j.compscitech.2004.05.020 ↗
3. Rozman HD, Tay GS (2008) The effects of NCO/OH ratio on propylene oxide-modified oil palm empty fruit bunch-based polyurethane composites. J Appl Polym Sci 110(6):3647–365410.1002/app.28881 ↗
4. Abdelwahab MA, Misra M, Mohanty AK (2015) Epoxidized pine oil–siloxane: crosslinking kinetic study and thermomechanical properties. J Appl Polym Sci 132(37):42451. https://doi.org/10.1002/app.4245110.1002/app.42451 ↗
5. Hsia HC, Ma CCM, Chen DS (1994) Adhesion properties and phase separation behavior of glycidyl-terminated polyurethanes. Angew Makromol Chem 220(1):133–14910.1002/apmc.1994.052200112 ↗
6. Yeganeh H, Mehdipour-Ataei S, Ghaffari M (2008) Preparation and properties of novel poly (urethane-imide) s via blending of reactive polyimide and epoxy-terminated urethane prepolymers. High Perform Polym 20(2):126–14510.1177/0954008307082743 ↗
7. Yeganeh H, Razavi-Nouri M, Ghaffari M (2008) Synthesis and properties of polybenzoxazine modified polyurethanes as a new type of electrical insulators with improved thermal stability. Polym Eng 48(7):1329–133810.1002/pen.21098 ↗
8. Sahraro M, Yeganeh H, Sorayya M (2016) Guanidine hydrochloride embedded polyurethanes as antimicrobial and absorptive wound dressing membranes with promising cytocompatibility. Mater Sci Eng C 59:1025–103710.1016/j.msec.2015.11.038 ↗
9. Edwards PA (2016) Oxirane (ethylene oxide) polyurethane coatings. U.S. Patent Application No. 15/015, 648
10. Hanoosh WS, Abdelrazaq EM (2009) Polydimethyl siloxane toughened epoxy resins: tensile strength and dynamic mechanical analysis. Malays Polym J 4(2):52–61
11. Hou SS, Chung YP, Chan CK, Kuo PL (2000) Function and performance of silicone copolymer. Part IV. Curing behavior and characterization of epoxy–siloxane copolymers blended with diglycidyl ether of bisphenol-A. Polymer 41(9):3263–327210.1016/S0032-3861(99)00525-X ↗
12. Wang LF, Ji Q, Glass TE, Ward TC, McGrath JE, Muggli M, Burns G, Sorathia U (2000) Synthesis and characterization of organosiloxane modified segmented polyether polyurethanes. Polymer 41(13):5083–509310.1016/S0032-3861(99)00570-4 ↗
13. Byczyński Ł (2014) Thermal degradation studies of poly (urethane–siloxane) thermosets based on co-poly (dimethyl)(methyl, 3-glycidoxypropyl) siloxane and epoxy-terminated urethane oligomer. Thermochim Acta 592:58–6610.1016/j.tca.2014.08.018 ↗
14. Burger C (1996) Silicon in polymer synthesis: with 73 tables. Springer, Heidelberg, p 19
15. Mathew A, Kurmvanshi S, Mohanty S, Nayak SK (2017) Influence of structure-property relationship on the optical, thermal and mechanical properties of castor oil based transparent polyurethane for catheter applications. J Macromol Sci, Part A: Pure Appl Chem 54(11):772–78110.1080/10601325.2017.1332468 ↗
16. Mathew A, Kurmvanshi S, Mohanty S, Nayak SK (2017) Influence of diisocyanate, glycidol and polyol molar ratios on the mechanical and thermal properties of glycidyl terminated biobased polyurethanes. Polym Int. https://doi.org/10.1002/pi.541210.1002/pi.5412 ↗
17. Mathew A, Kurmvanshi S, Mohanty S, Nayak SK (2017) Mechanical behavior of castor oil based advanced polyurethane functionalized with glycidol and siloxanes. JOM. https://doi.org/10.1007/s11837-017-2572-710.1007/s11837-017-2572-7 ↗
18. Prabu AA, Alagar M (2005) Thermal and morphological properties of silicone-polyurethane-epoxy intercrosslinked matrix materials. J Macromol Sci Part A Pure Appl Chem 42(2):175–18810.1081/MA-200046974 ↗
19. Soulas DN, Sanopoulou M, Papadokostaki KG (2013) Hydrophilic modification of silicone elastomer films: thermal, mechanical and theophylline permeability properties. Mater Sci Eng C 33(4):2122–213010.1016/j.msec.2013.01.031 ↗
20. Oktay B, Kayaman-Apohan N (2013) Polydimethylsiloxane (PDMS)-based antibacterial organic–inorganic hybrid coatings. J Coat Technol Res 10(6):785–79810.1007/s11998-013-9505-3 ↗
21. Harani H, Fellahi S, Bakar M (1999) Toughening of epoxy resin using hydroxyl-terminated polyesters. J Appl Polym Sci 71(1):29–3810.1002/(SICI)1097-4628(19990103)71:1<29::AID-APP5>3.0.CO;2-7 ↗
22. Chikhi N, Fellahi S, Bakar M (2002) Modification of epoxy resin using reactive liquid (ATBN) rubber. Eur Polym J 38(2):251–26410.1016/S0014-3057(01)00194-X ↗
23. Yang J, Gao Y, Li J, Ding M, Chen F, Tan H, Fu Q (2013) Synthesis and microphase separated structures of polydimethylsiloxane/polycarbonate-based polyurethanes. RSC Adv. 3(22):8291–829710.1039/c3ra40515j ↗
24. Denchev Z, Alagar M (2006) Synthesis and thermal characterization of phosphorus containing siliconized epoxy resins. Eur Polym J 42(10):2419–242910.1016/j.eurpolymj.2006.06.010 ↗
25. Florea NM, Lungu A, Badica P, Craciun L, Enculescu M, Ghita DG, Ionescu C, Zgirian RG, Iovu H (2015) Novel nanocomposites based on epoxy resin/epoxy-functionalized polydimethylsiloxane reinforced with POSS. Compos B 75:226–23410.1016/j.compositesb.2015.01.043 ↗
26. Yeganeh H, Hojati-Talemi P (2007) Preparation and properties of novel biodegradable polyurethane networks based on castor oil and poly (ethylene glycol). Polym Degrad Stab 92(3):480–48910.1016/j.polymdegradstab.2006.10.011 ↗