Skip to main content

Advertisement

SpringerLink
Log in

Sustainable production of polyurethane from castor oil, functionalized with epoxy- and hydroxyl-terminated poly(dimethyl siloxane) for biomedical applications

  • Biomaterials
  • Published:
Journal of Materials Science Aims and scope Submit manuscript

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Figure 1
Figure 2
Figure 3
Figure 4
Figure 5
Figure 6
Figure 7
Figure 8
Figure 9

Similar content being viewed by others

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):2287–2294

    Article  Google Scholar 

  2. Husić S, Javni I, Petrović ZS (2005) Thermal and mechanical properties of glass reinforced soy-based polyurethane composites. Compos Sci Technol 65(1):19–25

    Article  Google Scholar 

  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):3647–3654

    Article  Google Scholar 

  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.42451

  5. Hsia HC, Ma CCM, Chen DS (1994) Adhesion properties and phase separation behavior of glycidyl-terminated polyurethanes. Angew Makromol Chem 220(1):133–149

    Article  Google Scholar 

  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):126–145

    Article  Google Scholar 

  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):1329–1338

    Article  Google Scholar 

  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 59:1025–1037

    Article  Google Scholar 

  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

    Google Scholar 

  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):3263–3272

    Article  Google Scholar 

  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):5083–5093

    Article  Google Scholar 

  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 592:58–66

    Article  Google Scholar 

  14. Burger C (1996) Silicon in polymer synthesis: with 73 tables. Springer, Heidelberg, p 19

    Google Scholar 

  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):772–781

  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.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/s11837-017-2572-7

    Google Scholar 

  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):175–188

    Article  Google Scholar 

  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):2122–2130

    Article  Google Scholar 

  20. Oktay B, Kayaman-Apohan N (2013) Polydimethylsiloxane (PDMS)-based antibacterial organic–inorganic hybrid coatings. J Coat Technol Res 10(6):785–798

    Article  Google Scholar 

  21. Harani H, Fellahi S, Bakar M (1999) Toughening of epoxy resin using hydroxyl-terminated polyesters. J Appl Polym Sci 71(1):29–38

    Article  Google Scholar 

  22. Chikhi N, Fellahi S, Bakar M (2002) Modification of epoxy resin using reactive liquid (ATBN) rubber. Eur Polym J 38(2):251–264

    Article  Google Scholar 

  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):8291–8297

    Article  Google Scholar 

  24. Denchev Z, Alagar M (2006) Synthesis and thermal characterization of phosphorus containing siliconized epoxy resins. Eur Polym J 42(10):2419–2429

    Article  Google Scholar 

  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 75:226–234

    Article  Google Scholar 

  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):480–489

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Central Institute of Plastics Engineering & Technology, Guindy, Chennai, 600032, India

    Aiswarea Mathew & Sanjay K. Nayak

  2. Laboratory for Advanced Research in Polymeric Materials (LARPM), Central Institute of Plastics Engineering and Technology, Bhubaneswar, 751024, India

    Surendra Kurmvanshi, Smita Mohanty & Sanjay K. Nayak

Authors
  1. Aiswarea Mathew
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Surendra Kurmvanshi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Smita Mohanty
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Sanjay K. Nayak
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Aiswarea Mathew.

Ethics declarations

Conflict of interest

The authors declare that they have no conflict of interest.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Mathew, A., Kurmvanshi, S., Mohanty, S. et al. Sustainable production of polyurethane from castor oil, functionalized with epoxy- and hydroxyl-terminated poly(dimethyl siloxane) for biomedical applications. J Mater Sci 53, 3119–3130 (2018). https://doi.org/10.1007/s10853-017-1757-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10853-017-1757-3

Keywords

Search

Navigation