2024 (2) 5

https://doi.org/10.15407/polymerj.46.02.119

POLYURETHANES BASED ON MODIFIED HEMP OIL

Liudmyla Robota^* (ORCID: 0000-0001-5463-4816), Olena Akhranovych^** (ORCID: 0000-0002-5112-2329), Oleksandra Brykova (ORCID: 0000-0003-1652-9323), Oleksii Honchar (ORCID: 0000-0001-8356-9283), Yurii Saveliev (ORCID: 0000-0003-3356-9087)
Institute of Macromolecular Chemistry of the NAS of Ukraine, 48 Kharkivske Highway, Kyiv 02155, Ukraine,
*e-mail: L49robota@gmail.com,
**e-mail: elena_akh@ukr.net

Polym. J., 2024, 46, no. 2: 119-126.

Section: Polymer synthesis.

Language: Ukrainian.

Abstract:

Polyurethane materials of different composition and structure were prepared using diisocyanates of different nature, native and functionalized vegetable oils. Hydroxylated derivatives of hemp oil, namely lineoyl diethanolamide (LDEA), whose structure was confirmed by IR spectroscopic studies, were obtained by amidation of hemp oil with diethanolamine. LDEA is used as an isocyanate extender of functionalized castor oil with the formation of film-forming materials (content of components of naturally renewable origin up to 70%). A decrease in the strength characteristics of synthesized polyurethanes from 31 to 18.8 MPa and an increase in their elasticity is due to the presence of the fatty acid fragment in LDEA. The content of LDEA (internal plasticizer) can be a factor in regulating the level of strength-elastic properties, and its presence in the composition of polyurethane contributes to increased resistance in an acidic environment. Analogues of the specified material were prepared using diethanolamine as an extender. Aggregatively stable (more than 12 months) film-forming aqueous polyurethane dispersions containing LDEA (10 and 20 wt.% in the composition of oligomeric diols) were prepared. The size of their dispersed phase is 460–328 nm, which decreases with increasing LDEA content. The breaking strength indicators of film materials obtained based on IPU increase with the increase of LDEA content from 4.76 MPa to 5.86 MPa, respectively, and the relative elongation decreases from 469 to 430% with the content of LDEA 6.8 and 13.5 wt.%, respectively. Since the weight loss in alkaline and acidic environments decreases with increasing content of lineoyl diethanolamide in the dispersion, its presence in the composition of anionic polyurethanes is a factor in increasing their stability in aggressive environments.

Key words: hemp oil, castor oil, amidation, lineoyl diethanolamide, polyurethanes, anionic aqueous dispersion.

REFERENCES

1. Desroches M., Escouvois M., Auvergne R. et al. From vegetable oils to polyurethanes: synthetic routes to polyols and main industrial products. Polym.Rev., 2012, 52: 38–79. doi.org/10.1080/15583724.2011.640443.
2. Sharmin E., Zafar F., Akram D. et al. Recent advances in vegetable oils based environment friendly coatings: a review Ind. Crops Prod., 2015, 76: 215–229. https://doi.org/10.1016/j.indcrop.2015.06.022.
3. Paraskar P. M., Prabhudesai M. S., Hatkar V. M., Kulkarni R. D. Vegetable oil based polyurethane coatings – A sustainable approach: A review. Progress in Organic Coatings, 2021, 156: 106267–106285. https://doi.org/10.1016/j.porgcoat.2021.106267.
4. Papageorgiou George Z. Thinking Green: Sustainable Polymers from Renewable Resources. Polymers, 2018, 10: 952-957. https://doi.org/10.3390/polym10090952.
5. Liang H., Feng Y., Lu J., Liu L., Yang Z., Luo Y., et al. Bio-based cationic waterborne polyurethanes dispersions prepared from different vegetable oils. Industrial Crops and Products, 2018, 122: 448–455. https://doi.org/10.1016/j.indcrop.2018.06.006.
6. Gultekin G., Atalay-Oral C., Erkal S., Sahin F., Karastova D., Tantekin-Ersolmaz S. B., Guner F. S. Fatty acid-based polyurethane films for wound dressing applications. Journal of Materials Science: Materials in Medicine, 2009, 20: 421–431. https://doi.org/ 10.1007/s10856-008-3572-5.
7. Paraskar P. M., Kulkarni R. D. Synthesis of isostearic acid/dimer fatty acid-based polyesteramide polyol for the development of green polyurethane coatings. Journal of Polymers and the Environment, 2021, 29, 54–70. https://doi.org/10.1007/s10924-020-01849-x.
8. Kovács, E., Turczel, G., Szabó, L., Varga, R., Tóth, I., Anastas, P. T., Tuba, R. Synthesis of 1, 6-Hexandiol, polyurethane monomer derivatives via isomerization metathesis of methyl linolenate. ACS Sustainable Chemistry & Engineering, 2017, 5(12), 11215–11220. https://doi.org/10.1021/acssuschemeng.7b03309.
9. Gómez-Jiménez-Aberasturi O., Ochoa‐Gómez J. R. New approaches to producing polyols from biomass. Journal of Chemical Technology & Biotechnology, 2017, 92(4): 705–711. https://doi.org/10.1002/jctb.5149.
10. Zuber M., Shah S.A.A., Jamil T. et al. Performance behavior of modified cellulosic fabrics using polyurethane acrylate copolymer Int. J. Biol. Macromol., 2014, 67: 254–259. doi.org/10.1016/j.ijbiomac.2014.03.021.
11. Wang Y., Deng L., Fan Y. Preparation of soy-based adhesive enhanced by waterborne polyurethane: optimization by response surface methodology Hindawi Adv. Mater. Sci. Eng., 2018(1): 9253670. https://doi.org/10.1155/2018/9253670.
12. Xia Y., Larock R. C. Vegetable oil-based polymeric materials: Synthesis, properties, and applications Green Chemistry, 2010, 12: 1893−1909. https://doi.org/10.1039/C0GC00264J.
13. Tsujimoto T., Uyama H., Kobayashi S. et al. Green Nanocomposites from Renewable Plant Oils and Polyhedral Oligomeric Silsesquioxanes. Metals, 2015, 5: 1136–1147.
14. Samadzadeh M., Boura S. H., Peikari M. et al. Tung oil: an autonomous repairing agent for self-healing epoxy coatings Progress in Organic Coatings., 2011, 7(4): 383–387. https://doi.org/10.1016/j.porgcoat.2010.08.017.
15. Moreno M., Lampard C., Williams N., Lago E., Emmett S., Goikoetxea, M., Barandiaran M. J. Eco-paints from bio-based fatty acid derivative latexes. Progress in Organic Coatings, 2015, 81: 101–106. https://doi.org/10.1016/j.porgcoat.2015.01.001.
16. Adekunle K.F. Review of Vegetable Oil-Based Polymers: Synthesis and Applications Journal of Polymer Chemistry, 2015, 5: 34–40. http://doi.org/10.4236/ojpchem.2015.53004.
17. Williams C. K., Hillmyer M. A. Polymers from renewable resources: a perspective for a special issue of polymer reviews. Polymer reviews, 2008, 48(1): 1–10. https://doi.org/10.1080/15583720701834133.
18. Djordjevic I., Choudhury N. R., Dutta N. K., Kumar, S. Synthesis and characterization of novel citric acid-based polyester elastomers. Polymer, 2009, 50(7): 1682–1691. https://doi.org/10.1016/j.polymer.2009.01.045.
19. Guner F. S., Yagci Y., Erciyes A. T. Polymers from triglyceride oils Progress in Polymer Science, 2006, 31: 633−670. https://doi.org/10.1016/j.progpolymsci.2006.07.001.
20. Sharma V., Kundu P. P. Addition polymers from natural oils—A review. Progress in polymer science, 2006 31(11): 983–1008. https://doi.org/10.1016/j.progpolymsci.2006.09.003.
21. Pat. US 9,216,940 B2 USA C08G 18/36 (2013.01) Polyol synthesis from fatty acids and oils Curtis J.M., Liu G.G., Omonov T., Kharraz E. Publ. 22.12.2015.
22. Silverstein R.M., Webster F.X., Kiemkle D.J. Spectrometric identification of organic compounds. New York: John Wiley & Sons, 2005: 512. ISBN 0-471-39362-2.