Use of microwave aminolytic destruction products of polyethylene terephthalate in rubbers based on chloroprene rubber
https://doi.org/10.20914/2310-1202-2021-3-182-190
Abstract
In this paper, a method of recycling polyethylene terephthalate (PET) waste with a mixture of amino-alcohols - mo-noethanolamine and triethanolamine, taken in a certain ratio, is considered. As a result, of the degradation reaction, terephthalic acid diamide (N, N'-bis (2-hydroxyethyl) terephthalamide) is formed. To accelerate the destruction process, microwave radiation of various powers was used. The optimal conditions for PET decomposition have been determined: the time and power of microwave radiation with the yield of the target product (terephthalic acid diamide) 80-85%. The destruction process was carried out without the use of catalysts and at atmospheric pressure. The aminolytic degradation product of PET (terephthalic acid diamide) was used as a monomer in the polycondensation reaction to obtain a new oligomer. The obtained oligomer and the PET degradation product were investigated as new components in rubbers based on three grades of chloroprene rubber with different crystallization rates. The accelerating effect of new ingredients on the process of sulfur vulcanization of rubbers based on chloroprene rubber has been revealed. It has been demonstrated that the introduction of an oligomer based on a PET degradation product reduces the viscosity of rubber compounds by 25-35%. The effect on the elastic-strength properties of the obtained rubbers be-fore and after thermal aging is considered. It is shown that terephthalic acid diamide and oligomer based on it have an effect on the elastic-strength properties of the studied rubbers before and after thermal aging. In the future, a more detailed consideration of the effect of the new obtained ingredients in rubbers based on polar rubbers and thermoplastics on the physicochemical and physicomechanical parameters is planned.
About the Authors
M. A. VokhmyaninRussian Federation
postgraduate student, chemistry and technology of polymer processing department, Moscow str., 36. Kirov, 610020, Russia
R. L. Vesnin
Cand. Sci. (Engin.), head of the department of chemistry and technology of polymer processing, Moscow str., 36. Kirov, 610020, Russia
A. D. Kraev
postgraduate student, chemistry and technology of polymer processing department, Moscow str., 36. Kirov, 610020, Russia
V. A. Sedykh
Cand. Sci. (Engin.), chemistry and chemical technology of organic compounds and polymer processing department, Revolution Av., 19, Voronezh, 394036, Russia
References
1. Yun X., Xin-Yi Y., Dun-Hong G., Yong-Bo D. et al. Preparation and characterization of waterborne alkyd-amino baking coatings based on waste polyethylene terephthalate. Royal Society open science. 2020. vol. 7. no. 1. pp. 191447. doi: 10.1098/rsos.191447
2. Vesnin R.L., Alalykin A.A., Vokhmyanin M.A. Technology of recycling polyethylene terephthalate waste with the production of terephthalic acid amide. Bulletin of higher educational institutions. Series "Chemistry and Chemical Technology". 2020. no. 2. pp. 99–104. (in Russian).
3. Al-Sabagh A.M., Yehia F.Z., Eshaq G., Rabie A.M. et al. Greener routes for recycling of polyethylene terephthalate. Egyptian Journal of Petroleum. 2016. vol. 25. no. 1. pp. 53–64. doi: 10.1016/j.ejpe.2015.03.001
4. Jamdar V., Kathalewar M., Sabnis A. Depolymeriza-tion study of PET waste using aminoethylethanolamine and recycled product application as polyesteramide synthesis. Journal of Polymers and the Environment. 2018. vol. 26. no. 6. pp. 2601–2618. doi: 10.1007/s10924-017-1149-4
5. Loginova A.V., Tishin D.E., Kasyanova O.V. Modern methods of recycled polyethylene terephthalate processing and areas of application of the obtained materials. Globalization of environmental problems: past, present and future. 2017. pp. 221–221. (in Russian).
6. Woortman, A.J.J.; Loos, K.; Popovic, I.G. High Performance Alkyd Resins Synthesized from Postconsumer PET Bottles. RSC Advances. 2015. vol. 5. no. 76. pp. 62273-62283. doi: 10.1039/C5RA11777A
7. Scremin D.M., Miyazaki D.Y., Lunelli C.E., Silva S.A. et al. PET recycling by alcoholysis using a new heterogeneous catalyst: study and its use in polyurethane adhesives preparation. Macromolecular Symposia. 2019. vol. 383. no. 1. pp. 1800027. doi: 10.1002/masy.201800027
8. Zhou L., Lu X., Ju Z., Liu B. et al. Alcoholysis of polyethylene terephthalate to produce dioctyl terephthalate using choline chloride-based deep eutectic solvents as efficient catalysts. Green Chemistry. 2019. vol. 21. no. 4. pp. 897–906.
9. Zhou X., Wang C., Fang C., Yu R. et al. Structure and thermal properties of various alcoholysis products from waste poly (ethylene terephthalate). Waste management. 2019. vol. 85. pp. 164–174. doi: 10.1016/j.wasman.2018.12.032
10. Li Y., Li M., Lu J., Li X. et al. Decoloration of waste PET alcoholysis liquid by an electrochemical method. Water Science and Technology. 2018. vol. 77. no. 10. pp. 2463–2473. doi: 10.2166/wst.2018.191
11. Linlin D.Y.M.Y.Z. Study on the chemical recycling technologies on hydrolysis and alcoholysis of PET waste [J]. Plastics Manufacture. 2011. vol. 7.
12. Teotia M., Tarannum N., Soni R.K. Depolymerization of PET waste to potentially applicable aromatic amides: Their characterization and DFT study. Journal of Applied Polymer Science. 2017. no. 31. pp. 45153.
13. Panfilov D.A., Dvorko I.M. Chemical destruction of secondary polyethylene terephthalate as a method of obtaining resin-modifiers of polymers. Scientific Almanac. 2018. no. 3-2. pp. 183-186. (in Russian).
14. Tawfik M.E., Eskander S.B. Chemical Recycling of Poly(Ethylene Terephthalate) Waste Using Ethanolamine. Sorting of the End Products. Polymer Degradation and Stability. 2010. vol. 95. no. 2. pp. 187-194.
15. Parab Y.S., Shukla S.R. Novel synthesis, characterization of N1, N1, N4, N4-tetrakis (2-hydroxyethyl) terephthalamide (THETA) and terephthalic Acid (TPA) by depolymerization of PET bottle waste using diethanolamine. Journal of Macromolecular Science, Part A. 2013. vol. 50. no. 11. pp. 1149-1156. doi: 10.1080/10601325.2013.830004
16. Aguado A., Mart?nez L., Becerra L., Arieta-Araunabe?a M. et al. Chemical depolymerisation of PET complex waste: hydrolysis vs. glycolysis. Journal of Material Cycles and Waste Management. 2014. vol. 16. no. 2. pp. 201–210. doi: 10.1007/s10163-013-0177-y
17. Malik N., Kumar P., Shrivastava S., Ghosh S.B. An overview on PET waste recycling for application in packaging. International Journal of Plastics Technology. 2017. vol. 21. no. 1. pp. 1–24. doi: 10.1007/s12588-016-9164-1
18. Sinha V., Patel M.R., Patel J.V. PET waste management by chemical recycling: a review. Journal of Polymers and the Environment. 2010. vol. 18. no. 1. pp. 8–25.
19. Singh S., Sharma S., Umar A., Mehta S.K. et al. Recycling of waste poly (ethylene terephthalate) bottles by alkaline hydrolysis and recovery of pure nanospindle-shaped terephthalic acid. Journal of nanoscience and nanotechnology. 2018. vol. 18. no. 8. pp. 5804–5809. doi: 10.1166/jnn.2018.15363
20. Sreeram A., Leng Z., Padhan R.K., Qu X. Eco-friendly paving materials using waste PET and reclaimed asphalt pavement. HKIE Transactions. 2018. vol. 25. no. 4. pp. 237–247. doi: 10.1080/1023697X.2018.1534617
21. Padhan R.K., Mohanta C., Sreeram A., Gupta A. Rheological evaluation of bitumen modified using antistripping additives synthesised from waste polyethylene terephthalate (PET). International Journal of Pavement Engineering. 2020. vol. 21. no. 9. pp. 1083–1091. doi: 10.1080/10298436.2018.1519192
22. Merkel D.R., Kuang W., Malhotra D., Petrossian G. et al. Waste PET chemical processing to terephthalic amides and their effect on asphalt performance. ACS Sustainable Chemistry & Engineering. 2020. vol. 8. no. 14. pp. 5615–5625. doi: 10.1021/acssuschemeng.0c00036
23. D?bska B., Licho?ai L. The effect of the type of curing agent on selected properties of epoxy mortar modified with PET glycolisate. Construction and Building Materials. 2016. vol. 124. pp. 11–19.
24. D?bska B., Licho?ai L. The selected mechanical properties of epoxy mortar containing PET waste. Construction and Building materials. 2015. vol. 94. pp. 579–588.
25. D?bska B., Licho?ai L., Szyszka J. Innovative compo-site on the basis of an aerogel mat with an epoxy resin modified with PET waste and PCM. E3S Web of Conferences. EDP Sciences, 2018. vol. 44. pp. 31.
26. More A., Mhaske S. Epoxy-based anticorrosive coating developed with modified poly (o-anisidine) and depolymerized product of PET waste. Iranian Polymer Journal. 2018. vol. 27. no. 6. pp. 359–370.
27. Saidi N.M., Shafaamri A.S., Ma I.A.W., Kasi R. et al. Development of anti-corrosion coatings using the disposable waste material. Pigment & Resin Technology. 2018. vol. 47. no. 6. pp. 478-484. doi: 10.1108/PRT-03-2018-0030
28. Yun X., Xin-Yi Y., Dun-Hong G., Yong-Bo D. et al. Preparation and characterization of waterborne alkyd-amino baking coatings based on waste polyethylene terephthalate. Royal Society open science. 2020. vol. 7. no. 1. pp. 191447. doi: 10.1098/rsos.191447
29. Sadeghi G.M.M., Shamsi R., Sayaf M. From aminolysis product of PET waste to novel biodegradable polyurethanes. Journal of Polymers and the Environment. 2011. vol. 19. no. 2. pp. 522–534. doi: 10.1007/s10924-011-0283-7
30. Sadeghi G.M., Sayaf M. From PET waste to novel polyurethanes. Material Recycling–Trends and Perspectives. 2012. pp. 357–390.
31. Cakic S.M., Risti? I.S., Milena M., Nikoli? N.?. et al. Glycolyzed products from PET waste and their application in synthesis of polyurethane dispersions. Progress in Organic Coatings. 2012. vol. 74. no. 1. pp. 115–124. doi: 10.1016/j.porgcoat.2011.11.024
32. Luo X., Li Y. Synthesis and characterization of polyols and polyurethane foams from PET waste and crude glycerol. Journal of Polymers and the Environment. 2014. vol. 22. no. 3. pp. 318–328. doi: 10.1007/s10924-014-0649-8
33. Palekar V.S., Shah R.V., Shukla S.R. Ionic liquid?catalyzed aminolysis of poly (ethylene terephthalate) waste. Journal of applied polymer science. 2012. vol. 126. no. 3. pp. 1174–1181. doi: 10.1002/app.36878
34. Shojaei B., Abtahi M., Najafi M. Chemical recycling of PET: A stepping?stone toward sustainability. Polymers for Advanced Technologies. 2020. vol. 31. no. 12. pp. 2912–2938. doi: 10.1002/pat.5023
35. Fukushima K., Lecuyer J.M., Wei D.S., Horn H.W. et al. Advanced chemical recycling of poly (ethylene terephthalate) through organocatalytic aminoly-sis. Polymer Chemistry. 2013. vol. 4. no. 5. pp. 1610–1616.
36. Wang Y., Zhang Y., Song H., Wang Y. et al. Zinc-catalyzed ester bond cleavage: Chemical degradation of polyethylene terephthalate. Journal of Cleaner Production. 2019. vol. 208. pp. 1469–1475. doi: 10.1016/j.jclepro.2018.10.117
37. Delle Chiaie K.R. et al. Dual-catalytic depolymerization of polyethylene terephthalate (PET). Polymer Chemistry. 2020. vol. 11. no. 8. pp. 1450–1453.
38. B?ckstr?m E., Odelius K., Hakkarainen M. Ultrafast microwave assisted recycling of PET to a family of functional precursors and materials. European Polymer Journal. 2021. vol. 151. pp. 110441. doi: 10.1016/j.eurpolymj.2021.110441
39. Achilias D.S., Tsintzou G.P., Nikolaidis A.K., Bikiaris D.N. et al. Aminolytic depolymerization of poly (ethylene terephthalate) waste in a microwave reactor. Polymer International. 2011. vol. 60. no. 3. pp. 500–506. doi: 10.1002/pi.2976
40. Parab Y.S., Pingale N.D., Shukla S.R. Aminolytic depolymerization of poly (ethylene terephthalate) bottle waste by conventional and microwave irradiation heating. Journal of applied polymer science. 2012. vol. 125. no. 2. pp. 1103–1107. doi: 10.1002/app.34855
41. Shah R.V., Borude V.S., Shukla S.R. Recycling of PET waste using 3?amino?1?propanol by conventional or microwave irradiation and synthesis of bis?oxazin there from. Journal of Applied Polymer Science. 2013. vol. 127. no. 1. pp. 323–328. doi: 10.1002/app.37900
42. Park R., Sridhar V., Park H. Taguchi method for optimization of reaction conditions in microwave glycolysis of waste PET. Journal of Material Cycles and Waste Management. 2020. vol. 22. no. 3. pp. 664–672. doi: 10.1007/s10163-019-00958-7
43.
Review
For citations:
Vokhmyanin M.A., Vesnin R.L., Kraev A.D., Sedykh V.A. Use of microwave aminolytic destruction products of polyethylene terephthalate in rubbers based on chloroprene rubber. Proceedings of the Voronezh State University of Engineering Technologies. 2021;83(3):182-190. (In Russ.) https://doi.org/10.20914/2310-1202-2021-3-182-190




























