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Synthesis of novel propylene carbonate diol(PCD)and application in CO2-based polyols waterborne polyurethane

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Abstract

Propylene carbonate diols (PCD) were synthesized from propylene carbonate and ethylenediamine (EDA), iso-phorone diamine (IPDA) and diethylenetriamine (DETA), respectively. The obtained PCDs were used as extenders to prepare the waterborne polyurethane (WPU). The properties of PCD based WPUs were compared to the that of WPU used butane-1,4-diol (BDO) as extender. The structures of PCDs were characterized by Fourier transform infrared (FTIR) and nuclear magnetic resonance (NMR). The yields, melting points and viscosity of PCDs were tested. The mechanical properties, water absorption, water contact angle, adhesion, pencil hardness, thermal gravimetric analysis (TGA), differential scanning calorimeter (DSC) and dynamic mechanical analysis (DMA) of WPU films were also characterized. The results showed that PCDs with urethane bond in the structure were successfully synthesized and the yields were approximately 99% after 3 h of reaction. Compared to the WPU used BDO as extender, WPU films derived from PCDs exhibited superior tensile strength, outstanding adhesion and pencil hardness, lower water contact angle and water absorption, and higher initial thermal decomposition temperature.

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References

  1. Cao H, Liu S, Wang X (2022) Environmentally benign metal catalyst for the ring-opening copolymerization of epoxide and CO2: state-of-the-art, opportunities, and challenges. Green Chem Eng 3:111–124

    Article  Google Scholar 

  2. Li Y, Dai M, Chen X, Yang YP, Yang Mo WJ, Huang PC (2022) Synergetic effect and mechanism between propylene carbonate and polymer rich in ester and ether groups for CO2 physical absorption. J Clean Prod 336:130389

    Article  CAS  Google Scholar 

  3. North M, Pasquale R, Young C (2010) Synthesis of cyclic carbonates from epoxides and CO2. Green Chem 12:1514–1539

    Article  CAS  Google Scholar 

  4. Musa SG, Zulkifli MA, Merican OA (2021) Study on Selected Metal-Organic Framework-Based Catalysts for Cycloaddition Reaction of CO2 with Epoxides: A Highly Economic Solution for Carbon Capture and Utilization. Polymers 13:3905

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. Aouissi A, Aldhayan D, Naaser AY, Abduh AA, Kahtani, (2020) Propylene carbonate synthesis from propylene oxide and CO2 over Ga-Silicate-1 catalyst. Green Process Synthesis 9:440–450

    Article  Google Scholar 

  6. Kumar N, Srivastava VC (2020) Dimethyl carbonate synthesis via transesterification of propylene carbonate using efficient reduced graphene oxide supported ZnO nanocatalyst. Energy Fuels 34:7455–7464

    Article  CAS  Google Scholar 

  7. Wang J, Zhang H, Miao Y, Qiao L, Wang X, Wang F (2016) Waterborne polyurethanes from CO2 based polyols with comprehensive hydrolysis/oxidation resistance. Green Chem 18:524–530

    Article  Google Scholar 

  8. Xian W, Yuan J, Xie Z, Ou W, Liu X, Liu B (2021) Synthesis and properties of CO2 copolymer-based waterborne polyurethane with high solid content. J Polym Res 28:254

    Article  CAS  Google Scholar 

  9. Lu XL, Du FG, Ge XC, Xiao M, Meng YZ (2006) Biodegradability and thermal stability of poly (propylene carbonate)/starch composites. J Biomed Mater Res 77:653–658

    Article  CAS  Google Scholar 

  10. Kim G, Ree M, Kim H, Kim IJ, Kim JR, Lee JI (2008) Biological affinity and biodegradability of poly (propylene carbonate) prepared from copolymerization of carbon dioxide with propylene oxide. Macromol Res 16:473–480

    Article  CAS  Google Scholar 

  11. Langanke J, Wolf A, Hofmann J, Böhm K, Subhani MA, Müller TE, Leitner W, Gürtler C (2014) Carbon dioxide (CO2) as sustainable feedstock for polyurethane production. Green Chem 16:1865–1870

    Article  CAS  Google Scholar 

  12. Liu Z, Huang J, Chen S, Huang Y, Ding F, Guo W, Lei D, Yang L, Qing F, You Z (2020) CO2-based poly (propylene carbonate) with various carbonate linkage content for reactive hot-melt polyurethane adhesives. Int J Adhes Adhes 96:102456

    Article  CAS  Google Scholar 

  13. Dai S, Li P, Li X, Ning C, Kong L, Fang L, Liu Y, Liu L, Ao Y (2021) Waterborne polyurethanes from self-catalytic tartaric acid-based polyols for environmentally-friendly sizing agents. Compos Commun 27:100849

    Article  Google Scholar 

  14. Xian W, Song L, Liu B, Ding H, Le M (2017) Rheological and mechanical properties of thermoplastic polyurethane elastomer derived from co2 copolymer diol. J Appl Polym Sci 135:45974

    Article  Google Scholar 

  15. Chattopadhyay DK, Raju KVSN (2007) Structural engineering of polyurethane coatings for high performance applications. Prog Polym Sci 32:352–418

    Article  CAS  Google Scholar 

  16. Ma L, Song L, Li F, Wang H, Liu B (2017) Preparation and properties of poly (propylene carbonate)-based waterborne polyurethane-acrylate composite emulsion. Colloid Polym Sci 295:2299–2307

    CAS  Google Scholar 

  17. Jang JY, Jhon YK, Cheong IW, Kim JH (2002) Effect of process variables on molecular weight and mechanical properties of water-based polyurethane dispersion. Colloids Surf 196:135–143

    Article  CAS  Google Scholar 

  18. Chen Y, Liu Z, Han S, Han J, Jiang D (2016) Poly(propylene carbonate) polyurethane self-polishing coating for marine antifouling application. J Appl Polym Sci 133:43367

    Article  Google Scholar 

  19. Wang J, Zhang H, Miao Y, Qiao L, Wang X, Wang F (2016) UV-curable waterborne polyurethane from CO2-polyol with high hydrolysis resistance. Polymer 100:219–226

    Article  CAS  Google Scholar 

  20. Ma L, Song L, Wang H, Fan L, Liu B (2018) Synthesis and characterization of poly (propylene carbonate) glycol-based waterborne polyurethane with a high solid content. Prog Org Coat 122:38–44

    Article  CAS  Google Scholar 

  21. Webster DC (2003) Cyclic carbonate functional polymers and their applications. Prog Org Coat 47:77–86

    Article  CAS  Google Scholar 

  22. Mamat S, Abdullah LC, Aung MM, Rashid SA, Salleh MZ, Saalah S, Jusoh ER, Rayung M (2022) Synthesis and Characterization UV-Curable Waterborne Polyurethane Acrylate/Al2O3 Nanocomposite Coatings Derived from Jatropha Oil Polyol. Biointerface Res Appl Chem 13:193

    Article  Google Scholar 

  23. Kwon YR, Kim HC, Moon SK, Kim JS, Chang Y-W, Kim DH (2022) Facile preparation and characterization of low-gloss waterborne polyurethane coatings using amine-based chain extenders. Polym Int. https://doi.org/10.1002/pi.6446

    Article  Google Scholar 

  24. Liu B, Chen L, Zhang M, Yu A (2002) Degradation and Stabilization of Poly (propylene carbonate). Macromolecular 23:881–884

    CAS  Google Scholar 

  25. Pan H, Hao Y, Hao Y, Lang X, Zhang Y, Wang Z, Zhang H, Dong L (2017) Improved mechanical properties, barrier properties and degradation behavior of poly (butylenes adipate-co-terephthalate) /poly (propylene carbonate) films. Korean J Chem Eng 34:1294–1304

    Article  CAS  Google Scholar 

  26. Gholami M, Shakeri A, Zolghadr M, Yamini G (2021) Non-Isocyanate polyurethane from the extracted tannin of sumac leaves: Synthesis, characterization, and optimization of the reaction parameters. Ind Crops Prod 161:113195

    Article  CAS  Google Scholar 

  27. Cakić SM, Valcic MD, Ristić IS, Radusin T, Cvetinov MJ, Budinski-Simendić J (2019) Waterborne polyurethane-silica nanocomposite adhesives based on castor oil-recycled polyols: Effects of (3aminopropyl) triethoxysilane (APTES) content on properties. Int J Adhes Adhes 90:22–31

    Article  Google Scholar 

  28. Li R, Shan Z (2022) Annealing treatment on waterborne polyurethane film-forming and structural features induced heat conduction performance in conductive adhesive. Int J Adhes Adhes 117:103173

    Article  CAS  Google Scholar 

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Correspondence to Lina Song or Baohua Liu.

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We declare that we have no financial and personal relationships with other people or organizations that can inappropriately influence our work, there is no professional or other personal interest of any nature or kind in any product, service and/or company that could be construed as influencing the position presented in, or the review of, the manuscript entitled “Synthesis of novel propylene carbonate diol(PCD)and application in CO2-based polyols waterborne polyurethane”.

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He, Z., Xian, W., Ding, Z. et al. Synthesis of novel propylene carbonate diol(PCD)and application in CO2-based polyols waterborne polyurethane. J Polym Res 29, 445 (2022). https://doi.org/10.1007/s10965-022-03288-9

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