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Wood Science and Technology

, Volume 54, Issue 1, pp 103–121 | Cite as

Liquefaction of alder wood as the source of renewable and sustainable polyols for preparation of polyurethane resins

  • Kamila GoszEmail author
  • Daria Kowalkowska-Zedler
  • Józef Haponiuk
  • Łukasz PiszczykEmail author
Original
  • 76 Downloads

Abstract

Liquefaction of wood-based biomass gives different polyol properties depending on the reagents used. In this article, alder wood sawdust was liquefied with glycerol and poly(ethylene glycol) solvents. Liquefaction reactions were carried out at temperatures of 120, 150 and 170 °C. The obtained bio-polyols were analyzed in order to establish the process efficiency, hydroxyl number, acid value, viscosity and structural characteristics using Fourier transform infrared (FTIR), carbon (13C) and proton (1H) NMR analyses. The results indicate that the optimal conditions for the liquefaction process are at 150 °C for 6 h. The results of the FTIR spectra analysis and the hydroxyl number in the range of 214–687 mg KOH/g showed that the obtained bio-polyols are a potential substitute for petrochemical polyols commonly used for the synthesis of polyurethane polymers. Polyurethane resins containing 90 wt% of bio-polyol were obtained by a one-step method using a hydraulic press. The material was pressed for 15 min (5 MPa) at 100 °C with an NCO/OH ratio in the range of 0.9–1.2. Dynamic mechanical thermal analysis (DMA) showed high cross-linking density and modulus of elasticity in a wide range of 62–1362 MPa.

Notes

References

  1. Abdel Hakim AA, Nassar M, Emam A, Sultan M (2015) Mater Chem Phys 129:301–307.  https://doi.org/10.1016/j.matchemphys.2011.04.008 CrossRefGoogle Scholar
  2. Amran UA, Zakaria S, Chia CH et al (2019) Polyols and rigid polyurethane foams derived from liquefied lignocellulosic and cellulosic biomass. Cellulose.  https://doi.org/10.1007/s10570-019-02271-w CrossRefGoogle Scholar
  3. Behrendt F, Neubauer Y, Oevermann M et al (2012) European Psychiatric Association (EPA) guidance on suicide treatment and prevention. Eur Psychiatry 27(2):129–677.  https://doi.org/10.1002/ceat.200800077 CrossRefGoogle Scholar
  4. Budarin VL, Clark JH, Lanigan BA et al (2010) Microwave assisted decomposition of cellulose: a new thermochemical route for biomass exploitation. Bioresour Technol 101:3776–3779.  https://doi.org/10.1016/j.biortech.2009.12.110 CrossRefPubMedGoogle Scholar
  5. Budija F, Tavzes Č, Zupančič-Kralj L, Petrič M (2009) Self-crosslinking and film formation ability of liquefied black poplar. Bioresour Technol 100(2):(2):3316–3323–3323.  https://doi.org/10.1016/j.biortech.2009.02.004 CrossRefPubMedGoogle Scholar
  6. Cai Z, Gao J, Li X, Xiang B (2007) Synthesis and characterization of symmetrical benzodifuranone compounds with femtosecond time-resolved degenerate four-wave mixing technique. Opt Commun 272:503–508.  https://doi.org/10.1016/j.optcom.2006.11.056 CrossRefGoogle Scholar
  7. Calvo-Correas T, Gabilondo N, Alonso-Varona A et al (2016) Shape-memory properties of crosslinked biobased polyurethanes. Eur Polym J 78:253–263.  https://doi.org/10.1016/j.eurpolymj.2016.03.030 CrossRefGoogle Scholar
  8. Carballo-Meilan A, Goodman AM, Baron MG, Gonzalez-Rodriguez J (2014) A specific case in the classification of woods by FTIR and chemometric : discrimination of Fagales from Malpighiales. Cellulose 21:261–273.  https://doi.org/10.1007/s10570-013-0093-2 CrossRefGoogle Scholar
  9. Chaikumpollert O, Methacanon P, Suchiva K (2004) Structural elucidation of hemicelluloses from Vetiver grass. Carbohydr Polym 57:191–196.  https://doi.org/10.1016/j.carbpol.2004.04.011 CrossRefGoogle Scholar
  10. Chen F, Lu Z (2009) Liquefaction of wheat straw and preparation of rigid polyurethane foam from the liquefaction products. J Appl Polym Sci 111:508–516.  https://doi.org/10.1002/app.29107 CrossRefGoogle Scholar
  11. Collier WE, Schultz TP, Kalasinsky VF (1992) Infrared study of lignin: reexamination of aryl-alkyl ether C—O stretching peak assignments. Holzforschung 46:523–528.  https://doi.org/10.1515/hfsg.1992.46.6.523 CrossRefGoogle Scholar
  12. D’Souza J, Yan N (2013) Producing bark-based polyols through liquefaction: effect of liquefaction temperature. ACS Sustain Chem Eng 1:534–540.  https://doi.org/10.1021/sc400013e CrossRefGoogle Scholar
  13. Daneshvar S, Behrooz R, Najafi SK et al (2019) Characterization of polyurethane wood adhesive prepared from liquefied sawdust by ethylene carbonate. BioResour 14:796–815.  https://doi.org/10.15376/biores.14.1.796-815 CrossRefGoogle Scholar
  14. Delebecq E, Pascault J-P, Boutevin B, Ganachaud F (2013) On the versatility of urethane/urea bonds: reversibility, blocked isocyanate, and non-isocyanate polyurethane. Chem Rev 113:80–118.  https://doi.org/10.1021/cr300195n CrossRefPubMedGoogle Scholar
  15. De Oliveira F, Ramires EC, Frollini E, Belgacem MN (2015) Lignopolyurethanic materials based on oxypropylated sodium lignosulfonate and castor oil blends. Ind Crops Prod 72:77–86.  https://doi.org/10.1016/j.indcrop.2015.01.023 CrossRefGoogle Scholar
  16. Deng S, Ting Y-P (2005) Characterization of PEI-modified biomass and biosorption of Cu(II), Pb(II) and Ni(II). Water Res 39:2167–2177.  https://doi.org/10.1016/j.watres.2005.03.033 CrossRefPubMedGoogle Scholar
  17. Gaikwad MS, Gite VV, Mahulikar PP et al (2015) Eco-friendly polyurethane coatings from cottonseed and karanja oil. Prog Org Coat 86:164–172.  https://doi.org/10.1016/j.porgcoat.2015.05.014 CrossRefGoogle Scholar
  18. Hassan EM, Shukry N (2007) Polyhydric alcohol liquefaction of some lignocellulosic agricultural residues. Ind Crops Prod 7:33–38.  https://doi.org/10.1016/j.indcrop.2007.07.004 CrossRefGoogle Scholar
  19. Heredia-Guerrero JA, Benítez JJ, Domínguez E et al (2014) Infrared and Raman spectroscopic features of plant cuticles: a review. Front Plant Sci 5:1–15.  https://doi.org/10.3389/fpls.2014.00305 CrossRefGoogle Scholar
  20. Hu S, Wan C, Li Y (2012) Production and characterization of biopolyols and polyurethane foams from crude glycerol based liquefaction of soybean straw. Bioresour Technol 103:227–233.  https://doi.org/10.1016/j.biortech.2011.09.125 CrossRefPubMedGoogle Scholar
  21. Hu S, Luo X, Li Y (2014) Polyols and polyurethanes from the liquefaction of lignocellulosic biomass. Chemsuschem 7:66–72.  https://doi.org/10.1002/cssc.201300760 CrossRefPubMedGoogle Scholar
  22. Jasiukaityte-Grojzdek E, Kunaver M, Crestini C (2012) Lignin structural changes during liquefaction in acidified ethylene glycol. J Wood Chem Technol 32:342–360.  https://doi.org/10.1080/02773813.2012.698690 CrossRefGoogle Scholar
  23. Javni I, Petrović ZS, Guo A, Fuller R (2000) Thermal stability of polyurethanes based on vegetable oils. J Appl Polym Sci 77:1723–1734.  https://doi.org/10.1002/1097-4628(20000822)77:8%3c1723:AID-APP9%3e3.0.CO;2-K CrossRefGoogle Scholar
  24. Jin Y, Ruan X, Cheng X, Lü Q (2011) Liquefaction of lignin by polyethyleneglycol and glycerol. Bioresour Technol 102:3581–3583.  https://doi.org/10.1016/j.biortech.2010.10.050 CrossRefPubMedGoogle Scholar
  25. Kobayashi M, Asano T, Kajiyama M, Tomita B (2004) Analysis on residue formation during wood liquefaction with polyhydric alcohol. J Wood Sci 50:407–414.  https://doi.org/10.1007/s10086-003-0596-9 CrossRefGoogle Scholar
  26. Kong X, Liu G, Curtis JM (2011) Characterization of canola oil based polyurethane wood adhesives. Int J Adhes Adhes 31:559–564.  https://doi.org/10.1016/j.ijadhadh.2011.05.004 CrossRefGoogle Scholar
  27. Kržan A, Kunaver M, Tišler V (2005) Wood liquefaction using dibasic organic acids and glycols. Acta Chim Slov 52:253–258Google Scholar
  28. Kunaver M, Jasiukaityte E, Čuk N, Guthrie JT (2010) Liquefaction of wood, synthesis and characterization of liquefied wood polyester derivatives. J Appl Polym Sci 115:1265–1271.  https://doi.org/10.1002/app.31277 CrossRefGoogle Scholar
  29. Kurimoto Y, Doi S, Tamura Y (1999) Species effects on wood-liquefaction in polyhydric alcohols. Holzforschung 53:617–622.  https://doi.org/10.1515/HF.1999.102 CrossRefGoogle Scholar
  30. Kurimoto Y, Takeda M, Koizumi A et al (2000) Mechanical properties of polyurethane films prepared from liquefied wood with polymeric MDI. Bioresour Technol 74:151–157.  https://doi.org/10.1016/S0960-8524(00)00009-2 CrossRefGoogle Scholar
  31. Kurimoto Y, Koizumi A, Doi S et al (2001) Wood species effects on the characteristics of liquefied wood and the properties of polyurethane films prepared from the liquefied wood. Biomass Bioenerg 21:381–390.  https://doi.org/10.1016/S0961-9534(01)00041-1 CrossRefGoogle Scholar
  32. Lee W-J, Chao C-Y (2018) Effect of containing polyhydric alcohol liquefied wood on the properties of thermoplastic polyurethane resins. Eur J Wood Prod 76:1745–1752.  https://doi.org/10.1007/s00107-018-1338-4 CrossRefGoogle Scholar
  33. Lee W, Lin M (2008) Preparation and application of polyurethane adhesives made from polyhydric alcohol liquefied Taiwan acacia and China fir. J Appl Polym Sci 109:23–31.  https://doi.org/10.1002/app.28007 CrossRefGoogle Scholar
  34. Lee S-H, Yoshioka M, Shiraishi N (2000) Liquefaction of corn bran (CB) in the presence of alcohols and preparation of polyurethane foam from its liquefied polyol. J Appl Polym Sci 78:319–325.  https://doi.org/10.1002/1097-4628(20001010)78:2%3c319:AID-APP120%3e3.0.CO;2-Z CrossRefGoogle Scholar
  35. Lee SH, Teramoto Y, Shiraishi N (2002) Acid-catalyzed liquefaction of waste paper in the presence of phenol and its application to Novolak-type phenolic resin. J Appl Polym Sci 83:1473–1481.  https://doi.org/10.1002/app.10038 CrossRefGoogle Scholar
  36. Lee CS, Ooi TL, Chuah CH, Ahmad S (2007) Synthesis of palm oil-based diethanolamides. J Am Oil Chem Soc 84:945–952.  https://doi.org/10.1007/s11746-007-1123-8 CrossRefGoogle Scholar
  37. Lee W, Kuo E-S, Chao C-Y, Kao Y-P (2015) Properties of polyurethane (PUR) films prepared from liquefied wood (LW) and ethylene glycol (EG). Holzforschung 69:547–554.  https://doi.org/10.1515/hf-2014-0142 CrossRefGoogle Scholar
  38. Li H, Xu C, Yuan Z, Wei Q (2018) Synthesis of bio-based polyurethane foams with liquefied wheat straw: process optimization. Biomass Bioenergy 111:134–140.  https://doi.org/10.1016/j.biombioe.2018.02.011 CrossRefGoogle Scholar
  39. Li H, Feng S, Yuan Z et al (2017) Highly efficient liquefaction of wheat straw for the production of bio-polyols and bio-based polyurethane foams. Ind Crop Prod 109:426–433.  https://doi.org/10.1016/j.indcrop.2017.08.060 CrossRefGoogle Scholar
  40. Lu X, Wang Y, Zhang Y et al (2016) Preparation of bio-polyols by liquefaction of hardwood residue and their application in the modification of polyurethane foams. J Wuhan Univ Technol Sci Ed 31:918–924.  https://doi.org/10.1007/s11595-016-1468-7 CrossRefGoogle Scholar
  41. Luo X, Hu S, Zhang X, Li Y (2013) Thermochemical conversion of crude glycerol to biopolyols for the production of polyurethane foams. Bioresour Technol 139:323–329.  https://doi.org/10.1016/j.biortech.2013.04.011 CrossRefPubMedGoogle Scholar
  42. Mori R (2015) Inorganic–organic hybrid biodegradable polyurethane resin derived from liquefied Sakura wood. Wood Sci Technol 49:507–516.  https://doi.org/10.1007/s00226-015-0707-y CrossRefGoogle Scholar
  43. Ni B, Yang L, Wang C et al (2010) Synthesis and thermal properties of soybean oil-based waterborne polyurethane coatings. J Therm Anal Calorim 100:239–246.  https://doi.org/10.1007/s10973-009-0418-4 CrossRefGoogle Scholar
  44. Pan X, Webster DC (2012) New biobased high functionality polyols and their use in polyurethane coatings. Chemsuschem 5:419–429.  https://doi.org/10.1002/cssc.201100415 CrossRefPubMedGoogle Scholar
  45. Ristić IS, Budinski-Simendić J, Krakovsky I et al (2012) The properties of polyurethane hybrid materials based on castor oil. Mater Chem Phys 132:74–81.  https://doi.org/10.1016/j.matchemphys.2011.10.053 CrossRefGoogle Scholar
  46. Ruppert AM, Meeldijk JD, Kuipers BWM et al (2016) Glycerol etherification over highly active cao-based materials: new mechanistic aspects and related colloidal particle formation. Chem A Eur J 14:2016–2024.  https://doi.org/10.1002/chem.200701757 CrossRefGoogle Scholar
  47. Saidur R, Abdelaziz EA, Demirbas A et al (2011) A review on biomass as a fuel for boilers. Renew Sustain Energy Rev 15:2262–2289.  https://doi.org/10.1016/j.rser.2011.02.015 CrossRefGoogle Scholar
  48. Sequeiros A, Serrano L, Briones R, Labidi J (2013) Lignin liquefaction under microwave heating. Appl Polym.  https://doi.org/10.1002/app.39577 CrossRefGoogle Scholar
  49. Stefanidis SD, Kalogiannis KG, Iliopoulou EF et al (2014) A study of lignocellulosic biomass pyrolysis via the pyrolysis of cellulose, hemicellulose and lignin. J Anal Appl Pyrolysis 105:143–150.  https://doi.org/10.1016/j.jaap.2013.10.013 CrossRefGoogle Scholar
  50. Tavares LB, Boas CV, Schleder GR et al (2016) Bio-based polyurethane prepared from Kraft lignin and modified castor oil. Express Polym Lett 10:927–940.  https://doi.org/10.3144/expresspolymlett.2016.86 CrossRefGoogle Scholar
  51. Taylor P, Petrovi ZS (2008) Polyurethanes from vegetable oils. Polym Rev 48:37–41.  https://doi.org/10.1080/15583720701834224 CrossRefGoogle Scholar
  52. Trovati G, Sanches EA, De SSM et al (2014) Rigid and semi rigid polyurethane resins: a structural investigation using DMA, SAXS and Le Bail method. J Mol Struct 1075:589–593.  https://doi.org/10.1016/j.molstruc.2014.07.024 CrossRefGoogle Scholar
  53. Wang H, Chen H (2007) A novel method of utilizing the biomass resource: rapid liquefaction of wheat straw and preparation of biodegradable polyurethane foam (PUF). J Chin Inst Chem Eng 38:95–102.  https://doi.org/10.1016/j.jcice.2006.10.004 CrossRefGoogle Scholar
  54. Wang Y, Wu J, Wan Y et al (2009) Liquefaction of corn stover using industrial biodiesel glycerol. Int J Agric Biol Eng 2:32–40.  https://doi.org/10.3965/j.issn.1934-6344.2009.02.032-040 CrossRefGoogle Scholar
  55. Wang H, Ni Y, Jahan MS et al (2011) Stability of cross-linked acetic acid lignin-containing polyurethane. J Therm Anal Calorim 103:293–302.  https://doi.org/10.1007/s10973-010-1052-x CrossRefGoogle Scholar
  56. Wei Y, Cheng F, Li H, Yu J (2004) Synthesis and properties of polyurethane resins based on liquefied wood. J Appl Polym Sci 92:351–356.  https://doi.org/10.1002/app.20023 CrossRefGoogle Scholar
  57. Xu F, Sun JX, Liu CF, Sun RC (2006) Comparative study of alkali- and acidic organic solvent-soluble hemicellulosic polysaccharides from sugarcane bagasse. Carbohydr Res 341:253–261.  https://doi.org/10.1016/j.carres.2005.10.019 CrossRefPubMedGoogle Scholar
  58. Xue B, Wen J, Sun R (2015) Producing lignin-based polyols through microwave-assisted liquefaction for rigid polyurethane foam production. Materials (Basel) 8:586–599.  https://doi.org/10.3390/ma8020586 CrossRefGoogle Scholar
  59. Yao Y, Yoshioka M, Shiraishi N (1996) Water-absorbing polyurethane foams from liquefied starch. J Appl Polym Sci 60:1939–1949.  https://doi.org/10.1002/(SICI)1097-4628(19960613)60:11%3c1939:AID-APP18%3e3.0.CO;2-W CrossRefGoogle Scholar
  60. Ye L, Zhang J, Zhao J, Tu S (2014) Liquefaction of bamboo shoot shell for the production of polyols. Bioresour Technol 153:147–153.  https://doi.org/10.1016/j.biortech.2013.11.070 CrossRefPubMedGoogle Scholar
  61. Yue D, Oribayo O, Rempel GL, Pan Q (2017) Liquefaction of waste pine wood and its application in the synthesis of a flame retardant polyurethane foam. RSC Adv 7:30334–30344.  https://doi.org/10.1039/C7RA03546B CrossRefGoogle Scholar
  62. Zhang Y, Ikeda A, Hori N et al (2006) Characterization of liquefied product from cellulose with phenol in the presence of sulfuric acid. Bioresour Technol 97:313–321.  https://doi.org/10.1016/j.biortech.2005.02.019 CrossRefPubMedGoogle Scholar
  63. Zhang T, Zhou Y, Liu D, Petrus L (2007) Qualitative analysis of products formed during the acid catalyzed liquefaction of bagasse in ethylene glycol. Bioresour Technol 98:1454–1459.  https://doi.org/10.1016/j.biortech.2006.03.029 CrossRefPubMedGoogle Scholar
  64. Zhang H, Ding F, Luo C et al (2012) Liquefaction and characterization of acid hydrolysis residue of corncob in polyhydric alcohols. Ind Crop Prod 39:47–51.  https://doi.org/10.1016/j.indcrop.2012.02.010 CrossRefGoogle Scholar
  65. Zhao Y, Yan N, Feng M (2012) Polyurethane foams derived from liquefied mountain pine beetle-infested barks. J Appl Polym Sci 123:2849–2858.  https://doi.org/10.1002/app.34806 CrossRefGoogle Scholar
  66. Zou X, Qin T, Huang L et al (2009) Mechanisms and main regularities of biomass liquefaction with alcoholic solvents. Energy Fuels 23:5213–5218.  https://doi.org/10.1021/ef900590b CrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Department of Polymers Technology, Chemical FacultyGdansk University of TechnologyGdańskPoland
  2. 2.Department of Inorganic Chemistry, Chemical FacultyGdańsk University of TechnologyGdańskPoland

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