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High-Performance Bio-Based Non-Isocyanate Polyurethane Adhesive: A Solvent and Catalyst-Free Synthesis Approach

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Abstract

Adhesives are used to bond two surfaces together and thus find extensive applications in industry and everyday life. Most of the commercial adhesives are manufactured using formaldehyde which makes them toxic to humans and the environment. In addition, the low bonding strength of adhesives in humid environments and underwater needs to be improved for their wider applications. This work prepared and tested a green adhesive using soybean oil. The bio-based non-isocyanate polyurethane (NIPU) adhesives were synthesized by reacting carbonated soybean oil (CSBO) with different amines such as 1,2-ethylenediamine (EDA), 1,4-butylenediamine (BDA), and 1,6-hexamethylenediamine (HDA) in a solvent and catalyst-free approach. The effect of amines on the bonding characteristics such as swelling percentage, adhesion strength, and thermal properties of the adhesives were explored. The dry lap shear strength of the adhesives prepared using EDA, BDA, and HDA showed a bonding strength of 6.23, 8.26, and 7.22 MPa, respectively. Interestingly, the wet lap shear strength of HDA-based adhesive was observed to be around 7.49 MPa while it was 5.8 MPa for BDA and 2.8 MPa for EDA. The increasing chain length of diamines exhibits a decreasing trend in swelling percentage in different solvents which suggests a stronger crosslinking of NIPU adhesives. However, HDA has lower tensile strength than BDA due to its brittleness nature. The high bonding strength of soybean oil-based adhesives suggests that these green adhesives could be used to produce high-quality interior-grade plywood.

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No datasets were generated or analysed during the current study.

References

  1. Pilar M, Blasco C, Silvestre CR (2022) Sustainable Reactive Polyurethane Hot Melt Adhesives Based on Vegetable Polyols for Footwear Industry

  2. Wang YZ, Hsu YC, Wu RR, Kao HM (2003) Synthesis and structure properties of polyurethane based conducting copolymer I. 13 C NMR analysis. Synth Met 132:151–160

    Article  CAS  Google Scholar 

  3. Khatoon H, Ahmad S (2017) A review on conducting polymer reinforced polyurethane composites. J Ind Eng Chem 53:1–22

    Article  CAS  Google Scholar 

  4. Blattmann H, Fleischer M, Bähr M, Mülhaupt R (2014) Isocyanate- and phosgene-free routes to polyfunctional cyclic carbonates and green polyurethanes by fixation of carbon dioxide, Macromol. Rapid Commun 35:1238–1254

    Article  CAS  Google Scholar 

  5. Panchal U, Chaudhary ML, Patel P, Patel J, Gupta RK (2024) Soybean-Based Bio-Adhesives : Role of Diamine on the Adhesive Properties

  6. Kote P, Asare M, Chaudhary S, de Souza FM, Patel P, Gupta RK (2023) Synergistic Effect of P and N-Based Flame Retardants on Bio-Based Polyurethane Foams, in: Polyurethanes Prep. Prop. Appl. Vol. 2 Adv. Appl., American Chemical Society, : pp. 5–71

  7. Acuña P, Zhang J, Yin G-Z, Liu X-Q, Wang D-Y (2021) Bio-based rigid polyurethane foam from castor oil with excellent flame retardancy and high insulation capacity via cooperation with carbon-based materials. J Mater Sci 56:2684–2701

    Article  Google Scholar 

  8. Poussard L, Mariage J, Grignard B, Detrembleur C, Jéroîme C, Calberg C, Heinrichs B, De Winter J, Gerbaux P, Raquez JM, Bonnaud L, Dubois P (2016) Non-isocyanate polyurethanes from carbonated soybean oil using Monomeric or Oligomeric diamines to achieve thermosets or thermoplastics. Macromolecules 49:2162–2171

    Article  CAS  Google Scholar 

  9. Beniah G, Fortman DJ, Heath WH, Dichtel WR, Torkelson JM (2017) Non-isocyanate polyurethane Thermoplastic Elastomer: Amide-based chain extender yields enhanced nanophase separation and Properties in Polyhydroxyurethane. Macromolecules 50:4425–4434

    Article  CAS  Google Scholar 

  10. Bossion A, Jones GO, Taton D, Mecerreyes D, Hedrick JL, Ong ZY, Yang YY, Sardon H (2017) Non-isocyanate polyurethane soft nanoparticles obtained by surfactant-assisted interfacial polymerization. Langmuir 33:1959–1968

    Article  CAS  PubMed  Google Scholar 

  11. Jazi ME, Al-Mohanna T, Aghabozorgi F (2016) Synthesis and applications of isocyanate free polyurethane materials. Glob J Sci Front Res B Chem 16:1–20

    Google Scholar 

  12. Cornille A, Michaud G, Simon F, Fouquay S, Auvergne R, Boutevin B, Caillol S (2016) Promising mechanical and adhesive properties of isocyanate-free poly(hydroxyurethane). Eur Polym J 84:404–420

    Article  CAS  Google Scholar 

  13. Khatoon H, Iqbal S, Irfan M, Darda A, Rawat NK (2021) A review on the production, properties and applications of non-isocyanate polyurethane: a greener perspective. Prog Org Coat 154:106124

    Article  CAS  Google Scholar 

  14. Patel P, De Souza FM, Gupta RK (2024) Study of soybean oil-based non-isocyanate polyurethane films. via a Solvent and Catalyst-Free Approach

  15. Doley S, Dolui SK (2018) Solvent and catalyst-free synthesis of sunflower oil based polyurethane through non-isocyanate route and its coatings properties. Eur Polym J 102:161–168

    Article  CAS  Google Scholar 

  16. Polyurethane N, Zhang B, Yang X, Lin X, Shang H, Liu Q, Wang H, Liu S (2023) High-Strength, Self-Healing, Recyclable, and Catalyst-Free Bio-Based Non-Isocyanate Polyurethane

  17. Maisonneuve L, Lebarbé T, Grau E, Cramail H (2013) Structure-properties relationship of fatty acid-based thermoplastics as synthetic polymer mimics. Polym Chem 4:5472–5517

    Article  CAS  Google Scholar 

  18. Maisonneuve L, Lamarzelle O, Rix E, Grau E, Cramail H (2015) Isocyanate-free routes to polyurethanes and poly(hydroxy urethane)s. Chem Rev 115:12407–12439

    Article  CAS  PubMed  Google Scholar 

  19. Foltran S, Maisonneuve L, Cloutet E, Gadenne B, Alfos C, Tassaing T, Cramail H (2012) Solubility in CO 2 and swelling studies by in situ IR spectroscopy of vegetable-based epoxidized oils as polyurethane precursors. Polym Chem 3:525–532

    Article  CAS  Google Scholar 

  20. Maisonneuve L, More AS, Foltran S, Alfos C, Robert F, Landais Y, Tassaing T, Grau E, Cramail H (2014) Novel green fatty acid-based bis-cyclic carbonates for the synthesis of isocyanate-free poly(hydroxyurethane amide)s. RSC Adv 4:25795–25803

    Article  CAS  Google Scholar 

  21. Maisonneuve L, Wirotius AL, Alfos C, Grau E, Cramail H (2014) Fatty acid-based (bis) 6-membered cyclic carbonates as efficient isocyanate free poly(hydroxyurethane) precursors. Polym Chem 5:6142–6147

    Article  CAS  Google Scholar 

  22. Ochiai B, Inoue S, Endo T (2005) One-pot non-isocyanate synthesis of polyurethanes from bisepoxide, carbon dioxide, and diamine. J Polym Sci Part Polym Chem 43:6613–6618

    Article  CAS  Google Scholar 

  23. Paddock RL, Nguyen ST (2001) Chemical CO2 fixation: CR(III) salen complexes as highly efficient catalysts for the coupling of CO2 and epoxides. J Am Chem Soc 123:11498–11499

    Article  CAS  PubMed  Google Scholar 

  24. Yang Z, Peng H, Wang W, Liu T (2010) Crystallization behavior of poly(ε-caprolactone)/layered double hydroxide nanocomposites. J Appl Polym Sci 116:2658–2667

    Article  CAS  Google Scholar 

  25. Tamami B, Sohn S, Wilkes GL (2004) Incorporation of carbon dioxide into soybean oil and subsequent preparation and studies of nonisocyanate polyurethane networks. J Appl Polym Sci 92:883–891

    Article  CAS  Google Scholar 

  26. Bähr M, Mülhaupt R (2012) Linseed and soybean oil-based polyurethanes prepared via the non-isocyanate route and catalytic carbon dioxide conversion. Green Chem 14:483–489

    Article  Google Scholar 

  27. Javni I, Hong DP, Petrovic̈ ZS (2013) Polyurethanes from soybean oil, aromatic, and cycloaliphatic diamines by nonisocyanate route. J Appl Polym Sci 128:566–571

    Article  CAS  Google Scholar 

  28. Asare M.A., Kote P, Chaudhary S, de Souza F.M., Gupta R.K. (2022) Sunflower Oil as a renewable resource for polyurethane foams: effects of Flame-Retardants. Polym (Basel) 14:5282

  29. Teo L, Chen C, Kuo J (1997) Fourier Transform Infrared Spectroscopy Study on effects of temperature on Hydrogen Bonding in Amine-containing polyurethanes and poly (urethane - urea) s, 9297 1793–1799

  30. Panchireddy S, Grignard B, Thomassin J-M, Jerome C, Detrembleur C (2018) Bio-based poly(hydroxyurethane) glues for metal substrates. Polym Chem 9:2650–2659

    Article  CAS  Google Scholar 

  31. Bähr M, Bitto A, Mülhaupt R (2012) Cyclic limonene dicarbonate as a new monomer for non-isocyanate oligo- and polyurethanes (NIPU) based upon terpenes. Green Chem 14:1447–1454

    Article  Google Scholar 

  32. Nielsen LE (2008) Journal of Macromolecular Science, Part C : polymer reviews cross-linking – effect on Physical properties of polymers. J Macromol Sci Part C Polym Rev 3:69–103

    Article  Google Scholar 

  33. Gomez-Lopez A, Grignard B, Calvo I, Detrembleur C, Sardon H (2020) Monocomponent Non-isocyanate polyurethane adhesives based on a Sol-Gel process. ACS Appl Polym Mater 2:1839–1847

    Article  CAS  Google Scholar 

  34. Yang H, Du G, Li Z, Ran X, Zhou X, Li T, Gao W, Li J, Lei H, Yang L (2021) Superstrong Adhesive of Isocyanate-Free Polyurea with a branched structure. ACS Appl Polym Mater 3:1638–1651

    Article  CAS  Google Scholar 

  35. Kawalerczyk J, Dziurka D, Mirski R, Trociński A (2019) Flour fillers with urea-formaldehyde resin in plywood. BioResources 14:6727–6735

    Article  CAS  Google Scholar 

  36. Peng J, Liu F, Feng F, Feng X, Cui J (2023) Enhancing environmentally friendly tannin Adhesive for Plywood through Hyperbranched Polyamide. ACS Sustain Chem Eng 11:13805–13811

    Article  CAS  Google Scholar 

  37. Pichelin F, Kamoun C, Pizzi A (1999) Hexamine hardener behaviour: effects on wood glueing, tannin and other wood adhesives. Holz Als Roh - Und Werkst 57:305–307

    Article  CAS  Google Scholar 

  38. Pizzi A, Cameron FA (1981) Decrease of pressing temperature and adhesive content by metallic ion catalysis in tannin-bonded particleboard, Holz Als Roh- Und Werkst. 39 463–467

  39. Li K, Geng X, Simonsen J, Karchesy J (2004) Novel wood adhesives from condensed tannins and polyethylenimine. Int J Adhes Adhes 24:327–333

    Article  Google Scholar 

  40. Chen X, Pizzi A, Fredon E (2021) C. Gerardin, curing temperature polyurethane (NIPU) wood adhesives : Preparation and properties evaluation Abstract :, 1–28

  41. Xi X, Pizzi A, Frihart CR, Lorenz L, Gerardin C (2020) Tannin plywood bioadhesives with non-volatile aldehydes generation by specific oxidation of mono- and disaccharides. Int J Adhes Adhes 98

  42. Dong T, Dheressa E, Wiatrowski M, Pereira AP, Zeller A, Laurens LML, Pienkos PT (2021) Assessment of Plant and Microalgal Oil-Derived Nonisocyanate polyurethane products for potential commercialization, ACS sustain. Chem Eng 9:12858–12869

    CAS  Google Scholar 

  43. He X, Xu X, Wan Q, Bo G, Yan Y (2019) Solvent- and Catalyst-free synthesis, hybridization and characterization of Biobased Nonisocyanate polyurethane (NIPU), polymers (Basel). 11

  44. Mó O, Yáñez M, Eckert-Maksić M, Maksić ZB, Alkorta I, Elguero J (2005) Periodic trends in Bond Dissociation energies. A theoretical study. J Phys Chem A 109:4359–4365

    Article  PubMed  Google Scholar 

  45. Aung MM, Yaakob Z, Kamarudin S, Abdullah LC (2014) Synthesis and characterization of Jatropha (Jatropha curcas L.) oil-based polyurethane wood adhesive. Ind Crops Prod 60:177–185

    Article  CAS  Google Scholar 

  46. Ang KP, Lee CS, Cheng SF, Chuah CH (2014) Synthesis of palm oil-based polyester polyol for polyurethane adhesive production. J Appl Polym Sci 131:1–8

    Article  Google Scholar 

  47. Tenorio-Alfonso A, Sánchez MC, Franco JM (2017) Preparation, characterization and mechanical properties of bio-based polyurethane adhesives from isocyanate-functionalized cellulose acetate and castor oil for bonding wood. Polym (Basel) 9:1–14

    Google Scholar 

  48. Vieira FR, Gama N, Magina S, Barros-Timmons A, Evtuguin DV, Pinto PCOR (2022) Polyurethane Adhesives Based on Oxyalkylated Kraft Lignin, Polymers (Basel). 14

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Authors and Affiliations

  1. Department of Chemistry, Pittsburg State University, 1701 S. Broadway Street, Pittsburg, KS, 66762, USA

    Pratik Patel, Rutu Patel, Mayankkumar L. Chaudhary, Niyatiben Chaudhary & Ram K. Gupta

  2. National Institute for Materials Advancement, Pittsburg State University, 1204 Research Road, Pittsburg, KS, 66762, USA

    Pratik Patel, Rutu Patel, Mayankkumar L. Chaudhary, Niyatiben Chaudhary & Ram K. Gupta

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  1. Pratik Patel
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Contributions

PP, RP, MLC and NC performed all the experiments, analyzed the data, and wrote the first draft. RKG conceived and supervised the project, and finalized the draft.

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Correspondence to Ram K. Gupta.

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Patel, P., Patel, R., Chaudhary, M.L. et al. High-Performance Bio-Based Non-Isocyanate Polyurethane Adhesive: A Solvent and Catalyst-Free Synthesis Approach. J Polym Environ (2024). https://doi.org/10.1007/s10924-024-03277-7

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