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Kinetic study of Diels–Alder reaction involving in maleimide–furan compounds and linear polyurethane

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Abstract

Linear polyurethane was synthesized by Diels–Alder (DA) reaction between a polyurethane prepolymer end-capped with furan rings (MPF) and bismaleimide (BMI). The polymerization kinetics were studied following a preliminary kinetic study of the DA reaction between furfuryl alcohol (FA) and BMI compounds by attenuated total reflection infrared, ultraviolet–visible and in situ 1H NMR spectroscopies, where in situ 1H NMR spectroscopy was selected as the analytical method of choice to study the DA reaction between MPF and BMI. The results showed that the reaction followed second-order kinetics, and the most beneficial experimental conditions to maximize conversion were identified.

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References

  1. Moses JE, Moorhouse AD (2007) The growing applications of click chemistry. Chem Soc Rev 36:1249–1262

    Article  CAS  Google Scholar 

  2. Binder WH, Sachsenhofer R (2007) ‘Click’ chemistry in polymer and materials science. Macromol Rapid Commun 28:15–54

    Article  CAS  Google Scholar 

  3. Nandivada H, Jiang XW, Lahann J (2007) Click chemistry: versatility and control in the hands of materials scientists. Adv Mater 19:2197–2208

    Article  CAS  Google Scholar 

  4. Gheneim R, Perez-Berumen C, Gandini A (2002) Diels–Alder reactions with novel polymeric dienes and dienophiles: synthesis of reversibly cross-linked elastomers. Macromolecules 35:7246–7253

    Article  CAS  Google Scholar 

  5. Gandini A (2008) Polymers from renewable resources: a challenge for the future of macromolecular materials. Macromolecules 41:9491–9504

    Article  CAS  Google Scholar 

  6. Liu Y, Hsieh C (2006) Crosslinked epoxy materials exhibiting thermal remendablility and removability from multifunctional maleimide and furan compounds. J Polym Sci Part A: Polym Chem 44:905–913

    Article  CAS  Google Scholar 

  7. Liu Y, Hsieh CY, Chen YW (2006) Thermally reversible cross-linked polyamides and thermoresponsive gels by means of Diels–Alder reaction. Polymer 47:2581–2586

    Article  CAS  Google Scholar 

  8. Liu Y, Chen YW (2007) Thermally reversible cross-linked polyamides with high toughness and self-repairing ability from maleimide and furan-functionalized aromatic polyamides. Macro Chem Phys 208:224–232

    Article  CAS  Google Scholar 

  9. Gousse C, Gandini A, Hodge P (1998) Application of the Diels–Alder reaction to polymers bearing furan moieties. 2. Diels–Alder and retro-Diels–Alder reactions involving furan rings in some styrene copolymers. Macromolecules 31:314–321

    Article  CAS  Google Scholar 

  10. Mcelhanon JR, Russick EM, Wheeler DR et al (2002) Removable foams based on an epoxy resin incorporating reversible Diels–Alder adducts. J Appl Polym Sci 85:1496–1502

    Article  CAS  Google Scholar 

  11. Ax J, Wenz G (2012) Thermoreversible networks by Diels–Alder reaction of cellulose furoates with bismaleimides. Macromol Chem Phys 213:182–186

    Article  CAS  Google Scholar 

  12. Watanabe M, Yoshie N (2006) Synthesis and properties of readily recyclable polymers from bisfuranic terminated poly (ethylene adipate) and multi-maleimide linkers. Polymer 47:4946–4952

    Article  CAS  Google Scholar 

  13. Wu DY, Meure S, Solomon D (2008) Self-healing polymeric materials: a review of recent developments. Prog Polym Sci 33:479–522

    Article  CAS  Google Scholar 

  14. Yoshie N, Saito S, Oya N (2011) A thermally-stable self-mending polymer networked by Diels–Alder cycloaddition. Polymer 52:6074–6079

    Article  CAS  Google Scholar 

  15. Dispinar T, Sanyal R, Sanyal A (2007) A Diels–Alder/retro Diels–Alder strategy to synthesize polymers bearing maleimide side chains. J Polym Sci Part A: Polym Chem 45:4545–4551

    Article  CAS  Google Scholar 

  16. Burattini S, Greenland BW, Chappell D et al (2010) Healable polymeric materials: a tutorial review. Chem Soc Rev 39:1973–1985

    Article  CAS  Google Scholar 

  17. Kavitha AA, Singha NK (2010) Smart “All Acrylate” ABA triblock copolymer bearing reactive functionality via atom transfer radical polymerization (ATRP): demonstration of a “Click Reaction” in thermoreversible property. Macromolecules 43:3193–3205

    Article  CAS  Google Scholar 

  18. Zhang Y, Broekhuis AA, Picchioni F (2009) Thermally self-healing polymeric materials: the next step to recycling thermoset polymers. Macromolecules 42:1906–1912

    Article  CAS  Google Scholar 

  19. Wagener KB, Engle LP (1993) Thermally reversible polymer linkages. II. Linear addition polymers. J Polym Sci A Polym Chem 31(4):865–875

    Article  CAS  Google Scholar 

  20. Harris FW, Stille JK (1968) Diels–Alder polymers. Polyimides from a biscyclopentadienone and bismaleimides. Macromolecules 1(5):463–464

    Article  CAS  Google Scholar 

  21. Laita H, Boufi S, Gandini A (1997) The application of the Diels–Alder reaction copolymers bearing furan moieties 1. Reactions with maleimides. Eur Polymer J 33(8):1203

    Article  CAS  Google Scholar 

  22. Brand T, Klapper M (1999) Control of viscosity through reversible addition of telechelics via repetitive Diels–Alder reaction in bulk. Des Monomers Polym 2(4):287–309

    Article  CAS  Google Scholar 

  23. Tian Q, Rong MZ, Zhang MQ et al (2010) Synthesis and characterization of epoxy with improved thermal remendability based on Diels–Alder reaction. Polym Int 59:1339–1345

    Article  CAS  Google Scholar 

  24. Amalin Kavitha A, Singha NK (2007) A tailor-made polymethacrylate bearing a reactive diene in reversible Diels–Alder reaction. J Polym Sci Part A: Polym Chem 45:4441–4449

    Article  Google Scholar 

  25. Canadell J, Fischer H et al (2010) Stereoisomeric effects in thermo-remendable polymer networks based on Diels–Alder crosslink reactions. J Polym Sci Part A: Polym Chem 48:3456–3467

    Article  CAS  Google Scholar 

  26. Kennedy J, Carlson G (1983) Synthesis, characterization, and Diels–Alder extension of cyclopentadiene telechelic polyisobutylene. IV. alpha, omega-Di(3-cyclopentadienylpropyldimethylsilyl) polyisobutylene. J Polym Sci: Polym Chem Ed 21(12):3551–3561

    Article  CAS  Google Scholar 

  27. Gandini A, Coelho D, Silvestre AJD (2008) Reversible click chemistry at the service of macromolecular materials. Part 1: kinetics of the Diels–Alder reaction applied to furan-maleimide model compounds and linear polymerizations. Eur Polym J 44:4029–4036

    Article  CAS  Google Scholar 

  28. Gacal B, Durmaz H, Tasdelen MA et al (2006) Anthracene-maleimide-based Diels–Alder “Click Chemistry” as a novel route to graft copolymers. Macromolecules 39:5330–5336

    Article  CAS  Google Scholar 

  29. Kwart H, Burchuk I (1952) Isomerism and adduct stability in the Diels–Alder reaction. I. The adducts of furan and maleimide. J Am Chem Soc 74:3094–3097

    Article  CAS  Google Scholar 

  30. Kavitha AA, Singha NK (2009) “Click Chemistry” in tailor-made polymethacrylates bearing reactive furfuryl functionality: a new class of self-healing polymeric material. Appl Mater Interfaces 1:1427–1436

    Article  CAS  Google Scholar 

  31. Tian Q, Yuan YC, Rong MZ, Zhang MQ (2009) A thermally remendable epoxy resin. J Mater Chem 19:1289–1296

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by Huntsman Polyurethanes (China) Ltd. This project is also supported by the Shanghai Leading Academic Discipline Project (No. B202).

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Authors and Affiliations

  1. School of Chemistry and Chemical Technology, State Key Laboratory of Metal Matrix Composites, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240, People’s Republic of China

    Xuanxuan Liu, Pengfei Du, Li Liu, Zhen Zheng & Xinling Wang

  2. Huntsman Polyurethanes (China) Limited, 455 WenJing Road, Shanghai, 200245, China

    Yuefan Zhang

  3. Huntsman (Europe) BVBA, 3078, Everberg, Belgium

    Thomas Joncheray

Authors
  1. Xuanxuan Liu
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  2. Pengfei Du
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  3. Li Liu
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  4. Zhen Zheng
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  5. Xinling Wang
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  6. Thomas Joncheray
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  7. Yuefan Zhang
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Correspondence to Xinling Wang.

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Liu, X., Du, P., Liu, L. et al. Kinetic study of Diels–Alder reaction involving in maleimide–furan compounds and linear polyurethane. Polym. Bull. 70, 2319–2335 (2013). https://doi.org/10.1007/s00289-013-0954-8

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  • DOI: https://doi.org/10.1007/s00289-013-0954-8

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