Investigation on the thermal properties of new thermo-reversible networks based on poly(vinyl furfural) and multifunctional maleimide compounds

Express Polymer Letters

Volumn 6, Issue 2, 2012, Pages 129-141

  Gaina, C ^a   Ursache, O ^a   Gaina, V ^a   Buruiana, E ^a   Ionita, D ^a  

^a PETRU PONI INSTITUTE OF MACROMOLECULAR CHEMISTRY   (Romania)

Author keywords

Diels Alder polymers; Networks; Polymer synthesis; Thermal properties

Indexed keywords

EID: 82755196300     PISSN: 1788618X     EISSN: None     Source Type: Journal    
DOI: 10.3144/expresspolymlett.2012.14     Document Type: Article

References (44)

1. Bergman S. D., Wudl F.: Re-mendable polymers. in 'Self healing materials: An alternative approach to 20 centuries of materials science' (ed.: van der Zwaag S.) Springer, Dordrecht, 45-68 (2007).
2. Bergman, S. D., Wudl F.: Mendable polymers. Journal of Materials Chemistry, 18, 41-62 (2008). DOI: 10.1039/B713953P
3. Goiti E., Huglin M. B., Rego J. M.: Some properties of networks produced by the Diels-Alder reaction between poly(styrene-co-furfuryl methacrylate) and bismaleimide. European Polymer Journal, 40, 219-226 (2004). DOI: 10.1016/j.eurpolymj.2003.09.017
4. Wu D. Y., Meure S., Solomon D.: Self-healing polymeric materials: A review of recent developments. Progress in Polymer Science, 33, 479-522 (2008). DOI: 10.1016/j.progpolymsci.2008.02.001
5. Chen X., Dam M. A., Ono K., Mal A., Shen H., Nutt S. R., Sheran K., Wudl F.: A thermally re-mendable crosslinked polymeric material. Science, 295, 1698-1702 (2002). DOI: 10.1126/science.1065879
6. Boul P. J., Reutenauer P., Lehn J-M.: Reversible Diels-Alder reactions for the generation of dynamic combinatorial libraries. Organic Letters, 7, 15-18 (2005). DOI: 10.1021/ol048065k
7. Mcelhanon J. R., Russick E. M., Wheeler D. R., Loy D. A., Aubert J. H.: Removable foams based on an epoxy resin incorporating reversible Diels-Alder adducts. Journal of Applied Polymer Science, 85, 1496-1502 (2002). DOI: 10.1002/app.10753
8. Chen X., Wudl F., Mal A. K., Shen H., Nutt S. R.: New thermally remendable highly cross-linked polymeric materials. Macromolecules, 36, 1802-1807 (2003). DOI: 10.1021/ma0210675
9. Goiti E., Heatley F., Huglin M. B., Rego J. M.: Kinetic aspects of the Diels-Alder reaction between poly (styrene-co-furfuryl methacrylate) and bismaleimide. European Polymer Journal, 40, 1451-1460 (2004). DOI: 10.1016/j.eurpolymj.2004.01.036
10. Watanabe M., Yoshie N.: Synthesis and properties of readily recyclable polymers from bisfuranic terminated poly(ethylene adipate) and multi-maleimide linkers. Polymer, 47, 4946-4952 (2006). DOI: 10.1016/j.polymer.2006.05.036
11. Liu Y-L., Hsieh C-Y.: Crosslinked epoxy materials exhibiting thermal remendablility and removability from multifunctional maleimide and furan compounds. Journal of Polymer Science Part A: Polymer Chemistry, 44, 905-913 (2006). DOI: 10.1002/pola.21184
12. Tian Q., Rong M. Z., Zhang M. Q., Yuan Y. C.: Synthesis and characterization of epoxy with improved thermal remendability based on Diels-Alder reaction. Polymer International, 59, 1339-1345 (2010). DOI: 10.1002/pi.2872
13. Tian Q., Yuan Y. C., Rong M. Z., Zhang M. Q.: A thermally remendable epoxy resin. Journal of Materials Chemistry, 19, 1289-1296 (2009) DOI: 10.1039/B811938D
14. Ishida K., Yoshie N.: Two-way conversion between hard and soft properties of semicrystalline cross-linked polymer. Macromolecules, 41, 4753-4757 (2008). DOI: 10.1021/ma8008383
15. Aumsuwan N., Urban M. W.: Reversible releasing of arms from star morphology polymers. Polymer, 50, 33-36 (2009). DOI: 10.1016/j.polymer.2008.10.048
16. Gousé C., Gandini A., Hodge P.: 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 (1998). DOI: 10.1021/ma9710141
17. Goiti E., Huglin M. B., Rego J. M.: Some observations on the copolymerization of styrene with furfuryl methacrylate. Polymer, 42, 10187-10193 (2001). DOI: 10.1016/S0032-3861(01)00577-8
18. Goiti E., Huglin M. B., Rego J. M.: Thermal breakdown by the retro Diels-Alder reaction of crosslinking in poly[styrene-co-(furfuryl methacrylate)]. Macromolecular Rapid Communications, 24, 692-696 (2003). DOI: 10.1002/marc.200350013
19. Gheneim R., Perez-Berumen C., Gandini A.: Diels-Alder reactions with novel polymeric dienes and dienophiles: Synthesis of reversibly cross-linked elastomers. Macromolecules, 35, 7246-7253 (2002). DOI: 10.1021/ma020343c
20. Kavitha A. A., Singha N. K.: A tailor-made polymethacrylate bearing a reactive diene in reversible Diels-Alder reaction. Journal of Polymer Science Part A: Polymer Chemistry, 45, 4441-4449 (2007). DOI: 10.1002/pola.22195
21. Liu Y-L., Chen Y-W.: Thermally reversible crosslinked polyamides with high toughness and self-repairing ability from maleimide-and furan-functionalized aromatic polyamides). Macromolecular Chemistry and Physics, 208, 224-232 (2007). DOI: 10.1002/macp.200600445
22. Kavitha A. A., Singha N. K.: Atom-transfer radical copolymerization of furfuryl methacrylate (FMA) and methyl methacrylate (MMA): A thermally-amendable copolymer. Macromolecular Chemistry and Physics, 208, 2569-2577 (2007). DOI: 10.1002/macp.200700239
23. Zhu J., Kell A. J., Workentin M. S.: A retro-Diels-Alder reaction to uncover maleimide-modified surfaces on monolayer-protected nanoparticles for reversible covalent assembly. Organic Letters, 8, 4993-4996 (2006). DOI: 10.1021/ol0615937
24. Imai Y., Itoh H., Naka K., Chujo Y.: Thermally reversible IPN organic-inorganic polymer hybrids utilizing the Diels-Alder reaction. Macromolecules, 33, 4343-4346 (2000). DOI: 10.1021/ma991899b
25. Adachi K., Achimuthu A. K., Chujo Y.: Synthesis of organic-inorganic polymer hybrids controlled by Diels-Alder reaction. Macromolecules, 37, 9793-9797 (2004). DOI: 10.1021/ma0400618
26. Liu Y-L., Hsieh C-Y., Chen Y-W.: Thermally reversible cross-linked polyamides and thermo-responsive gels by means of Diels-Alder reaction. Polymer, 47, 2581-2586 (2006). DOI: 10.1016/j.polymer.2006.02.057
27. Zhang Y., Broekhuis A. A., Picchioni F.: Thermally self-healing polymeric materials: The next step to recycling thermoset polymers? Macromolecules, 42, 1906-1912 (2009). DOI: 10.1021/ma8027672
28. Teramoto N., Arai Y., Shibata M.: Thermo-reversible Diels-Alder polymerization of difurfurylidene trehalose and bismaleimides. Carbohydrate Polymers, 64, 78-84 (2006). DOI: 10.1016/j.carbpol.2005.10.029
29. Gandini A., Coelho D., Silvestre A. J. D.: 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. European Polymer Journal, 44, 4029-4036 (2008). DOI: 10.1016/j.eurpolymj.2008.09.026
30. Jegat C., Mignard N.: Effect of the polymer matrix on the thermal behaviour of a furan-maleimide type adduct in the molten state. Polymer Bulletin, 60, 799-808 (2008). DOI: 10.1007/s00289-008-0913-y
31. Canadell J., Fischer H., De With G., Van Benthem R. A. T. M.: Stereoisomeric effects in thermo-remendable polymer networks based on Diels-Alder crosslink reactions. Journal of Polymer Science Part A: Polymer Chemistry, 48, 3456-3467 (2010). DOI: 10.1002/pola.24134
32. Mikroyannidis J. A.: Thermostable laminating resins based on aromatic diketone bis-and tetramaleimides. Journal of Polymer Science Part A: Polymer Chemistry, 28, 679-691 (1990). DOI: 10.1002/pola.1990.080280317
33. Cristea M., Gaina C., Gheorghiu Ionita D., Gaina V.: Dynamic mechanical analysis on modified bismaleimide resins. Journal of Thermal Analysis and Calorimetry, 93, 69-76 (2008). DOI: 10.1007/s10973-007-8802-4
34. Gaina V., Gaina C., Sava M., Stoleriu A., Rusu M.: Bismaleimide resins containing urethanic moieties. Journal of Macromolecular Science Part A: Pure and Applied Chemistry, 34, 2435-2449 (1997). DOI: 10.1080/10601329708010058
35. Gousse C., Gandini A.: Acetalization of polyvinyl alcohol with furfural. European Polymer Journal, 33, 667-671 (1997). DOI: 10.1016/S0014-3057(96)00234-0
36. Chetri P., Dass N. N.: Synthesis of poly(vinyl benzal) from poly(vinyl alcohol) in nonaqueous medium. Journal of Applied Polymer Science, 62, 2139-2145 (1996). DOI: 10.1002/(SICI)1097-4628(19961219)62:12<2139::AID-APP16>3.0.CO;2-0
37. Fernández M. D., Fernández M. J., Hoces P.: Poly (vinyl acetal)s containing electron-donor groups: Synthesis in homogeneous phase and their thermal properties. Reactive and Functional Polymers, 68, 39-56 (2008). DOI: 10.1016/j.reactfunctpolym.2007.10.012
38. Adriaensens P., Pollers I., Carleer R., Vanderzande D., Gelan J.: Solid-state NMR study of different types of poly(vinyl formal). Macromolecules, 32, 440-447 (1999). DOI: 10.1021/ma981216c
39. Cerrada M. L., Benavente R., Pérez E., Pereña J. M.: The effect of orientation on the morphology and viscoelastic response of vinyl alcohol-ethylene copolymers. Macromolecular Chemistry and Physics, 201, 1858-1868 (2000). DOI: 10.1002/1521-3935(20000901)201:14<1858:: AID-MACP1858>3.0.CO;2-A
40. Park J-S., Park J-W., Ruckenstein E.: On the viscoelastic properties of poly(vinyl alcohol) and chemically crosslinked poly(vinyl alcohol). Journal of Applied Polymer Science, 82, 1816-1823 (2001). DOI: 10.1002/app.2023
41. Park J-S., Park J-W., Ruckenstein E.: A dynamic mechanical and thermal analysis of unplasticized and plasticized poly(vinyl alcohol)/methylcellulose blends. Journal of Applied Polymer Science, 80, 1825-1834 (2001). DOI: 10.1002/app.1278
42. Tian Q., Rong M. Z., Zhang M. Q., Yuan Y. C.: Optimization of thermal remendability of epoxy via blending. Polymer, 51, 1779-1785 (2010). DOI: 10.1016/j.polymer.2010.02.004
43. Shaulov A. Yu., Lomakin S. M., Zarkhina T. S., Rakhimkulov A. D., Shilkina N. G., Muravlev Yu. B., Berlin Al. Al.: Carbonization of poly(vinyl alcohol) in blends with boron polyoxide. Doklady Physical Chemistry, 403, 154-158 (2005). DOI: 10.1007/s10634-005-0048-x
44. Alexy P., Káchová D., Kriak M., Bako D., imková B.: Poly(vinyl alcohol) stabilisation in thermoplastic processing. Polymer Degradation and Stability, 78, 413-421 (2002). DOI: 10.1016/S0141-3910(02)00177-5