DOI QR코드

DOI QR Code

Structural investigations of toluene diisocyanate (TDI) and trimethylolpropane (TMP)-based polyurethane prepolymer

  • He, Yong (School of Chemistry and Chemical Engineering, South China University of Technology) ;
  • Zhang, Xinya (School of Chemistry and Chemical Engineering, South China University of Technology) ;
  • Zhang, Xinfang (School of Chemistry and Chemical Engineering, South China University of Technology) ;
  • Huang, Hong (School of Chemistry and Chemical Engineering, South China University of Technology) ;
  • Chang, Jie (School of Chemistry and Chemical Engineering, South China University of Technology) ;
  • Chen, Huanqin (School of Chemistry and Chemical Engineering, South China University of Technology)
  • Published : 2012.09.25

Abstract

Polyurethane prepolymer prepared from nonequivalent amounts of toluene diisocyanate (TDI) over trifunctional trimethylolpropane (TMP) was followed by gel permeation chromatography (GPC). Steric hindrance of TMP was considered as the main factor affecting the molar mass distribution, especially in the higher molecular weight region. An optimum reaction condition was the initial NCO/OH ratio of 3 and the reaction temperature of $50^{\circ}C$.Then polyurethane prepolymer could be purified through the thin film evaporator with excellent properties. A combination of mass spectrometry (MS) and $^1H$ nuclear magnetic resonance (NMR) spectroscopy was employed to identify and confirm the individual compounds presented from GPC analysis.

Keywords

References

  1. D.K. Chattopadhyay, B. Sreedhar, K.V.S.N. Raju, J. Appl. Polym. Sci. 95 (2005) 1509. https://doi.org/10.1002/app.21404
  2. R.A. Potyrailo, B.J. Chisholm, W.G. Morris, J.N. Cawse, W.P. Flanagan, L. Hassib, C.A. Molaison, K. Ezbiansky, G. Medford, H. Reitz, J. Comb. Chem. 5 (2003) 472. https://doi.org/10.1021/cc030022s
  3. H.S. Choi, C.H. Lim, S.T. Noh, J. Ind. Eng. Chem. 8 (2002) 524.
  4. P. Krol, Prog. Mater Sci. 52 (2007) 915. https://doi.org/10.1016/j.pmatsci.2006.11.001
  5. D.K. Chattopadhyay, K.V.S.N. Raju, Prog. Polym. Sci. 32 (2007) 352. https://doi.org/10.1016/j.progpolymsci.2006.05.003
  6. J. Zhang, C.P. Hu, Eur. Polym. J. 44 (2008) 3708. https://doi.org/10.1016/j.eurpolymj.2008.08.019
  7. M.A. Semsarzadeh, A.H. Navarchian, J. Appl. Polym. Sci. 90 (2003) 963. https://doi.org/10.1002/app.12691
  8. H.J. Oh, W.Y. Kim, D.S. Lee, Y.S. Lee, J. Ind. Eng. Chem. 6 (2000) 425.
  9. K.C. Frisch, S.L. Reegen, B. Thir, J. Polym. Sci. Part C: Polym. Symp. 16 (1967) 2191.
  10. F. Willeboordse, J. Phys. Chem. 74 (1970) 601. https://doi.org/10.1021/j100698a020
  11. P. Krol, H. Galina, K. Kaczmarski, Macromol. Theory Simul. 8 (1999) 129. https://doi.org/10.1002/(SICI)1521-3919(19990301)8:2<129::AID-MATS129>3.0.CO;2-D
  12. P. Krol, J. Appl. Polym. Sci. 61 (1996) 2207. https://doi.org/10.1002/(SICI)1097-4628(19960919)61:12<2207::AID-APP21>3.0.CO;2-2
  13. P. Krol, J. Appl. Polym. Sci. 69 (1998) 169. https://doi.org/10.1002/(SICI)1097-4628(19980705)69:1<169::AID-APP20>3.0.CO;2-U
  14. C.F. Bartelink, M. De Pooter, H.J.M. Grunbauer, U. Beginn, M. Moller, J. Polym. Sci. Part A: Polym. Chem. 38 (2000) 2555. https://doi.org/10.1002/1099-0518(20000715)38:14<2555::AID-POLA60>3.0.CO;2-Z
  15. P. Krol, B. Pilch-Pitera, Polymer 44 (2003) 5075. https://doi.org/10.1016/S0032-3861(03)00431-2
  16. G. Alois, Isocyanates and method of preparing same, U.S. Patent 3183112, 1965.
  17. M. Spirkova, M. Kubin, K. Dusek, J. Macromol. Sci. Pure Appl. Chem. 27 (1990) 509.
  18. J.T. Garrett, C.A. Siedlecki, J. Runt, Macromolecules 34 (2001) 7066. https://doi.org/10.1021/ma0102114
  19. P. Barbeau, J.F. Gerard, B. Magny, J.P. Pascault, J. Polym. Sci. Part B: Polym. Phys. 38 (2000) 2750. https://doi.org/10.1002/1099-0488(20001101)38:21<2750::AID-POLB50>3.0.CO;2-B
  20. L.I. Majoros, B. Dekeyser, R. Hoogenboom, M.W.M. Fijten, J. Geeraert, N. Haucourt, U.S. Schubert, J. Polym. Sci. Part A: Polym. Chem. 48 (2010) 570. https://doi.org/10.1002/pola.23768
  21. L.I. Majoros, B. Dekeyser, R. Hoogenboom, M.W.M. Fijten, N. Haucourt, U.S. Schubert, J. Polym. Sci. Part A: Polym. Chem. 47 (2009) 3729. https://doi.org/10.1002/pola.23382
  22. C.M. Thompson, S.G. Taylor, W.W. McGee, J. Polym. Sci. Part A: Polym. Chem. 32 (1994) 113. https://doi.org/10.1002/pola.1994.080320113
  23. F. Prochazka, T. Nicolai, D. Durand, Macromolecules 33 (2000) 1703. https://doi.org/10.1021/ma9901543
  24. A. Prabhakar, D.K. Chattopadhyay, B. Jagadeesh, K.V.S.N. Raju, J. Polym. Sci. Part A: Polym. Chem. 43 (2005) 1196. https://doi.org/10.1002/pola.20583
  25. B. Grepinet, F. Pla, P. Hobbes, T. Monge, P. Swaels, J. Appl. Polym. Sci. 81 (2001) 3149. https://doi.org/10.1002/app.1767
  26. P. Krol, B. Pilch-Pitera, Eur. Polym. J. 37 (2001) 251. https://doi.org/10.1016/S0014-3057(00)00116-6
  27. E. Esser, C. Keil, D. Braun, P. Montag, H. Pasch, Polymer 41 (2000) 4039. https://doi.org/10.1016/S0032-3861(99)00646-1
  28. R. Murgasova, D. Hercules, Anal. Bioanal. Chem. 373 (2002) 481. https://doi.org/10.1007/s00216-002-1332-9
  29. L.H. Peebles, Macromolecules 7 (1974) 872. https://doi.org/10.1021/ma60042a034
  30. L.H. Peebles, Macromolecules 9 (1976) 58. https://doi.org/10.1021/ma60049a010
  31. M. Moller, H.U. Moritz, J. Appl. Polym. Sci. 101 (2006) 4090. https://doi.org/10.1002/app.23374
  32. K. Dusek, M. Spirkova, I. Havlicek, Macromolecules 23 (1990) 1774. https://doi.org/10.1021/ma00208a036
  33. A.M. Heintz, D.J. Duffy, S.L. Hsu, W. Suen, W. Chu, C.W. Paul, Macromolecules 36 (2003) 2695. https://doi.org/10.1021/ma021559h
  34. I. Yilgor, E. Yilgor, I.G. Guler, T.C. Ward, G.L. Wilkes, Polymer 47 (2006) 4105. https://doi.org/10.1016/j.polymer.2006.02.027
  35. S. Pongkitwitoon, R. Hernandez, J. Weksler, A. Padsalgikar, T. Choi, J. Runt, Polymer 50 (2009) 6305. https://doi.org/10.1016/j.polymer.2009.10.067
  36. J. Mattia, P. Painter, Macromolecules 40 (2007) 1546. https://doi.org/10.1021/ma0626362
  37. G. Rokicki, A. Piotrowska, Polymer 43 (2002) 2927. https://doi.org/10.1016/S0032-3861(02)00071-X
  38. D.J. Yontz, S.L. Hsu, Macromolecules 33 (2000) 8415. https://doi.org/10.1021/ma000454g
  39. M. Sumi, Y. Chokki, Y. Nakai, M. Nakabayashi, T. Kanzawa, Die Makromolekulare Chemie 78 (1964) 146. https://doi.org/10.1002/macp.1964.020780112
  40. M. Pegoraro, A. Galbiati, G. Ricca, J. Appl. Polym. Sci. 87 (2003) 347. https://doi.org/10.1002/app.10958

Cited by

  1. Reaction Monitoring of Toluenediisocyanate (TDI) Polymerization on a Non-Mixable Aqueous Surface by MALDI Mass Spectrometry vol.29, pp.7, 2012, https://doi.org/10.2116/analsci.29.703
  2. 폴리우레탄 접착제의 물성에 미치는 PPG, MDI, 2-HEMA 및 butyl acrylate량의 영향 vol.49, pp.3, 2012, https://doi.org/10.7473/ec.2014.49.3.245
  3. Combined effect of thermoplastic and thermosetting adhesives on properties of particleboard with rice husk core vol.17, pp.5, 2012, https://doi.org/10.1590/1516-1439.286314
  4. 용제를 사용하지 않는 친환경 폴리우레탄 접착제의 합성 및 물성 : DPE-41, TDI, 개시제 및 가소제량의 영향 vol.23, pp.11, 2012, https://doi.org/10.5322/jesi.2014.23.11.1909
  5. Tailoring the hard domain cohesiveness in polyurethanes by interplay between the functionality and the content of chain extender vol.5, pp.94, 2012, https://doi.org/10.1039/c5ra15190b
  6. Synthesis and characterization of solvent-free waterborne polyurethane dispersion with both sulfonic and carboxylic hydrophilic chain-extending agents for matt coating applications vol.5, pp.130, 2012, https://doi.org/10.1039/c5ra21471h
  7. Evaluation of AgHAP-containing polyurethane foam dressing for wound healing: synthesis, characterization, in vitro and in vivo studies vol.3, pp.39, 2012, https://doi.org/10.1039/c5tb00995b
  8. Process investigating and modelling for the self-polymerization of toluene diisocyanate (TDI)-based polyurethane prepolymer vol.50, pp.17, 2012, https://doi.org/10.1007/s10853-015-9134-6
  9. Study of the correlation between flexible food packaging peeling resistance and surface composition for aluminum-metallized BOPP films aged at 60°C vol.93, pp.1, 2012, https://doi.org/10.1080/00218464.2016.1176921
  10. A Simple and Low‐Cost Synthesis of Antibacterial Polyurethane with High Mechanical and Antibacterial Properties vol.218, pp.20, 2012, https://doi.org/10.1002/macp.201700203
  11. A Study on Synthesis and Properties of Polyurethane Dispersion Adhesives vol.52, pp.4, 2012, https://doi.org/10.7473/ec.2017.52.4.295
  12. The peeling resistance of flexible laminated food packaging: Roles of the NCO:OH ratio and aluminum surface aging times vol.94, pp.10, 2012, https://doi.org/10.1080/00218464.2017.1387777
  13. Synthesis and characterization of alicyclic two-component waterborne polyurethane vol.47, pp.4, 2012, https://doi.org/10.1108/prt-07-2017-0064
  14. One-Step and Solvent-Free Synthesis of Polyethylene Glycol-Based Polyurethane As Solid-Solid Phase Change Materials for Solar Thermal Energy Storage vol.58, pp.8, 2012, https://doi.org/10.1021/acs.iecr.8b05903
  15. A Simple Method for the Quantification of Free Isocyanates on the Surface of Cellulose Nanocrystals upon Carbamation using Toluene Diisocyanate vol.2, pp.2, 2012, https://doi.org/10.3390/surfaces2020032
  16. Research on the interfacial reaction between amine group in urea and the coating materials of polyurethane coated urea vol.200, pp.1, 2012, https://doi.org/10.1080/10584587.2019.1592616
  17. High-performance thermosets with heat resistant properties derived from methacrylated isosorbide and epoxy-based vinyl ester vol.6, pp.12, 2012, https://doi.org/10.1088/2053-1591/ab63c5
  18. The Current Versatility of Polyurethane Three-Dimensional Printing for Biomedical Applications vol.26, pp.3, 2012, https://doi.org/10.1089/ten.teb.2019.0224
  19. Comparative effects of two different crosslinkers on the properties of vegetable oil‐based polyurethanes vol.137, pp.22, 2012, https://doi.org/10.1002/app.48741
  20. Improving the Low-Temperature Performance of RET Modified Asphalt Mixture with Different Modifiers vol.10, pp.11, 2012, https://doi.org/10.3390/coatings10111070
  21. Preparation of branched polyurethane curing agent by condensation polymerization and radical polymerization vol.2, pp.12, 2012, https://doi.org/10.1007/s42452-020-03841-5
  22. Synthesis of Piperazine Quaternary Ammonium Alkali Catalyst and Its Application in Isocyanate Polymerization vol.79, pp.9, 2012, https://doi.org/10.6023/a21060300
  23. Self-healing materials enable free-standing seamless large-scale 3D printing vol.64, pp.7, 2012, https://doi.org/10.1007/s40843-020-1603-y
  24. Adhesives for the Installation of Cast Basalt Elements on Metal and Comparison of Properties when Using Different Types of Fillers vol.898, pp.None, 2012, https://doi.org/10.4028/www.scientific.net/kem.898.35