Citation: Jie Miao, Zhen Wang, Xiao-dong Ji, Jing-ling Yan. Synthesis and Properties of Creosol-derived Polyimides[J]. Acta Polymerica Sinica, ;2019, 50(3): 261-270. doi: 10.11777/j.issn1000-3304.2019.18201 shu

Synthesis and Properties of Creosol-derived Polyimides

Jie Miao ^1,2 ,
Zhen Wang ¹ ,
Xiao-dong Ji ¹ ,
Jing-ling Yan ^1,3,,

1.
Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022
2.
College of Applied Chemistry and Engineering, University of Science and Technology of China, Hefei 230026
3.
Ningbo Institute of Material Technology and Engineering, Chinese Academy of Sciences, Ningbo 315201

Corresponding author: Jing-ling Yan, jyan@ciac.ac.cn
Received Date: 21 September 2018
Revised Date: 14 October 2018
Available Online: 15 November 2018

The development of high-performance polymers using bio-renewable feedstocks will promote a sustainable society. However, it remains a challenge to fabricate polyimides rich in bio-based component while high in heat resistance. In this work, three types of bio-based dianhydrides were synthesized using bio-renewable creosol as the raw material, which were then applied for preparing three series of polyimides via polycondensation with petroleum- or bio-based diamines. The molecular weights of these bio-based polyimides were in the range of 14 – 233 kg mol⁻¹. The inherent viscosity of these polymers spanned a range 0.4 – 2.06 dL g⁻¹. Most of the polyimides were soluble in common organic solvents, and flexible films could be readily cast from their solutions. The bio-based contents of these polymers ranged from 31.8% to 56.4%. The temperatures at 5% weight loss (T_5%) and the glass transition temperatures (T_g) of bio-based polyetherimides (PI-I and PI-II series) were 406 – 453 °C and 213 – 235 °C, respectively, while PI-III series containing dioxin segments exhibited a T_5% at 490 – 508 °C and T_g at 378 – 424 °C due to the existence of fused aromatic rings. The tensile strength, modulus, and elongation at break of these polyimides were 70 – 115 MPa, 1.80 – 2.8 GPa, and 3.5% – 20.4%, respectively. The above mentioned results indicated comparable thermal and mechanical properties between the bio-based polyimies in this study and those made from petroleum-based monomers, such as Ultem^® and Kapton^®. Due to an excellent combination of high bio-based contents and outstanding thermal and mechanical properties, these polyimides showed great potential in various applications as films and engineering plastics, replacing petroleum-based polyimides.
- Bio-based polyimides,
- Creosol,
- Dianhydrides,
- Thermal and mechanical properties
1. [1]
  Sroog C E. Prog Polym Sci, 1991, 16: 561 − 694 doi: 10.1016/0079-6700(91)90010-I
2. [2]
  Abajo J D, Campa J G D L. J Appl Polym Sci, 1985, 30: 2401 − 2411 doi: 10.1002/app.1985.070300611
3. [3]
  Belgacem N M. Monomers, Polymers and Composites from Renewable Resources. Oxford: Elsevier Ltd, 2008. 43 − 46
4. [4]
  Hu J H, Wang Z P, Lu Z, Chen C, Shi M, Wang J B, Zhao E J, Zeng K, Yang G. Polymer, 2017, 119: 59 − 65 doi: 10.1016/j.polymer.2017.05.012
5. [5]
  Hu J H, Chen C, Yang F, He B, Lu Z, Li R K, Yang G, Zeng K. Polymer, 2018, 146: 407 − 419 doi: 10.1016/j.polymer.2018.05.006
6. [6]
  Suvannasara P, Tateyama S, Miyasato A, Matsumura K, Shimoda T, Ito T, Yamagata Y, Fujita T, Takaya N, Kaneko T. Macromolecules, 2014, 47: 1586 − 1593 doi: 10.1021/ma402499m
7. [7]
  Ji X D, Wang Z K, Yan J L, Wang Z. Polymer, 2015, 74: 38 − 45 doi: 10.1016/j.polymer.2015.07.051
8. [8]
  Mi Z M, Liu Z X, Tian C S, Zhao X G, Zhou H W, Wang D M, Chen C H. J Polym Sci, Part A: Polym Chem, 2017, 55: 3253 − 3265 doi: 10.1002/pola.v55.19
9. [9]
  Yang G L, Zhang R, Huang H H, Liu L X, Wang L, Chen Y M. RSC Adv, 2015, 5: 67574 − 67582 doi: 10.1039/C5RA14526K
10. [10]
  Kuhire S S, Sharma P, Chakrabarty S, Wadgaonkar P P. J Polym Sci, Part A: Polym Chem, 2017, 55: 3636 − 3645 doi: 10.1002/pola.v55.21
11. [11]
  Raquez J M, Deléglise M, Lacrampe M F, Krawczak P. Prog Polym Sci, 2010, 35: 487 − 509 doi: 10.1016/j.progpolymsci.2010.01.001
12. [12]
13. [13]
  Laurichesse S, Avérous L. Prog Polym Sci, 2014, 39: 1266 − 1290 doi: 10.1016/j.progpolymsci.2013.11.004
14. [14]
  Pion F, Ducrot P H, Allais F. Macromol Chem Phys, 2014, 215: 431 − 439 doi: 10.1002/macp.v215.5
15. [15]
  Mialon L, Vanderhenst R, Pemba A G, Miller S A. Macromol Rapid Commun, 2011, 32: 1386 − 1392 doi: 10.1002/marc.201100242
16. [16]
  Kuhire S S, Avadhani C V, Wadgaonkar P P. Eur Polym J, 2015, 71: 547 − 557 doi: 10.1016/j.eurpolymj.2015.08.021
17. [17]
  Fache M, Montérémal C, Boutevin B, Caillol S. Eur Polym J, 2015, 73: 344 − 362 doi: 10.1016/j.eurpolymj.2015.10.032
18. [18]
  Meylemans H A, Harvey B G, Reams J T, Guenthner A J, Cambrea L R, Groshens T J, Baldwin L C, Garrison M D, Mabry J M. Biomacromolecules, 2013, 14: 771 − 780 doi: 10.1021/bm3018438
19. [19]
  Hocking M B. J Chem Educ, 1997, 74: 1055 − 1059 doi: 10.1021/ed074p1055
20. [20]
  Wang Q, Yang Y, Li Y, Yu W, Hou Z J. Tetrahedron, 2006, 62: 6107 − 6112 doi: 10.1016/j.tet.2006.03.111
21. [21]
  Meylemans H A, Groshens T J, Harvey B G. ChemSusChem, 2012, 5: 206 − 210 doi: 10.1002/cssc.201100402
22. [22]
  Garrison M D, Harvey B G. J Appl Polym Sci, 2016, 133: 43621 − 43623
23. [23]
  Harvey B G, Guenthner A J, Koontz T A, Storch P J, Reams J T, Groshens T J. Green Chem, 2016, 18: 2416 − 2423 doi: 10.1039/C5GC02893K
24. [24]
  Thiyagarajan S, Gootjes L, Vogelzang W, Wu J, van Haveren J, van Es D S. Tetrahedron, 2011, 67: 383 − 389 doi: 10.1016/j.tet.2010.11.031
25. [25]
  Li Q X, Fang X Z, Wang Z, Gao L X, Ding M X. J Polym Sci, Part A: Polym Chem, 2003, 41: 3249 − 3260
26. [26]
  Norton G A, Devlin S L. Bioresour Technol, 2006, 97: 2084 − 2090 doi: 10.1016/j.biortech.2005.08.017
27. [27]
  Saini A K, Carlin C M, Patterson H H. J Polym Sci, Part A: Polym Chem, 1993, 31: 2751 − 2758 doi: 10.1002/pola.1993.080311111
28. [28]
  Sazanov Y N, Shibaev L A. Thermochim Acta, 1976, 15: 43 − 54 doi: 10.1016/0040-6031(76)80090-1
29. [29]
  Wu J, Jasinskawalc L, Dudenko D, Rozanski A, Hansen M R, Es D V, Koning C E. Macromolecules, 2012, 45: 9333 − 9346 doi: 10.1021/ma302126b
30. [30]
  Ding M X. Prog Polym Sci, 2007, 32: 623 − 668 doi: 10.1016/j.progpolymsci.2007.01.007
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