Citation: Hai-Mu Ye, Xiao-Tong Chen, Ping Liu, Na Yan. Prominently Promoting the Formation of Poly(butylene adipate) α-Form Crystals by Coalescing from Inclusion Complex[J]. Chinese Journal of Polymer Science, ;2018, 36(7): 866-870. doi: 10.1007/s10118-018-2095-x shu

Prominently Promoting the Formation of Poly(butylene adipate) α-Form Crystals by Coalescing from Inclusion Complex

Department of Materials Science and Engineering, China University of Petroleum, Beijing 102249, China

Corresponding author: Hai-Mu Ye, yehaimu@cup.edu.cn
Received Date: 12 October 2017
Accepted Date: 23 November 2017
Available Online: 11 July 2018

We successfully use a co-precipitation method to prepare inclusion complex between poly(butylene adipate) (PBA) chains (guest component) and urea molecules (host component). The PBA/urea inclusion complex is confirmed to adopt a hexagonal crystal modification with lattice parameters of a = 8.14 Å and c = 10.92 Å, and the interaction between PBA chains and urea is van der Waals force. The singly isolated PBA chains are suggested to take some gauche conformation, which is different from the all-trans conformation in β-form PBA. Furthermore, we employ the isolated PBA chains which are uniformly pre-established in a specific conformation in urea channels to regulate the crystal form of PBA for the first time. After removing the host urea molecules, the coalesced PBA chains are found to solely crystallize into α-form crystals at different coalescing temperatures. By comparing the FTIR spectra, it is found that PBA chains in inclusion complex plausibly contain some similar conformers as those in α-form crystal, which is suggested to be the intrinsic reason for the sole formation of α-form crystals. This research proves that inclusion complex can be used as a very effective method to regulate polymorphism of semi-crystalline polymers.
- Poly(butylene adipate),
- Inclusion complex,
- Polymorphism,
- Chain conformation
1. [1]
  Minke, R.; Blackwell, J. Polymorphic structures of poly(tetramethylene adipate). J. Macromol. Sci., Part B: Phys. 1979, 16(3), 407-417. doi: 10.1080/00222347908212305
2. [2]
  Minke, R.; Blackwell, J. Single crystals of poly(tetramethylene adipate). J. Macromol. Sci., Part B: Phys. 1980, 18(2), 233-255. doi: 10.1080/00222348008241380
3. [3]
  Gan, Z.; Kuwabara, K.; Abe, H.; Iwata, T.; Doi, Y. The role of polymorphic crystal structure and morphology in enzymatic degradation of melt-crystallized poly(butylene adipate) films. Polym. Degrad. Stab. 2005, 87(1), 191-199. doi: 10.1016/j.polymdegradstab.2004.08.007
4. [4]
  Song, Y. Y.; Ye, H. M.; Xu, J.; Hou, K.; Zhou, Q.; Lu, G. W. Stretch-induced bidirectional polymorphic transformation of crystals in poly(butylene adipate). Polymer 2014, 55(13), 3054-3061. doi: 10.1016/j.polymer.2014.05.011
5. [5]
  Pouget, E.; Almontassir, A.; Casas, M. T.; Puiggalí, J. On the crystalline structures of poly(tetramethylene adipate). Macromolecules 2003, 36(3), 698-705. doi: 10.1021/ma0214052
6. [6]
  Iwata, T.; Kobayashi, S.; Tabata, K.; Yonezawa, N.; Doi, Y. Crystal structure, thermal behavior and enzymatic degradation of poly(tetramethylene adipate) solution-grown chain-folded lamellar crystals. Macromol. Biosci. 2004, 4(3), 296-307. doi: 10.1002/(ISSN)1616-5195
7. [7]
  Noguchi, K.; Kondo, H.; Ichikawa, Y.; Okuyama K.; Washiyama, J. Molecular and crystal structure of poly(tetramethylene adipate) α form based on synchrotron X-ray fiber diffraction. Polymer 2005, 46(24), 10823-10830. doi: 10.1016/j.polymer.2005.09.010
8. [8]
  Gan, Z.; Kuwabara, K.; Abe, H.; Iwata, T.; Doi, Y. Metastability and transformation of polymorphic crystals in biodegradable poly(butylene adipate). Biomacromolecules 2004, 5(2), 371-378. doi: 10.1021/bm0343850
9. [9]
  Gan, Z.; Abe, H.; Doi, Y. Temperature-induced polymorphic crystals of poly(butylene adipate). Macromol. Chem. Phys. 2002, 203(16), 2369-2374. doi: 10.1002/macp.200290007
10. [10]
  Woo, E. M.; Wu, M. C. Thermal and X-ray analysis of polymorphic crystals, melting, and crystalline transformation in poly(butylene adipate). J. Polym. Sci., Part B: Polym. Phys. 2005, 43(13), 1662-1672. doi: 10.1002/(ISSN)1099-0488
11. [11]
  Liang, R.; Chen, Y. C.; Zhang, C. Q.; Yin, J.; Liu, X. L.; Wang, L. K.; Kong, R.; Feng, X.; Yang, J. J. Crystallization behavior of biodegradable poly(ethylene adipate) modulated by a benign nucleating agent: Zinc phenylphosphonate. Chinese J. Polym. Sci. 2017, 35(4), 558-568. doi: 10.1007/s10118-017-1917-6
12. [12]
  Tang, Y. R.; Xu, J.; Guo, B. H. Polymorphic behavior and enzymatic degradation of poly(butylene adipate) in the presence of hexagonal boron nitride nanosheets. Ind. Eng. Chem. Res. 2015, 54(6), 1832-1841. doi: 10.1021/ie504593z
13. [13]
  Yang, J.; Liang, R.; Chen, Y.; Zhang, C.; Zhang, R.; Wang, X.; Kong, R.; Chen, Q. Using a self-assemblable nucleating agent to tailor crystallization behavior, crystal morphology, polymorphic crystalline structure, and biodegradability of poly(1,4-butylene adipate). Ind. Eng. Chem. Res. 2017, 56(28), 7910-7919. doi: 10.1021/acs.iecr.7b01783
14. [14]
  Yang, J.; Pan, P.; Hua, L.; Zhu, B.; Dong, T.; Inoue Y. Polymorphic crystallization and phase transition of poly(butylene adipate) in its miscible crystalline/crystalline blend with poly(vinylidene fluoride). Macromolecules 2010, 43(20), 8610-8618. doi: 10.1021/ma1015566
15. [15]
  Sun, X.; Pi, F.; Zhang, J.; Takahashi, I.; Wang, F.; Yan, S.; Ozaki, Y. Study on the phase transition behavior of poly(butylene adipate) in its blends with poly(vinyl phenol). J. Phys. Chem. B 2011, 115(9), 1950-1957. doi: 10.1021/jp110003m
16. [16]
  Wang, H. J.; Feng, H. P.; Wang, X. C.; Guo, P. Y.; Zhao, T. S.; Ren, L. F.; Qiang, X. H.; Xiang, Y. H.; Yan, C. Effects of crystallization temperature and blend ratio on the crystal structure of poly(butylene adipate) in the poly(butylene adipate)/poly(butylene succinate) blends. Chinese J. Polym. Sci. 2014, 32(4), 488-496. doi: 10.1007/s10118-014-1420-2
17. [17]
  Liang, Z.; Pan, P.; Zhu, B.; Inoue, Y. Isomorphic crystallization of poly(hexamethylene adipate-co-butylene adipate): regulating crystal modification of polymorphic polyester from internal crystalline lattice. Macromolecules 2010, 43(15), 6429-6437. doi: 10.1021/ma1008989
18. [18]
  Zhao, L.; Gan, Z. Effect of copolymerized butylene terephthalate chains on polymorphism and enzymatic degradation of poly(butylene adipate). Polym. Degrad. Stab. 2006, 91(10), 2429-2436. doi: 10.1016/j.polymdegradstab.2006.03.012
19. [19]
  Sun, Y.; Li, H.; Huang, Y.; Chen, E.; Zhao, L.; Gan, Z.; Yan, S. Epitaxial crystallization of poly(butylene adipate) on highly oriented polyethylene thin film. Macromolecules 2005, 38(7), 2739-2743. doi: 10.1021/ma0474269
20. [20]
  Ning, Z. B.; Nielsen, R.; Zhao, L. F.; Yu, D. H.; Gan, Z. H. Influence of teflon substrate on crystallization and enzymatic degradation of polymorphic poly(butylene adipate). Chinese J. Polym. Sci. 2014, 32(9), 1243-1252. doi: 10.1007/s10118-014-1503-0
21. [21]
  Tang, Y. R.; Li, T.; Ye, H. M.; Xu, J.; Guo, B. H. The effect of polymer-substrate interaction on the nucleation property: comparing study of graphene and hexagonal boron nitride nanosheets. Chinese J. Polym. Sci. 2016, 34(8), 1021-1031. doi: 10.1007/s10118-016-1816-2
22. [22]
  Imai, M.; Kaji, K.; Kanaya, T.; Sakai, Y. Ordering process in the induction period of crystallization of poly(ethylene terephthalate). Phys. Rev. B 1995, 52(17), 12696. doi: 10.1103/PhysRevB.52.12696
23. [23]
  Wang, C. X.; Zhang, X. C.; Song, Y. Y.; Zhou, Q.; Ye, H. M. Regulating the polymorphism behaviour and crystal transformation of poly(butylene adipate) by incorporating butylene fumarate units into the crystal lattice. RSC Adv. 2016, 6(1), 607-616. doi: 10.1039/C5RA21203K
24. [24]
  Song, Y. Y.; Ye, H. M.; Meng, X. Y.; Zhou, Q.; Lu, G. W. Novel polymorphism behavior of poly(butylene adipate) in its nanocomposites with carbon nanofibers. RSC Adv. 2015, 5(124), 102384-102391. doi: 10.1039/C5RA19099A
25. [25]
  Ye, H. M.; Song, Y. Y.; Meng, X.; Zhou, Q. Fractionated crystallization, polymorphism and crystal transformation of poly(butylene adipate) confined in electrospun immiscible blend fibers with polystyrene. RSC Adv. 2016, 6(61), 55961-55969. doi: 10.1039/C6RA09117B
26. [26]
  Lu, J.; Mirau, P. A.; Tonelli, A. E. Chain conformations and dynamics of crystalline polymers as observed in their inclusion compounds by solid-state NMR. Prog. Polym. Sci. 2002, 27(2), 357-401. doi: 10.1016/S0079-6700(01)00045-4
27. [27]
  Gurarslan, A.; Shen, J.; Tonelli, A. E. Behavior of poly(ε-caprolactone)s (PCLs) coalesced from their stoichiometric urea inclusion compounds and their use as nucleants for crystallizing PCL melts: Dependence on PCL molecular weights. Macromolecules 2012, 45(6), 2835-2840. doi: 10.1021/ma300270g
28. [28]
  Zhong, Z.; Yang, X.; Guo, B. H.; Xu, J., Huang, Y. Dissolution behavior of the crystalline inclusion complex formed by the drug diflunisal and poly(ε-caprolactone). Cryst. Growth Des. 2016, 17(1), 355-362.
29. [29]
  Ye, H. M.; Chen, X. T.; Liu, P.; Wu, S. Y.; Jiang, Z.; Xiong, B.; Xu, J. Preparation of poly(butylene succinate) crystals with exceptionally high melting point and crystallinity from its inclusion complex. Macromolecules 2017, 50(14), 5425-5433. doi: 10.1021/acs.macromol.7b00656
30. [30]
  Ye, H. M.; Song, Y. Y.; Xu, J.; Guo, B. H.; Zhou, Q. Melting behavior of inclusion complex formed between polyethylene glycol oligomer and urea. Polymer 2013, 54(13), 3385-3391. doi: 10.1016/j.polymer.2013.04.026
31. [31]
  Chenite, A.; Brisse, F. Structural investigations of urea-aliphatic polyester adducts. Macromolecules 1993, 26(12), 3055-3061. doi: 10.1021/ma00064a010
32. [32]
  Smith, A. E. The crystal structure of the urea-hydrocarbon complexes. Acta Crystallogr. 1952, 5(2), 224-235. doi: 10.1107/S0365110X52000629
33. [33]
  Meaurio, E., López-Rodríguez, N.; Sarasua, J. R. Infrared spectrum of poly(L-lactide): application to crystallinity studies. Macromolecules 2006, 39(26), 9291-9301. doi: 10.1021/ma061890r
34. [34]
  Meaurio, E., Zuza, E., López-Rodríguez, N.; Sarasua, J. R. Conformational behavior of poly(L-lactide) studied by infrared spectroscopy. J. Phys. Chem. B 2006, 110(11), 5790-5800. doi: 10.1021/jp055203u
35. [35]
  Ma, W.; Zhang, J.; Wang, X. Formation of poly(vinylidene fluoride) crystalline phases from tetrahydrofuran/N,N-dimethylformamide mixed solvent. J. Mater. Sci. 2008, 43(1), 398-401. doi: 10.1007/s10853-007-2211-8
36. [36]
  Yan, C.; Zhang, Y.; Hu, Y.; Ozaki, Y.; Shen, D.; Gan, Z.; Yan, S.; Takahashi, I. Melt crystallization and crystal transition of poly(butylene adipate) revealed by infrared spectroscopy. J. Phys. Chem. B 2008, 112(11), 3311-3314. doi: 10.1021/jp077195i
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