Citation: Fei Liu, De-Quan Chi, Hai-Ning Na, Jin Zhu. Isothermal Crystallization Kinetics and Crystalline Morphologies of Poly(butylene adipate-co-butylene 1, 4-cyclohexanedicarboxylate) Copolymers[J]. Chinese Journal of Polymer Science, ;2018, 36(6): 756-764. doi: 10.1007/s10118-018-2051-9 shu

Isothermal Crystallization Kinetics and Crystalline Morphologies of Poly(butylene adipate-co-butylene 1, 4-cyclohexanedicarboxylate) Copolymers

Fei Liu ^a ,
De-Quan Chi ^a,b ,
Hai-Ning Na ^a,, ,
Jin Zhu ^a

a.
Ningbo Key Laboratory of Polymer Materials, Ningbo Institute of Materials Technology and Engineering, Chinese Academy of Sciences, Ningbo 315201, China
b.
College of Materials Science and Engineering, Qingdao University of Science and Technology, Qingdao 266042, China

Corresponding author: Hai-Ning Na, nahaining@nimte.ac.cn
Received Date: 1 September 2017
Accepted Date: 25 September 2017
Available Online: 8 February 2018

In this study, the isothermal crystallization kinetics and crystalline morphology of poly(butylene adipate-co-butylene 1, 4-cyclohexanedicarboxylate) (PBAC), which refers to a copolyester containing a non-planar ring structure, were investigated by differential scanning calorimetry and polarized optical microscopy, and compared with those of neat poly(butylene 1, 4-cyclohexanedicarboxylate) (PBC). The results indicate that the introduction of butylene adipate (BA) unit into PBAC did not change the intrinsical crystallization mechanism. But, the crystallization rate and ability, and equilibrium melting temperature of PBAC copolymers were reduced. All PBC and PBAC copolymers could only form high density of nucleation from melt at given supercooling, while no Maltese cross or ring-banded spherulites could be observed. PBAC copolymers with a high amount of BA unit became amorphous after quenching with liquid nitrogen from melt, while PBC and PBAC copolymers with a low amount of BA unit could still form a large amount of nuclei under the same treatment.
1. [1]
  Tserki V., Matzinos P., Pavlidou E., Vachliotis D., Panayiotou C.. Biodegradable aliphatic polyesters. part Ⅰ. properties and biodegradation of poly(butylene succinate-co-butylene adipate)[J]. Polym. Degrad. Stab., 2006,91:367-376. doi: 10.1016/j.polymdegradstab.2005.04.035
2. [2]
  Gan Z., Kuwabara K., Abe H., Iwata T., Doi Y.. Metastability and transformation of polymorphic crystals in biodegradable poly(butylene adipate)[J]. Biomacromolecules, 2004,5:371-378. doi: 10.1021/bm0343850
3. [3]
  Xu J., Guo B. H.. Poly(butylene succinate) and its copolymers:research, development and industrialization[J]. Biotechnol. J., 2010,5(11):1149-1163. doi: 10.1002/biot.v5.11
4. [4]
  Gan Z., Abe H., Kurokawa H., Doi Y.. Solid-state microstructures, thermal properties, and crystallization of biodegradable poly(butylene succinate) (PBS) and its copolyesters[J]. Biomacromolecules, 2001,2(2):605-613. doi: 10.1021/bm015535e
5. [5]
  Kint D., Munoz-Guerra S.. A review on the potential biodegradability of poly(ethylene terephthalate)[J]. Polym. Int., 1999,48(5):346-352. doi: 10.1002/(SICI)1097-0126(199905)48:5<346::AID-PI156>3.0.CO;2-N
6. [6]
  Stein R. S., Misra A.. Morphological studies on polybutylene terephthalate[J]. J. Polym. Sci. Polym. Phys. Ed., 1980,18(2):327-342. doi: 10.1002/pol.1980.180180215
7. [7]
  Herrera R., Franco L., Rodríguez-Galán A., Puiggalí J.. Characterization and degradation behavior of poly(butylene adipate-co-terephthalate)s[J]. J. Polym. Sci., Part A:Polym. Chem., 2002,40(23):4141-4157. doi: 10.1002/pola.v40:23
8. [8]
  Yokouchi M., Sakakibara Y., Chatani Y., Tadokoro H., Tanaka T.. Structures of two crystalline forms of poly(buty1ene terephthalate) and reversible transition between them by mechanical deformation[J]. Macromolecules, 1975,9:266-273.
9. [9]
  Kai W., Zhu B., He Y., Inoue Y.. Crystallization of poly(butylene adipate) in the presence of nucleating agents[J]. J. Polym. Sci., Part B:Polym. Phys., 2005,43(17):2340-2351. doi: 10.1002/(ISSN)1099-0488
10. [10]
  Yang J., Pan P., Dong T., Inoue Y.. Crystallization kinetics and crystalline structure of biodegradable poly(ethylene adipate)[J]. Polymer, 2010,51(3):807-815. doi: 10.1016/j.polymer.2009.11.065
11. [11]
  Vasanthan N., Ozkaya S., Yaman M.. Morphological and conformational changes of poly(trimethylene terephthalate) during isothermal melt crystallization[J]. J. Phys. Chem. B, 2010,114:13069-13075.
12. [12]
  Yang J., Pan P., Hua L., Xie Y., Dong T., Zhu B., Inoue Y., Feng X.. Fractionated crystallization, polymorphic crystalline structure, and spherulite morphology of poly(butylene adipate) in its miscible blend with poly(butylene succinate)[J]. Polymer, 2011,52(15):3460-3468. doi: 10.1016/j.polymer.2011.05.041
13. [13]
  Chen Y. A., Wu T. M.. Crystallization kinetics of poly(1, 4-butylene adipate) with stereocomplexed poly(lactic acid) serving as a nucleation agent[J]. Ind. Eng. Chem. Res., 2014,53:16689-16695. doi: 10.1021/ie503303u
14. [14]
  Milani A., Galimberti D.. Polymorphism of poly(butylene terephthalate) investigated by means of periodic density functional theory calculations[J]. Macromolecules, 2014,47(3):1046-1052. doi: 10.1021/ma402602f
15. [15]
  Androsch R., Rhoades A. M., Stolte I., Schick C.. Density of heterogeneous and homogeneous crystal nuclei in poly(butylene terephthalate)[J]. Eur. Polym. J., 2015,66:180-189. doi: 10.1016/j.eurpolymj.2015.02.013
16. [16]
  Cui Z., Qiu Z.. Thermal properties and crystallization kinetics of poly(butylene suberate)[J]. Polymer, 2015,67:12-19. doi: 10.1016/j.polymer.2015.04.069
17. [17]
  Park S. S., Chae S. H., Im S. S.. Transesterification and crystallization behavior of poly(butylene succinate)/poly(butylene terephthalate) block copolymers[J]. J. Polym. Sci., Part A:Polym. Chem., 1998,36(1):147-156. doi: 10.1002/(ISSN)1099-0518
18. [18]
  Nikolic M. S., Djonlagic J.. Synthesis and characterization of biodegradable poly(butylene succinate-co-butylene adipate)s[J]. Polym. Degrad. Stab., 2001,74:263-270. doi: 10.1016/S0141-3910(01)00156-2
19. [19]
  Kuwabara K., Gan Z., Nakamura T., Abe H., Doi Y.. Crystalline/amorphous phase structure and molecular mobility of biodegradable poly(butylene adipate-co-butylene terephthalate) and related polyesters[J]. Biomacromolecules, 2002,3(2):390-396. doi: 10.1021/bm0156476
20. [20]
  Cranston E., Kawada J., Raymond S., Morin F. G., Marchessault R. H.. Cocrystallization model for synthetic biodegradable poly(butylene adipate-co-butylene terephthalate)[J]. Biomacromolecules, 2003,4:995-999. doi: 10.1021/bm034089n
21. [21]
  Gan Z., Kuwabara K., Yamamoto M., Abe H., Doi Y.. Solid-state structures and thermal properties of aliphatic-aromatic poly(butylene adipate-co-butylene terephthalate) copolyesters[J]. Polym. Degrad. Stab., 2004,83:289-300. doi: 10.1016/S0141-3910(03)00274-X
22. [22]
  Ren M., Song J., Song C., Zhang H., Sun X., Chen Q., Zhang H., Mo Z.. Crystallization kinetics and morphology of poly(butylene succinate-co-adipate)[J]. J. Polym. Sci., Part B:Polym. Phys., 2005,43(22):3231-3241. doi: 10.1002/(ISSN)1099-0488
23. [23]
  Shi X. Q., Ito H., Kikutani T.. Characterization on mixed-crystal structure and properties of poly(butylene adipate-co-terephthalate) biodegradable fibers[J]. Polymer, 2005,46:11442-11450. doi: 10.1016/j.polymer.2005.10.065
24. [24]
  Qiu Z., Yan C., Lu J., Yang W., Ikehara T., Nishi T.. Various crystalline morphology of poly(butylene succinate-co-butylene adipate) in its miscible blends with poly(vinylidene fluoride)[J]. J. Phys. Chem. B, 2007,111(11):2783-2789. doi: 10.1021/jp067606f
25. [25]
  Hwang S. Y., Jin X. Y., Yoo E. S., Im S. S.. Synthesis, physical properties and enzymatic degradation of poly(oxyethylene-b-butylene succinate) ionomers[J]. Polymer, 2011,52(13):2784-2791. doi: 10.1016/j.polymer.2011.04.065
26. [26]
  Ojijo V., Sinha Ray S., Sadiku R.. Role of specific interfacial area in controlling properties of immiscible blends of biodegradable polylactide and poly[(butylene succinate)-coadipate][J]. ACS Appl. Mater. Interfaces, 2012,4(12):6690-6701. doi: 10.1021/am301842e
27. [27]
  Wang X., Shi J., Chen Y., Fu Z., Shi Y.. Nonisothermal crystallization kinetics of poly(butylene adipate-co-terephthalate) Copolyester[J]. China Pet. Process. Petrochemical Technol., 2012,14(1):74-79.
28. [28]
  Dil E. J., Carreau P. J., Favis B.D.. Morphology, miscibility and continuity development in poly(lactic acid)/poly(butylene adipate-co-terephthalate) blends[J]. Polymer, 2015,68:202-212. doi: 10.1016/j.polymer.2015.05.012
29. [29]
  Liu F., Zhang J., Wang J., Liu X., Zhang R., Hu G., Na H., Zhu J.. Soft segment free thermoplastic polyester elastomers with high performance[J]. J. Mater. Chem. A, 2015,3:13637-13641. doi: 10.1039/C5TA03325J
30. [30]
  Brunelle D. J., Jang T.. Optimization of poly(1, 4-cyclohexylidene cyclohexane-1, 4-dicarboxylate) (PCCD) preparation for increased crystallinity[J]. Polymer, 2006,47(11):4094-4104. doi: 10.1016/j.polymer.2006.02.070
31. [31]
  Berti C., Celli A., Marchese P., Marianucci E., Barbiroli G., Di Credico F.. Influence of molecular structure and stereochemistry of the 1, 4-cyclohexylene ring on thermal and mechanical behavior of poly(butylene 1, 4-cyclohexanedicarboxylate)[J]. Macromol. Chem. Phys., 2008,209(13):1333-1344. doi: 10.1002/macp.v209:13
32. [32]
  Gigli M., Lotti N., Vercellino M., Visai L., Munari A.. Novel ether-linkages containing aliphatic copolyesters of poly(butylene 1, 4-cyclohexanedicarboxylate) as promising candidates for biomedical applications[J]. Mater. Sci. Eng. C Mater. Biol. Appl., 2014,34:86-97. doi: 10.1016/j.msec.2013.08.013
33. [33]
  Gigli M., Lotti N., Gazzano M., Siracusa V., Finelli L., Munari A., Dalla Rosa M.. Fully aliphatic copolyesters based on poly(butylene 1, 4-cyclohexanedicarboxylate) with promising mechanical and barrier properties for food packaging applications[J]. Ind. Eng. Chem. Res., 2013,52(36):12876-12886. doi: 10.1021/ie401781d
34. [34]
  Commereuc S., Askanian H., Verney V., Celli A., Marchese P., Berti C.. About the end life of novel aliphatic and aliphatic-aromatic (co)polyesters after UV-weathering:structure/degradability relationships[J]. Polym. Degrad. Stab., 2013,98(7):1321-1328. doi: 10.1016/j.polymdegradstab.2013.03.030
35. [35]
  Berti C., Binassi E., Celli A., Colonna M., Fiorini M., Marchese P., Marianucci E., Gazzano M., Credico F. D. I., Brunelle D.J.. Poly(1, 4-cyclohexylenedimethylene 1, 4-cyclohexanedicarboxylate):influence of stereochemistry of 1, 4-cyclohexylene units on the thermal properties[J]. J. Polym. Sci., Part B:Polym. Phys, 2008,46:619-630. doi: 10.1002/(ISSN)1099-0488
36. [36]
  Chen L. P., Yee A. F., Goetz J. M., Schaefer J.. Molecular structure effects on the secondary relaxation and impact strength of a series of polyester copolymer glasses[J]. Macromolecules, 1998,31(16):5371-5382. doi: 10.1021/ma971671t
37. [37]
  Gong Y., Hu C. W., Li H., Huang K. L., Tang W.. Isomer transformation and photoluminescence in novel coordination polymers constructed from 1, 4-cyclohexanedicarboxylic acid and imidazole[J]. J. Solid State Chem., 2005,178(10):3152-3158. doi: 10.1016/j.jssc.2005.07.023
38. [38]
  Liu F., Qiu J., Wang J., Zhang J., Na H., Zhu J.. Role of cis-1, 4-cyclohexanedicarboxylic acid in the regulation of the structure and properties of a poly(butylene adipate-co-butylene 1, 4-cyclohexanedicarboxylate) copolymer[J]. RSC Adv, 2016,6(70):65889-65897. doi: 10.1039/C6RA13495E
39. [39]
  Qiu J., Liu F., Zhang J., Na H., Zhu J.. Non-planar ring contained polyester modifying polylactide to pursue high toughness[J]. Compos. Sci. Technol., 2016,128:41-48. doi: 10.1016/j.compscitech.2016.03.014
40. [40]
  Celli A., Marchese P., Sullalti S., Berti C., Barbiroli G.. Eco-friendly poly(butylene 1, 4-cyclohexanedicarboxylate):relationships between stereochemistry and crystallization behavior[J]. Macromol. Chem. Phys., 2011,212(14):1524-1534. doi: 10.1002/macp.v212.14
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