Citation: Chanita Sungkapreecha, Walter W. Focke, René Androsch. Competition between Liquid-liquid De-mixing, Crystallization, and Glass Transition in Solutions of PLA of Different Stereochemistry and DEET[J]. Chinese Journal of Polymer Science, ;2020, 38(2): 174-178. doi: 10.1007/s10118-019-2314-0 shu

Competition between Liquid-liquid De-mixing, Crystallization, and Glass Transition in Solutions of PLA of Different Stereochemistry and DEET

a.
Interdisciplinary Center for Transfer-oriented Research in Natural Sciences, Martin Luther University Halle-Wittenberg, 06099 Halle/Saale, Germany
b.
University of Pretoria Institute for Sustainable Malaria Control and MRC Collaborating Centre for Malaria Research, Department of Chemical Engineering, University of Pretoria, Private Bag X20, Hatfield 0028, South Africa

Corresponding author: René Androsch, rene.androsch@iw.uni-halle.de
Received Date: 17 May 2019
Revised Date: 4 June 2019
Available Online: 26 July 2019

Liquid-liquid (L-L) de-mixing and vitrification of solutions of either crystallizable poly(L-lactic acid) (PLLA) or non-crystallizable poly(D/L-lactic acid) (PDLLA) with 50 m% N,N-diethyl-3-methylbenzamide (DEET) were analyzed by calorimetry and cloud-point measurements, which allows drawing conclusions about the effect of polymer stereochemistry on the phase behavior. Regardless of the PLA stereochemistry, vitrification of the solutions on fast cooling, hindering crystallization of PLLA, occurred below −20 °C and suppressed prior L-L de-mixing. The experimental results prove that crystallization in samples containing crystallizable PLLA, observed at around 55 °C on slow cooling, is not preceded by L-L de-mixing.
- Crystallization,
- PLA,
- DEET,
- Liquid-liquid phase separation,
- Thermally-induced phase separation (TIPS)
1. [1]
  Sungkapreecha, C.; Iqbal, N.; Gohn, A. M.; Focke, W. W.; Androsch, R. Phase behavior of the polymer/drug system PLA/DEET. Polymer 2017, 126, 116−125. doi: 10.1016/j.polymer.2017.08.031
2. [2]
  Sungkapreecha, C.; Beily, M. J.; Kressler, J.; Focke, W. W.; Androsch, R. Phase behavior of the polymer/drug system PLA/DEET: effect of PLA molar mass on subambient liquid-liquid phase separation. Thermochim. Acta 2018, 660, 77−81. doi: 10.1016/j.tca.2017.12.021
3. [3]
  Martínez-Pérez, C. A.; Olivas-Armendariz, I.; Castro-Carmona, J. S.; García-Casillas, P. E. Scaffolds for tissue engineering via thermally induced phase separation. Adv. Regenerative Med.: InTech 2011, 275−294.
4. [4]
  Lloyd, D. R.; Kinzer, K. E.; Tseng, H. S. Microporous membrane formation via thermally induced phase separation. I. Solid-liquid phase separation. J. Membr. Sci. 1990, 52, 239−261. doi: 10.1016/S0376-7388(00)85130-3
5. [5]
  Lloyd, D. R.; Kim, S. S.; Kinzer, K. E. Microporous membrane formation via thermally-induced phase separation. II. Liquid-liquid phase separation. J. Membr. Sci. 1991, 64, 1−11. doi: 10.1016/0376-7388(91)80073-F
6. [6]
  Katz, T. M.; Miller, J. H.; Hebert, A. A. Insect repellents: historical perspectives and new developments. J. Am. Acad. Dermatol. 2008, 58, 865−871. doi: 10.1016/j.jaad.2007.10.005
7. [7]
  Roberts, J. R.; Reigart, J. R. Does anything beat DEET? Pediatr. Ann. 2004, 33, 443−453.
8. [8]
  Huggins, M. L. Solutions of long chain compounds. J. Chem. Phys. 1941, 9, 440−440.
9. [9]
  Flory, P. J. Thermodynamics of high polymer solutions. J. Chem. Phys. 1942, 10, 51−61. doi: 10.1063/1.1723621
10. [10]
  Shultz, A. R.; Flory, P. J. Phase equilibria in polymer-solvent systems. J. Am. Chem. Soc. 1952, 74, 4760−4767. doi: 10.1021/ja01139a010
11. [11]
  Shultz, A. R.; Flory, P. J. Phase equilibria in polymer-solvent systems. II. Thermodynamic interaction parameters from critical miscibility data. J. Am. Chem. Soc. 1953, 75, 3888−3892. doi: 10.1021/ja01112a005
12. [12]
  Mandelkern, L. Crystallization kinetics in high polymers. II. Polymer-diluent mixtures. J. Appl. Phys. 1955, 26, 443−451. doi: 10.1063/1.1722016
13. [13]
  Product information, Sulzer Chemtec Ltd. https://www.sulzer.com/-/media/files/products/polymer_production_technology/brochures/fact_sheet_polylactides.ashx?la=en: accessed 14/06/2019.
14. [14]
  Androsch, R.; Di Lorenzo, M. L.; Schick, C. Crystal nucleation of random L/D-lactide copolymers. Eur. Polym. J. 2016, 75, 474−485. doi: 10.1016/j.eurpolymj.2016.01.020
15. [15]
  Product information, Evonik Nutrition & Care GmbH; https://healthcare.evonik.com/product/health-care/en/products/biomaterials/resomer/pages/controlled-release.aspx: accessed 13/06/2019.
16. [16]
  Product information, Sigma-Aldrich Chemie GmbH; http://www.sigmaaldrich.com/catalog/product/aldrich/d100951: accessed 13/06/2019.
17. [17]
  Di Lorenzo, M. L.; Rubino, P.; Luijkx, R.; Hélou, M. Influence of chain structure on crystal polymorphism of poly(lactic acid). Part 1: effect of optical purity of the monomer. Colloid Polym. Sci. 2014, 292, 399−409. doi: 10.1007/s00396-013-3081-z
18. [18]
  Sungkapreecha, C.; Iqbal, N.; Focke, W. W.; Androsch, R. Crystallization of poly(L-lactic acid) (PLLA) in solution with the mosquito-repellent N,N-diethyl-3-methyl-benzamide (DEET). Polym. Cry. 2019, 2, e10029.
19. [19]
  Androsch, R.; Schick, C.; Di Lorenzo, M. L. Kinetics of nucleation and growth of crystals of poly(L-lactic acid). Adv. Polym. Sci. 2018, 279, 235−272.
20. [20]
  Androsch, R.; Schick, C. Interplay between the relaxation of the glass of random L/D-lactide copolymers and homogeneous crystal nucleation: evidence for segregation of chain defects. J. Phys. Chem. B 2016, 120, 4522−4528. doi: 10.1021/acs.jpcb.6b03022
21. [21]
  Righetti, M. C.; Gazzano, M.; Di Lorenzo, M. L.; Androsch, R. Enthalpy of melting of α′-and α-crystals of poly (L-lactic acid). Eur. Polym. J. 2015, 70, 215−220.
22. [22]
  Hu, W. B.; Mathot, V. B. F.; Frenkel, D. Lattice model study of the thermodynamic interplay of polymer crystallization and liquid-liquid demixing. J. Chem. Phys. 2003, 118, 10343−10348. doi: 10.1063/1.1572462
23. [23]
  Zha, L. Y.; Hu, W. B. Homogeneous crystal nucleation triggered by spinodal decomposition in polymer solutions. J. Phys. Chem. B 2007, 111, 11373−11378. doi: 10.1021/jp068431c
1. [1]
  Wangyan Hu , Ke Li , Xiangnan Dou , Ning Li , Xiayan Wang . Nano-sized stationary phase packings retained by single-particle frit for microchip liquid chromatography. Chinese Chemical Letters, 2024, 35(4): 108806-. doi: 10.1016/j.cclet.2023.108806
2. [2]
  Jun Lu , Jinrui Yan , Yaohao Guo , Junjie Qiu , Shuangliang Zhao , Bo Bao . Controlling solid form and crystal habit of triphenylmethanol by antisolvent crystallization in a microfluidic device. Chinese Chemical Letters, 2024, 35(4): 108876-. doi: 10.1016/j.cclet.2023.108876
3. [3]
  Ce Liang , Qiuhui Sun , Adel Al-Salihy , Mengxin Chen , Ping Xu . Recent advances in crystal phase induced surface-enhanced Raman scattering. Chinese Chemical Letters, 2024, 35(9): 109306-. doi: 10.1016/j.cclet.2023.109306
4. [4]
  Xingyu Chen , Sihui Zhuang , Weiyao Yan , Zhengli Zeng , Jianguo Feng , Hongen Cao , Lei Yu . Synthesis, antibacterial evaluation, and safety assessment of Se@PLA as a potent bactericide against Xanthomonas oryzae pv. oryzae. Chinese Chemical Letters, 2024, 35(10): 109635-. doi: 10.1016/j.cclet.2024.109635
5. [5]
  Hongxia Li , Xiyang Wang , Du Qiao , Jiahao Li , Weiping Zhu , Honglin Li . Mechanism of nanoparticle aggregation in gas-liquid microfluidic mixing. Chinese Chemical Letters, 2024, 35(4): 108747-. doi: 10.1016/j.cclet.2023.108747
6. [6]
  Pengcheng Su , Shizheng Chen , Zhihong Yang , Ningning Zhong , Chenzi Jiang , Wanbin Li . Vapor-phase postsynthetic amination of hypercrosslinked polymers for efficient iodine capture. Chinese Chemical Letters, 2024, 35(9): 109357-. doi: 10.1016/j.cclet.2023.109357
7. [7]
  Lingling Su , Qunyan Wu , Congzhi Wang , Jianhui Lan , Weiqun Shi . Theoretical design of polyazole based ligands for the separation of Am(Ⅲ)/Eu(Ⅲ). Chinese Chemical Letters, 2024, 35(8): 109402-. doi: 10.1016/j.cclet.2023.109402
8. [8]
  Jingwen Zhao , Jianpu Tang , Zhen Cui , Limin Liu , Dayong Yang , Chi Yao . A DNA micro-complex containing polyaptamer for exosome separation and wound healing. Chinese Chemical Letters, 2024, 35(9): 109303-. doi: 10.1016/j.cclet.2023.109303
9. [9]
  Huangjie Lu , Yingzhe Du , Peng Lin , Jian Lin . Separation of americium from lanthanides based on oxidation state control. Chinese Journal of Structural Chemistry, 2024, 43(10): 100344-100344. doi: 10.1016/j.cjsc.2024.100344
10. [10]
  Tian Feng , Yun-Ling Gao , Di Hu , Ke-Yu Yuan , Shu-Yi Gu , Yao-Hua Gu , Si-Yu Yu , Jun Xiong , Yu-Qi Feng , Jie Wang , Bi-Feng Yuan . Chronic sleep deprivation induces alterations in DNA and RNA modifications by liquid chromatography-mass spectrometry analysis. Chinese Chemical Letters, 2024, 35(8): 109259-. doi: 10.1016/j.cclet.2023.109259
11. [11]
  Haoyang Wang , Ronghao Zhang , Yanlun Ren , Li Zhang . A convenient method for measuring gas-liquid volumetric mass transfer coefficient in micro reactors. Chinese Chemical Letters, 2024, 35(4): 108833-. doi: 10.1016/j.cclet.2023.108833
12. [12]
  Cheng Guo , Xiaoxiao Zhang , Xiujuan Hong , Yiqiu Hu , Lingna Mao , Kezhi Jiang . Graphene as adsorbent for highly efficient extraction of modified nucleosides in urine prior to liquid chromatography-tandem mass spectrometry analysis. Chinese Chemical Letters, 2024, 35(4): 108867-. doi: 10.1016/j.cclet.2023.108867
13. [13]
  Luyu Zhang , Zirong Dong , Shuai Yu , Guangyue Li , Weiwen Kong , Wenjuan Liu , Haisheng He , Yi Lu , Wei Wu , Jianping Qi . Ionic liquid-based in situ dynamically self-assembled cationic lipid nanocomplexes (CLNs) for enhanced intranasal siRNA delivery. Chinese Chemical Letters, 2024, 35(7): 109101-. doi: 10.1016/j.cclet.2023.109101
14. [14]
  Shengyu Zhao , Qinhao Shi , Wuliang Feng , Yang Liu , Xinxin Yang , Xingli Zou , Xionggang Lu , Yufeng Zhao . Suppression of multistep phase transitions of O3-type cathode for sodium-ion batteries. Chinese Chemical Letters, 2024, 35(5): 108606-. doi: 10.1016/j.cclet.2023.108606
15. [15]
  Xue Xin , Qiming Qu , Islam E. Khalil , Yuting Huang , Mo Wei , Jie Chen , Weina Zhang , Fengwei Huo , Wenjing Liu . Hetero-phase zirconia encapsulated with Au nanoparticles for boosting electrocatalytic nitrogen reduction. Chinese Chemical Letters, 2024, 35(5): 108654-. doi: 10.1016/j.cclet.2023.108654
16. [16]
  Tian Yang , Yi Liu , Lina Hua , Yaoyao Chen , Wuqian Guo , Haojie Xu , Xi Zeng , Changhao Gao , Wenjing Li , Junhua Luo , Zhihua Sun . Lead-free hybrid two-dimensional double perovskite with switchable dielectric phase transition. Chinese Chemical Letters, 2024, 35(6): 108707-. doi: 10.1016/j.cclet.2023.108707
17. [17]
  Shu Lin , Kezhen Qi . Phase-dependent lithium-alloying reactions for lithium-metal batteries. Chinese Chemical Letters, 2024, 35(4): 109431-. doi: 10.1016/j.cclet.2023.109431
18. [18]
  Zhaohong Chen , Mengzhen Li , Jinfei Lan , Shengqian Hu , Xiaogang Chen . Organic ferroelastic enantiomers with high T_c and large dielectric switching ratio triggered by order-disorder and displacive phase transition. Chinese Chemical Letters, 2024, 35(10): 109548-. doi: 10.1016/j.cclet.2024.109548
19. [19]
  Zhi-Yuan Yue , Hua-Kai Li , Na Wang , Shan-Shan Liu , Le-Ping Miao , Heng-Yun Ye , Chao Shi . Dehydration-triggered structural phase transition-associated ferroelectricity in a hybrid perovskite-type crystal. Chinese Chemical Letters, 2024, 35(10): 109355-. doi: 10.1016/j.cclet.2023.109355
20. [20]
  Zhuoer Cai , Yinan Zhang , Xiu-Ni Hua , Baiwang Sun . Phase transition arising from order-disorder motion in stable layered two-dimensional perovskite. Chinese Journal of Structural Chemistry, 2024, 43(11): 100426-100426. doi: 10.1016/j.cjsc.2024.100426

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1894)
HTML views(54)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142