Enhancing the Crystallization Performance of Poly(L-lactide) by Intramolecular Hybridizing with Tunable Self-assembly-type Oxalamide Segments

Man-Man Yu; Wei-Jun Yang; De-Yu Niu; Xiao-Xia Cai; Yun-Xuan Weng; Wei-Fu Dong; Ming-Qing Chen; Peng-Wu Xu; Yang Wang; Hong Chu; Pi-Ming Ma

doi:10.1007/s10118-020-2461-3

Your Location：

Home >

Browse articles >

Enhancing the Crystallization Performance of Poly(L-lactide) by Intramolecular Hybridizing with Tunable Self-assembly-type Oxalamide Segments

ARTICLE | Updated：2020-08-17

- Enhancing the Crystallization Performance of Poly(L-lactide) by Intramolecular Hybridizing with Tunable Self-assembly-type Oxalamide Segments
- Enhancing the Crystallization Performance of Poly(L-lactide) by Intramolecular Hybridizing with Tunable Self-assembly-type Oxalamide Segments
- Chinese Journal of Polymer Science 2021年39卷第1期页码：122-132
- Affiliations：
  
  a.The Key Laboratory of Synthetic and Biological Colloids, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi 214122, China
  b.Beijing Key Laboratory of Quality Evaluation Technology for Hygiene and Safety of Plastics, Beijing Technology and Business University, Beijing 100048, China
- Author bio：
  
  wyxuan@th.btbu.edu.cn (Y.X.W.)
  p.ma@jiangnan.edu.cn (P.M.M.)
- Funds：
  
  This work was financially supported by the National Natural Science Foundation of China (No. 51873082), the MOE & SAFEA 111 Project (No. B13025), the Opening Project of Beijing Key Laboratory of Quality Evaluation Technology for Hygiene and Safety of Plastics (Beijing Technology and Business University) (No. QETHSP2019003), and the Postgraduate Research & Practice Innovation Program of Jiangnan University (No. JNKY19_020).
- DOI：10.1007/s10118-020-2461-3
  中图分类号：
- 收稿：2020-04-20，
  
  修回：2020-5-20，
  
  录用：2020-5-22，
  
  网络首发：2020-08-17，
  
  纸质出版：2021-01-01
- Accepted：
Scan QR Code
Yu, M. M.; Yang, W. J.; Niu, D. Y.; Cai, X. X.; Weng, Y. X.; Dong, W. F.; Chen, M. Q.; Xu, P. W.; Wang, Y.; Chu, H.; Ma, P. M. Enhancing the crystallization performance of poly(L-lactide) by intramolecular hybridizing with tunable self-assembly-type oxalamide segments. Chinese J. Polym. Sci. 2021, 39, 122–132

Man-Man Yu, Wei-Jun Yang, De-Yu Niu, et al. Enhancing the Crystallization Performance of Poly(L-lactide) by Intramolecular Hybridizing with Tunable Self-assembly-type Oxalamide Segments[J]. Chinese Journal of Polymer Science, 2021, 39(1): 122-132.
Yu, M. M.; Yang, W. J.; Niu, D. Y.; Cai, X. X.; Weng, Y. X.; Dong, W. F.; Chen, M. Q.; Xu, P. W.; Wang, Y.; Chu, H.; Ma, P. M. Enhancing the crystallization performance of poly(L-lactide) by intramolecular hybridizing with tunable self-assembly-type oxalamide segments. Chinese J. Polym. Sci. 2021, 39, 122–132 DOI： 10.1007/s10118-020-2461-3.

Man-Man Yu, Wei-Jun Yang, De-Yu Niu, et al. Enhancing the Crystallization Performance of Poly(L-lactide) by Intramolecular Hybridizing with Tunable Self-assembly-type Oxalamide Segments[J]. Chinese Journal of Polymer Science, 2021, 39(1): 122-132. DOI： 10.1007/s10118-020-2461-3.

摘要

Abstract

In this work

hydroxyl-terminated oxalamide compounds

-bis(2-hydroxyethyl)oxalamide (OXA1) and

′

-(ethane-1

2-diyl)bis(

-(2-hydroxyethyl)oxalamide (OXA2) were synthesized to initiate the ring-opening polymerization of L-lactide for preparation of oxalamide-hybridized poly(L-lactide) (PLA

OXA

)

i.e.

PLA

OXA1

and PLA

OXA2

. The crystallization properties of PLA were improved by the self-assembly of the oxalamide segments in PLA

OXA

which served as the initial heterogeneous nuclei. The crystal growth kinetics was studied by Hoffman-Lauritzen theory and it revealed that the nucleation energy barrier of PLA

OXA1

and PLA

OXA2

was lower than that of PLA. Consequently

PLA

OXA

could crystallize much faster than PLA

accompanied with a decrease in spherulite size and half-life crystallization time by 74.8% and 86.5% (

=125 °C)

respectively. In addition

the final crystallinity of PLA

OXA1

and PLA

OXA2

was 6 and 8 times higher

respectively

in comparison with that of neat PLA under a controlled cooling rate of 10 °C/min. The results demonstrate that the hybridization of oxalamide segments in PLA backbone will serve as the self-heteronucleation for promoting the crystallization rate. The higher the content of oxalamide segments (PLA

OXA2

compared with PLA

OXA1

) is

the stronger the promotion effect will be. Therefore

this study may provide a universal approach by hybridizing macromolecular structure to facilitate the crystallization of semi-crystalline polymer materials.

关键词

Keywords

references

Rankin, J. . European parliament votes to ban single-use plastics . The Guardian , 2019 . 27 .

Trache, D.; Hussin, M. H.; Haafiz, M. K. M.; Thakur, V. K. . Recent progress in cellulose nanocrystals: sources and production . Nanoscale , 2017 . 9 1763 - 1786 . DOI: 10.1039/C6NR09494E http://doi.org/10.1039/C6NR09494E .

Gu, J.; Peng, X.; Peng, C.; Lei, Z.; Wang, H.; Dai, L.; Song, L.; Huang, Y.; Zhang, J.; Tao, C. . Functionalization of biodegradable PLA non-woven fabric as superoleophilic and superhydrophobic material for efficient oil absorption and oil/water separation . ACS Appl. Mater. Interfaces , 2017 . 9 5968 DOI: 10.1021/acsami.6b13547 http://doi.org/10.1021/acsami.6b13547 .

Tenn, N.; Follain, N.; Soulestin, J.; Crétois, R.; Bourbigot, S.; Marais, S. . Effect of nanoclay hydration on barrier properties of PLA/montmorillonite based nanocomposites . J. Phys. Chem. C , 2013 . 117 12117 - 12135 . DOI: 10.1021/jp401546t http://doi.org/10.1021/jp401546t .

Saiwaew, R.; Suppakul, P.; Boonsupthip, W.; Pechyen, C.; Saiwaew, R. . Development and characterization of poly(lactic acid)/fish water soluble protein composite sheets: a potential approach for biodegradable packaging . Energy Procedia , 2014 . 56 280 - 298 . DOI: 10.1016/j.egypro.2014.07.159 http://doi.org/10.1016/j.egypro.2014.07.159 .

Chen, Y.; Wang, W.; Qiu, Y.; Li, L.; Qian, L.; Xin, F. . Terminal group effects of phosphazene-triazine bi-group flame retardant additives in flame retardant polylactic acid composites . Polym. Degrad. Stab. , 2017 . 140 166 - 175 . DOI: 10.1016/j.polymdegradstab.2017.04.024 http://doi.org/10.1016/j.polymdegradstab.2017.04.024 .

Zhang, X.; Meng, L.; Li, G.; Liang, N.; Zhang, J.; Zhu, Z.; Wang, R. . Effect of nucleating agents on the crystallization behavior and heat resistance of poly(L-lactide) . J. Appl. Polym. Sci. , 2016 . 133 42999 .

Zhu, B.; Wang, Y.; Liu, H.; Ying, J.; Liu, C.; Shen, C. . Effects of interface interaction and microphase dispersion on the mechanical properties of PCL/PLA/MMT nanocomposites visualized by nanomechanical mapping . Compos. Sci. Technol. , 2020 . 190 108048 DOI: 10.1016/j.compscitech.2020.108048 http://doi.org/10.1016/j.compscitech.2020.108048 .

Chen, P.; Lian, H.; Shih, Y.; Chenwei, S.; Jeng, R. . Preparation, characterization and crystallization kinetics of Kenaf fiber/multi-walled carbon nanotube/polylactic acid (PLA) green composites . Mater. Chem. Phys. , 2017 . 196 249 - 255 . DOI: 10.1016/j.matchemphys.2017.05.006 http://doi.org/10.1016/j.matchemphys.2017.05.006 .

Xu, P.; Cui, Z.; Ruan, G.; Ding, Y. . Enhanced crystallization kinetics of PLLA by ethoxycarbonyl ionic liquid modified graphene . Chinese J. Polym. Sci. , 2019 . 37 243 - 252 . DOI: 10.1007/s10118-019-2192-5 http://doi.org/10.1007/s10118-019-2192-5 .

Bhoje Gowd, E.; Nagendra, B.; Sivaprasad, V. P.; Sijla Rosely, C. . Influence of boron nitride nanosheets on the crystallization and polymorphism of poly(L-lactide) . J. Phys. Chem. B , 2018 . 122 6442 - 6451 . DOI: 10.1021/acs.jpcb.8b03211 http://doi.org/10.1021/acs.jpcb.8b03211 .

Nam, J. Y.; Okamoto, M.; Okamoto, H.; Nakano, M.; Usuki, A.; Matsuda, M. . Morphology and crystallization kinetics in a mixture of low-molecular weight aliphatic amide and polylactide . Polymer , 2006 . 47 1340 - 1347 . DOI: 10.1016/j.polymer.2005.12.066 http://doi.org/10.1016/j.polymer.2005.12.066 .

Pan, P.; Shan, G.; Bao, Y. . Enhanced nucleation and crystallization of poly(L-lactic acid) by immiscible blending with poly(vinylidene fluoride) . Ind. Eng. Chem. Res. , 2014 . 53 3148 - 3156 . DOI: 10.1021/ie404085a http://doi.org/10.1021/ie404085a .

Yuan, B. C.; Zou, L. G. . Effect of orotic acid on the crystallization kinetics and morphology of biodegradable poly(L-lactide) as an efficient nucleating agent . Thermochim. Acta , 2014 . 577 41 - 45 . DOI: 10.1016/j.tca.2013.12.011 http://doi.org/10.1016/j.tca.2013.12.011 .

Pan, P.; Yang, J.; Shan, G.; Bao, Y.; Weng, Z.; Inoue, Y. . Nucleation effects of nucleobases on the crystallization kinetics of poly(L-lactide) . Macromol. Mater. Eng. , 2012 . 297 670 - 679 . DOI: 10.1002/mame.201100266 http://doi.org/10.1002/mame.201100266 .

Shi, Y.; Shao, L.; Yang, J.; Huang, T.; Wang, Y.; Zhang, N.; Wang, Y. . Highly improved crystallization behavior of poly(L-lactide) induced by a novel nucleating agent: substituted-aryl phosphate salts . Polym. Adv. Technol. , 2013 . 24 42 - 50 . DOI: 10.1002/pat.3047 http://doi.org/10.1002/pat.3047 .

Xie, Q.; Han, L.; Shan, G.; Bao, Y.; Pan, P. . Polymorphic crystalline structure and crystal morphology of eenantiomeric poly(lactic acid) blends tailored by a self-assemblable aryl amide nucleator . ACS Sustain. Chem. Eng. , 2016 . 4 2680 - 2688 . DOI: 10.1021/acssuschemeng.6b00191 http://doi.org/10.1021/acssuschemeng.6b00191 .

Ma, P.; Xu, Y.; Wang, D.; Dong, W.; Chen, M. . Rapid crystallization of poly(lactic acid) by using tailor-made oxalamide derivatives as novel soluble-type nucleating agents . Ind. Eng. Chem. Res. , 2014 . 53 12888 - 12892 . DOI: 10.1021/ie502211j http://doi.org/10.1021/ie502211j .

Ma, P.; Xu, Y.; Shen, T.; Dong, W.; Chen, M.; Lemstra, P. J. . Tailoring the crystallization behavior of poly(L-lactide) with self-assembly-type oxalamide compounds as nucleators: 1. Effect of terminal configuration of the nucleators . Eur. Polym. J. , 2015 . 70 400 - 411 . DOI: 10.1016/j.eurpolymj.2015.07.040 http://doi.org/10.1016/j.eurpolymj.2015.07.040 .

Kamal, M. R.; Khoshkava, V. . Effect of cellulose nanocrystals (CNC) on rheological and mechanical properties and crystallization behavior of PLA/CNC nanocomposites . Carbohydr. Polym. , 2015 . 123 105 - 114 . DOI: 10.1016/j.carbpol.2015.01.012 http://doi.org/10.1016/j.carbpol.2015.01.012 .

Bai, H.; Zhang, W.; Deng, H.; Zhang, Q.; Fu, Q. . Control of crystal morphology in poly(L-lactide) by adding nucleating agent . Macromolecules , 2011 . 44 1233 - 1237 . DOI: 10.1021/ma102439t http://doi.org/10.1021/ma102439t .

Bai, H.; Huang, C.; Xiu, H.; Zhang, Q.; Fu, Q. . Enhancing mechanical performance of polylactide by tailoring crystal morphology and lamellae orientation with the aid of nucleating agent . Polymer , 2014 . 55 6924 - 6934 . DOI: 10.1016/j.polymer.2014.10.059 http://doi.org/10.1016/j.polymer.2014.10.059 .

Shen, T.; Xu, Y.; Cai, X.; Ma, P.; Dong, W.; Chen, M. . Enhanced crystallization kinetics of poly(lactide) with oxalamide compounds as nucleators: effect of spacer length between the oxalamide moieties . RSC Adv. , 2016 . 6 48365 - 48374 . DOI: 10.1039/C6RA04050K http://doi.org/10.1039/C6RA04050K .

Bao, J.; Chang, X.; Xie, Q.; Yu, C.; Shan, G.; Bao, Y.; Pan, P. . Preferential formation of β -form crystals and temperature-dependent polymorphic structure in supramolecular poly(L-lactic acid) bonded by multiple hydrogen bonds . Macromolecules , 2017 . 50 8619 - 8630 . DOI: 10.1021/acs.macromol.7b01705 http://doi.org/10.1021/acs.macromol.7b01705 .

Kodal, M.; Sirin, H.; Ozkoc, G. . Non-isothermal crystallization kinetics of PEG plasticized PLA/G-POSS nanocomposites . Polym. Compos. , 2017 . 38 1378 - 1389 . DOI: 10.1002/pc.23704 http://doi.org/10.1002/pc.23704 .

Dave, V.; Srivastava, P.; Sharma, S.; Bajaj, J.; Tak, K. . PEGylated PLA-Phospholipon 90G complex hybrid nanoparticles loaded with etoricoxib for effective treatment pain relief potential . Int. J. Polym. Mater. Polym. Biomater. , 2019 . 69 640 - 652 . .

Xia, S.; Liu, X.; Wang, J.; Kan, Z.; Chen, H.; Fu, W.; Li, Z. . Role of poly(ethylene glycol) grafted silica nanoparticle shape in toughened PLA-matrix nanocomposites . Compos. Part B , 2019 . 168 398 - 405 . DOI: 10.1016/j.compositesb.2019.03.050 http://doi.org/10.1016/j.compositesb.2019.03.050 .

Södergård, A.; Stolt, M. . Properties of lactic acid based polymers and their correlation with composition . Prog. Polym. Sci. , 2002 . 27 1123 - 1163 . DOI: 10.1016/S0079-6700(02)00012-6 http://doi.org/10.1016/S0079-6700(02)00012-6 .

Sijbrandi, N. J.; Kimenai, A. J.; Mes, E. P. C.; Broos, R.; Bar, G.; Rosenthal, M.; Odarchenko, Y. I.; Ivanov, D. A.; Feijen, J.; Dijkstra, P. J. . Synthesis, morphology and properties of segmented poly(ether ester amide)s comprising uniform glycine or β -alanine extended bisoxalamide hard segments . Polymer , 2012 . 53 4033 - 4044 . DOI: 10.1016/j.polymer.2012.07.015 http://doi.org/10.1016/j.polymer.2012.07.015 .

Harings, J. A.; van Asselen, O.; Graf, R.; Broos, R.; Rastogi, S. . The role of superheated water on the crystallization of N , N ′-1, 2-ethanediyl-bis(6-hydroxy-hexanamide): implications on crystallography and phase transitions . Cryst. Growth Des. , 2008 . 8 2469 - 2477 . DOI: 10.1021/cg8001064 http://doi.org/10.1021/cg8001064 .

Tsuji, H. . In vitro hydrolysis of blends from enantiomeric poly(lactide)s. Part 4: well-homo-crystallized blend and nonblended films . Biomaterials , 2003 . 24 537 - 547 . DOI: 10.1016/S0142-9612(02)00365-4 http://doi.org/10.1016/S0142-9612(02)00365-4 .

Takahiko, K.; Nelly, R.; Go, M.; Koji, N.; Toshiji, K.; Mitsuru, N.; Hirotaka, O.; Jumpei, K.; Arimitsu, U.; Nobutaka, H. . Crystallization and melting behavior of poly(L-lactic acid) . Macromolecules , 2013 . 40 9463 - 9469 . .

Zhang, R. C.; Sun, D.; Lu, A.; Zhong, M.; Xiong, G.; Wan, Y. . Equilibrium melting temperature of polymorphic poly(L-lactide) and its supercooling dependence on growth kinetics . Polymers , 2017 . 9 625 DOI: 10.3390/polym9110625 http://doi.org/10.3390/polym9110625 .

Dobreva, A.; Gutzow, I. . Activity of substrates in the catalyzed nucleation of glass-forming melts. II. Experimental evidence . J. Non-Cryst. Solids , 1993 . 162 13 - 25 . DOI: 10.1016/0022-3093(93)90737-I http://doi.org/10.1016/0022-3093(93)90737-I .

Avrami, M. . Granulation, phase change, and microstructure kinetics of phase change. III . J. Phys. Chem. , 1941 . 9 177 - 184 . DOI: 10.1063/1.1750872 http://doi.org/10.1063/1.1750872 .

Tsuji, H.; Yamashita, Y. . Highly accelerated stereocomplex crystallization by blending star-shaped 4-armed stereo diblock poly(lactide)s with poly(D-lactide) and poly(L-lactide) cores . Polymer , 2014 . 55 6444 - 6450 . DOI: 10.1016/j.polymer.2014.10.024 http://doi.org/10.1016/j.polymer.2014.10.024 .

Shen, T.; Xu, Y.; Wang, L.; Dong, W.; Chen, M.; Ma, P. . High-performance poly(lactide) composites by construction of network-like shish-kebab crystals . RSC Adv. , 2016 . 6 71046 - 71051 . DOI: 10.1039/C6RA11815A http://doi.org/10.1039/C6RA11815A .

Hoffman, J. D. . Theoretical aspects of polymer crystallization with chain folds: bulk polymers . Polym. Eng. Sci. , 1964 . 4 315 - 362 . DOI: 10.1002/pen.760040413 http://doi.org/10.1002/pen.760040413 .

Shen, T.; Ma, P.; Yu, Q.; Dong, W.; Chen, M. . The effect of thermal history on the fast crystallization of poly(L-lactide) with soluble-type nucleators and shear flow . Polymers , 2016 . 8 431 DOI: 10.3390/polym8120431 http://doi.org/10.3390/polym8120431 .

Tsuji, H.; Miyase, T.; Tezuka, Y.; Saha, S. K. . Physical properties,crystallization,and spherulite growth of linear and 3-arm poly(L-lactide)s . Biomacromolecules , 2007 . 100 944 - 947 . .

Zhang, M.; Guo, B. H.; Xu, J. . A review on polymer crystallization theories . Crystals , 2017 . 7 4 .

Tang, X.; Chen, W.; Li, L. . The tough journey of polymer crystallization: battling with chain flexibility and connectivity . Macromolecules , 2019 . 52 3575 - 3591 . DOI: 10.1021/acs.macromol.8b02725 http://doi.org/10.1021/acs.macromol.8b02725 .

Okada, K.; Watanabe, K.; Urushihara, T.; Toda, A.; Hikosaka, M. . Role of epitaxy of nucleating agent (NA) in nucleation mechanism of polymers . Polymer , 2007 . 48 401 - 408 . DOI: 10.1016/j.polymer.2006.10.048 http://doi.org/10.1016/j.polymer.2006.10.048 .

Legras, R.; Mercier, J.; Nield, E. . Polymer crystallization by chemical nucleation . Nature , 1983 . 304 432 DOI: 10.1038/304432a0 http://doi.org/10.1038/304432a0 .

Xing, Q.; Li, R.; Dong, X.; Luo, F.; Kuang, X.; Wang, D.; Zhang, L. . Enhanced crystallization rate of poly(L-lactide) mediated by a hydrazide compound: nucleating mechanism study . Macromol. Chem. Phys. , 2015 . 216 1134 - 1145 . DOI: 10.1002/macp.201500002 http://doi.org/10.1002/macp.201500002 .

浏览量

142

Downloads

CSCD

文章被引用时，请邮件提醒。

Submit

工具集

关联资源

Regulating Intermolecular Interactions through Phenyl-alkyl Side-chain Engineering for High-efficiency Organic Solar Cells

Impact of Annealing on the Melt Recrystallization of a-PDLA/α-PLLA Double-layered Films

Influence of Freezing Layer on the Crystallization Kinetics of PCL on Oriented PE Film

Enhanced Phase Transition in Poly(ethylene glycol) Grafted Butene-1 Copolymers

Tunable Circularly Polarized Luminescence of Helical Poly(phenylacetylene)s via Side-chain-to-Backbone Förster Resonance Energy Transfer