

FOLLOWUS
a.State Key Laboratory of Chemical Engineering, College of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, China
b.Université de Strasbourg, CNRS, CHIMIE UMR 7177, Laboratoire de Chimie de Coordination, 4 rue Blaise Pascal, 67081 Strasbourg Cedex, France
jiesy@zju.edu.cn
Received:28 May 2019,
Revised:2019-8-6,
Accepted:29 August 2019,
Online First:12 October 2019,
Published:2020-03
Scan QR Code
Hu, Q.; Jie, S. Y.; Braunstein, P.; Li, B. G. Ring-opening copolymerization of , ε,-caprolactone and , δ,-valerolactone catalyzed by a 2,6-bis(amino)phenol zinc complex. Chinese J. Polym. Sci. 2020, 38, 240–247.
Qian Hu, Su-Yun Jie, Pierre Braunstein, et al. Ring-opening Copolymerization of
Hu, Q.; Jie, S. Y.; Braunstein, P.; Li, B. G. Ring-opening copolymerization of , ε,-caprolactone and , δ,-valerolactone catalyzed by a 2,6-bis(amino)phenol zinc complex. Chinese J. Polym. Sci. 2020, 38, 240–247. DOI: 10.1007/s10118-020-2347-4.
Qian Hu, Su-Yun Jie, Pierre Braunstein, et al. Ring-opening Copolymerization of
In combination with methyllithium
a 2
6-bis(amino)phenol zinc complex
1
was used in the ring-opening polymerization of
δ
-valerolactone in the absence or presence of benzyl alcohol and showed high efficiency
mainly producing cyclic and linear polyvalerolactones
respectively. On the basis of homopolymerization
the ring-opening copolymerization of
ε
-caprolactone and
δ
-valerolactone was investigated. The P(CL-
co
-VL) random copolymers
PCL-
b
-PVL and PVL-
b
-PCL diblock copolymers
were prepared by varying the feeding strategy (premixing or sequential feeding). The copolymer composition was adjusted by varying the feeding ratio of two monomers. The structure and thermal properties of obtained polymers were characterized by GPC
1
H-NMR
13
C-NMR
MALDI-TOF mass spectroscopy
and DSC
respectively.
Sangeetha, V. H.; Deka, H.; Varghese, T. O.; Nayak, S. K . State of the art and future prospectives of poly(lactic acid) based blends and composites . Polym. Compos. , 2018 . 39 81 - 101 . DOI: 10.1002/pc.23906 http://doi.org/10.1002/pc.23906 .
Pant, H. R.; Kim, H. J.; Bhatt, L. R.; Joshi, M. K.; Kim, E. K.; Kim, J. I.; Abdal-hay, A.; Hui, K. S.; Kim, C. S . Chitin butyrate coated electrospun nylon-6 fibers for biomedical applications . Appl. Surf. Sci. , 2013 . 285 538 - 544 . DOI: 10.1016/j.apsusc.2013.08.089 http://doi.org/10.1016/j.apsusc.2013.08.089 .
Cameron, D. J. A.; Shaver, M. P . Aliphatic polyester polymer stars: Synthesis, properties and applications in biomedicine and nanotechnology . Chem. Soc. Rev. , 2011 . 40 1761 - 1776 . DOI: 10.1039/C0CS00091D http://doi.org/10.1039/C0CS00091D .
Shin, E. J.; Brown, H. A.; Gonzalez, S.; Jeong, W.; Hedrick, J. L.; Waymouth, R. M . Zwitterionic copolymerization: synthesis of cyclic gradient copolymers . Angew. Chem. Int. Ed. , 2011 . 50 6388 - 6391 . DOI: 10.1002/anie.201101853 http://doi.org/10.1002/anie.201101853 .
Stirling, E.; Champouret, Y.; Visseaux, M . Catalytic metal-based systems for controlled statistical copolymerisation of lactide with a lactone . Polym. Chem. , 2018 . 9 2517 - 2531 . DOI: 10.1039/C8PY00310F http://doi.org/10.1039/C8PY00310F .
Rad'Kova, N.; Rad'Kov, V.; Cherkasov, A.; Kovylina, T.; Trifonov, A . Lanthanide bis(borohydride) complexes coordinated by tetradentate phenoxide ligand: synthesis, structure, and catalytic activity in ring-opening polymerization of rac -lactide and ε -caprolactone . Inorg. Chim. Acta , 2019 . 489 132 - 139 . DOI: 10.1016/j.ica.2019.02.014 http://doi.org/10.1016/j.ica.2019.02.014 .
Cho, J.; Chun, M. K.; Nayab, S.; Jeong, J. H . Synthesis and structures of copper(II) complexes containing N , N -bidentate N -substituted phenylethanamine derivatives as pre-catalysts for heterotactic-enriched polylactide . Polyhedron , 2019 . 163 54 - 62 . DOI: 10.1016/j.poly.2019.02.014 http://doi.org/10.1016/j.poly.2019.02.014 .
Caballero-Jiménez, D.; García-de-Jesús, O.; Lopez, N.; Reyes-Ortega, Y. Muñoz-Hernández, M . Tetranuclear complexes of group 12 and 13 supported on a polynucleating ligand and activity studies in the ROP of rac -lactide . Inorg. Chim. Acta , 2019 . 489 120 - 125 . DOI: 10.1016/j.ica.2019.02.007 http://doi.org/10.1016/j.ica.2019.02.007 .
Dou, J.; Zhu, D.; Zhang, W.; Wang, R.; Wang, S.; Zhang, Q.; Zhang, X.; Sun, W. H . Highly efficient iron(II) catalysts toward ring opening polymerization of ε -caprolactone through in situ initiation . Inorg. Chim. Acta , 2019 . 488 299 - 303 . DOI: 10.1016/j.ica.2019.01.040 http://doi.org/10.1016/j.ica.2019.01.040 .
Munzeiwa, W. A.; Nyamori, V. O.; Omondi, B . N , O -amino-phenolate Mg(II) and Zn(II) Schiff base complexes: synthesis and application in ring-opening polymerization of ε -caprolactone and lactides . Inorg. Chim. Acta , 2019 . 487 264 - 274 . DOI: 10.1016/j.ica.2018.12.028 http://doi.org/10.1016/j.ica.2018.12.028 .
Chen, X.; Wang, B.; Pan, L.; Li, Y . Homoleptic, bis-ligated magnesium complexes for ring-opening polymerization of lactide and lactones: synthesis, structure, polymerization behavior and mechanism studies . Appl. Organomet. Chem. , 2019 . 33 e4770 DOI: 10.1002/aoc.4770 http://doi.org/10.1002/aoc.4770 .
Steiniger, P.; Schäfer, P. M.; Wölper, C.; Henkel, J.; Ksiazkiewicz, A. N.; Pich, A.; Herres-Pawlis, S.; Schulz, S . Synthesis, structures, and catalytic activity of homo- and heteroleptic ketoiminate zinc complexes in lactide polymerization . Eur. J. Inorg. Chem. , 2018 . 2018 4014 - 4021 . DOI: 10.1002/ejic.201800504 http://doi.org/10.1002/ejic.201800504 .
González, D. M.; Cisterna, J.; Brito, I.; Roisnel, T.; Hamon, J.; Manzur, C . Binuclear Schiff-base zinc(II) complexes: synthesis, crystal structures and reactivity toward ring opening polymerization of rac -lactide . Polyhedron , 2019 . 162 91 - 99 . DOI: 10.1016/j.poly.2019.01.043 http://doi.org/10.1016/j.poly.2019.01.043 .
Yang, Z.; Hu, C.; Duan, R.; Sun, Z.; Zhang, H.; Pang, X.; Li, L . Salen-manganese complexes and their application in the ring-opening polymerization of lactide and ε -caprolactone . Asian J. Org. Chem. , 2019 . 8 376 - 384 . DOI: 10.1002/ajoc.201800695 http://doi.org/10.1002/ajoc.201800695 .
Li, M.; Behzadi, S.; Chen, M.; Pang, W.; Wang, F.; Tan, C . Phenoxyimine ligands bearing nitrogen-containing second coordination spheres for zinc catalyzed stereoselective ring-opening polymerization of rac -lactide . Organometallics , 2019 . 38 461 - 468 . DOI: 10.1021/acs.organomet.8b00788 http://doi.org/10.1021/acs.organomet.8b00788 .
Saeed, W.; Al-Odayni, A.; Alghamdi, A.; Alrahlah, A.; Aouak, T . Thermal properties and non-isothermal crystallization kinetics of poly( δ -valerolactone) and poly( δ -valerolactone)/titanium dioxide nanocomposites . Crystals , 2018 . 8 452 DOI: 10.3390/cryst8120452 http://doi.org/10.3390/cryst8120452 .
D’auria, I.; Mazzeo, M.; Pappalardo, D.; Lamberti, M.; Pellecchia, C . Ring-opening polymerization of cyclicesters promoted by phosphido-diphosphine pincergroup 3 complexes . J. Polym. Sci., Part A: Polym. Chem. , 2011 . 49 403 - 413 . DOI: 10.1002/pola.24447 http://doi.org/10.1002/pola.24447 .
Khalil, M. I.; Al-Shamary, D. O. H.; Al-Deyab, S. S . Synthesis of poly( δ -valerolactone) by activated monomer polymerization, its characterization and potential medical application . Asian J. Biochem. Pharm. Res. , 2015 . 5 137 - 147 . .
Woodruff, M. A.; Hutmacher, D. W . The return of a forgotten polymer—polycaprolactone in the 21 st century . Prog. Polym. Sci. , 2010 . 35 1217 - 1256 . DOI: 10.1016/j.progpolymsci.2010.04.002 http://doi.org/10.1016/j.progpolymsci.2010.04.002 .
Duale, K.; Zięba, M.; Chaber, P.; Di Fouque, D.; Memboeuf, A.; Peptu, C.; Radecka, I.; Kowalczuk, M.; Adamus, G . Molecular level structure of biodegradable poly( δ -valerolactone) obtained in the presence of boric acid . Molecules , 2018 . 23 2034 DOI: 10.3390/molecules23082034 http://doi.org/10.3390/molecules23082034 .
Saeed, W. S.; Al-Odayni, A.; Ali Alghamdi, A.; Abdulaziz Al-Owais, A.; Semlali, A.; Aouak, T . Miscibility of poly(ethylene- co -vinylalcohol)/poly( δ -valerolactone) blend and tissue engineering scaffold fabrication using naphthalene as porogen . Polym. Plast. Technol. Eng. , 2018 . 58 1 - 23 . .
Lee, H.; Zeng, F.; Dunne, M.; Allen, C . Methoxy poly(ethylene glycol)-block-poly( δ -valerolactone) copolymer micelles for formulation of hydrophobic drugs . Biomacromolecules , 2005 . 6 3119 - 3128 . DOI: 10.1021/bm050451h http://doi.org/10.1021/bm050451h .
Nair, K. L.; Jagadeeshan, S.; Nair, S. A.; Kumar, G. S. V . Evaluation of triblock copolymeric micelles of δ -valerolactone and poly(ethylene glycol) as a competent vector for doxorubicin delivery against cancer . J. Nanobiotechnol. , 2011 . 9 42 DOI: 10.1186/1477-3155-9-42 http://doi.org/10.1186/1477-3155-9-42 .
Alonso, D. M.; Wettstein, S. G.; Dumesic, J. A . Gamma-valerolactone. A sustainable platform molecule derived from lignocellulosic biomass . Green Chem. , 2013 . 15 584 - 595 . DOI: 10.1039/c3gc37065h http://doi.org/10.1039/c3gc37065h .
Alghamdi, A. A.; Saeed, W. S.; Al-Odayni, A.; Alharthi, F. A.; Semlali, A.; Aouak, T . Poly(ethylene- co -vinylalcohol)/poly( δ -valerolactone)/aspirin composite: model for a new drug-carrier system . Polymers , 2019 . 11 439 DOI: 10.3390/polym11030439 http://doi.org/10.3390/polym11030439 .
Wu, T.; Wei, Z.; Ren, Y.; Yu, Y.; Leng, X.; Li, Y . Highly branched linear-comb random copolyesters of ε -caprolactone and δ -valerolactone: isodimorphism, mechanical properties and enzymatic degradation behavior . Polym. Degrad. Stab. , 2018 . 155 173 - 182 . DOI: 10.1016/j.polymdegradstab.2018.07.018 http://doi.org/10.1016/j.polymdegradstab.2018.07.018 .
Zhang, L.; Dong, H.; Li, M.; Wang, L.; Liu, Y.; Wang, L.; Fu, S . Fabrication of polylactic acid-modified carbon black composites into improvement of levelness and mechanical properties of spun-dyeing polylactic acid composites membrane . ACS Sustain. Chem. Eng. , 2018 . 7 688 - 696 . .
Xiao, Y.; Pan, J.; Wang, D.; Heise, A.; Lang, M . Chemo-enzymatic synthesis of poly(4-piperidine lactone- b - ω -pentadecalactone) block copolymers as biomaterials with antibacterial properties . Biomacromolecules , 2018 . 19 2673 - 2681 . DOI: 10.1021/acs.biomac.8b00296 http://doi.org/10.1021/acs.biomac.8b00296 .
Wilson, J. A.; Hopkins, S. A.; Wright, P. M.; Dove, A. P . Synthesis of ω -pentadecalactone copolymers with independently tunable thermal and degradation behavior . Macromolecules , 2015 . 48 950 - 958 . DOI: 10.1021/ma5022049 http://doi.org/10.1021/ma5022049 .
Hong, M.; Tang, X.; Newell, B. S.; Chen, E. Y. X . “Nonstrained” γ -butyrolactone-based copolyesters: copolymerization characteristics and composition-dependent (thermal, eutectic, cocrystallization, and degradation) properties . Macromolecules , 2017 . 50 8469 - 8479 . DOI: 10.1021/acs.macromol.7b02174 http://doi.org/10.1021/acs.macromol.7b02174 .
Fernández, J.; Etxeberria, A.; Sarasua, J . In vitro degradation studies and mechanical behavior of poly( ε -caprolactone- co - δ -valerolactone) and poly( ε -caprolactone- co -L-lactide) with random and semi-alternating chain microstructures . Eur. Polym. J. , 2015 . 71 585 - 595 . DOI: 10.1016/j.eurpolymj.2015.09.001 http://doi.org/10.1016/j.eurpolymj.2015.09.001 .
Hunley, M. T.; Beers, K. L . Nonlinear method for determining reactivity ratios of ring-opening copolymerizations . Macromolecules , 2013 . 46 1393 - 1399 . DOI: 10.1021/ma302015e http://doi.org/10.1021/ma302015e .
Fernández, J.; Etxeberria, A.; Sarasua, J. R . Synthesis, structure and properties of poly(L-lactide- co -caprolactone) statistical copolymers . J. Mech. Behav. Biomed. Mater. , 2012 . 9 100 - 112 . DOI: 10.1016/j.jmbbm.2012.01.003 http://doi.org/10.1016/j.jmbbm.2012.01.003 .
Chandra, R.; Rustgi, R . Biodegradable polymers . Prog. Polym. Sci. , 1998 . 23 1273 - 1335 . DOI: 10.1016/S0079-6700(97)00039-7 http://doi.org/10.1016/S0079-6700(97)00039-7 .
Faÿ, F.; Renard, E.; Langlois, V.; Linossier, I.; Vallée-Rehel, K . Development of poly( ε -caprolactone- co -L-lactide) and poly( ε -caprolactone- co - δ -valerolactone) as new degradable binder used for antifouling paint . Eur. Polym. J. , 2007 . 43 4800 - 4813 . DOI: 10.1016/j.eurpolymj.2007.07.045 http://doi.org/10.1016/j.eurpolymj.2007.07.045 .
Hu, Q.; Jie, S.; Braunstein, P.; Li, B . Highly active tridentate amino-phenol zinc complexes for the catalytic ring-opening polymerization of ε -caprolactone . J. Organomet. Chem. , 2019 . 882 1 - 9 . DOI: 10.1016/j.jorganchem.2018.12.013 http://doi.org/10.1016/j.jorganchem.2018.12.013 .
Hunley, M. T.; Sari, N.; Beers, K. L . Microstructure analysis and model discrimination of enzyme-catalyzed copolyesters . ACS Macro Lett. , 2013 . 2 375 - 379 . DOI: 10.1021/mz300659h http://doi.org/10.1021/mz300659h .
Save, M.; Schappacher, M.; Soum, A . Controlled ring-opening polymerization of lactones and lactides initiated by lanthanum isopropoxide, 1. General aspects and kinetics . Macromol. Chem. Phys. , 2002 . 203 889 - 899 . DOI: 10.1002/1521-3935(20020401)203:5/6<889::AID-MACP889>3.0.CO;2-O http://doi.org/10.1002/1521-3935(20020401)203:5/6<889::AID-MACP889>3.0.CO;2-O .
Piedra-Arroni, E.; Ladavière, C.; Amgoune, A.; Bourissou, D . Ring-opening polymerization with Zn(C 6 F 5 ) 2 -based lewis pairs: original and efficient approach to cyclic polyesters . J. Am. Chem. Soc. , 2013 . 135 13306 - 13309 . DOI: 10.1021/ja4069968 http://doi.org/10.1021/ja4069968 .
0
Views
101
Downloads
3
CSCD
Publicity Resources
Related Articles
Related Author
Related Institution
京公网安备11010802046900号