Poly(lactide)-block-poly([epsilon]-caprolactone-co-[epsilon]-decalactone)-block-poly(lactide) copolymer elastomers

Schneiderman, Deborah K.; Hill, Erin M.; Martello, Mark T.; Hillmyer, Marc A.

doi:10.1039/C5PY00202H

Title: Poly(lactide)-block-poly([epsilon]-caprolactone-co-[epsilon]-decalactone)-block-poly(lactide) copolymer elastomers

Journal Article · Fri Aug 28 00:00:00 EDT 2015 · Polym. Chem. - UK

DOI:https://doi.org/10.1039/C5PY00202H· OSTI ID:1183618

Schneiderman, Deborah K.; Hill, Erin M.; Martello, Mark T.; Hillmyer, Marc A. ^[1]

Batch ring opening transesterification copolymerization of ε-caprolactone and ε-decalactone was used to generate statistical copolymers over a wide range of compositions and molar masses. Reactivity ratios determined for this monomer pair, r_CL = 5.9 and r_DL = 0.03, reveal ε-caprolactone is added preferentially regardless of the propagating chain end. Relative to poly(ε-caprolactone) the crystallinity and melting point of these statistical copolymers were depressed by the addition of ε-decalactone; copolymers containing greater than 31 mol% (46 wt%) ε-decalactone were amorphous. Poly(lactide)-block-poly(ε-caprolactone-co-ε-decalactone)-block-poly(lactide) triblock polymers were also prepared and used to explore the influence of midblock composition on the temperature dependent Flory-Huggins interaction parameter (χ). In addition, uniaxial extension tests were used to determine the effects of midblock composition, poly(lactide) content, and molar mass on the mechanical properties of these new elastomeric triblocks.

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Research Organization:: Argonne National Laboratory (ANL), Argonne, IL (United States). Advanced Photon Source (APS)

Sponsoring Organization:: NSFUNIVERSITY

OSTI ID:: 1183618

Journal Information:: Polym. Chem. - UK, Vol. 6, Issue (19) ; 2015

Country of Publication:: United States

Language:: ENGLISH

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Cited by: 69 works

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References (66)

Effect of Architecture on the Phase Behavior of AB-Type Block Copolymer Melts Matsen, M. W. Macromolecules, Vol. 45, Issue 4 https://doi.org/10.1021/ma202782s	journal	February 2012
Block Copolymers—Designer Soft Materials Bates, Frank S.; Fredrickson, Glenn H. Physics Today, Vol. 52, Issue 2 https://doi.org/10.1063/1.882522	journal	February 1999
Block copolymer micelles for drug delivery: design, characterization and biological significance Kataoka, Kazunori; Harada, Atsushi; Nagasaki, Yukio Advanced Drug Delivery Reviews, Vol. 47, Issue 1 https://doi.org/10.1016/S0169-409X(00)00124-1	journal	March 2001
Conjugated Block Copolymer Photovoltaics with near 3% Efficiency through Microphase Separation Guo, Changhe; Lin, Yen-Hao; Witman, Matthew D. Nano Letters, Vol. 13, Issue 6 https://doi.org/10.1021/nl401420s	journal	May 2013
Block copolymer electrolytes for rechargeable lithium batteries Young, Wen-Shiue; Kuan, Wei-Fan; Epps, Thomas H. Journal of Polymer Science Part B: Polymer Physics, Vol. 52, Issue 1 https://doi.org/10.1002/polb.23404	journal	November 2013
High-Modulus, High-Conductivity Nanostructured Polymer Electrolyte Membranes via Polymerization-Induced Phase Separation Schulze, Morgan W.; McIntosh, Lucas D.; Hillmyer, Marc A. Nano Letters, Vol. 14, Issue 1 https://doi.org/10.1021/nl4034818	journal	December 2013
Block Copolymer Thin Films: Physics and Applications Fasolka, Michael J.; Mayes, Anne M. Annual Review of Materials Research, Vol. 31, Issue 1, p. 323-355 https://doi.org/10.1146/annurev.matsci.31.1.323	journal	August 2001
Block Copolymer Nanostructures for Technology Tseng, Yu-Chih; Darling, Seth B. Polymers, Vol. 2, Issue 4 https://doi.org/10.3390/polym2040470	journal	October 2010
Self-Assembled Block Copolymer Thin Films as Water Filtration Membranes Phillip, William A.; O’Neill, Brandon; Rodwogin, Marc ACS Applied Materials & Interfaces, Vol. 2, Issue 3 https://doi.org/10.1021/am900882t	journal	February 2010
Nanoporous Membranes Derived from Block Copolymers: From Drug Delivery to Water Filtration Jackson, Elizabeth A.; Hillmyer, Marc A. ACS Nano, Vol. 4, Issue 7 https://doi.org/10.1021/nn1014006	journal	June 2010
Sustainable Poly(lactide- b -butadiene) Multiblock Copolymers with Enhanced Mechanical Properties Lee, Intaek; Panthani, Tessie R.; Bates, Frank S. Macromolecules, Vol. 46, Issue 18 https://doi.org/10.1021/ma401508b	journal	September 2013
ε-Decalactone: A Thermoresilient and Toughening Comonomer to Poly( l -lactide) Olsén, Peter; Borke, Tina; Odelius, Karin Biomacromolecules, Vol. 14, Issue 8 https://doi.org/10.1021/bm400733e	journal	July 2013
Triblock Copolymers Based on 1,3-Trimethylene Carbonate and Lactide as Biodegradable Thermoplastic Elastomers Zhang, Zheng; Grijpma, Dirk W.; Feijen, Jan Macromolecular Chemistry and Physics, Vol. 205, Issue 7 https://doi.org/10.1002/macp.200300184	journal	May 2004
Homo- and Block Copolymerizations of ε-Decalactone with l -Lactide Catalyzed by Lanthanum Compounds Lin, Jin-Ou; Chen, Wanli; Shen, Zhiquan Macromolecules, Vol. 46, Issue 19 https://doi.org/10.1021/ma401218p	journal	September 2013
Polylactide–Poly(6-methyl-ε-caprolactone)–Polylactide Thermoplastic Elastomers Martello, Mark T.; Hillmyer, Marc A. Macromolecules, Vol. 44, Issue 21 https://doi.org/10.1021/ma201063t	journal	November 2011
Resorbable and Highly Elastic Block Copolymers from 1,5-Dioxepan-2-one and l -Lactide with Controlled Tensile Properties and Hydrophilicity Ryner, Maria; Albertsson, Ann-Christine Biomacromolecules, Vol. 3, Issue 3 https://doi.org/10.1021/bm015658z	journal	May 2002
Renewable-Resource Thermoplastic Elastomers Based on Polylactide and Polymenthide Wanamaker, Carolyn L.; O'Leary, Leslie E.; Lynd, Nathaniel A. Biomacromolecules, Vol. 8, Issue 11 https://doi.org/10.1021/bm700699g	journal	November 2007
Scalable production of mechanically tunable block polymers from sugar Xiong, M.; Schneiderman, D. K.; Bates, F. S. Proceedings of the National Academy of Sciences, Vol. 111, Issue 23 https://doi.org/10.1073/pnas.1404596111	journal	May 2014
Synthesis and Melt Processing of Sustainable Poly(ε-decalactone)- block -Poly(lactide) Multiblock Thermoplastic Elastomers Martello, Mark T.; Schneiderman, Deborah K.; Hillmyer, Marc A. ACS Sustainable Chemistry & Engineering, Vol. 2, Issue 11 https://doi.org/10.1021/sc500412a	journal	October 2014
Controlled Polymerization of Next-Generation Renewable Monomers and Beyond Yao, Kejian; Tang, Chuanbing Macromolecules, Vol. 46, Issue 5 https://doi.org/10.1021/ma3019574	journal	February 2013
Biobased building blocks for the rational design of renewable block polymers Holmberg, Angela L.; Reno, Kaleigh H.; Wool, Richard P. Soft Matter, Vol. 10, Issue 38 https://doi.org/10.1039/C4SM01220H	journal	January 2014
Biodegradable Polyesters from Renewable Resources Tsui, Amy; Wright, Zachary C.; Frank, Curtis W. Annual Review of Chemical and Biomolecular Engineering, Vol. 4, Issue 1 https://doi.org/10.1146/annurev-chembioeng-061312-103323	journal	June 2013
The battle for the “green” polymer. Different approaches for biopolymer synthesis: bioadvantaged vs. bioreplacement Hernández, Nacú; Williams, R. Christopher; Cochran, Eric W. Org. Biomol. Chem., Vol. 12, Issue 18 https://doi.org/10.1039/C3OB42339E	journal	January 2014
PLA-based biodegradable and tunable soft elastomers for biomedical applications Harrane, Amine; Leroy, Adrien; Nouailhas, Hélène Biomedical Materials, Vol. 6, Issue 6 https://doi.org/10.1088/1748-6041/6/6/065006	journal	November 2011
Synthesis, preparation, in vitro degradation, and application of novel degradable bioelastomers—A review Liu, Quanyong; Jiang, Lei; Shi, Rui Progress in Polymer Science, Vol. 37, Issue 5 https://doi.org/10.1016/j.progpolymsci.2011.11.001	journal	May 2012
Dependence of the Ultimate Tensile Strength of Thermoplastic Elastomers of the Triblock Type on the Molecular Weight between Chain Entanglements of the Central Block Tong, Jiang-Dong; Jerôme, Robert Macromolecules, Vol. 33, Issue 5 https://doi.org/10.1021/ma990404f	journal	March 2000
Aliphatic polyesters II. The degradation of poly (DL-lactide), poly (ε-caprolactone), and their copolymers in vivo Pitt, G.; Gratzl, M.; Kimmel, G. Biomaterials, Vol. 2, Issue 4 https://doi.org/10.1016/0142-9612(81)90060-0	journal	October 1981
Triblock copolymers of -caprolactone, trimethylene carbonate, and L-lactide: Effects of using random copolymer as hard-block Widjaja, Leonardus Kresna; Kong, Jen Fong; Chattopadhyay, Sujay Journal of the Mechanical Behavior of Biomedical Materials, Vol. 6 https://doi.org/10.1016/j.jmbbm.2011.11.001	journal	February 2012
Designing biodegradable multiblock PCL/PLA thermoplastic elastomers Cohn, D.; Hotovely Salomon, A. Biomaterials, Vol. 26, Issue 15 https://doi.org/10.1016/j.biomaterials.2004.07.052	journal	May 2005
Synthesis and Properties of Poly[isobornyl methacrylate (IBMA)- b -butadiene (BD)- b -IBMA] Copolymers: New Thermoplastic Elastomers of a Large Service Temperature Range Yu, Jian Ming; Dubois, Philippe; Jérôme, Robert Macromolecules, Vol. 29, Issue 23 https://doi.org/10.1021/ma960710i	journal	January 1996
Triblock copolymers of ε-caprolactone, L-lactide, and trimethylene carbonate: Biodegradability and elastomeric behavior Widjaja, Leonardus Kresna; Kong, Jen Fong; Chattopadhyay, Sujay Journal of Biomedical Materials Research Part A, Vol. 99A, Issue 1 https://doi.org/10.1002/jbm.a.33161	journal	July 2011
Synthesis of biodegradable thermoplastic elastomers (BTPE) based on ε-caprolactone Lipik, V. T.; Widjaja, L. K.; Liow, S. S. Express Polymer Letters, Vol. 4, Issue 1 https://doi.org/10.3144/expresspolymlett.2010.6	journal	January 2010
Poly(CL/DLLA-b-CL) multiblock copolymers as biodegradable thermoplastic elastomers Ryynanen, T.; Nykanen, A.; Seppala, J. V. Express Polymer Letters, Vol. 2, Issue 3 https://doi.org/10.3144/expresspolymlett.2008.23	journal	January 2008
Resilient Bioresorbable Copolymers Based on Trimethylene Carbonate, l -Lactide, and 1,5-Dioxepan-2-one Andronova, Natalia; Albertsson, Ann-Christine Biomacromolecules, Vol. 7, Issue 5 https://doi.org/10.1021/bm060081c	journal	May 2006
Biodegradable elastomers based on ABA triblocks: influence of end-block crystallinity on elastomeric character: Biodegradable elastomers based on ABA triblocks Kong, Jen Fong; Lipik, Vitali; Abadie, Marc JM Polymer International, Vol. 61, Issue 1 https://doi.org/10.1002/pi.3130	journal	July 2011
Thermoplastic elastomers based on poly(lactide)–poly(trimethylene carbonate-co-caprolactone)–poly(lactide) triblock copolymers and their stereocomplexes Zhang, Z.; Grijpma, D. W.; Feijen, J. Journal of Controlled Release, Vol. 116, Issue 2 https://doi.org/10.1016/j.jconrel.2006.09.033	journal	November 2006
Enhancement of mechanical properties of triblock copolymers by random copolymer middle blocks Staudinger, Ulrike; Satapathy, Bhabani K.; Thunga, Mahendra European Polymer Journal, Vol. 43, Issue 6 https://doi.org/10.1016/j.eurpolymj.2007.03.022	journal	June 2007
Regular Mixing Thermodynamics of Hydrogenated Styrene–Isoprene Block–Random Copolymers Beckingham, Bryan S.; Register, Richard A. Macromolecules, Vol. 46, Issue 8 https://doi.org/10.1021/ma4002512	journal	April 2013
Mixing Thermodynamics of Ternary Block–Random Copolymers Containing a Polyethylene Block Beckingham, Bryan S.; Burns, Adam B.; Register, Richard A. Macromolecules, Vol. 46, Issue 7 https://doi.org/10.1021/ma400311p	journal	March 2013
Synthesis of biodegradable thermoplastic elastomers from ε -caprolactone and lactide Nakayama, Yuushou; Aihara, Kazuki; Yamanishi, Hitomi Journal of Polymer Science Part A: Polymer Chemistry, Vol. 53, Issue 3 https://doi.org/10.1002/pola.27463	journal	November 2014
Topological behavior mimicking ethylene–hexene copolymers using branched lactones and macrolactones Jasinska-Walc, Lidia; Hansen, Michael Ryan; Dudenko, Dmytro Polym. Chem., Vol. 5, Issue 10 https://doi.org/10.1039/C3PY01754K	journal	January 2014
Achieving Micelle Control through Core Crystallinity Glavas, Lidija; Olsén, Peter; Odelius, Karin Biomacromolecules, Vol. 14, Issue 11 https://doi.org/10.1021/bm401312j	journal	October 2013
Effect of composition on the entanglement density in random copolymers Lomellini, Paolo; Rossi, Anna Grazia Die Makromolekulare Chemie, Vol. 191, Issue 7, p. 1729-1737 https://doi.org/10.1002/macp.1990.021910723	journal	July 1990
Kinetics and Mechanism of the Stannous Octoate-Catalyzed Bulk Polymerization of ε-Caprolactone Storey, Robson F.; Sherman, John W. Macromolecules, Vol. 35, Issue 5 https://doi.org/10.1021/ma010986c	journal	February 2002
Crystallization kinetics of poly(ε-caprolactone) in miscible thermosetting polymer blends of epoxy resin and poly(ε-caprolactone) Guo, Qipeng; Groeninckx, Gabriel Polymer, Vol. 42, Issue 21 https://doi.org/10.1016/S0032-3861(01)00348-2	journal	October 2001
Crystal structure of poly-ε-caprolactone Bittiger, H.; Marchessault, R. H.; Niegisch, W. D. Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry, Vol. 26, Issue 12 https://doi.org/10.1107/S0567740870005198	journal	December 1970
Synthesis, characterization, and miscibility of caprolactone random copolymers Vion, Jean Marc; Jerome, Robert; Teyssie, Philippe Macromolecules, Vol. 19, Issue 7 https://doi.org/10.1021/ma00161a009	journal	July 1986
Crystallization kinetics and melting of caprolactone random copolymers Goulet, Louise; Prud'homme, Robert E. Journal of Polymer Science Part B: Polymer Physics, Vol. 28, Issue 12 https://doi.org/10.1002/polb.1990.090281212	journal	November 1990
Lactone polymers. VIII. Dynamic mechanical properties of ε-caprolactone and γ-(tert-butyl)-ε-caprolactone copolymers Seefried, C. G.; Koleske, J. V.; Critchfield, F. E. Journal of Polymer Science: Polymer Physics Edition, Vol. 14, Issue 11 https://doi.org/10.1002/pol.1976.180141107	journal	November 1976
Ring-Opening Polymerization of l -Lactide and ε-Caprolactone Utilizing Biocompatible Zinc Catalysts. Random Copolymerization of l -Lactide and ε-Caprolactone Darensbourg, Donald J.; Karroonnirun, Osit Macromolecules, Vol. 43, Issue 21 https://doi.org/10.1021/ma101784y	journal	November 2010
Crystallization behavior of poly(ε-caprolactone) chains confined in lamellar nanodomains Nakagawa, Shintaro; Tanaka, Takumi; Ishizone, Takashi Polymer, Vol. 55, Issue 16 https://doi.org/10.1016/j.polymer.2014.06.049	journal	August 2014
Rheology of ordered and disordered symmetric poly(ethylenepropylene)-poly(ethylethylene) diblock copolymers Rosedale, J. H.; Bates, F. S. Macromolecules, Vol. 23, Issue 8 https://doi.org/10.1021/ma00210a032	journal	April 1990
Crystallization Kinetics and Morphology of Biodegradable Double Crystalline PLLA- b -PCL Diblock Copolymers Castillo, Reina Verónica; Müller, Alejandro J.; Raquez, Jean-Marie Macromolecules, Vol. 43, Issue 9 https://doi.org/10.1021/ma100201g	journal	May 2010
Crystallization in Poly( l -lactide)- b -poly(ε-caprolactone) Double Crystalline Diblock Copolymers: A Study Using X-ray Scattering, Differential Scanning Calorimetry, and Polarized Optical Microscopy Hamley, I. W.; Castelletto, V.; Castillo, R. V. Macromolecules, Vol. 38, Issue 2 https://doi.org/10.1021/ma0481499	journal	January 2005
Melt Structure and its Transformation by Sequential Crystallization of the Two Blocks within Poly(L-lactide)-block-Poly(ɛ-caprolactone) Double Crystalline Diblock Copolymers Hamley, I. W.; Parras, P.; Castelletto, V. Macromolecular Chemistry and Physics, Vol. 207, Issue 11 https://doi.org/10.1002/macp.200600085	journal	June 2006
Crystallization-Induced Orientation for Microstructures of Poly( l -lactide)- b -poly(ε-caprolactone) Diblock Copolymers Ho, Rong-Ming; Hsieh, Ping-Yen; Tseng, Wen-Hsien Macromolecules, Vol. 36, Issue 24 https://doi.org/10.1021/ma0347868	journal	December 2003
Synthesis and crystallization behavior of poly( l -lactide)- block -poly(ϵ-caprolactone) copolymer Kim, Jin Kon; Park, Dong-Jin; Lee, Myung-Se Polymer, Vol. 42, Issue 17 https://doi.org/10.1016/S0032-3861(01)00217-8	journal	August 2001
Thermal properties of di- and triblock copolymers of poly(l-lactide) with poly(oxyethylene) or poly(ε-caprolactone) Maglio, Giovanni; Migliozzi, Anna; Palumbo, Rosario Polymer, Vol. 44, Issue 2 https://doi.org/10.1016/S0032-3861(02)00764-4	journal	January 2003
Synthesis and Characterization of Poly( l -lactide)−Poly(ε-caprolactone) Multiblock Copolymers Jeon, Oju; Lee, Soo-Hong; Kim, Soo Hyun Macromolecules, Vol. 36, Issue 15 https://doi.org/10.1021/ma034006v	journal	July 2003
Structure and mechanical properties of poly(?,?-lactic acid)/poly(ɛ-caprolactone) blends Broz, M. Biomaterials, Vol. 24, Issue 23 https://doi.org/10.1016/S0142-9612(03)00314-4	journal	October 2003
Nanoporous Linear Polyethylene from a Block Polymer Precursor Pitet, Louis M.; Amendt, Mark A.; Hillmyer, Marc A. Journal of the American Chemical Society, Vol. 132, Issue 24 https://doi.org/10.1021/ja100985d	journal	June 2010
Pressure-Sensitive Adhesives from Renewable Triblock Copolymers Shin, Jihoon; Martello, Mark T.; Shrestha, Mona Macromolecules, Vol. 44, Issue 1 https://doi.org/10.1021/ma102216d	journal	January 2011
Consequences of Polylactide Stereochemistry on the Properties of Polylactide-Polymenthide-Polylactide Thermoplastic Elastomers Wanamaker, Carolyn L.; Bluemle, Michael J.; Pitet, Louis M. Biomacromolecules, Vol. 10, Issue 10 https://doi.org/10.1021/bm900721p	journal	October 2009
A correlation between critical tensile strength and polymer cross-sectional area Vincent, P. I. Polymer, Vol. 13, Issue 12 https://doi.org/10.1016/0032-3861(72)90116-4	journal	December 1972
Bulk polymerization of ε-caprolactone: Rheological predictive laws Gimenez, Jérôme; Cassagnau, Philippe; Michel, Alain Journal of Rheology, Vol. 44, Issue 3 https://doi.org/10.1122/1.551099	journal	May 2000
Block copolymer micelles for drug delivery: Design, characterization and biological significance Kataoka, Kazunori; Harada, Atsushi; Nagasaki, Yukio Advanced Drug Delivery Reviews, Vol. 64 https://doi.org/10.1016/j.addr.2012.09.013	journal	December 2012

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