Bulk Ring-Opening Transesterification Polymerization of the Renewable δ-Decalactone Using an Organocatalyst
Abstract
The bulk ring-opening polymerization of renewable δ-decalactone using 1,5,7-triazabicyclo[4.4.0]dec-5-ene was carried out at temperatures between 7 and 110 °C. The equilibrium monomer concentration for reactions within this temperature range was used to determine the polymerization thermodynamic parameters (Δ H p = -17.1 ± 0.6 kJ mol -1 , Δ S p = -54 ± 2 J mol -1 K -1 ) for δ-decalactone. The polymerization kinetics were established and high molar mass poly(δ-decalactone) was prepared with a glass transition temperature of -51 °C. Poly(δ-decalactone) samples with controlled molar mass and narrow molar mass distributions were realized by controlling the monomer conversion and initiator concentration. A high molar mass poly(lactide)-poly(δ-decalactone)-poly(lactide) triblock copolymer with a low polydispersity index was prepared by simple sequential addition of monomers. The product triblock exhibited two distinct glass transitions temperatures consistent with microphase segregation.
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The effect of alkyl substituent size and location on the standard state enthalpy and entropy of polymerization has not been experimentally studied in a systematic manner.
“Although thermodynamic parameters have been reported for the polymerization of several substituted δ -valerolactone monomers, the e ff ect of alkyl substituent size and location on the standard state enthalpy ( Δ H p ° ) and entropy ( Δ S p ° ) of polymerization has not been experimentally studied in a systematic manner.”
From Aliphatic Polyester Block Polymer Design (2016) · cites this paper as [33]
The effect of alkyl substituent size and location on bulk polymerization rate has not been systematically studied.
“The e ff ect of alkyl substituent size and location on bulk polymerization rate has not been systematically studied.”
From Aliphatic Polyester Block Polymer Design (2016) · cites this paper as [33]
Cites
Influence of Polydispersity on the Self-Assembly of Diblock Copolymers
Lynd, N. A., & Hillmyer, M. A. (2005) · Macromolecules · doi:10.1021/ma051025r · Cited by 309 · see citing works
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Aliphatic Polyester Block Polymer Design
Schneiderman, D. K., & Hillmyer, M. A. (2016) · Macromolecules · doi:10.1021/acs.macromol.6b00211 · Cited by 290 · see citing works
Self-citationThermodynamic Presynthetic Considerations for Ring-Opening Polymerization
Olsén, P., Odelius, K., & Albertsson, A.-C. (2016) · Biomacromolecules · doi:10.1021/acs.biomac.5b01698 · Cited by 244 · see citing works
Recent Developments in Lactone Monomers and Polymer Synthesis and Application
Bińczak, J., Dziuba, K., & Chrobok, A. (2021) · Materials · doi:10.3390/ma14112881 · Cited by 43 · see citing works
Deokar, M. D., Garnaik, B., & Sivaram, S. (2022) · ACS Omega · doi:10.1021/acsomega.1c04486 · Cited by 21 · see citing works
Progress in Catalytic Ring-Opening Polymerization of Biobased Lactones
Al-Shok, L., Haddleton, D. M., & Adams, F. (2022) · Advances in Polymer Science · doi:10.1007/12_2021_111 · Cited by 10 · see citing works
- Authors
- Martello, M. T., Burns, A., & Hillmyer, M.
- Affiliations
- University of Minnesota (US)
- Corresponding author
- Hillmyer, Marc
- Venue
- ACS Macro Letters
- Publisher
- American Chemical Society (ACS)
- Published
- 2011-11-30
- Volume
- 1
- Issue
- 1
- Pages
- 131-135
- ISSN
- 2161-1653 (ISSN-L)
- OpenAlex
- W2317621330
- Cited by
- 113
- References
- 1
- Citations by year
- 2026: 4 · 2025: 4 · 2024: 11 · 2023: 8 · 2022: 7 · 2021: 12 · 2020: 5 · 2019: 7 · 2018: 9 · 2017: 9 · 2016: 9 · 2015: 10 · 2014: 10 · 2013: 5 · 2012: 3
- FWCI
- 2.36
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- ACS Macro Letters (publishedVersion)
- PubMed (publishedVersion)
- Funders
- Center for Sustainable Polymers, University of Minnesota
- Topics
- Physical Sciences › Materials Science › Biomaterials › biodegradable polymer synthesis and properties
- Physical Sciences › Chemistry › Organic Chemistry › Advanced Polymer Synthesis and Characterization
- Physical Sciences › Materials Science › Polymers and Plastics › Polymer composites and self-healing
- Keywords
- δ-decalactone, ring-opening polymerization, organocatalysis, 1,5,7-triazabicyclo[4.4.0]dec-5-ene, polymerization thermodynamics, polymerization kinetics, glass transition temperature, molecular weight control, microphase separation, renewable monomers
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