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Cited by 83biodegradable polymer synthesis and propertiesPolymer crystallization and propertiesPolymer composites and self-healing

Physical properties and hydrolytic degradability of polyethylene-like polyacetals and polycarbonates

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Ortmann, Patrick, Heckler, Ilona, Mecking, Stefan·2014·Green Chemistry
DOI 10.1039/c3gc42592d
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Abstract

Long-chain polyacetals and polycarbonates were prepared by polycondensation of α,ω-diols (C18, C19, C23) derived from fatty acids as a renewable feedstock with diethoxymethane and dimethyl carbonate, respectively, in one step. Studies of hydrolytic degradation of the solid polymers show a much higher stability compared to their shorter-chain counterparts. Long-chain polyacetals were found to degrade slowly under acidic conditions, while the long-chain polycarbonates also degraded in a basic environment. To rationalize the impact of acetal and carbonate groups on the thermal and crystalline properties of polyacetals and polycarbonates, additional model polymers with a further reduced and systematically varied functional group density were generated by ADMET copolymerization of the unfunctionalized undeca-1,10-diene with bis(undec-10-en-1-yloxy)methane or di(undec-10-en-1-yl) carbonate, respectively, followed by exhaustive hydrogenation. Long-chain polycarbonates possess polyethylene-like solid state structures. By comparison to polyesters, a given density of carbonate groups in the polymer chain reduces melting and crystallization temperatures significantly more strongly. By contrast, long-chain polyacetals possess more complex non-uniform crystal structures, and only adopt a polyethylene-like structure at very low densities of acetal groups. Also, acetal groups more strongly impact melting and crystallization temperatures vs. carbonates.

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  • The key challenge of achieving polyethylene-like mechanical properties had not been addressed in previous preparations of PE-18,18 and PC-18.

    “Samples of polyester-18,18 (PE-18,18) and polycarbonate-18 (PC-18) had been prepared previously based on other feedstocks, 19,20 but the key challenge of achieving polyethylene-like mechanical properties had not been addressed.”

    From Closed-loop recycling of polyethylene-like materials (2021) · cites this paper as [19]

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Authors
Ortmann, P., Heckler, I., & Mecking, S.
Affiliations
University of Konstanz (DE)
Corresponding author
Mecking, Stefan
ORCID
Mecking, Stefan
Venue
Green Chemistry
Publisher
Royal Society of Chemistry (RSC)
Published
2014
Volume
16
Issue
4
Pages
1816
ISSN
  • 1463-9262 (ISSN-L)
  • 1463-9270
DOI
10.1039/c3gc42592d
OpenAlex
W2068467020
Cited by
83
References
53
Citations by year
2026: 10 · 2025: 13 · 2024: 11 · 2023: 5 · 2022: 2 · 2021: 11 · 2020: 4 · 2019: 5 · 2018: 6 · 2016: 4 · 2015: 8 · 2014: 4
FWCI
2.02
Type
journal article
Language
en
Open access
Licence
cc-by
Locations
  • Green Chemistry (publishedVersion, cc-by)
  • KOPS (University of Konstanz) (submittedVersion)
Topics
  • Physical Sciences › Materials Science › Biomaterials › biodegradable polymer synthesis and properties
  • Physical Sciences › Materials Science › Polymers and Plastics › Polymer crystallization and properties
  • Physical Sciences › Materials Science › Polymers and Plastics › Polymer composites and self-healing
Keywords
polyoxymethylene, polycarbonate, hydrolytic degradation, long-chain polymers, diethoxymethane, dimethyl carbonate, hydrogenation, melting point, crystallization temperature, crystal structure, functional group density, renewable raw materials, biodegradable polymers

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