Jump to main content
Jump to site search

Issue 4, 2014
Previous Article Next Article

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

Author affiliations

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.

Graphical abstract: Physical properties and hydrolytic degradability of polyethylene-like polyacetals and polycarbonates

Back to tab navigation

Supplementary files

Article information


Submitted
20 Dec 2013
Accepted
24 Jan 2014
First published
12 Feb 2014

This article is Open Access

Green Chem., 2014,16, 1816-1827
Article type
Paper

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

P. Ortmann, I. Heckler and S. Mecking, Green Chem., 2014, 16, 1816
DOI: 10.1039/C3GC42592D

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material.

Reproduced material should be attributed as follows:

  • For reproduction of material from NJC:
    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
  • For reproduction of material from PCCP:
    [Original citation] - Published by the PCCP Owner Societies.
  • For reproduction of material from PPS:
    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
  • For reproduction of material from all other RSC journals:
    [Original citation] - Published by The Royal Society of Chemistry.

Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.


Social activity

Search articles by author

Spotlight

Advertisements