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Issue 11, 2019
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Enhanced reduction of polymerization-induced shrinkage stress via combination of radical ring opening and addition fragmentation chain transfer

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Abstract

Polymerization-induced shrinkage stress within bulk photopolymer networks represents one of the most pressing challenges for their application in 3D-printing, microelectronics and dentistry. The occurring shrinkage stress within commercial (meth)acrylate-based networks results from a combination of the covalent attachment of monomers and the gelation at early stages of the reaction. Alternatively, cyclic monomers (e.g. 1,1-disubstituted 2-vinylcyclopropanes, VCPs) have been reported as a possible monomer class yielding reduced polymerization shrinkage and consequently shrinkage stress due to a radical ring opening reaction. Another way to reduce the occurring shrinkage stress is to regulate the radical network formation via an addition fragmentation chain transfer (AFCT) concept. Herein, the light-induced radical polymerization of a combination of VCP monomers with variable amounts of an AFCT reagent (an ester-activated vinyl sulfonate ester EVS) was investigated. A high reactivity towards light-induced radical polymerization is confirmed for VCP/EVS mixtures via photoreactor, photo-DSC and real time (RT)-NIR-photorheology accompanied by a significant increase in C[double bond, length as m-dash]C double bond conversion with increasing amounts of EVS. Most importantly, both systems (VCPs and AFCT reagents) combined lead to an enhanced reduction of polymerization-induced shrinkage stress. The resulting materials showed, even at low concentrations of EVS, a high network homogeneity (indicated by a narrow loss factor plot in DMTA). Also, filled systems performed well with respect to reduced shrinkage force while maintaining sufficient E-modulus and flexural strength. The presented material concept has great potential for dental materials and lithography-based 3D-printing.

Graphical abstract: Enhanced reduction of polymerization-induced shrinkage stress via combination of radical ring opening and addition fragmentation chain transfer

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Supplementary files

Article information


Submitted
29 Oct 2018
Accepted
26 Jan 2019
First published
29 Jan 2019

This article is Open Access

Polym. Chem., 2019,10, 1357-1366
Article type
Paper

Enhanced reduction of polymerization-induced shrinkage stress via combination of radical ring opening and addition fragmentation chain transfer

S. Schoerpf, Y. Catel, N. Moszner, C. Gorsche and R. Liska, Polym. Chem., 2019, 10, 1357
DOI: 10.1039/C8PY01540F

This article is licensed under a Creative Commons Attribution-NonCommercial 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 and it is not used for commercial purposes.

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    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
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    [Original citation] - Published by the PCCP Owner Societies.
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    [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.

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