Dual‐Cure Coatings: Spiroorthoesters as Volume‐Controlling Additives in Thiol–Ene Reactions

Philipp Marx, Angelo Romano, Roland Fischer, Ignazio Roppolo, Marco Sangermano, Frank Wiesbrock

Publikation: Beitrag in einer FachzeitschriftArtikelForschungBegutachtung

Abstract

Most thiol–ene systems exhibit shrinkage during cross-linking, potentially resulting in micro-cracks and delamination. Oligocyclic monomers like spiroorthoesters (SOEs), on the contrary, show expansion during the ring-opening polymerization. In this communication, a photocurable thiol–ene system composed of a trifunctional thiol, a bisfunctional allyl-bisphenol A compound, and an SOE compound bearing one olefin function shows expansion in the range from −3.07 to +1.70 vol% if the SOE content is increased from 0–30 wt%. Network formation can be accomplished under visible light if a radical as well as a cationic photoinitiator (dual-cure mechanism) and a sensitizer are used. The elasticity of the cured resin increases upon the addition of the SOE; correspondingly, the glass-transition temperature shows a (minor) decrease from 16 to 3 °C. A tailor-made combination of the allyl-bisphenol A compound (90 wt%) and the SOE (10 wt%) yields networks that are volume-neutral during curing.

Originalspracheenglisch
Aufsatznummer1800627
Seitenumfang5
FachzeitschriftMacromolecular materials and engineering
Jahrgang304
Ausgabenummer4
DOIs
PublikationsstatusVeröffentlicht - 2019

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Bearings (structural)
Coatings
Ring opening polymerization
Alkenes
Sulfhydryl Compounds
Delamination
Olefins
Curing
Elasticity
Resins
Monomers
Cracks
Communication
bisphenol A
Glass transition temperature

Schlagwörter

    ASJC Scopus subject areas

    • !!Materials Chemistry
    • !!Chemical Engineering(all)
    • !!Polymers and Plastics
    • Organische Chemie

    Fields of Expertise

    • Advanced Materials Science

    Kooperationen

    • NAWI Graz

    Dies zitieren

    Dual‐Cure Coatings: Spiroorthoesters as Volume‐Controlling Additives in Thiol–Ene Reactions. / Marx, Philipp; Romano, Angelo; Fischer, Roland; Roppolo, Ignazio; Sangermano, Marco; Wiesbrock, Frank.

    in: Macromolecular materials and engineering, Jahrgang 304, Nr. 4, 1800627, 2019.

    Publikation: Beitrag in einer FachzeitschriftArtikelForschungBegutachtung

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    abstract = "Most thiol–ene systems exhibit shrinkage during cross-linking, potentially resulting in micro-cracks and delamination. Oligocyclic monomers like spiroorthoesters (SOEs), on the contrary, show expansion during the ring-opening polymerization. In this communication, a photocurable thiol–ene system composed of a trifunctional thiol, a bisfunctional allyl-bisphenol A compound, and an SOE compound bearing one olefin function shows expansion in the range from −3.07 to +1.70 vol{\%} if the SOE content is increased from 0–30 wt{\%}. Network formation can be accomplished under visible light if a radical as well as a cationic photoinitiator (dual-cure mechanism) and a sensitizer are used. The elasticity of the cured resin increases upon the addition of the SOE; correspondingly, the glass-transition temperature shows a (minor) decrease from 16 to 3 °C. A tailor-made combination of the allyl-bisphenol A compound (90 wt{\%}) and the SOE (10 wt{\%}) yields networks that are volume-neutral during curing.",
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    AU - Roppolo, Ignazio

    AU - Sangermano, Marco

    AU - Wiesbrock, Frank

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    KW - volumetric expansion

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    KW - thiol-ene reactions

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