Polymethylferrocene-induced photopolymerization of cyanoacrylates using visible and near-infrared light
Faggi, Enrico (Universitat Autònoma de Barcelona. Departament de Química)
Gascó-Catalán, Carolina (Universitat Autònoma de Barcelona. Departament de Química)
Aguilera-Sigalat, Jordi (CUANTUM Medical Cosmetics S.L.)
Guirado López, Gonzalo (Universitat Autònoma de Barcelona. Departament de Química)
Ortego, Sara (CUANTUM Medical Cosmetics S.L.)
Sáez, Rubén (CUANTUM Medical Cosmetics S.L.)
Pujol Vila, Ferran (CUANTUM Medical Cosmetics S.L.)
Marquet, Jordi (Universitat Autònoma de Barcelona. Departament de Química)
Hernando Campos, Jordi (Universitat Autònoma de Barcelona. Departament de Química)
Sebastián Pérez, Rosa Maria (Universitat Autònoma de Barcelona. Departament de Química)

Date:	2019
Abstract:	Metallocene-induced photopolymerization of cyanoacrylates based on electron transfer processes has been proposed as an alternative to more conventional light-curing strategies relying on photobase generators. However, successful application of this methodology has so far only been achieved for very reactive cyanoacrylates under UV illumination and long irradiation times, which eventually hampers its practical use. To overcome these limitations, we describe in this work the use of electron-rich polymethylferrocenes as photoinitiators, with which fast light-induced polymerization of commercial formulations of less reactive, but more relevant long alkyl chain cyanoacrylates has been accomplished by illumination with visible and even near-infrared light. In addition, generalization of this technology to other electron-deficient, noncyanoacrylate monomers has been demonstrated. The low oxidation potential of polymethylferrocenes accounts for these excellent results, which strongly favors the formation of radical anions by electron transfer that initiate the polymerization reaction. Because of the high molecular weight and superior adhesive behavior of the resulting polymer materials as well as the facile access to polymethylferrocenes, they emerge as very attractive photoinitiators for the light-curing of cyanoacrylate (and other) glues in real applications.
Grants:	Ministerio de Economía y Competitividad RTC-2016-5683-1 Ministerio de Economía y Competitividad CTQ2015-65439-R Agència de Gestió d'Ajuts Universitaris i de Recerca 2017/SGR-465 Ministerio de Ciencia e Innovación BES-2016-078179
Rights:	Tots els drets reservats.
Language:	Anglès
Document:	Article ; recerca ; Versió acceptada per publicar
Subject:	Electron transfer process ; Electron-deficient ; High molecular weight ; Low oxidation potential ; Near infrared light ; Photobase generator ; Polymerization reaction ; Visible and near infrared
Published in:	Macromolecules, Vol. 52, Issue 15 (August 2019) , p. 5602-5610, ISSN 1520-5835

DOI: 10.1021/acs.macromol.9b00745

Postprint 55 p, 2.2 MB

The record appears in these collections:
Research literature > UAB research groups literature > Research Centres and Groups (research output) > Experimental sciences > Group in Electrochemistry, Photochemistry and Organic Reactivity (GEFRO)
Articles > Research articles
Articles > Published articles