New allyl-functional catalytic comonomers for sequential thiol-Michael and radical thiol-ene reactions

Soft poly(thioether) thermosets have been synthesized by employing a two-step curing procedure based on click chemistry. The first stage of curing is a thiol-Michael addition between acrylates (or methacrylates) and thiols in excess, catalyzed by a set of novel tertiary amine catalyst comonomers wit...

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Detalles Bibliográficos
Autores: Konuray, Ali Osman|||0000-0001-7281-006X, Fernández Francos, Xavier|||0000-0002-3492-2922, Ramis Juan, Xavier|||0000-0003-2550-7185, Serra Albet, Maria Àngels|||0000-0003-1387-0358
Tipo de recurso: artículo
Fecha de publicación:2018
País:España
Institución:Universitat Politècnica de Catalunya (UPC)
Repositorio:UPCommons. Portal del coneixement obert de la UPC
Idioma:inglés
OAI Identifier:oai:upcommons.upc.edu:2117/117314
Acceso en línea:https://hdl.handle.net/2117/117314
https://dx.doi.org/10.1016/j.polymer.2018.01.073
Access Level:acceso abierto
Palabra clave:Catalysis
Heat resistant plastics
Michael addition
Dual-curing
Thiol
Acrylate
Methacrylate
Click reaction
Catàlisi
Plàstics termostables
Àrees temàtiques de la UPC::Enginyeria dels materials::Materials plàstics i polímers
Àrees temàtiques de la UPC::Enginyeria química
Descripción
Sumario:Soft poly(thioether) thermosets have been synthesized by employing a two-step curing procedure based on click chemistry. The first stage of curing is a thiol-Michael addition between acrylates (or methacrylates) and thiols in excess, catalyzed by a set of novel tertiary amine catalyst comonomers with allyl functionality. Subsequently, the pendant allyl groups of the comonomer get incorporated into the polymer network by undergoing thiol-ene UV photopolymerization with the remaining thiols. The strong catalysis by the high concentration of tertiary amine groups facilitates quantitative conversions at the end of the first stage. All remaining functional groups are depleted after a short period of UV irradiation. Final materials are clear, transparent, and exhibit homogeneous network structures with alpha relaxation temperatures in the range 3–25¿°C. This sub-ambient relaxation temperature range suggests these materials may be suitable for coating applications where delicate substrates are involved such as plastic, wood and paper.