Exploring Aromatic S-Thioformates as Photoinitiators

Paul Rieger; Sabrina Pueschmann; Michael Haas; Max Schmallegger; Gema Guedes de la Cruz; Thomas Griesser

doi:10.3390/polym15071647

Exploring Aromatic S-Thioformates as Photoinitiators

Paul Rieger, Sabrina Pueschmann, Michael Haas, Max Schmallegger, Gema Guedes de la Cruz^*, Thomas Griesser^*

^*Korrespondierende/r Autor/-in für diese Arbeit

Publikation: Beitrag in einer Fachzeitschrift › Artikel › Begutachtung

Abstract

Thiyl radicals were generated from aromatic S-thioformates by photolysis. The corresponding photo-initiated decarbonylation allows initiating polymerization reactions in both acrylate- and thiol-acrylate-based resin systems. Compared to aromatic thiols, the introduction of the photolabile formyl group prevents undesired reactions with acrylate monomers allowing photoinitiators (PIs) with constant reactivity over storage. To demonstrate the potential of S-thioformates as PIs, the bifunctional molecule S,S′-(thiobis(4,1-phenylene))dimethanethioate (2b) was synthesized, providing reactivity under visible light excitation. Consequently, acrylate-based formulations could successfully be processed by digital light processing (DLP)-based stereolithography at 405 nm in high resolution.

Originalsprache	englisch
Aufsatznummer	1647
Fachzeitschrift	Polymers
Jahrgang	15
Ausgabenummer	7
DOIs	https://doi.org/10.3390/polym15071647
Publikationsstatus	Veröffentlicht - Apr. 2023

ASJC Scopus subject areas

Chemie (insg.)
Polymere und Kunststoffe

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10.3390/polym15071647Lizenz: CC BY 4.0

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abstract = "Thiyl radicals were generated from aromatic S-thioformates by photolysis. The corresponding photo-initiated decarbonylation allows initiating polymerization reactions in both acrylate- and thiol-acrylate-based resin systems. Compared to aromatic thiols, the introduction of the photolabile formyl group prevents undesired reactions with acrylate monomers allowing photoinitiators (PIs) with constant reactivity over storage. To demonstrate the potential of S-thioformates as PIs, the bifunctional molecule S,S′-(thiobis(4,1-phenylene))dimethanethioate (2b) was synthesized, providing reactivity under visible light excitation. Consequently, acrylate-based formulations could successfully be processed by digital light processing (DLP)-based stereolithography at 405 nm in high resolution.",

keywords = "photochemistry, photoinitiator, thiol-ene",

author = "Paul Rieger and Sabrina Pueschmann and Michael Haas and Max Schmallegger and {Guedes de la Cruz}, Gema and Thomas Griesser",

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AU - Rieger, Paul

AU - Pueschmann, Sabrina

AU - Haas, Michael

AU - Schmallegger, Max

AU - Guedes de la Cruz, Gema

AU - Griesser, Thomas

PY - 2023/4

Y1 - 2023/4

N2 - Thiyl radicals were generated from aromatic S-thioformates by photolysis. The corresponding photo-initiated decarbonylation allows initiating polymerization reactions in both acrylate- and thiol-acrylate-based resin systems. Compared to aromatic thiols, the introduction of the photolabile formyl group prevents undesired reactions with acrylate monomers allowing photoinitiators (PIs) with constant reactivity over storage. To demonstrate the potential of S-thioformates as PIs, the bifunctional molecule S,S′-(thiobis(4,1-phenylene))dimethanethioate (2b) was synthesized, providing reactivity under visible light excitation. Consequently, acrylate-based formulations could successfully be processed by digital light processing (DLP)-based stereolithography at 405 nm in high resolution.

AB - Thiyl radicals were generated from aromatic S-thioformates by photolysis. The corresponding photo-initiated decarbonylation allows initiating polymerization reactions in both acrylate- and thiol-acrylate-based resin systems. Compared to aromatic thiols, the introduction of the photolabile formyl group prevents undesired reactions with acrylate monomers allowing photoinitiators (PIs) with constant reactivity over storage. To demonstrate the potential of S-thioformates as PIs, the bifunctional molecule S,S′-(thiobis(4,1-phenylene))dimethanethioate (2b) was synthesized, providing reactivity under visible light excitation. Consequently, acrylate-based formulations could successfully be processed by digital light processing (DLP)-based stereolithography at 405 nm in high resolution.

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KW - thiol-ene

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Exploring Aromatic S-Thioformates as Photoinitiators

Abstract

ASJC Scopus subject areas

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