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Polymers 2017, 9(9), 400; https://doi.org/10.3390/polym9090400

Carbanion as a Superbase for Catalyzing Thiol–Epoxy Photopolymerization

1
Key Laboratory of Synthetic and Biological Colloids, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi 214122, Jiangsu, China
2
Collaborative Innovation Centre for Petrochemical New Materials, AnHui Province Key Laboratory of Optoelectronic and Magnetism Functional Materials, School of Chemistry and Chemical Engineering, Anqing Normal University, Anqing 246013, Anhui, China
*
Author to whom correspondence should be addressed.
Received: 21 July 2017 / Revised: 22 August 2017 / Accepted: 25 August 2017 / Published: 29 August 2017
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Abstract

Photobase generator (PBG)-mediated thiol–epoxy photopolymerization has received widedspread attention due to its versatility in various applications. Currently, nearly all reported PBGs release amines as active species. The formed amines induce odor, yellowing, and potential toxicity. In this study, a series of novel thioxanthone-based PBGs, which were able to generate carbanion via decarboxylation under LED light irradiation, were designed and straightforwardly prepared. The formed carbanion can be used as a superbase to catalyze thiol–epoxy polymerization efficiently. Investigation on 1H NMR and FT-IR confirmed the generation of carbanion intermediates. The counteranion significantly affected the photodecarboxylation efficiency. The study of photopolymerization tests, based on real-time FT-IR and dielectric analysis measurements, indicated that the generated carbanion exhibited faster polymerization rate and higher epoxy conversion than traditional superbase 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). In differential scanning calorimeter, thermogravimetric, and nanoindentation tests, comparable thermal and mechanical properties of the photocured films catalyzed by novel PBGs were obtained. The high initiation ability combined with straightforward synthesis makes these PBGs promising candidates for commercialization. View Full-Text
Keywords: photopolymerization; thiol–epoxy; carbanion; superbase; decarboxylation; thioxanthone photopolymerization; thiol–epoxy; carbanion; superbase; decarboxylation; thioxanthone
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Dong, X.; Hu, P.; Shen, W.; Li, Z.; Liu, R.; Liu, X. Carbanion as a Superbase for Catalyzing Thiol–Epoxy Photopolymerization. Polymers 2017, 9, 400.

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