Quaternary ammonium salts of phenylglyoxylic acid as photobase generators for thiol-promoted epoxide photopolymerization

Salmi, Hanène; Allonas, Xavier; Ley, Christian; Defoin, Albert; Ak, Antosik

doi:10.1039/c4py00927d

Cited by 62 publications

(82 citation statements)

References 51 publications

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“…The resulting precipitate was filtered off and dried in vacuum to obtain 0.21g (Yield, 51%) colourless crystals. 1 …”

Section: Synthesis Of Compound (9-oxo-9h-thioxanthen-2-yl)-acetate12mentioning

confidence: 97%

“…The disappeared colour confirmed the release of CO 2 when TX-DBU solution was irradiated. 1 Based on the photolysis results combined with the previous report by other groups, 12, 29 a possible mechanism of photoinduced decomposition was proposed (Scheme 2). After irradiation, the excited PBG underwent decarboxylation, releasing CO 2 and basic species which were responsible for the subsequent thiol-epoxy polymerization.…”

Section: Photolysis Studymentioning

confidence: 98%

“…[1][2][3] Polymerization based on thiol-epoxy reaction has long been employed in commercial applications including adhesives and high performance coatings. 4 Photoinduced thiol-epoxy polymerization provides additional advantages of spatial and temporal control of the process.…”

Section: Introductionmentioning

confidence: 99%

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Thioxanthone acetic acid ammonium salts: highly efficient photobase generators based on photodecarboxylation

Dong

Zhu

et al. 2015

RSC Adv.

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Novel photobase generators, which contain thioxanthone as the chromophore and different quaternary ammonium salts as latent active species, can efficiently catalyze thiol-epoxy polymerization via photoinduced decarboxylation.A series of photobase generators (PBGs), which contain thioxanthone as the chromophore and different quaternary ammonium salts as latent active species, were straightforwardly synthesized in two steps and their structures were characterized. Investigation on the photophysical properties of the PBGs indicated that the PBGs were photosensitive to long wavelength due to the characteristic absorption of thioxanthone at 380 nm. The study on photolysis confirmed the photoinduced decarboxylation mechanism, through which the PBGs released active basic species efficiently. All the novel PBGs showed high activity in catalysing thiol-epoxy polymerization without postexposure baking. This is especially true for the PBG containing 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD), which exhibited faster polymerization rate and higher epoxy conversion than the previously described highly active PBG system.

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“…The resulting precipitate was filtered off and dried in vacuum to obtain 0.21g (Yield, 51%) colourless crystals. 1 …”

Section: Synthesis Of Compound (9-oxo-9h-thioxanthen-2-yl)-acetate12mentioning

confidence: 97%

Section: Photolysis Studymentioning

confidence: 98%

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Thioxanthone acetic acid ammonium salts: highly efficient photobase generators based on photodecarboxylation

Dong

Zhu

et al. 2015

RSC Adv.

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“…[42] Seit dieser Verçffentlichung wurden mehrere andere Klassen von PBGs entwickelt, darunter O-Acyloxime und Salze.D iese photolabilen Verbindungen wurden als Vernetzer verwendet und in jüngster Zeit als Basenkatalysatoren eingesetzt. [44] In diesem Zusammenhang haben Forscher im vergangenem Jahrzehnt effizientere PBGs entwickelt, die in der Lage sind, starke Amidine,G uanidine,C arbene und sogar Phosphazene freizusetzen, die sich als wirksame Katalysatoren fürb asenvermittelte Polymerisationen erwiesen haben. Darüber hinaus beschreiben die meisten Berichte in der Literatur Verbindungen mit Quantenausbeuten, die nur in der Lage sind, relativ schwach basische primäre und sekundäre Amine freizusetzen, die bei der Initiierung anionischer Polymerisationen unzureichend sind.…”

Section: Photobasenbildnerunclassified

Organische Photosäuren‐ und Photobasenbildner für Polymerisationen: Jüngste Fortschritte und Herausforderungen

et al. 2019

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Photopolymerisation, oder in anderen Worten die Nutzung von Licht als Auslöser einer Polymerisationsreaktion, ist eine der vielversprechendsten Technologien zur Herstellung anspruchsvoller Polymere. Eine der Schlüsselkomponenten der Photopolymerisation ist die photoaktive Spezies. Diese ist in der Lage, durch die Absorption von Licht die aktive Verbindung zu generieren, welche die Polymerisation der Monomere einleitet und einen großen Einfluss auf die Eigenschaften des finalen Produkts hat. In der Vergangenheit war das Forschungsfeld der Photopolymerisation von photoaktiven Radikalbildnern zur Einleitung radikalischer Reaktionen dominiert. Um das Spektrum der Polymere, die durch eine Photopolymerisation hergestellt werden können zu erweitern, wurde im letzten Jahrzehnt intensive Forschungsarbeit zur Synthese und Verwendung photoaktiver Moleküle geleistet, die in der Lage sind, unter Einfluss von Licht Säuren oder Basen zu bilden. Diese Verbindungen sind nicht nur dafür bekannt, die ringöffnende Polymerisation verschiedenster heterozyklischer Monomere, wie Laktone, Carbonate oder Epoxide einzuleiten, sondern auch die Stufenwachstumsreaktion von Polyurethanen zu initiieren. Dieser Kurzaufsatz hebt die jüngsten Fortschritte zur Entwicklung organischer, photoaktiver Säuren‐ und Basenbildner hervor, mit dem Ziel, eine breitere Anwendung der photoaktiven Verbindung im Bereich der Photopolymerisation zu fördern und die Verwendung der daraus resultierenden Polymere für anspruchsvolle Produktionsprozesse zu ermöglichen.

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“…Tetramethylguanidine phenylglyoxylate and N-methylnifedipine derivative are prepared according to the procedure described in the literature. 15,16 Preparation of the hydrolysed sol Trifunctional organosilane compound methyltriethoxysilane (MTEOS) possess three hydrolysable ethoxy groups (OC 2 H 5 ) and one non-hydrolysable methyl group (CH 3 ). In the rst step of the process a 60 mL of MTES precursor and 70 mL of water (pH ¼ 3.5, HCl) are combined in 250 mL ask.…”

Section: Methodsmentioning

confidence: 99%

Two-photon controlled sol–gel condensation for the microfabrication of silica based microstructures. The role of photoacids and photobases

et al. 2017

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Two-photon excitation of photobases is used to induce pH changes and control the condensation step of the sol-gel process at the focal point of a laser beam in a confocal configuration. This two-photon microfabrication process, which is usually used in the polymerization of organic monomers, enables the generation of 2D and 3D inorganic Si-O-Si networks of silica based materials with micron resolution.Different variables for the formulation are studied, including the mechanism of condensation, the type of photo initiator, the solvent and the concentration used, as well as the laser parameters.

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Quaternary ammonium salts of phenylglyoxylic acid as photobase generators for thiol-promoted epoxide photopolymerization

Cited by 62 publications

References 51 publications

Thioxanthone acetic acid ammonium salts: highly efficient photobase generators based on photodecarboxylation

Thioxanthone acetic acid ammonium salts: highly efficient photobase generators based on photodecarboxylation

Organische Photosäuren‐ und Photobasenbildner für Polymerisationen: Jüngste Fortschritte und Herausforderungen

Two-photon controlled sol–gel condensation for the microfabrication of silica based microstructures. The role of photoacids and photobases

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