Photo-polymerization properties of type-II photoinitiator systems based on 2-chlorohexaaryl biimidazole (o-Cl-HABI) and various N-phenylglycine (NPG) derivatives!

Chen, Yung‐Chung; Kuo, Yuan-Tsung; Ho, Te-Wei

doi:10.1039/c8pp00300a

Cited by 24 publications

(15 citation statements)

References 32 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Hexaarylbiimidazole (HABI) derivatives, such as BCIM, are commonly used as PIs in the industrial production of DFRs [ 59 ]. However, because of their short-wavelength absorption, which is below 350 nm, and as one kind of type II PI, this kind of compound is usually used together with hydrogen donors such as NPG and longer wavelength photosensitizers such as 4,4′-bis(dimethylamino)benzophenone [ 60 , 61 , 62 ]. In this section, we found that COXEs can be used to improve the photoreactivity of the BCIM/NPG coinitiator system upon 450 nm LED irradiation.…”

Section: Resultsmentioning

confidence: 99%

Coumarin Ketoxime Ester with Electron-Donating Substituents as Photoinitiators and Photosensitizers for Photopolymerization upon UV-Vis LED Irradiation

Fan

Sun

et al. 2022

Polymers

View full text Add to dashboard Cite

High-performance photoinitiators (PIs) are essential for ultraviolet–visible (UV-Vis) light emitting diode (LED) photopolymerization. In this study, a series of coumarin ketoxime esters (COXEs) with electron-donating substituents (tert-butyl, methoxy, dimethylamino and methylthio) were synthesized to study the structure/reactivity/efficiency relationships for substituents for the photoinitiation performance of PIs. The introduction of heteroatom electron-donating substituents leads to a redshift in the COXE absorption of more than 60 nm, which matches the UV-Vis LED emission spectra. The PIs also show acceptable thermal stability via differential scanning calorimetry (DSC) and thermal gravimetric analysis (TGA). The results from real-time Fourier transform infrared (RT-FTIR) measurements indicate that COXEs show an excellent photoinitiation efficiency for free radical polymerization under UV-Vis LED irradiation (365–450 nm); in particular, the conversion efficiency for tri-(propylene glycol) diacrylate (TPGDA) polymerization initiated by COXE-O and COXE-S (4.8 × 10−5 mol·g–1) in 3 s can reach more than 85% under UV-LED irradiation (365, 385 nm). Moreover, the photosensitization of COXEs in the iodonium hexafluorophosphate (Iod-PF6) and hexaarylbiimidazole/N-phenylglycine (BCIM/NPG) systems was investigated via RT-FTIR. As a coinitiator, COXEs show excellent performance in dry film photoresist (DFR) photolithography. This excellent performance of COXEs demonstrates great potential for UV-curing and photoresist applications, providing a new idea for the design of PIs.

show abstract

Section: Resultsmentioning

confidence: 99%

Coumarin Ketoxime Ester with Electron-Donating Substituents as Photoinitiators and Photosensitizers for Photopolymerization upon UV-Vis LED Irradiation

Fan

Sun

et al. 2022

Polymers

View full text Add to dashboard Cite

show abstract

“…Hexaarylbiimidazoles are also characterized by a low sensitivity to oxygen, which has stimulated the industrial interest for this family of structures. [288][289][290][291] To end, the high yield of lophyl radicals i.e. 2,4,5-triarylimidazolyl radicals make these structures appealing candidates to initiate the FRP of acrylates when combined to hydrogen donor (See Scheme 6).…”

Section: Hexaarylbiimidazole Derivativesmentioning

confidence: 99%

Recent advances on visible light Triphenylamine-based photoinitiators of polymerization

Dumur

2022

European Polymer Journal

View full text Add to dashboard Cite

“…Other mechanisms of photoinduced cleavage of photoinitiator, derivatives HABI have also been proposed. Their schemes with an explanation are presented in Figure 16 and Figure 17 [ 154 , 159 ].…”

Section: Commonly Used Photoinitiating Systems For Dental Applicatmentioning

confidence: 99%

“…The radical-mediated thiol-ene polymerization mechanism.Other mechanisms of photoinduced cleavage of photoinitiator, derivatives HABI have also been proposed. Their schemes with an explanation are presented inFigures 16 and 17[154,159].Materials 2020, 13, x FOR PEER REVIEW 14 of Proposed mechanism of the photolysis of the carbon-nitrogen (C-N) bond between the imidazole rings of HABI.…”

mentioning

confidence: 99%

Moving Towards a Finer Way of Light-Cured Resin-Based Restorative Dental Materials: Recent Advances in Photoinitiating Systems Based on Iodonium Salts

Topa

Ortyl

2020

Materials

View full text Add to dashboard Cite

The photoinduced polymerization of monomers is currently an essential tool in various industries. The photopolymerization process plays an increasingly important role in biomedical applications. It is especially used in the production of dental composites. It also exhibits unique properties, such as a short time of polymerization of composites (up to a few seconds), low energy consumption, and spatial resolution (polymerization only in irradiated areas). This paper describes a short overview of the history and classification of different typical monomers and photoinitiating systems such as bimolecular photoinitiator system containing camphorquinone and aromatic amine, 1-phenyl-1,2-propanedione, phosphine derivatives, germanium derivatives, hexaarylbiimidazole derivatives, silane-based derivatives and thioxanthone derivatives used in the production of dental composites with their limitations and disadvantages. Moreover, this article represents the challenges faced when using the latest inventions in the field of dental materials, with a particular focus on photoinitiating systems based on iodonium salts. The beneficial properties of dental composites cured using initiation systems based on iodonium salts have been demonstrated.

show abstract

Photo-polymerization properties of type-II photoinitiator systems based on 2-chlorohexaaryl biimidazole (o-Cl-HABI) and various N-phenylglycine (NPG) derivatives!

Abstract: A series of p-substituted NPG derivatives (Cl-NPG, OMe-NPG and NO2-NPG) comprising different push–pull characteristics have been synthesized and characterized.

Cited by 24 publications

References 32 publications

Coumarin Ketoxime Ester with Electron-Donating Substituents as Photoinitiators and Photosensitizers for Photopolymerization upon UV-Vis LED Irradiation

Coumarin Ketoxime Ester with Electron-Donating Substituents as Photoinitiators and Photosensitizers for Photopolymerization upon UV-Vis LED Irradiation

Recent advances on visible light Triphenylamine-based photoinitiators of polymerization

Moving Towards a Finer Way of Light-Cured Resin-Based Restorative Dental Materials: Recent Advances in Photoinitiating Systems Based on Iodonium Salts

Contact Info

Product

Resources

About