Large-molecular-weight acyldiphenylphosphine oxides as low-mobility type I photoinitiator for radical polymerization

Wu, Yinping; Ke, Jiasheng; Dai, Changxiang; Wang, Jiuwu; Huang, Chenguang; Situ, Yue; Huang, Hong

doi:10.1016/j.eurpolymj.2022.111380

Cited by 11 publications

(4 citation statements)

References 27 publications

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“…( 4) [55]. Based on the absorptions at λ abs max of the leaching solution, the concentration of the photoinitiators were calculated, and low leaching of photoinitiator compounds favor the increase of the hardness of the cured lms [30,33]. The molecular weight of PyBF is 704.3 g mol − 1 , which is larger than that of commercial TPO (348.4 g mol − 1 ).…”

Section: Photopolymerizations Incorporation With Commercial Tpomentioning

confidence: 99%

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A pyrrolo[3,2-b]pyrrole derivative used for one- and two-component radical photoinitiators for photopolymerization under 405 nm

Liu,

Xu,

Liu

et al. 2023

Preprint

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The new design is generally based on the improvement of existing commercial photoinitiators as well as the introduction of new building blocks aimed at improving the properties of polymerized materials. A photoinitiator named 1,4-bis(4-bromophenyl)-2,5-bis(4-(trifluoromethyl)phenyl)-1,4-dihydropyrrolo[3,2-b]pyrrole (PyBF) with a symmetric trifluoromethyl (-CF3) end groups was synthesized through a one-step aldehyde–ketone condensation reaction. The -CF3 groups are introduced on the 2,5-position phenyl rings of the pyrrolo[3,2-b]pyrrole core, and PyBF shows visible light photoinitiation ability that matching with light-emitting diode (LED) of 405 nm. Both acrylate prepolymer and monomer have been applied to our photopolymerization formulas using PyBF as one-component photoinitiator. The thermal stability of PyBF is compared with commercial photointiator (diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide, TPO) with a comparable thermal decomposition temperature (Td) temperature above 300 oC. The SEM results show that the cured materials of PyBF/TPO/PEGDA mixture using PyBF/TPO as two-component photoinitiator system have smooth surface, instead of PyBF/PEGDA and TPO/PEGDA systems. Therefore, both the potential pyrrole-based one- and two-component photoinitiator for rational design is worth expected for visible light photopolymerization.

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Section: Photopolymerizations Incorporation With Commercial Tpomentioning

confidence: 99%

“…Conventional commercial photoinitiators ensure the wide development of photopolymerizations in practical applications in terms of rapid photoinitiation speed and high photopolymerization conversion [29]. Under 405 nm LED irradiation, commercial phosphine oxide (TPO) is commonly used [30,31].…”

Section: Introductionmentioning

confidence: 99%

A pyrrolo[3,2-b]pyrrole derivative used for one- and two-component radical photoinitiators for photopolymerization under 405 nm

Liu,

Xu,

Liu

et al. 2023

Preprint

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“…In order to respond to the requirements of faster photoreactivity, suitable for different light exposure wavelengths (especially near UV or visible-light region) and other purposes, various Type I photoinitiators have been recently developed. [8,[10][11][12][13][14][15][16][17] Among all Type I PIs, oxime esters (OXEs) are well known due to their very high efficiency by the homolytic cleavage of the NÀ O bond. [18] Then, the iminyl and acyloxy radicals can be produced for photopolymerization.…”

Section: Introductionmentioning

confidence: 99%

Effect of Terminal Alkyl Chains for Free Radical Photopolymerization Based on Triphenylamine Oxime Ester Visible‐Light Absorbing Type I Photoinitiators

et al. 2023

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In order to investigate the photopolymerization properties of the alkyl chain length dependence Type I photoinitiators, in this study, a series of visible‐light‐absorbing triphenylamine oxime esters (Peko‐A‐D, and reference TP‐1M) containing various alkyl chain length in the periphery were synthesized. That is, an alkane segment contains isopropyl for Peko‐A, butyl for Peko‐B, undecane for Peko‐C, pentadecane for Peko‐D and methyl for TP‐1M, respectively. Except for Peko‐D, all of them have good organo‐solubility and can dissolve in testing monomer (trimethylolpropane triacrylate, TMPTA). All the oxime esters give from near UV to visible‐light absorption regions with maximum absorption peaks at around 360 nm and show rather red‐shifted compared to the commercial OXE‐01 compound. Accordingly, the photochemical reaction behavior was studied by cyclic voltammograms (CV), electron spin resonance (ESR) and steady‐state photolysis. In addition, the oxime esters based photoinitiating systems are studied through photo‐DSC experiment based on various light exposure wavelengths (UV lamp, LED@365 nm and LED@405 nm). Under different light source, the penetration affects the final double conversion efficiencies. As a result, all the oxime esters‐based formulation shows better double conversion efficiencies upon LED@405 nm as an irradiation source. Finally, the new oxime ester photoinitiating system was capable applied in direct laser write to generate 3D patterns using a laser diode @405 nm.

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“…Currently, two methods are being studied to limit the migration of photoinitiators. 30 Either by adding polymerisable functions to the photoinitiators, so that they participate in the photopolymerization and are trapped in the materials, 30,31 or by adding massive groups to the photoinitiators to limit their diffusion in the polymers (e.g., macromolecular photoinitiators). 32 Thus, the modification of phosphine oxides has these two interests.…”

Section: Introductionmentioning

confidence: 99%

Towards safe phosphine oxides photoinitiators with good cytocompatibility for 3D printing of thermoplastics

Buchon,

Becht,

Rubatat

et al. 2023

J of Applied Polymer Sci

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Abstract3D printing is the technology of choice for the rapid production of objects with complex morphologies and controlled physical and chemical properties. 3D printing by photopolymerization is of great interest because of its ability to access very small scales and its high resolution. In the case of recent 3D printers, the preferred wavelength for light irradiation is 405 nm since it is a safe and energy‐economical irradiation. For 3D printing to be effective, it is therefore necessary to develop easily accessible, stable and highly efficient photoinitiating systems at the 405 nm wavelength. Beside, with the increasing use of photoinitiators, it is essential to develop structures with low cytotoxicity. Hence, the development of new photoinitiators is currently of major interest. To this end, the photochemical properties (triplet energy, bond dissociation energy, cleavage reaction enthalpy, and absorption properties) of several molecules have been calculated by molecular modeling and the most promising compounds have been synthesized. In this paper, four phosphine oxides photoinitiators (ADPO‐1, CPO‐2, CPO‐3, and FPO‐1) are synthesized and characterized. Subsequently, their absorption properties are measured and their efficiencies in photopolymerization under LED irradiation at 405 nm are evaluated. It is important to note that these structures have never been reported in 3D printing. Markedly, among the obtained photoinitiators, two of them show better efficiency than the commercially available and widely used phenylbis(2,4,6‐trimethylbenzoyl)phosphine oxide (BAPO) in photopolymerization (i.e., (Rp/[M0]) x100 values are 6.94, 12.95, and 4.93 s−1 for CPO‐2, ADPO‐1, and BAPO; with [M0] the initial acrylate function concentration). Furthermore, one of the synthesized photoinitiators is successfully used in 3D printing of thermoplastics for potential recycling ability. Finally, one of the obtained structures shows a lower cytotoxicity than the benchmark structure diphenyl(2,4,6‐trimethylbenzoyl)phosphine oxide (TPO).

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Large-molecular-weight acyldiphenylphosphine oxides as low-mobility type I photoinitiator for radical polymerization

Cited by 11 publications

References 27 publications

A pyrrolo[3,2-b]pyrrole derivative used for one- and two-component radical photoinitiators for photopolymerization under 405 nm

A pyrrolo[3,2-b]pyrrole derivative used for one- and two-component radical photoinitiators for photopolymerization under 405 nm

Effect of Terminal Alkyl Chains for Free Radical Photopolymerization Based on Triphenylamine Oxime Ester Visible‐Light Absorbing Type I Photoinitiators

Towards safe phosphine oxides photoinitiators with good cytocompatibility for 3D printing of thermoplastics

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