Synthesis and characterization of low-migration bisacylphenylphosphine oxide photoinitiators

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

doi:10.1016/j.porgcoat.2022.107396

Cited by 5 publications

(6 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…However, the acyl radical has not been captured and observed using this method consistent with previous literature reports. [38,39] Upon irradiation, [40] which is indeed isolated in pure form after irradiation of 4 a in toluene. Single crystals of 5 were obtained for the first time via slow evaporation of a saturated toluene solution.…”

Section: Synthesis and Characterization Of Cbaposmentioning

confidence: 99%

Cyclo‐Bis(Acyl)phosphine Oxides as Efficient Photoinitiators for Radical Polymerization

Peng,

Shen,

Chen

2024

Eur J Inorg Chem

View full text Add to dashboard Cite

Acyclic acylphosphine oxides have been extensively utilized in industrial applications as typical photoinitiators (PIs). In this study, we demonstrate the efficiency of their cyclic analogues, cyclo‐bis(acyl)phosphine oxides (CBAPOs), as efficient PIs. We present the isolation and X‐ray crystallographic characterization of CBAPOs. These compounds exhibit a long maximum absorption wavelength ranging between 415 and 420 nm, extending well into the near 500 nm region. Radical trapping experiments suggest that CBAPOs undergo homolytic P–C(O) bond α‐cleavage. Steady‐state photolysis conducted with LED light at 390 nm, monitored by UV‐Vis spectroscopy, confirms the gradual decay of CBAPOs over time. Additionally, all CBAPOs are capable of initiating radical polymerization under irradiation at 365 nm. Notably, one of the CBAPOs (4a) demonstrates comparable photoinitiating efficiency to one of commercially available bis(acyl)phosphine oxides (Irgacure 819).

show abstract

Section: Synthesis and Characterization Of Cbaposmentioning

confidence: 99%

Cyclo‐Bis(Acyl)phosphine Oxides as Efficient Photoinitiators for Radical Polymerization

Peng,

Shen,

Chen

2024

Eur J Inorg Chem

View full text Add to dashboard Cite

show abstract

“…Users demand to develop more migration‐resistant materials to minimize the risk on top of the surface where it could directly harm humans [10] . Binding the light‐sensitive group to a polymer chain presents one possibility [11] to reduce diffusion that causes migration [12] …”

Section: Figurementioning

confidence: 99%

“…[10] Binding the light-sensitive group to a polymer chain presents one possibility [11] to reduce diffusion that causes migration. [12] Photoinitiating systems generating initiating radicals according to a unimolecular homolytic bond cleavage mechanism have received great attention in recent decades. [1a,b,e-h] Here, materials following a homolytic bond cleavage possess the widest distribution.…”

mentioning

confidence: 99%

Type I Photoinitiator Based on Sustainable Carbon Dots

Li,

Guo,

Luo

et al. 2024

Angew Chem Int Ed

View full text Add to dashboard Cite

Sustainable carbon dots comprising surficial oxime ester groups following homolytic bond cleavage exhibit potential as photoinitiators for traditional free radical photopolymerization. Carbon dots were made following a solvothermal procedure from sustainable furfural available from lignocellulose. Surficial aldehyde moieties reacted with hydroxylamine to the respective oxime while reaction with benzoyl chloride resulted in a biobased Type I photoinitiator comprising sustainable carbon dot (CD‐PI). Photoinitiating ability was compared with the traditional photoinitiator (PI) ethyl (2,4,6‐trimethyl benzoyl) phenyl phosphinate (TPO‐L) by real‐time FTIR with UV exposure at 365 nm. Photopolymer composition based on a mixture of urethane dimethacrylate (UDMA) and tripropylene glycol diethacrylate (TPGDA) resulted in a similar final conversion of about 70% using either CD‐PI or TPO‐L. Nevertheless, it appeared homogeneous in the case of compositions processed with CD‐PI, while those made with TPO‐L were heterogeneous as shown by two glass transition temperatures. Moreover, the migration rate of CD‐PI in the cured samples was lower in comparison with those samples using TPO‐L as PI.

show abstract

“…Previously reported Type I PIs for LED-induced photopolymerization, such as oxime esters, [22] acylphosphine oxides, [23] 𝛼dicarbonyls, [5,24] and naphthalimide derivatives [25] possess drawbacks including a poor solubility in monomers, a limited penetration of light, and complex synthetic routes. These drawbacks severely limit their application in thick film curing systems and 3D printing.…”

Section: Introductionmentioning

confidence: 99%

Novel High‐Performance Glyoxylate Derivative‐Based Photoinitiators for Free Radical Photopolymerization and 3D Printing with Visible LED

Gao,

Zhang,

Morlet‐Savary

et al. 2024

Small

View full text Add to dashboard Cite

Investigations concerning the glyoxylate moiety as a photocleavable functional group for visible light photoinitiators, particularly in the initiation of free radical photopolymerization remain limited. This study introduces nine innovative carbazole‐based ethyl glyoxylate derivatives (CEGs), which are synthesized and found to exhibit excellent photoinitiation abilities as monocomponent photoinitiating systems. Notably, these structures demonstrate robust absorption in the near‐UV/visible range, surpassing the commercial photoinitiators. Moreover, the newly developed glyoxylate derivatives show higher acrylate function conversions compared to a benchmark photoinitiator (MBF) in free radical photopolymerization. Elucidation of the photoinitiation mechanism of CEGs is achieved through a comprehensive analysis involving the decarboxylation reaction and electron spin resonance spin trapping. Furthermore, their practical utility is confirmed during direct laser writing and 3D printing processes, enabling the successful fabrication of 3D printed objects. This study introduces pioneering concepts and effective strategies in the molecular design of novel photoinitiators, showcasing their potential for highly advantageous applications in 3D printing.

show abstract

Synthesis and characterization of low-migration bisacylphenylphosphine oxide photoinitiators

Cited by 5 publications

References 28 publications

Cyclo‐Bis(Acyl)phosphine Oxides as Efficient Photoinitiators for Radical Polymerization

Cyclo‐Bis(Acyl)phosphine Oxides as Efficient Photoinitiators for Radical Polymerization

Type I Photoinitiator Based on Sustainable Carbon Dots

Novel High‐Performance Glyoxylate Derivative‐Based Photoinitiators for Free Radical Photopolymerization and 3D Printing with Visible LED

Contact Info

Product

Resources

About