Strategies to develop α-aminoketone derivatives photoinitiators with low migration ability for UV–vis LED photopolymerization

Liao, Wen; Jin, Ming

doi:10.1016/j.eurpolymj.2023.111899

Cited by 16 publications

(1 citation statement)

References 42 publications

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“…UV photopolymerization has been well applied as an environmentally friendly tool to many fields including photoresist, optical imaging, adhesives, high-performance coatings and medical materials for many years due to its advantages of energy conservation, spatial and temporal control of rapid curing systems [1][2][3][4][5][6]. Among UV curing reactions, the base/nucleophile catalyzed thiol-epoxy UV photopolymerization has drawn intensive attentions because of many merits, such as better oxygen inhibition tolerance than radical photopolymerization [7][8][9][10], good reaction selectivity under mild conditions and low shrinkage of cured products [11][12][13][14].…”

Section: Introductionmentioning

confidence: 99%

Photobase generators with AIE property used for visual observations of thiol–epoxy near‐UV/visible photopolymerization

Xie,

Huang,

et al. 2023

Applied Research

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Photopolymerization of thiol–epoxy resins initiated by photobase generators (PBGs) is a very good way to prepare specific polymeric products. However, lack of near‐UV or visible LED light sensitive PBGs that can release strong bases to effectively catalyze this reaction and synchronously monitor the polymerization progress still is a problem. In this work, a series of such PBGs are successfully synthesized by modifying common AIE molecules including triphenylamine (TPA) and tetraphenylethylene (TPE) and then neutralizing them with strong bases like 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU), 1,5‐diazabicyclo[4.3.0]non‐5‐ene(DBN) and 1,5,7‐triazabicyclo[4.4.0]dec‐5‐ene (TBD). The obtained PBGs show very good light absorption ability from 365 to 405 nm. They can generate free strong bases under near‐UV/visible LED light radiations as a result of photodecarboxylation reaction to catalyze the rapid thiol‐epoxy photopolymerization. The TBD‐based PBGs have the best final monomer conversion above 60% due to their strongest alkalinity. Increasing viscosity during the polymerization process can trigger an AIE phenomenon of the PBGs. A linear correlation equation of the AIE intensity with the monomer conversion can be founded, which is helpful for quantitatively monitoring the photopolymerization progress. More importantly, qualitative observations of the brightness changes of the resulting AIE lights are very useful to visualize the photopolymerization progress, which may find some applied potentials in industry.This article is protected by copyright. All rights reserved.

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Section: Introductionmentioning

confidence: 99%

Photobase generators with AIE property used for visual observations of thiol–epoxy near‐UV/visible photopolymerization

Xie,

Huang,

et al. 2023

Applied Research

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Lignin‐Based Macromolecular Photoinitiator for Non‐Migration, Self‐Adhesive, and Water‐Resistant Eutectogels toward Underwater Reliable Communication

Luo,

Qi,

et al. 2024

Adv Funct Materials

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Hydrophobic conductive gels have attracted much attention in underwater sensing as the soft robots and wearable sensors. Among the various methods for preparing conductive gels, UV‐initiated polymerization shows advantages of rapid curing and significant energy savings. However, traditional commonly used photoinitiators in UV‐initiated polymerization often migrate or diffuse within conductive gels, especially with prolonged use or underwater, posing potential environmental and health risks. Herein, a novel lignin‐based macromolecular photoinitiator (L‐BF) is first designed by incorporating benzoylformate into the lignin backbone, demonstrating excellent UV absorption, high radical initiation efficiency, and hydrophobicity. Subsequently, hydrophobic eutectogels (HEG) are prepared via UV‐initiated polymerization using L‐BF as photoinitiator. The HEG shows excellent mechanical properties (toughness of 5.67 MJ m−3 and strain of 941%) and scarcely L‐BF migration underwater. Moreover, the hydrophobic network of L‐BF endowed HEG with hydrophobicity (water contact angle exceeds 110°; swelling ratio is <5.8%), superior underwater adhesion (255 kPa), even maintained excellent sensing performance (gauge factor of 4.69), and long‐term reproducibility (20 000 cycles) in air and underwater. Validation confirms the potential of HEG as an effective wearable sensor for underwater posture monitoring and communication, advancing the use of lignin and low‐migration conductive gels in marine exploration.

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Enhanced One/Two‐Photon Initiating Performance of Nitro‐Carbazole‐Styrene Based Oxime/Ketoxime Esters

Xie,

Wang,

Wang

et al. 2024

Chin. J. Chem.

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Comprehensive SummaryPhotoinitiators of the oxime ester (OXE) or ketoxime ester (OXE‐CO) type can rapidly undergo N—O bond cleavage and generate free radicals to initiate photopolymerization under LED excitation, occupying an important position in the field of photocuring. However, the commercial OXEs, e.g., OXE 01 and 02 with λmax's at 326 and 344 nm, respectively, still do not well match the emission spectra of LEDs. Developing novel OXEs/OXE‐COs with high photosensitivity for long‐wavelength LEDs has great significance. Here, four new OXEs/OXE‐COs with nitro‐carbazole‐styrene conjugated chromophore were designed, synthesized, and used as photoinitiators. Results demonstrated that all photoinitiators had strong absorption within the UV–vis range (λmax: 381—392 nm, εmax: 8200—11500 M−1·cm−1). Molecular design of the oxime ester cleavage to produce a small volume methyl group and a methacryl group with an unsaturated double bond brings high activity and low migration, respectively, in one‐photon polymerization under 365—450 nm LEDs excitation. Moreover, OXEs/OXE‐COs with PETA exhibited a wide processing window, high resolution (line accuracy~100 nm) and good nano‐patterning capability under 780 nm femtosecond laser irradiation in two‐photon polymerization, indicating their great potential in 2D/3D microfabrication technologies.

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Strategies to develop α-aminoketone derivatives photoinitiators with low migration ability for UV–vis LED photopolymerization

Cited by 16 publications

References 42 publications

Photobase generators with AIE property used for visual observations of thiol–epoxy near‐UV/visible photopolymerization

Photobase generators with AIE property used for visual observations of thiol–epoxy near‐UV/visible photopolymerization

Lignin‐Based Macromolecular Photoinitiator for Non‐Migration, Self‐Adhesive, and Water‐Resistant Eutectogels toward Underwater Reliable Communication

Enhanced One/Two‐Photon Initiating Performance of Nitro‐Carbazole‐Styrene Based Oxime/Ketoxime Esters

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