Magnolol-derived thiol-ene photo-polymerized membranes with intrinsic anti-flammability and high transparency

Guo, Wenwen; Liang, Fuwei; Chen, Shun; Yu, Kejing; Sun, Jie; Pang, Zengyuan; Fei, Bin

doi:10.1016/j.compositesb.2022.110074

Cited by 20 publications

(9 citation statements)

References 47 publications

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“…39 Moreover, the higher glass transition temperature of DDAB/4SH leads to the brittle and glassy state, thus reducing the toughness. Compared to previous reported works, 17,18,29,40,41 DDAB/3SH shows superior toughness, promising significant potential applications in the fields of electronic protection and encapsulation (see Figure 4c and Table S3). The outstanding toughness of DDAB/3SH holds tremendous potential for applications in electronic protection and electronic packaging.…”

Section: Mechanical Propertiesmentioning

confidence: 70%

“…Photocuring is a common method based on thiol–ene click chemistry for the synthesis of resin-type materials, , possessing a rapid curing speed, boasting advantages such as energy efficiency and straightforward operation, which are widely employed in photosensitive materials, coating, , three-dimensional (3D) printing, etc. For instance, Guo et al utilized magnolia phenol as a precursor to prepare phosphorus-containing biobased monomers (MBDPP). Subsequently, they adopted thiol compounds with three and four thiol groups, respectively, to undergo photopolymerization reactions with the monomers.…”

Section: Introductionmentioning

confidence: 99%

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Daidzein-Derived Thermosetting Resins via UV-Induced Thiol–Ene Click Reaction with Ultralow k and Tunable Mechanical Properties for Electronic Packaging

Dai,

Zhang,

Yang

et al. 2024

ACS Appl. Polym. Mater.

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The exploration of biomass-derived thermosetting resins for implementation in flexible electronic packaging has emerged as a central focus. Herein, a daidzein-derived monomer (DDAB) was synthesized, which featured carbon−carbon double bonds. Biobased resins, namely, DDAB/3SH and DDAB/4SH, were meticulously fabricated via photocuring process, entailing the amalgamation of DDAB with trithiol (TPTMP) and tetrathiol (PETMP) monomers, respectively. DDAB/4SH showed impressive mechanical properties with a tensile strength of 28.1 MPa and elongation at break of 21.3%. Notably, owing to the augmented free volume inherent within the system, DDAB/3SH exhibited an exceptional elongation at a break of 111.7%, thereby surpassing the performance metrics of the majority of previously documented thiol-containing compounds. Moreover, both DDAB/3SH and DDAB/4SH demonstrated desirable dielectric properties. Specifically, within the frequency range of 15−16 GHz, DDAB/3SH achieved a minimum dielectric constant of 2.58. The exceptional dielectric performance, coupled with the tunable mechanical properties, proves the substantial application potential of DDAB/SH biomass-derived resins for flexible electronic packaging applications.

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Section: Mechanical Propertiesmentioning

confidence: 70%

Section: Introductionmentioning

confidence: 99%

Daidzein-Derived Thermosetting Resins via UV-Induced Thiol–Ene Click Reaction with Ultralow k and Tunable Mechanical Properties for Electronic Packaging

Dai,

Zhang,

Yang

et al. 2024

ACS Appl. Polym. Mater.

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“…It is observed that all PVC films maintain a high energy storage modulus up to -20 °C, undergo a sharp decrease from -20 °C to 40 °C, and reach values close to 0 after 40 °C. Notably, DOP exhibits the largest energy storage modulus, signifying its capacity to absorb more energy for deformation and higher stiffness [24] . Comparatively, the compounded IDEO films exhibit lower energy storage modulus than DOP, suggesting greater susceptibility to deformation and enhanced flexibility.…”

Section: Molecular Dynamics Simulation Methodologymentioning

confidence: 99%

Synergistic plasticizing effect of bio-based isosorbide di-epoxidized oleate on poly(vinyl chloride) resins

Huang,

Nan,

et al. 2024

Polym. Bull.

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The strategic importance of developing environmentally friendly PVC biomass plasticizers with excellent anti-migration and plasticizing effects cannot be overstated. This paper delves into the synthesis and application of bio-based isosorbide di-epoxidized oleate (IDEO) as a secondary biomass plasticizer in polyvinyl chloride (PVC) films. Explored were the synergistic effects between IDEO and dioctyl phthalate (DOP), alongside an assessment of the influence of the compound plasticizer on the properties of PVC products. The partial substitution of DOP resulted in PVC films with improved thermal stability, flexibility, and migration resistance. IDEO-10/PVC, in particular, exhibited a 64% increase in tensile strength compared to DOP/PVC and maintained thermal stabilization for over 280 minutes at 180 ℃. With a glass transition temperature (Tg) of 33 °C, a plasticizing efficiency of 148%, and excellent cold resistance properties, IDEO-10/PVC outperformed DOP/PVC. IDEO-10/PVC migration resistance was significantly lower than in the original PVC resin with only DOP plasticizers under three different polar conditions. Transmittance remained above 87% after 10 days of UV irradiation. Molecular dynamics simulation further confirmed the synergistic plasticizing effect between IDEO and DOP at an IDEO addition of 10 phr. The environmentally friendly approach, holds significant promise for the scaled-up application of PVC.

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“…Magnolol, a naturally occurring compound found in Magnolia officinalis plants, possesses two allyl groups in its molecular makeup, making it a suitable contender as a UV curable monomer. Moreover, magnolol’s molecular structure features two phenolic hydroxyl groups, which makes it easily modifiable to be flame retardants . Magnolol-derived bis(diphenyl phosphate) (MBDPP) was effectively created by phosphorylation of the phenol groups (Scheme B) and then underwent thiol–ene polymerization with TTMP or PETMP monomers to achieve photocuring.…”

Section: Lignin-derived Photopolymersmentioning

confidence: 99%

“…Moreover, magnolol's molecular structure features two phenolic hydroxyl groups, which makes it easily modifiable to be flame retardants. 175 Magnolol-derived bis-(diphenyl phosphate) (MBDPP) was effectively created by phosphorylation of the phenol groups (Scheme 20B) and then underwent thiol−ene polymerization with TTMP or PETMP monomers to achieve photocuring. The photocured membranes showed good flexibility, high transparency, and excellent antiflammability.…”

Section: Lignin-derived Photopolymersmentioning

confidence: 99%

Renewable Photopolymers: Transformation of Biomass Resources into Value-Added Products Under Light

Lai,

Zhang,

Xiao

2023

ACS Sustainable Chem. Eng.

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Light-induced cross-linking of liquid monomers has found widespread applications in various fields, such as dentistry, coatings, tissue engineering, and 3D printing. These processes typically rely on monomers derived from petrochemicals, which are volatile in price and are becoming increasingly depleted, compelling researchers to explore alternative sources from forestry and agricultural crops. The renewability of these resources makes them a promising option for developing substitutive materials with similar or superior properties. The various structural subunits in biomass offer alternative building blocks for petroleum-based photopolymers including the double bond-containing and hydrophobic fatty acids and terpenes, hydrophilic carbohydrates and proteins, aromatic furfural compounds from carbohydrates, and phenolic moieties in lignin. They can be transformed into photopolymers by the inherent or chemically introduced photocurable bonds. This review seeks to highlight recent advancements in transforming renewable platform chemicals into photocurable systems for photopolymerization processes and examines the thermomechanical properties and applications of the resulting cured materials. Furthermore, potential issues for improvement are also identified, such as the cost-effectiveness of biomass-based photopolymers and the risk in competition with food production. The perspectives on future directions for improving the renewability in this area are also given.

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Magnolol-derived thiol-ene photo-polymerized membranes with intrinsic anti-flammability and high transparency

Cited by 20 publications

References 47 publications

Daidzein-Derived Thermosetting Resins via UV-Induced Thiol–Ene Click Reaction with Ultralow k and Tunable Mechanical Properties for Electronic Packaging

Daidzein-Derived Thermosetting Resins via UV-Induced Thiol–Ene Click Reaction with Ultralow k and Tunable Mechanical Properties for Electronic Packaging

Synergistic plasticizing effect of bio-based isosorbide di-epoxidized oleate on poly(vinyl chloride) resins

Renewable Photopolymers: Transformation of Biomass Resources into Value-Added Products Under Light

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