Photoreduction of 9,10-Phenanthrenequinone in the Presence of Dimethacrylate Oligomers and Their Polymers

Len’shina, N. A.; Zakharina, M. Yu.; Kovylin, Roman S.; Батенькин, М. А.; Kulikova, T. I.; Arsen’ev, M. V.; Чесноков, С. А.

doi:10.1134/s0018143918050090

Cited by 6 publications

(4 citation statements)

References 20 publications

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“…Porous polymer monoliths were prepared by photopolymerization of liquid compositions, consisting of dimethacrylates EGDMA or TEGDMA as polymerizable monomers, 1‐octanol (50 vol%) as a porogenic agent, and 9,10‐phenanthrenequinone as a photoinitiator. Polymerization initiation proceeds by the radicals generated during photoreduction of PQ by visible light: the PQ molecules are turned to the lowest excited triplet state under the action of light ( λ ≤ 520 nm), and the exited molecules abstract the hydrogen atom from H‐donor molecules such as alchohols and dimethacrylate molecules (polyEGDMA or polyTEGDMA) . The formed carbon‐centered radicals initiate the polymerization of methacrylic monomers accompanied by the formation of a three‐dimensional cross‐linked polymer.…”

Section: Resultsmentioning

confidence: 99%

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Facile Visible‐Light‐Induced Preparation and Hydrophobization of Porous polyEGDMA and polyTEGDMA Thick Monoliths

Len’shina

Arsenyev

Батенькин

et al. 2020

Polymer Engineering & Sci

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The simple low‐cost method for synthesis and post‐functionalization of thick macroporous polymer monoliths was proposed and realized by example of obtaining and hydrophobization of monoliths based on mono‐ and triethylene glycol dimethacrylates. Described procedures comprise using of ubiquitous visible‐light projection system and single photoinitiator (9,10‐phenanthrenequinone) in both cases. This approach eliminates the need in “material” photomasks and permit to operate with computer generated virtual photomask to form the pattern of functionalization. Macroporous polymer monoliths of 2 and 4 mm in thickness with a system of interconnected pores were synthesized and hydrophobized. The thick layers of functionalized porous polymer with wetting pattern through the entire sample thickness with the water contact angle for hydrophobic parts reaching120–125° were obtained. POLYM. ENG. SCI., 60:682–689, 2020. © 2020 Society of Plastics Engineers

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Section: Resultsmentioning

confidence: 99%

“…Another dicarbonyl photoinitiator (9,10‐phenanthrenquinone) is used for photopolymerization of mono‐ and dimethacrylates . 9,10‐Phenanthrenquinone is capable to react with polymer matrices based on the monomers EGDMA and TEGDMA in the excited state .…”

Section: Introductionmentioning

confidence: 99%

Facile Visible‐Light‐Induced Preparation and Hydrophobization of Porous polyEGDMA and polyTEGDMA Thick Monoliths

Len’shina

Arsenyev

Батенькин

et al. 2020

Polymer Engineering & Sci

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“…The mechanism of photopolymerization initiated by o-quinones can be described using the general Scheme 2 [23,36,55,56]. Photoinitiation of radical polymerization in the presence of o-quinones is based on their photoreduction reaction [23,[32][33][34]46,47,57]. The spectral sensitivity range of these systems is determined by the position of the quinone absorption bands.…”

Section: Kinetics Studiesmentioning

confidence: 99%

“…All three listed photoinitiators are useless without the addition of co-initiators, usually tertiary amines [24,44,45]. In contrast, PQ requires no co-initiator to photoinitiate polymerization [43,46,47]. A mixture of ethylene glycol dimethacrylate (EGDMA) and 1-butanol in a 30:70 mass ratio was used for photopolymerization, leading to the formation of porous polymers; this was the approach previously used to obtain biocompatible polymers in a 36Q photoinitiating system [16].…”

Section: Introductionmentioning

confidence: 99%

Pore Structure Tuning of Poly-EGDMA Biomedical Material by Varying the O-Quinone Photoinitiator

et al. 2023

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Porous polymer monoliths with thicknesses of 2 and 4 mm were obtained via polymerization of ethylene glycol dimethacrylate (EGDMA) under the influence visible-light irradiation in the presence of a 70 wt% 1-butanol porogenic agent and o-quinone photoinitiators. The o-quinones used were: 3,5-di-tret-butyl-benzoquinone-1,2 (35Q), 3,6-di-tret-butyl-benzoquinone-1,2 (36Q), camphorquinone (CQ), and 9,10-phenanthrenequinone (PQ). Porous monoliths were also synthesized from the same mixture but using 2,2′-azo-bis(iso-butyronitrile) (AIBN) at 100 °C instead o-quinones. According to the results of scanning electron microscopy, all the resulting samples were conglomerates of spherical, polymeric particles with pores between them. Use of mercury porometry showed that the interconnected pore systems of all the polymers were open. The average pore size, Dmod, in such polymers strongly depended on both the nature of the initiator and the method of initiation of polymerization. For polymers obtained in the presence of AIBN, the Dmod value was as low as 0.8 μm. For polymers obtained via photoinitiation in the presence of 36Q, 35Q, CQ, and PQ, the Dmod values were significantly greater, i.e., 9.9, 6.4, 3.6, and 3.7 μm, respectively. The compressive strength and Young’s modulus of the porous monoliths increased symbatically in the series PQ < CQ < 36Q < 35Q < AIBN with decreasing proportions of large pores (over 12 μm) in their polymer structures. The photopolymerization rate of the EGDMA and 1-butanol, 30:70 wt% mixture was maximal for PQ and minimal for 35Q. All polymers tested were non-cytotoxic. Based on the data from MTT testing, it can be noted that the polymers obtained via photoinitiation were characterized by their positive effect on the proliferative activity of human dermal fibroblasts. This makes them promising osteoplastic materials for clinical trials.

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Biocompatible Non‐Toxic Porous Polymeric Materials Based on Carbonate‐ and Phthalate‐Containing Dimethacrylates

et al. 2019

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Polymer monolith materials of 2 mm thickness with open interconnected pores were obtained by a visible light induced radical polymerization of carbonate-or phthalate containing dimethacrylate in the presence of aliphatic alcohols (60 to 70 wt %) as porogenic additives. Obtained materials absorb water easily and reveal a specific surface area of 3.1 to 21.5 m 2 g À 1 and a porosity of 55-72%. According SEM data the porous monoliths consist of polymer particles (size up to 1 μm) that form 3D structures with a pore size up to 5 μm for poly (carbonatedimethacrylate) and tens of microns for phthalatecontaining polydimethacrylates. Mesenchymal stem cells from the bone marrow (MSC-BM) of the pig were picked out and characterized. The MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) tests on polymers obtained have shown their non-cytotoxicity. MSC-BMs spread out well on the polymeric samples and retained their viability and typical morphology during 7 days. Adhesion and viability of MSCs on the surface of materials were detected by calcein staining. The data obtained indicate that the porous polymers derived from dimethacrylates might be promising for construction of plastics for bone grafting.

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Photoreduction of 9,10-Phenanthrenequinone in the Presence of Dimethacrylate Oligomers and Their Polymers

Cited by 6 publications

References 20 publications

Facile Visible‐Light‐Induced Preparation and Hydrophobization of Porous polyEGDMA and polyTEGDMA Thick Monoliths

Facile Visible‐Light‐Induced Preparation and Hydrophobization of Porous polyEGDMA and polyTEGDMA Thick Monoliths

Pore Structure Tuning of Poly-EGDMA Biomedical Material by Varying the O-Quinone Photoinitiator

Biocompatible Non‐Toxic Porous Polymeric Materials Based on Carbonate‐ and Phthalate‐Containing Dimethacrylates

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