Leaching and Biodegradation of Darocur 1173 used as a Photo-Initiator in the Production of Photocrosslinked Silicone Acrylates

Ouali, Salma; Louis, Yoann; Germain, Patrick; Gourdon, Rémy; Desjardin, Valérie

doi:10.1007/s10924-017-0939-z

Cited by 14 publications

(5 citation statements)

References 17 publications

(20 reference statements)

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“…However, combining photopatterning methods with photocleavable chemistries presents a key obstacle: standard commercial photoinitiators used in soft materials patterning are also UV-absorbing, and this overlap interferes with UV-light directed material responses. Furthermore, photoinitiators generally have poor water solubility and typically remain sequestered within cross-linked polymer networks after photopolymerization has completed, with leaching time scales on the order of tens of hours to days. − Specifically, the persistence of widely utilized UV-wavelength excitable photoinitiators in photolithographic applications, such as Darocur and OmniRad, diminishes the activity of large classes of UV photoswitchable chemistries during potential therapeutic applications. ,− …”

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confidence: 99%

Digital Maskless Photolithographic Patterning of DNA-Functionalized Poly(ethylene glycol) Diacrylate Hydrogels with Visible Light Enabling Photodirected Release of Oligonucleotides

et al. 2019

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Soft biomaterials possessing structural hierarchy have growing applications in lab-on-chip devices, artificial tissues, and micromechanical and chemomechanical systems. The ability to integrate sets of biomolecules, specifically DNA, within hydrogel substrates at precise locations could offer the potential to form and modulate complex biochemical processes with DNA-based molecular switches in such materials and provide a means of creating dynamic spatial patterns, thus enabling spatiotemporal control of a wide array of reaction-diffusion phenomena prevalent in biological systems. Here we develop a means of photopatterning two-dimensional DNA-functionalized poly(ethylene glycol) diacrylate (PEGDA) hydrogel architectures with an aim toward these applications. While PEGDA photopatterning methods are well-established for the fabrication of hydrogels, including those containing oligonucleotides, the photoinitiators typically used have significant crosstalk with many UV-photoswitchable chemistries including nitrobenzyl derivatives. We demonstrate the digital photopatterning of PEGDA-co-DNA hydrogels using a blue light-absorbing (470 nm peak) photoinitiator system and macromer comprised of camphorquinone, triethanolamine, and poly(ethylene glycol) diacrylate (M n = 575) that minimizes absorption in the UV-A wavelength range commonly used to trigger photoswitchable chemistries. We demonstrate this method using digital maskless photolithography within microfluidic devices that allows for the reliable construction of multidomain structures. The method achieves feature resolutions as small as 25 μm, and the resulting materials allow for lateral isotropic bulk diffusion of short single-stranded (ss) DNA oligonucleotides. Finally, we show how the use of these photoinitiators allows for orthogonal control of photopolymerization and UV-photoscission of acrylate-modified DNA containing a 1-(2-nitrophenyl) ethyl spacer to selectively cleave DNA from regions of a PEGDA substrate.

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confidence: 99%

Digital Maskless Photolithographic Patterning of DNA-Functionalized Poly(ethylene glycol) Diacrylate Hydrogels with Visible Light Enabling Photodirected Release of Oligonucleotides

et al. 2019

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“…To support this notion, Darocur 1173 leaching was also observed from crosslinked silica-acrylate films at acidic pH in another study. 26 Thus, Darocur 1173 leaching from the untreated chip could be possible. Meanwhile, MD700 still displays a small degree of swelling when in contact with organic liquids.…”

Section: Resultsmentioning

confidence: 99%

One-step flow synthesis of size-controlled polymer nanogels in a fluorocarbon microfluidic chip

Montalbo,

Wu,

2024

RSC Adv.

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“…Today acrylate oligomers are common constituent in UV-curable formulations. [1][2][3][4][5][6][7][8] Among them, epoxy acrylate resins are well known due to their distinct advantages: High reactivity, excellent adhesion onto polarsurfaces like metals, woods… due to the presence of pendant hydroxyl groups in their molecules. The main disadvantages of the resins are their low backbone flexibility leading to brittleness and low elongation at break of UV cured films on their base preventing the use in practice where high flexibility of coatings is needed.…”

Section: Introductionmentioning

confidence: 99%

Influence of the weight ratio of an epoxy resin modified by castor oil and an epoxidiacrylate oligomer on photocrosslinking and properties of UV‐cured coatings

Hien

Thanh

Tai

2019

Vietnam Journal of Chemistry

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The influence of the weight ratio of a castor oil modified epoxy resin (CE) and an epoxidiacrylate resin (EDA) on photocrosslinking and properties of the coatings containing these resins, hexandioldiacrylate monomer (HDDA) and photoinitiator Darocur 1173 (D.1173) upon UV‐exposure have been studied. The variation of acrylate groups during the photoinitiated polymerization was evaluated by FTIR analysis. The crosslinking of the UV‐cured coatings was proved by gel fraction and swelling degree determinations. In addition, some of the properties of the UV‐cured coatings such as relative hardness, flexibility, impact resistance, adhesion onto steel plates and gloss have also been examined. It was shown that the increase of the CE/EDA ratio from 10/40 to 40/10 in investigated coatings led to the decrease of the conversion rate of acrylate groups, and significantly changed some properties of the cured coatings after 14.4 s of UV irradiation: Decrease of gel fraction from 96 to 61 %, but improved the flexibility from 10 to 3 mm, impact resistance from 40 to 140 kG.cm, adhesion from 5 to 2 points. The gloss of the coatings remained to be 100 % in all cases. Long hydrocarbon chains of castor oil residue in CE, lower reactivity of double bonds and radicals formed in the chains compared with those of acrylate groups have been attributed to the obtained relationship between the CE/EDA ratio and photocrosslinking, properties of the cured coatings.

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Leaching and Biodegradation of Darocur 1173 used as a Photo-Initiator in the Production of Photocrosslinked Silicone Acrylates

Cited by 14 publications

References 17 publications

Digital Maskless Photolithographic Patterning of DNA-Functionalized Poly(ethylene glycol) Diacrylate Hydrogels with Visible Light Enabling Photodirected Release of Oligonucleotides

Digital Maskless Photolithographic Patterning of DNA-Functionalized Poly(ethylene glycol) Diacrylate Hydrogels with Visible Light Enabling Photodirected Release of Oligonucleotides

One-step flow synthesis of size-controlled polymer nanogels in a fluorocarbon microfluidic chip

Influence of the weight ratio of an epoxy resin modified by castor oil and an epoxidiacrylate oligomer on photocrosslinking and properties of UV‐cured coatings

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