Biocompatible photoinitiators based on poly‐α‐ketoesters

Taschner, Roland; Gauss, Paul; Knaack, Patrick; Liska, Robert

doi:10.1002/pol.20199929

Cited by 17 publications

(12 citation statements)

References 17 publications

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“…Linear polyester polyols from malic acid and 1,6‐hexanediol were synthesized in melt in the presence of scandium‐ 35 or tin‐based 36 catalysts. Poly(hexamethylene 2‐oxoglutarate), a polyester polyol prepared from 1,6‐hexanediol and α ‐ketoglutaric acid in the presence of p ‐toluenesulfonic acid, was used as a polymeric UV‐photoinitiator 37 . However, to the best of our knowledge, no attempts to utilize HT methods in the synthesis of these or similar bio‐based polyester polyols have been made so far.…”

Section: Resultsmentioning

confidence: 99%

“…Poly(hexamethylene 2-oxoglutarate), a polyester polyol prepared from 1,6-hexanediol and α-ketoglutaric acid in the presence of p-toluenesulfonic acid, was used as a polymeric UV-photoinitiator. 37 However, to the best of our knowledge, no attempts to utilize HT methods in the synthesis of these or similar bio-based polyester polyols have been made so far. Selected FTIR spectra of the polyester polyol products are given in Figure 5.…”

Section: Polyesterification Of Bio-based Acids In a High-throughput Reactormentioning

confidence: 99%

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Parallel esterification of bio‐based dicarboxylic acids in small scale film reactors: A high‐throughput study

Hevus

McNamara

Ricapito

et al. 2021

Journal of Polymer Science

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The applicability of polyesters across a wide range of fields creates a demand for novel polyester structures that can offer advanced product performance. Two critical factors to the development of unique polymer architectures are the speed at which new polymeric systems can be synthesized and the available selection of monomers from which polymers are designed. Herein, we successfully demonstrate the applicability of a high‐throughput (HT) approach to polyesterification reaction between dicarboxylic acids and diols in reaction conditions similar to those used in industry. Furthermore, we apply our HT design to a series of bio‐based monomers whose unique structures offer potential for enhanced properties in polyester‐based systems. Using a custom‐built array of small‐scale film reactors, we conducted a parallel screening of 13 bio‐based dicarboxylic acids as potential monomers in the synthesis of polyester polyols through copolymerization with 1,6‐hexanediol. The polyester polyols were characterized for their molecular weight and thermal properties. Carrying out polyesterification reactions in small‐scale film reactors is seen as a quick and powerful tool for screening the effectiveness of a series of potential monomers, as this method offers highly controllable and reproducible reaction conditions in every reactor coupled with the ability to use a minimum amount of reagents.

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Section: Resultsmentioning

confidence: 99%

Section: Polyesterification Of Bio-based Acids In a High-throughput Reactormentioning

confidence: 99%

Parallel esterification of bio‐based dicarboxylic acids in small scale film reactors: A high‐throughput study

Hevus

McNamara

Ricapito

et al. 2021

Journal of Polymer Science

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“…For biological applications, we anticipate that the firstgeneration DCPI will be limited by cytotoxicity and carcinogenicity, similar to its benzophenone precursor, but look forward to the development of biocompatible initiators for this uniquely enabling additive manufacturing technique. 77 Subtractive Manufacturing of Engineered Tissues. Subtractive manufacturing, whereby patterned removal of a subset of bulk starting material, also found utility for tissue fabrication; micrometer-scale resolution over complex void volumes have made these the strategy of choice for creating well-defined microvascular networks.…”

Section: ■ Fabricating Complex Tissue Structuresmentioning

confidence: 99%

“…This approach improves upon the resolution of stereolithography by an order of magnitude, while generating large-scale objects at 4–5 orders of magnitude faster than multiphoton lithography. For biological applications, we anticipate that the first-generation DCPI will be limited by cytotoxicity and carcinogenicity, similar to its benzophenone precursor, but look forward to the development of biocompatible initiators for this uniquely enabling additive manufacturing technique …”

Section: Fabricating Complex Tissue Structuresmentioning

confidence: 99%

The Art of Engineering Biomimetic Cellular Microenvironments

Bretherton

DeForest

2021

ACS Biomater. Sci. Eng.

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Cells and their surrounding microenvironment exist in dynamic reciprocity, where bidirectional feedback and feedforward crosstalk drives essential processes in development, homeostasis, and disease. With the ongoing explosion of customizable biomaterial innovation for dynamic cell culture, an ever-expanding suite of user-programmable scaffolds now exists to probe cell fate in response to spatiotemporally controlled biophysical and biochemical cues. Here, we highlight emerging trends in these efforts, emphasizing strategies that offer tunability over complex network mechanics, present biomolecular cues anisotropically, and harness cells as physiochemical actuators of the pericellular niche. Altogether, these material advances will lead to breakthroughs in our basic understanding of how cells interact with, integrate signals from, and influence their surrounding microenvironment.

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“…Notably, by increasing the molar extinction coefficients of photoinitiators, the quantity of the compound introduced into the photocurable resin can be drastically lowered while maintaining a constant absorption. This point is of crucial interest, as the extractability and the migratability of photoinitiators within the polymer films can be a major issue for numerous applications such as food packaging [18,19] or the design of biocompatible materials or safety equipment [20][21][22][23]. Parallel to the absorption, the excited state lifetime is another point to consider and an elongation of this latter is beneficial by providing more time for the photoinitiator to react with the different additives [24][25][26].…”

Section: Introductionmentioning

confidence: 99%

Free Radical Photopolymerization and 3D Printing Using Newly Developed Dyes: Indane-1,3-Dione and 1H-Cyclopentanaphthalene-1,3-Dione Derivatives as Photoinitiators in Three-Component Systems

et al. 2020

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The design of photoinitiating systems with excellent photochemical reactivities at 405nm LED is one of the obstacles to efficiently promote free radical polymerization in mild conditions (e.g., low light intensity, under air). Here, our actual search for new multicomponent photoinitiating systems at 405nm LED prompts us to develop new dyes based on push–pull structures. In the present paper, we chose two series of new dyes which possess indane-1,3-dione and 1H-cyclopenta naphthalene-1,3-dione groups as the electron-withdrawing groups, since they have the great potential to behave as sensitive and remarkable photoinitiators in vat photopolymerization/3D printing. When incorporated with a tertiary amine (ethyl dimethylaminobenzoate EDB, used as electron/hydrogen donor) and an iodonium salt (used as electron acceptor) as the three-component photoinitiating systems (PISs), and among a series of 21 dyes, 10 of them could efficiently promote the free radical photopolymerization of acrylates. Interestingly, steady state photolysis experiments revealed different behaviors of the dyes. Fluorescence experiments and free energy change calculations for redox processes were also carried out to investigate the relevant chemical mechanisms. Additionally, the formation of radicals from the investigated PISs was clearly observed by electron spin resonance (ESR) spin-trapping experiments. Finally, stereoscopic 3D patterns were successfully fabricated by the laser writing technique. In this work, the use of push–pull dyes based on the naphthalene scaffold as photoinitiators of polymerization is reported for the first time in a systematic study aiming at investigating the structure–performance relationship for irradiation carried out at 405 nm. By carefully selecting the electron donors used in the two series of push–pull dyes, novel and high-performance photoinitiating systems operating at 405 nm are thus proposed.

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Biocompatible photoinitiators based on poly‐α‐ketoesters

Cited by 17 publications

References 17 publications

Parallel esterification of bio‐based dicarboxylic acids in small scale film reactors: A high‐throughput study

Parallel esterification of bio‐based dicarboxylic acids in small scale film reactors: A high‐throughput study

The Art of Engineering Biomimetic Cellular Microenvironments

Free Radical Photopolymerization and 3D Printing Using Newly Developed Dyes: Indane-1,3-Dione and 1H-Cyclopentanaphthalene-1,3-Dione Derivatives as Photoinitiators in Three-Component Systems

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