Thiol‐ene photopolymerization for efficient curing of vinyl esters

Mautner, Andreas; Qin, Xiao‐Hua; Wutzel, Harald; Ligon, Samuel Clark; Kapeller, Barbara; Moser, Dominique; Russmueller, Guenter; Stampfl, Juergen; Liska, Robert

doi:10.1002/pola.26365

Cited by 63 publications

(104 citation statements)

References 23 publications

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“…For the thiol-ene reaction was demonstrated to boost the reactivity of the new types of vinyl carbonates, the influence of thiols onto the mechanical performance had to be analyzed as well ( Figure 5). The typical trend, already found for various types of photopolymers such as (meth)acrylates, [46] vinyl ester, [43] and vinyl carbonates, [39] that the addition of thiols leads to a decrease in both indentation modulus and hardness was found again. This is based on thiols rendering the polymer network more flexible, resulting in reduced stiffness and hardness but increased toughness.…”

Section: Mechanical Characterization By Nanoindentationsupporting

confidence: 59%

“…TTeGDMA, this value is usually well below 1 mM. [31,32,39,43] However, the dental formulation MA, which was the blueprint for the new types of vinyl carbonates and is known for its excellent for vinyl carbonates. [39] Thus, the influence of thiols onto the photoreactivity of the new vinyl carbonates was analyzed, too ( Figure 4).…”

Section: Toxicological Analysismentioning

confidence: 99%

“…eventually, the photoreactivity as expressed by t max was in the same range as those of acrylates. [43] This acceleration is based upon a combined chain and step-growth polymerization mechanism. [39] …”

Section: Toxicological Analysismentioning

confidence: 99%

“…To further boost the photoreactivity, nontoxic thiols, [39,43] via the thiol-ene reaction, have recently been demonstrated to be suitable polymerization accelerators biocompatibility as conventional vinyl carbonates. The photoreactivity of these monomers was similar to common vinyl carbonates, too, and could be improved through the addition of thiols via the thiol-ene reaction without losing much of the mechanical properties.…”

Section: Mechanical Characterization By Nanoindentationmentioning

confidence: 99%

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Vinyl carbonate photopolymers with improved mechanical properties for biomedical applications

Mautner

Steinbauer

Russmüller

et al. 2016

Designed Monomers and Polymers

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Recently, vinyl carbonates have been demonstrated to be a versatile alternative to acrylates and methacrylates in biomedical applications as they exhibit photoreactivity and mechanical properties on a level or even above (meth)acrylates. Furthermore, much lower cytotoxicity as well as degradation via a surface erosion mechanism qualify them for medical use. However, it is highly desirable to improve the mechanical properties of vinyl carbonates to reach the performance of PLA. Thus, the main focus of this study lies on designing vinyl carbonates with suitable functional groups that are capable of augmenting mechanical properties of vinyl carbonates, e.g. cyclic structures or urethane groups, and implementing them into the vinyl carbonate structures. Resulting monomers were tested regarding their photoreactivity and cytotoxicity. Furthermore, cured specimens were investigated concerning their mechanical properties. In addition, the thiol-ene reaction was utilized to further improve photoreactivity. The new vinyl carbonates exhibit excellent biocompatibility and photoreactivity that can be significantly enhanced through the addition of thiols onto the level of highly photoreactive acrylates. Most importantly, results showed that the mechanical properties could be improved onto the level of PLA and above.

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Section: Mechanical Characterization By Nanoindentationsupporting

confidence: 59%

Section: Toxicological Analysismentioning

confidence: 99%

Section: Toxicological Analysismentioning

confidence: 99%

Section: Mechanical Characterization By Nanoindentationmentioning

confidence: 99%

See 2 more Smart Citations

Vinyl carbonate photopolymers with improved mechanical properties for biomedical applications

Mautner

Steinbauer

Russmüller

et al. 2016

Designed Monomers and Polymers

Self Cite

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“…Furthermore, hydrogels formed by vinyl ester chemistry remain largely unexplored. We therefore synthesized PEG divinyl esters (PEGDVE) through a transesterification reaction between PEG dicarboxylic acids and vinyl acetate under the catalysis of palladium (II) acetate [37]. Table 2 presents a comparative analysis on the biocompatibility of acrylates and vinyl esters.…”

Section: Chemistry Of Hydrogel Formationmentioning

confidence: 99%

Additive manufacturing of photosensitive hydrogels for tissue engineering applications

et al. 2014

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Hydrogels are extensively explored as scaffolding materials for 2D/3D cell culture and tissue engineering. Owing to the substantial complexity of tissues, it is increasingly important to develop 3D biomimetic hydrogels with user-defined architectures and controllable biological functions. To this end, one promising approach is to utilize photolithography-based additive manufacturing technologies (AMTs) in combination with photosensitive hydrogels. We here review recent advances in photolithography-based additive manufacturing of 3D hydrogels for tissue engineering applications. Given the importance of materials selection, we firstly give an overview of water-soluble photoinitiators for single-and two-photon polymerization, photopolymerizable hydrogel precursors and light-triggered chemistries for hydrogel formation.Through the text we discuss the design considerations of hydrogel precursors and synthetic approaches to polymerizable hydrogel precursors of synthetic and natural origins. Next, we shift to how photopolymerizable hydrogels could integrate with photolithography-based AMTs for creating well-defined hydrogel structures. We illustrate the working-principles of both single-and two-photon lithography and case studies of their applications in tissue engineering. In particular, two-photon lithography is highlighted as a powerful tool for 3D functionalization/construction of hydrogel constructs with μm-scale resolution. Within the text we also explain the chemical reactions involved in two-photon-induced biofunctionalization and polymerization. In the end, we summarize the limitations of available hydrogel systems and photolithography-based AMTs as well as a future outlook on potential optimizations.

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Hydrogels for Two‐Photon Polymerization: A Toolbox for Mimicking the Extracellular Matrix

Torgersen

Qin

et al. 2013

Adv Funct Materials

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217

206

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The natural extracellular matrix (ECM) represents a complex and dynamic environment. It provides numerous spatio‐temporal signals mediating many cellular functions including morphogenesis, adhesion, proliferation and differentiation. The cell–ECM interaction is bidirectional. Cells dynamically receive and process information from the ECM and remodel it at the same time. Theses complex interactions are still not fully understood. For better understanding, it is indispensable to deconstruct the ECM up to the point of investigating isolated characteristics and cell responses to physical, chemical and topographical cues. Two‐photon polymerization (2PP) allows the exact reconstruction of cell specific sites in 3D at micro‐ and nanometer precision. Processing biocompatible synthetic and naturally‐derived hydrogels, the microenvironment of cells can be designed to specifically investigate their behavior in respect to key chemical, mechanical and topographical attributes. Moreover, 3D manipulation can be performed in the presence of cells, guiding biological tissue formation in all stages of its development. Here, advances in 2PP microfabrication of synthetic and naturally based hydrogels are reviewed. Key components of photopolymerizable hydrogel precursors, their structure–property relationships and their polymerization mechanisms are presented. Furthermore, it is shown how biocompatible 2PP fabricated constructs can act as biologically relevant matrices to study cell functions and tissue development.

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Thiol‐ene photopolymerization for efficient curing of vinyl esters

Cited by 63 publications

References 23 publications

Vinyl carbonate photopolymers with improved mechanical properties for biomedical applications

Vinyl carbonate photopolymers with improved mechanical properties for biomedical applications

Additive manufacturing of photosensitive hydrogels for tissue engineering applications

Hydrogels for Two‐Photon Polymerization: A Toolbox for Mimicking the Extracellular Matrix

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