Highly Stretchable Thermoset Fibers and Nonwovens Using Thiol–ene Photopolymerization

Shanmuganathan, Kadhiravan; Elliot, Steven M.; Lane, Austin P.; Ellison, Christopher J.

doi:10.1021/am503563q

Cited by 30 publications

(48 citation statements)

References 23 publications

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“…S14). It was concluded from these experiments that a high degree of functional group conversion had been reached (>98% conversion across all PILs for which a stoichiometric ratio of functional groups was employed).…”

Section: Resultsmentioning

confidence: 97%

“…Thiol (2570 cm −1 ) and double bond (1630 cm −1 ) conversions were determined from multiple FTIR spectra taken for each thiol–ene network specimen before and after UV curing. Functional group conversions were determined using FTIR following a literature method . Error in measurements was determined to be less than ±2%.…”

Section: Methodsmentioning

confidence: 99%

“…Functional group conversions were determined using FTIR following a literature method. 33 Error in measurements was determined to be less than ±2%. An overlay of representative FTIR spectra for each PIL can be found in the supporting information (Fig.…”

Section: Polymer Characterizationmentioning

confidence: 99%

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Correlating structure with ionic conductivity in bis(phosphonium)‐containing [NTf₂] thiol–ene networks

Sims

Bontrager

Whittaker

et al. 2019

Polymer International

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Thiol–ene photopolymerization was employed in order to prepare a series of covalently crosslinked bis(phosphonium)‐containing poly(ionic liquid) (PIL) networks. While the counteranion was held constant (NTf2), the structure of the bis(phosphonium)‐containing ‘ene’ monomer was varied in order to explore the breadth of thermal, mechanical and conductive properties available for this system. Towards this end, it was determined that more flexible spacers within the cationic monomer led to PIL networks with lower Tg values and higher conductivities. Most notable was a two‐ to three‐orders‐of‐magnitude increase in ionic conductivity (from 10−9 to 10−6 S cm−1 at 30 °C, 30% relative humidity) when the R group on phosphonium was changed from phenyl to isopropyl. Changing the functional group ratio to off‐stoichiometry also led to a slight increase in conductivity. Although the thermal stability (Td5%) of the phosphonium ionic liquid monomers was found to be significantly higher (>400 °C) than that of analogous imidazolium monomers, this improvement was not observed to directly transfer over to the polymer where a two‐step decomposition pathway was observed. The first step is attributed to the thiol monomer backbone while the second step correlates well with decomposition of the phosphonium portion of the PIL. © 2019 Society of Chemical Industry

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Section: Resultsmentioning

confidence: 97%

Section: Methodsmentioning

confidence: 99%

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Correlating structure with ionic conductivity in bis(phosphonium)‐containing [NTf₂] thiol–ene networks

Sims

Bontrager

Whittaker

et al. 2019

Polymer International

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“…Owing to the versatility of thiol-ene chemistry, fibers with drastically different mechanical, thermal, and network structural properties were fabricated by incorporating monomers with different chemical structures [21].…”

Section: Introductionmentioning

confidence: 99%

Manipulating characteristic timescales and fiber morphology in simultaneous centrifugal spinning and photopolymerization

Fang

Dulaney

Gadley

et al. 2015

Polymer

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a b s t r a c tIn this study, the fabrication of crosslinked nonwoven fibers via simultaneous thiol-ene photopolymerization and spinning of monomer jets has been demonstrated in centrifugal Forcespinning for the first time. We observed that simultaneous Forcespinning and photopolymerization resulted in a wide variety of fiber morphologies including beads, beads-on-string, uniform fiber, fused fibers, and wellcured fibers. To elucidate the underlying mechanisms and parameter interactions that give rise to these morphologies, we systematically varied the light intensity, solution elasticity, and spin speed of the Forcespinning process. From these experimental results, an operating diagram was constructed based on the measured process parameters, their respective timescales, and observed effects on fiber morphology. While numerous parameters can individually affect fiber formation and morphology, the interplay between curing kinetics, solution viscoelasticity, and orifice-to-collector processing time window is also crucial in this process. Smooth and well-cured fibers were formed only when the photopolymerization occurred sufficiently quickly, before both the breakup of fibers into droplets due to a surface tension driven Rayleigh instability and the deposition of fibers on the collector. Our findings can serve as a predictive guideline for the fabrication of crosslinked fibers with desired morphology, the implementation of the in-situ polymerization and spinning concept into other commercial fiber manufacturing technologies, and the adaptation of other functional or high performance monomer systems.

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“…In one example, Ellison reported a process in which a mixture of thioland ene-functional monomers was spun and simultaneously UV-crosslinked. 25 Hoogenboom and Sanyal produced crosslinked oxazoline fibres by a UV-triggered thiol-ene reaction, 26 while…”

mentioning

confidence: 99%

Direct UV-Triggered Thiol–ene Cross-Linking of Electrospun Polyester Fibers from Unsaturated Poly(macrolactone)s and Their Drug Loading by Solvent Swelling

et al. 2017

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Abstract. Electrospinning is considered a relative simple and versatile technique to form high porosity porous scaffolds with micron to nanoscale fibers for biomedical applications. Here, electrospinning of unsaturated aliphatic polyglobalide (PGl) into well-defined fibers with an average diameter of 9 µm is demonstrated. Addition of a dithiol crosslinker and a photoinitiator to the polymer solution enabled the UV-triggered intra-crosslinking of the fibers during the spinning process. The in-situ crosslinking of the fibers resulted in amorphous material able to swell up to 14% in tetrahydrofyrane (THF) without losing the fiber morphology. Seeding Mesenchymal Stem Cells (MSCs) onto both crosslinked and non-crosslinked PGl fibers proved their compatibility with MSCs and suitability as scaffolds for cell growth and proliferation of MSCs. Moreover, the ability to directly load crosslinked PGl with hydrophobic molecules by soaking the fiber mesh in solution is shown with Rhodamine B and Indomethacin, a hydrophobic anti-inflammatory drug. This marks an advantage over conventional aliphatic polyesters and opens opportunities for the design of drug loaded polyester scaffolds for biomedical applications or tissue engineering.

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Highly Stretchable Thermoset Fibers and Nonwovens Using Thiol–ene Photopolymerization

Cited by 30 publications

References 23 publications

Correlating structure with ionic conductivity in bis(phosphonium)‐containing [NTf₂] thiol–ene networks

Correlating structure with ionic conductivity in bis(phosphonium)‐containing [NTf₂] thiol–ene networks

Manipulating characteristic timescales and fiber morphology in simultaneous centrifugal spinning and photopolymerization

Direct UV-Triggered Thiol–ene Cross-Linking of Electrospun Polyester Fibers from Unsaturated Poly(macrolactone)s and Their Drug Loading by Solvent Swelling

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Highly Stretchable Thermoset Fibers and Nonwovens Using Thiol–ene Photopolymerization

Cited by 30 publications

References 23 publications

Correlating structure with ionic conductivity in bis(phosphonium)‐containing [NTf2] thiol–ene networks

Correlating structure with ionic conductivity in bis(phosphonium)‐containing [NTf2] thiol–ene networks

Manipulating characteristic timescales and fiber morphology in simultaneous centrifugal spinning and photopolymerization

Direct UV-Triggered Thiol–ene Cross-Linking of Electrospun Polyester Fibers from Unsaturated Poly(macrolactone)s and Their Drug Loading by Solvent Swelling

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Correlating structure with ionic conductivity in bis(phosphonium)‐containing [NTf₂] thiol–ene networks

Correlating structure with ionic conductivity in bis(phosphonium)‐containing [NTf₂] thiol–ene networks