Monolithic Scavenger Resins by Amine Functionalizations of Poly(4-vinylbenzyl chloride-<i>co</i>-divinylbenzene) PolyHIPE Materials

Krajnc, Peter; Brown, Jane F.; Cameron, Neil R.

doi:10.1021/ol026115k

Cited by 137 publications

(85 citation statements)

References 22 publications

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“…These materials, commonly termed polyHIPEs, have been prepared from a wide range of chemistries, including polystyrene 8,9 , polystyrene derivatives [10][11][12][13] , poly(meth)acrylates [14][15][16][17] , polyacrylamides [18][19][20] , poly(ether sulfone)s 21 , norbornenes 22 , poly(propylene fumarate) 23 , dicyclopentadiene 24,25 , polysaccharides 26 and proteins 27,28 .…”

Section: Introductionmentioning

confidence: 99%

Degradable emulsion-templated scaffolds for tissue engineering from thiol–ene photopolymerisation

et al. 2012

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Further information on publisher's website:http://dx.doi.org/10.1039/c2sm26250aPublisher's copyright statement:Additional information: Use policyThe full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-prot purposes provided that:• a full bibliographic reference is made to the original source • a link is made to the metadata record in DRO • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders.Please consult the full DRO policy for further details. AbstractEmulsion templating has been used to prepare highly porous polyHIPE materials by thiol-ene photoinitiated network formation. Commercially available multifunctional thiols and acrylates were formulated into water-in-oil high internal phase emulsions (HIPEs) using an appropriate surfactant, and the HIPEs were photo-cured. The temperature of the HIPE aqueous phase was found to influence the morphology of the resulting materials. In agreement with previous work, a higher aqueous phase temperature (80 o C) gave rise to a larger mean void and interconnect diameter. The influence of temperature on morphology was found to be reduced at higher porosity, but still significant. The Young's modulus of the porous materials was shown to be related to the functionality of the acrylate comonomer used. A mixture of penta-and hexa-acrylate gave rise to a 100-fold increase in modulus, compared to an analogous tri-functional acrylate. The materials could be functionalised conveniently by addition of mono-acrylates or thiols to the organic phase of the precursor HIPE. Degradation was observed to occur at a rate depending on the degradation conditions. Under cell culture conditions at 37 o C, 19% mass loss occurred over 15 weeks. The scaffolds were found to be capable of supporting the growth of keratinocytic cells (HaCaTs) over 11 days in culture. Some penetrative in-growth of the cells into the scaffold was observed.3

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Section: Introductionmentioning

confidence: 99%

Degradable emulsion-templated scaffolds for tissue engineering from thiol–ene photopolymerisation

et al. 2012

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“…It has been found previously that when diamino alkanes and multi functional amines were used to transform polyacrylates and polyvinylbenzyl chloride, a substantial amount of additional cross-linking took place. [16,17,18,19] This kind of side reaction is undesired when free amino groups are needed for further functionalisations or end applications. Site-site interactions can be strongly dependent on the temperature and also on the solvent polarity.…”

Section: Resultsmentioning

confidence: 99%

“…Rather low loadings of amines prompted us to perform the reaction at elevated temperatures (initially, we tried to avoid high temperatures as it has been shown previously that higher temperatures enable more post polymerisation cross-linking). In the case [16] and 4-nitrophenyl acrylate based supports [17] these loading are rather low, however it is very likely that due to the macroporous nature functionalised groups are positioned at the surface where they are most needed for the applications with convective mass transfer. Partial hydrolysis of epoxy groups may also be contributing to lower loadings of amine groups.…”

Section: Resultsmentioning

confidence: 99%

Amine Functionalisations of Glycidyl methacrylate Based PolyHIPE Monoliths

Majer

Krajnc

2010

Macromolecular Symposia

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Summary: High internal phase emulsions were employed to prepare highly porous (up to 80% pore volume) monoliths of poly(glycidyl methacrylate-co-ethylenegycol dimethacrylate) by free radical polymerisations of continuous phases of emulsions. Monoliths with cavities approximately 4 mm in diameter and with interconnecting pores approximately 0.7 mm in diameter were obtained. In order to obtain monoliths with ion exchange groups on the surface of pores for chromatography applications, functionalisations with different amines were performed and various reaction conditions tested. FTIR spectroscopy and nitrogen content analysis were used to monitor the functionalisation processes. Monoliths were succesfully functionalised with 1,2-diaminoethane, 1,4-diaminobuthane, 1,8-diaminooctane and tris(diethylamino)amine.

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“…Poly(styrene/divinylbenzene) materials were functionalized by sulfonation, bromination and nitration 14 . PolyHIPEs produced from 4-vinylbenzyl chloride (VBC) have also been functionalized post-polymerization with a wide range of nucleophiles, including the amines tris(2-aminoethyl)amine and hexamethylenetetramine 15 . Reactive methacrylates, such as glycidyl methacrylate (GMA) 16 , and acrylate esters, such as Nacryloxysuccinimide (NASI) 17 , have also been used in polyHIPE production in order to form polymer networks with reactive handles that can be functionalized post-polymerization.…”

Section: Introductionmentioning

confidence: 99%

Chemical functionalization of emulsion-templated porous polymers by thiol–ene “click” chemistry

2014

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A note on versions:The version presented here may differ from the published version or, version of record, if you wish to cite this item you are advised to consult the publisher's version. Please see the 'permanent WRAP URL' above for details on accessing the published version and note that access may require a subscription. Highly porous polymers (polyHIPEs) have been prepared by the photopolymerization of high internal phase emulsions (HIPEs) with varying ratios of thiol and acrylate monomers. The resulting polymers have a nominal porosity of 80%, and are seen to have a well-defined, interconnected pore morphology, with average pore diameters ranging from 30 to 60 µm. The polyHIPE polymers have been shown using a colourimetric (Ellman's) assay to contain residual thiols which are reactive towards a range of (meth)acrylates (hexfluoroisopropyl acrylate, fluorescein O-acrylate and poly(ethylene glycol) methyl ether methacrylate). Functionalization was explored using thermally-and UV-initiated radical-mediated "click" reactions and an amine-catalysed Michael addition reaction. The extent of functionalization was investigated qualitatively and quantitatively using a range of techniques (solid state NMR spectroscopy; FTIR spectroscopy; X-ray photoelectron spectroscopy (XPS); observation of fluorescence); high levels of conversion (up to 90-95%) were observed for the thermallyinitiated radical reaction and the Michael reaction.

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Monolithic Scavenger Resins by Amine Functionalizations of Poly(4-vinylbenzyl chloride-co-divinylbenzene) PolyHIPE Materials

Cited by 137 publications

References 22 publications

Degradable emulsion-templated scaffolds for tissue engineering from thiol–ene photopolymerisation

Degradable emulsion-templated scaffolds for tissue engineering from thiol–ene photopolymerisation

Amine Functionalisations of Glycidyl methacrylate Based PolyHIPE Monoliths

Chemical functionalization of emulsion-templated porous polymers by thiol–ene “click” chemistry

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