Photoinitiated Polymerization of Biomaterials

Fisher, John P.; Dean, David; Engel, Paul S.; Mikos, Antonios G.

doi:10.1146/annurev.matsci.31.1.171

Cited by 156 publications

(133 citation statements)

References 41 publications

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“…[1][2][3] However, the synthesis of multifunctional macromers that form these degradable networks commonly involves multiple functionalization and purification steps, which makes the development of large numbers of polymers with diverse properties difficult. Here, we develop the first combinatorial library of degradable photocrosslinked materials.…”

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confidence: 99%

“…The spatial and temporal control afforded during photoinitiated polymerizations has motivated their wide application in the general field of biomaterials. [1,2] For example, photocrosslinkable hydrogels are used for the delivery of cells to injured tissues, [4][5][6][7][8] for the encapsulation and controlled delivery of biological molecules, [9][10][11] and for controlled fluid flow and cell confinement in microfluidics. [12,13] Additionally, highly crosslinked photopolymers are currently used in dentistry [14] and are being developed as bone-replacement materials [15,16] and for the fabrication of microdevices.…”

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A Combinatorial Library of Photocrosslinkable and Degradable Materials

Anderson¹,

Tweedie²,

Hossain³

et al. 2006

Advanced Materials

137

191

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Photocrosslinkable and degradable polymers are finding a broad range of applications as drug-delivery vehicles, tissueengineering scaffolds, and in the fabrication of microdevices. [1][2][3] However, the synthesis of multifunctional macromers that form these degradable networks commonly involves multiple functionalization and purification steps, which makes the development of large numbers of polymers with diverse properties difficult. Here, we develop the first combinatorial library of degradable photocrosslinked materials. A library of acrylate-terminated poly(b-amino ester)s was synthesized in parallel via a condensation reaction that combines primary or secondary amines with diacrylates. This library of macromers was then photopolymerized to form degradable networks, with a wide range of degradation times (< 1 day to minimal mass loss after three months), mass-loss profiles, and mechanical properties (∼ 4 to 350 MPa). We believe this library approach will allow for the rapid screening and design of degradable polymers for a variety of applications. The spatial and temporal control afforded during photoinitiated polymerizations has motivated their wide application in the general field of biomaterials. [1,2] For example, photocrosslinkable hydrogels are used for the delivery of cells to injured tissues, [4][5][6][7][8] for the encapsulation and controlled delivery of biological molecules, [9][10][11] and for controlled fluid flow and cell confinement in microfluidics. [12,13] Additionally, highly crosslinked photopolymers are currently used in dentistry [14] and are being developed as bone-replacement materials [15,16] and for the fabrication of microdevices.[17] Many of these applications are only possible owing to the controlled nature of this type of polymerization. For example, photoinitiated control of polymerization allows for their application as injectable biomaterials [18,19] with a non-cytotoxic polymerization process.[20]Additionally, through use of masks and lasers, the spatial control of the polymerization process allows for unique patterning and construction of complex materials.[21]Numerous photopolymerizable and degradable materials have been developed, including polyanhydrides, poly(propylene fumarates), poly(ethylene glycol), and polysaccharides, [8,15,16,18] all utilizing multiple reaction and purification steps for synthesis of the photopolymerizable precursors. Despite this work, it has proven challenging to predict specific desirable properties (e.g., degradation and mechanics) from known chemical and structural details of the network precursors. These properties are essential in the design of degradable polymers. For instance, it may be desirable to synthesize a very hard material for some applications (e.g., orthopaedics), whereas a soft material is advantageous for other applications (e.g., tissue adhesive). [22,23] One potential solution to the inability to predict physical behavior is the generation of a higher-throughput approach to rapidly synthesize and screen photopolymerizable li...

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A Combinatorial Library of Photocrosslinkable and Degradable Materials

Anderson¹,

Tweedie²,

Hossain³

et al. 2006

Advanced Materials

137

191

View full text Add to dashboard Cite

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“…On the other hand, their development is limited by the availability of such precursors and in many cases a high degree of mechanical stability is not required. Three basic strategies have been adopted: (i) use of existing photoactive, water soluble precursors; (ii) addition of photoactive groups to existing non-photoactive hydrophilic precursors; (iii) combination of water-soluble photoinitiators with hydrophilic precursors with limited photoactivity [4]. The third strategy, based on the use of water-soluble photoinitiators, is the most versatile in terms of the range of potential precursors and may be adapted to suit specific wavelengths of UV light, with clear advantages for biomedical applications.…”

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confidence: 99%

Synthesis and Photopolymerization of Tween 20 Methacrylate/N-vinyl-2-Pyrrolidone Blends

Borges

Jayakrishnan

Bourban

et al. 2012

Materials Science and Engineering: C

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Poly(oxyethylene 20 sorbitan) monolaurate (Tween® 20) methacrylates were synthesized by coupling methacryloyl chloride (MeOCl) to Tween 20 in the presence of 4-(N,N-dimethylamino) pyridine, using THF as a solvent, in order to investigate their suitability as precursors for photopolymerizable hydrogels in tissue engineering applications. The degree of substitution could be controlled by adjusting the molar ratio of MeOCl and Tween 20, giving three different monomers: Tween 20 monomethacrylate, Tween 20 dimethacrylate and Tween 20 trimethacrylate. Combined 1 H NMR and MALDI-TOF MS confirmed these monomers to be of high purity and to have polydispersities less than 1.3. It was shown that aqueous solutions of the monomers were photoactive, all the methacrylate groups reacting within 30 minutes exposure to a UV light intensity of 145 mW/cm 2 . Aqueous Tween 20 trimethacrylate was then combined with N-vinyl-2-pyrrolidone (NVP), giving tough copolymer hydrogels on photopolymerization, whose swelling ratios and swelling rates could be tuned by varying the Tween 20 trimethacrylate content. The use of a flexible spacer with a multifunctional monomer gives a permanent three-dimensional network, whilst maintaining degrees of swelling of between 60 and 85%, with potential for a wide range of biological and non-biological applications.

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“…For instance, photoinitiated polymerization methods might accommodate room temperature or below synthesis conditions, which is deficient in synthesis methods employing thermal energy such as thermal curing and free-radical polymer synthesis with thermally degradable initiators [8,9]. In the literature, benzoin, 2-hydroxy-2-methyl-1-phenyl propan-1-one (Darocure 1173), 2-hydroxy-1-[4-(2-hydroxyethoxy)phenyl]-2-methyl propan-1-one (Irgacure 2959) photoinitiators were used in the synthesis of PCL based macrophotoinitiators via stannous octoate catalyzed living ring-opening polymerization (ROP) to induce photopolymerization of methyl methacrylate (MMA) resulting in block copolymers of ɛ-caprolactone (CL) and MMA [10].…”

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