Synthesis, Characterization, and Polymerization of Glycidyl Methacrylate Derivatized Dextran

Dijk-Wolthuis, W. N. E. Van; Franssen, O.; Talsma, H.; Steenbergen, M.J. van; Bosch, J. J. Kettenes‐van den; Hennink, W.E.

doi:10.1021/ma00122a044

Cited by 361 publications

(310 citation statements)

References 14 publications

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“…The availability of dextran with different molecular weights, its solubility in polar organic solvents, which enables chemical modification, and its biocompatibility make this natural polysaccharide synthetically useful. For example, dextran-based hydrogels have been obtained either in a single step using bi-functional crosslinking agents such as isocyanate-type monomers [8], or in two-steps involving the derivatization of dextran with polymerizable double bonds followed by radical [9] or UV [10][11][12] polymerization of the dextran derivatives. Although an extensive study was undertaken, few reports [13] dealt with regioselectivity in chemical modification.…”

Section: Introductionmentioning

confidence: 99%

“…Nonetheless, regioselectivity may be necessary to provide highly ordered, swellable and strong hydrogels [14]. Moreover, few attempts [4,8,9] were made to fully characterize the three-dimensional hydrogel structures, despite the need to obtain information on the crosslink density, the molecular weight between crosslinks, and the average mesh pore size of the gels to enable useful and tailorable hydrogel synthesis to be performed.…”

Section: Introductionmentioning

confidence: 99%

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Enzymatic synthesis of dextran-containing hydrogels

2002

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Dextran, a natural glucose-containing polysaccharide, has been acylated by Proleather FG-F and lipase AY, a protease and lipase from Bacillus sp. and Candida rugosa, respectively, in anhydrous dimethylsulfoxide in the presence of vinyl acrylate (VA). The efficiency of the reaction in the presence of Proleather FG-F and the isolated yields were ca. 71% and 45%, respectively. Dextran derivatized with VA (dexT70-VA) was characterized by gel permeation chromatography and its structure was established by NMR indicating two positional isomers at the 2 and 3 positions on the glucose moieties in equal amounts. Furthermore, the dextran glucopyranose residues were mono-substituted. The benefits of the biocatalytic synthesis of dextran acrylates was demonstrated using 4-dimethylaminopyridine as a chemical catalyst. Gels were prepared by free radical polymerization of aqueous solutions of dexT70-VA with different degrees of substitution and monomer concentrations. Intermolecular linkages and physical entanglements are predominantly formed by concentrated solutions, however, a part of the acrylate groups did not react. Gel pore sizes were calculated from swelling experiments and ranged from ca. 18 to 182 ( A. r

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Enzymatic synthesis of dextran-containing hydrogels

2002

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“…They suggested that the reaction occurred through the opening of the GMA epoxy ring (Martens and Anseth, 2000). Van Dijk-Wolthuis et al, 1995 andLo &Jiang, 2010, have investigated the chemical modification of dextran with GMA in DMSO as a solvent catalyzed by 4-(N, N-dimethylamino) pyridine (DMAP). They concluded that the addition of GMA to dextran might occur through the opening of the GMA epoxy ring, too.…”

Section: Introductionmentioning

confidence: 99%

“…They concluded that the addition of GMA to dextran might occur through the opening of the GMA epoxy ring, too. They found glycidol as a by-product, which resulted in the addition of methacrylate groups (Van Dijk-Wolthuis et al, 1995 andLo &Jiang, 2010). However, it was postulated that the trans-esterification reaction would be mainly favored because the formed glycidol is a good leaving group (Van Dijk-Wolthuis et al, 1995).…”

Section: Introductionmentioning

confidence: 99%

“…They found glycidol as a by-product, which resulted in the addition of methacrylate groups (Van Dijk-Wolthuis et al, 1995 andLo &Jiang, 2010). However, it was postulated that the trans-esterification reaction would be mainly favored because the formed glycidol is a good leaving group (Van Dijk-Wolthuis et al, 1995). Recently, GMA was used to modify alginate for producing thermal in-situ polymerizable hydrogels at physiological temperature for cell encapsulation (Wang et al, 2015).…”

Section: Introductionmentioning

confidence: 99%

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In-Situ UV-Photopolymerized PVA-g-GMA Hydrogels for Biomedical Applications: I. Synthesis, Characterizations and Grafting Optimization

2018

J App Pharm Sci

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This work explores the synthesis and grafting optimization of PVA-g-GMA hydrogels. The grafting of poly (vinyl alcohol) (PVA) with glycidyl methacrylate (GMA) was conducted by the trans-esterification reaction via introducing methacryloyl groups into PVA chains and glycidol was formed as by-product. The grafting reaction conditions of PVA-g-GMA e.g. GMA concentrations and reaction temperature were optimized. The kinetic parameters e.g. grafting efficiency (GE) and grafting percentage (GP%) were calculated to optimize the grafting reaction, while yield (%) was determined to monitor the hydrogels formation. The instrumental characterizations e.g. 1 H-NMR, FTIR, SEM and TGA/DSC, were investigated for verifying the grafting reaction. The UV-photopolymerization was used for photocrosslinking the water-soluble PVA-g-GMA using Irgacure 2959 (I 2959 ) as a photoinitiator. Results revealed that the grafting reaction dramatically increased with increase of both GMA concentration until 0.15M and reaction temperature at 60 o C. Also, the surface morphological of PVA-g-GMA freeze-dried gels was found more compacted, smooth and uniform due to the grafting process. A significant thermal stability was noticed, due to grafting reaction of PVA-g-GMA throughout TGA and DSC results. The obtained results are very promising and opening new area for conducting further investigations considering the very low price of the used UV crosslinking method compared to the chemical crosslinking method.

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Pore structure analysis of swollen dextran-methacrylate hydrogels by SEM and mercury intrusion porosimetry

Kim¹,

Chu²

2000

J. Biomed. Mater. Res.

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The objectives of this study were to visually examine the surface and interior morphology of a new class of biodegradable hydrogels based on dextran-methacrylate and to quantify the porous structure of these hydrogels in swollen state. Two techniques (scanning electron microscopy and mercury intrusion porosimetry) were used to analyze pore structure of dextran-methacrylate hydrogels as a function of the degree of methacrylate substitution. SEM was used to observe 3-dimensional network structure of cryofixed and fractured swollen dextran-methacrylate hydrogels. Image analysis of the SEM data revealed different pore shapes and sizes, depending on the degree of substitution and the location within the hydrogel. A higher methacrylate-substituted dextran hydrogel showed a compact and rigid pore structure, while a lower substituted hydrogel showed a delicate and fragile pore structure. Mercury intrusion porosimetry analysis of the pore structure of dextran-methacrylate hydrogels provided useful and more reliable quantitative data of pore characteristics, such as total pore area, average pore diameter, their distribution, and bulk density. The total pore area and average pore diameter of swollen dextran-methacrylate hydrogels decreased with an increase in degree of methacrylate substitution, while bulk density increased with an increase in degree of substitution.

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Synthesis, Characterization, and Polymerization of Glycidyl Methacrylate Derivatized Dextran

Cited by 361 publications

References 14 publications

Enzymatic synthesis of dextran-containing hydrogels

Enzymatic synthesis of dextran-containing hydrogels

In-Situ UV-Photopolymerized PVA-g-GMA Hydrogels for Biomedical Applications: I. Synthesis, Characterizations and Grafting Optimization

Pore structure analysis of swollen dextran-methacrylate hydrogels by SEM and mercury intrusion porosimetry

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