Studies on novel radiopaque methyl methacrylate: glycidyl methacrylate based polymer for biomedical applications (original) (raw)
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Acta Biomaterialia, 2008
The properties of copolymers (physical, chemical, biocompatibility, etc.) depend on their chemical structure and microstructural characteristics. We have prepared radio-opaque polymers based on the copolymers of methyl methacrylate (MMA) and 2-[2 0 ,3 0 ,5 0 -triiodobenzoyl]oxoethyl methacrylate (TIBOM). The copolymerization reaction between TIBOM and MMA showed that the reactivity ratios were r 1 = 0.00029 and r 2 = 1.2146. The composition diagram is typical for a practically non-homopolymerizable monomer (TIBOM) and a very reactive monomer (MMA). The copolymers were analyzed on an X-ray microcomputed tomograph and they proved to be radio-opaque even at low concentrations of TIBOM. The biocompatibility was tested both in vitro (with J774.2 macrophage and SaOS-2 osteoblast like cells) and in vivo in the rat. These materials were found to be non-toxic and were well tolerated by the organism. These combined results led to the suggestion that this type of polymer could be used as dental or bone cements in place of barium or zirconium particles, which are usually added to provide X-ray opacity.
Journal of Polymer Research
New radiopaque nanocomposites were prepared using iodinated copolymers and cloisite 20A, as reinforcement agent. Iodinated copolymers were prepared through copolymerization of Methyl methacrylate and acrylic acid and subsequently modification of the P(MMA-co-AA) via 4iodophenyl isocynate and 3,4,5-triiophenyl isocyanate for synthesis of 1I-P(MMA-co-AA) and 3I-P(MMA-co-AA) respectively. Preparation of the nanocomposites was carried out by the solution method using various amounts of organoclay. In order to investigate the effect of iodinated substituents on the morphology and thermal characteristics of the composite samples, the P(MMA-co-AA) was modified via phenyl isocyanate (PIC-P(MMA-co-AA)) and then the nanocomposites were prepared using cloisite 20A. All the nanocomposite samples were characterized by X-ray diffraction (XRD), scanning electron microscopoy (SEM), and thermogravimetric analysis (TGA). The X-ray visibility of the radiopaque nanocomposites was also explored using X-radiography. The results obtained indicated that the iodinated nanocomposites had an excellent radiopacity, and due to their biocompatibility, they could be used for medical applications.
Journal of Biomaterials Science, Polymer Edition, 2011
Radiopacity is required for embolic materials to be monitored by angiography during embolization. Covalently bound radio-opaque biomaterials would be ideal for embolization. Poly(N-isopropylacrylamideco-PEG-acrylate) modified with 2-iodobenzoyl chloride was synthesized and characterized by 1 H-NMR, differential scanning calorimetry and X-ray opacity. Poly(N-isopropylacrylamide-co-PEG-2-iodobenzoate) shows radiopacity, as well as thermo-sensitivity. Cytotoxicity testing on these co-polymers shows little cytotoxicity. Phase-transition temperature and radiopacity varied according to the content of NIPAAm and 2-iodobenzoate. Increasing the content of 2-iodobenzoate raised the radiopacity and lowered the LCST.
Journal of Macromolecular Science, Part A
A new methacrylate monomer 2-(4-nitrophenyl)-2-oxoethyl-2-methacrylate (NFM) was synthesized and its radical copolymerization with glycidyl methacrylate (GMA) was studied in 1,4-dioxane solution at 65 C using 2,2 0-azobisisobutyronitrile as an initiator. The synthesized monomer and copolymers were characterized by FTIR, 1 H and 13 C-NMR spectroscopy. The analysis of reactivity ratios revealed that NFM is less reactive than GMA, and copolymers formed are statistically in nature. Thermogravimetric analysis of the polymers reveals that the thermal stability of the copolymers increases with an increasing in the mole fraction of NFM in the copolymers. Glass transition temperatures of the copolymers decreased with an increasing of NFM molar fraction in copolymers. In addition, according to the results obtained from the contact angle and zeta potential measurements the hydrophobic character of the polymer decreases (it means surface free energy increases) and its zeta potential becomes more negative with increase of NFM ratio in the copolymer. Polymers with carbonyl functional groups have been particularly interesting because of their use as photoresists.
Synthesis and polymerization of some iodine-containing monomers for biomedical applications
Journal of Applied Polymer Science, 1992
Triiodophenol and iothalamic acid (5-acetamido-2,4,6-triio-N-methyl isophthalamic acid) were converted to their acrylic derivatives by esterfication with methacryloyl chloride and 2-hydroxyethyl methacrylate (HEMA), respectively. The monomers due to presence of heavy iodine atoms were expected to be radiopaque in nature. The monomers were characterized using TLC, IR, and 1H-NMR spectroscopy. Both monomers were highly resistant to homopolymerization and copolymerization with other acrylic monomers such as methyl methacrylate (MMA) or HEMA by initiators such as 2,2′-azobis isobutyronitriie (AIBN) or benzoyl peroxide (BPO) yielding only polymers of low molecular weight. The polymers obtained were charactrized by gel permeation chromatography (GPC) and differential thermal analysis (DTA). The resistance to polymerization is presumably due to the presence of bulky iodine atoms in the monomers sterically hindering the propagation step. The decomposition temperatures of the homopolymers and copolymers were close to 300°. Copolymers of HEMA with both radiopaque monomers incorporated to the extent of 25 wt % in the feed, however, produced polymers with good radiopacity. Copolymers with HEMA were also prepared in the form of microspheres by a solvent evaporation method with the aim of using them as particles in therapeutic embolization. While the polymer based on triiodophenol was found to cause extensive blood haemolysis in in vitro tests, polymer based on iothalamic acid was found to be nonhemolytic in character suggesting that copolymers based on iothalamic acid would be suitable for implantation in the living tissue.
Molecules, 2022
In this study, well-known oligomers containing ethyl methacrylate (EMA) and glycidyl methacrylate (GMA) components for the synthesis of the oligomeric network [P(EMA)-co-(GMA)] were used. In order to change the hydrophobic character of the [P(EMA)-co-(GMA)] to a more hydrophilic one, the oligomeric chain was functionalized with ethanolamine, xylitol (Xyl), and L-ornithine. The oligomeric materials were characterized by nuclear magnetic resonance and Fourier transform infrared spectroscopy, scanning electron microscopy, and differential thermogravimetric analysis. In the final stage, thanks to the large amount of -OH groups, it was possible to obtain a three-dimensional hydrogel (HG) network. The HGs were used as a matrix for the immobilization of methylene blue, which was chosen as a model compound of active substances, the release of which from the matrix was examined using spectrophotometric detection. The cytotoxic test was performed using fluid extracts of the HGs and human skin...
Radiation polymerisation of cyclohexyl methacrylate—I
International Journal of Radiation Applications and Instrumentation. Part C. Radiation Physics and Chemistry
AMtra~t-Radiation polymerisation of cyclobexyl methacrylate has been carried out at various doses, dose rates and temperatures. The radical yield determined by induction period method using benzoquinone as a scavenger is 6.25. The dose rate exponent is found to be 0.517 indicating a bimolccular termination. The (Kp/K[/2) value is 0.268, which is an order of magnitude higher than for methyl methacrylate under identical conditions of dose rate and temperature. Energy of activation calculated on the basis of kinetic data is found to be 2.06 kcal/mol, which is also quite low. These results indicate the probability of the existence of an anionic initiation in addition to free radical initiation. Chain transfer constant to the monomer (Ktr/Kp) is found to be 1.9 x 10-4.
Journal of the Chemical Society of Pakistan, 2011
Homopolymerization of 4-methoxybenzyl methacrylate (MBMA) and copolymerization with isobornyl methacrylate (IBMA) by the atom transfer radical polymerization method (ATRP) were performed at 90 °C. The homopolymer [poly(MBMA)] and copolymer [poly(MBMA-co-IBMA)] were characterized by Fourier transform infrared (FTIR), 1 H and 13 C NMR and gel permeation chromatography (GPC) techniques.. The compositions of the copolymers were calculated from 1 H NMR spectra. For the atom transfer radical copolymerization system, their monomer reactivity ratios were obtained by using the Kelen-Tüdos and Fineman-Ross equation, as r1: 0.88, r2: 0.63 (r1 is the monomer reactivity ratio of IBMA) and r1: 0,90, r2 :0,65.The initial decomposition temperatures of the resultant copolymers decreased with an increasing mol fraction of IBMA, which indicates that the heat resistance of the copolymer has been improved by decreasing the MBMA units.
Bulletin of Materials Science
New inherently radiopaque nanocomposites were prepared using iodine-containing poly(methyl methacrylateco-acrylamide) and graphene oxide. For this purpose, P(MMA-co-AA) was synthesized via copolymerization of methyl methacrylate and acrylic acid, and modified with 4-iodophenyl isocyanate and 3,4,5-triiodophenyl isocyanate to form poly[(methyl methacrylate-co-(N-4-iodophenyl)acrylamide)] (1I-P(MMA-co-AA)) and poly[(methyl methacrylate-co-(N-3,4,5-triiodophenyl)acrylamide)] (3I-P(MMA-co-AA)), respectively. For comparative evaluation, the non-iodinated copolymer (PIC-P(MMA-co-AA)) was prepared via reaction of the P(MMA-co-AA) with phenyl isocyanate to investigate the effect of iodinated substituents on the morphology and thermal characteristics of the nanocomposites. All the nanocomposites were characterized by X-ray diffraction analysis, scanning electron microscopy, X-radiography and thermogravimetric analysis. The results proved that thermal properties of the nanocomposites improved by the introduction of different amounts of graphene oxide into the copolymers' matrix. Radiopacity measurements showed the excellent radiopacity of iodinated nanocomposites and proved that 3I-GO-5 had radiopacity equivalent to that of an aluminium wedge with 2-mm thickness.