Synthesis and Characterization of Polymeric Soybean Oil-g-Methyl Methacrylate (and n-Butyl Methacrylate) Graft Copolymers:  Biocompatibility and Bacterial Adhesion

Abstract

Peroxidation, epoxidation, and/or perepoxidation reactions of soybean oil under air at room temperature resulted in cross-linked polymeric soybean oil peroxides on the surface along with the waxy soluble part, sPSB, with a molecular weight of 4690, containing up to 2.3 wt % peroxide. This soluble polymeric oil peroxide, sPSB, initiated the free radical polymerization of either methyl methacrylate (MMA) or n-butyl methacrylate (nBMA) to give PSB-g-PMMA and PSB-g-PnBMA graft copolymers. The polymers obtained were characterized by (1)H NMR, thermogravimetric analysis, differential scanning calorimetry, and gel permeation chromatography techniques. Polymeric oil as a plasticizer lowered the glass transition of the PSB-g-PMMA graft copolymers. PSB-g-PMMA and PSB-g-PnBMA graft copolymer film samples were also used in cell culture studies. Fibroblast and macrophage cells were strongly adhered and spread on the copolymer film surfaces, which is important in tissue engineering. Bacterial adhesion on PSB-g-PMMA graft copolymer was also studied. Both Staphylococcus epidermidis and Escherichia coli adhered on the graft copolymer better than on homo-PMMA. Furthermore, the latter adhered much better than the former.

Preparation of a bio-based epoxy with comparable properties to those of petroleum-based counterparts

“…The samples were dissolved in deuterated chloroform (CDCl 3 ). 1 H-NMR and 13 C-NMR were obtained at room temperature using Tetramethylsilane (TMS) as the internal standard. Fourier transform infrared (FT-IR) spectra were collected on a Nicolet 6700 FTIR spectrometer.…”

“…ppm) 5.5 (1H), 3.1 (2H), 2.7 (1H), 2.5 (1H), 2.2 (1H), 1.78-1.24 (13H), 1.2(3H), 1.0(6H), 0.6(3H). 13 …”

“…However, compared with the achieved progress on bio-based thermoplastics, the research on bio-based thermosetting resins, especially the thermosetting resins with high glass transition temperature (higher than 100°C) and comparable mechanical properties with petroleum-based counterparts are very limited. To the best of our knowledge, plant oil might be the most popular renewable resource in the synthesis of bio-based thermosetting resins [3,[11][12][13]. But unfortunately, due to the long soft aliphatic chain in triglyceride and its low crosslink density, the resulting resin always has a low glass transition temperature (lower than 100°C) and disappointing mechanical properties.…”

“…Javni et al [11] and Can et al [12] also prepared unsaturated polyester or polyurethane from soybean oil derivatives. But their results indicated that the properties of the oil-based resin strongly depended on the incorporation of rigid petroleum chemicals [11][12][13][14][15]. In order to obtain the acceptable mechanical and thermal properties for practical application, the content of the rigid co-monomer was usually as high as 50% or beyond.…”

New oil modified acrylic polymer for pH sensitive drug release: Experimental results and statistical analysis

“…However, the main disadvantage of hydogels and cytosan are their poor mechanical properties caused by extensive swelling. Cakmakh, et al [17,18] synthesized a graft polymer based on soya bean oil and methyl methacrylate and studied the biocompatibility of this sample in presence of bacterial adhesion. Polyurethane polymers are proven biocompatible and durable materials as recently shown by Bernacca, et al [19].…”