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Synthesis and characterization of poly(N-isopropyl acryl amide)-g-poly(LINOLEIC ACID)/poly(linolenic acid) graft copolymers

Allı, Abdulkadir | Hazer, Baki

Article | 2011 | JAOCS, Journal of the American Oil Chemists' Society88 ( 2 ) , pp.255 - 263

To diversify edible oil thermoresponsive polymer composites, polymeric linoleic acid peroxide (PLina) and polymeric linolenic acid peroxide (PLinl) were obtained by the autoxidation of linoleic acid (Lina) and linolenic acid (Linl), respectively. The autoxidation of Lina and Linl under air at room temperature rendered waxy soluble polymeric peroxide, having a soluble fraction in chloroform of more than 91 wt% and containing up to 1.0 wt% of peroxide. The soluble polymeric oil macro-peroxide was used to initiate the free radical polymerization of N-isopropylacrylamide, NIPAM, resulting in PLina-g-PNIPAM and PLinl-g-PNIPAM graft copol . . .ymers, respectively. The PNIPAM content of the graft copolymers was calculated using the elemental nitrogen analysis of graft copolymers. Thermal analysis, FTIR, 1H NMR, and SEM techniques were used in the characterization of the products. The hydrophobic effect of the fatty acid macro peroxides on the thermal response rate of the graft copolymers was investigated by means of swelling-deswelling behaviors in response to temperature change. They have a thermoresponsive character and exhibit a volume phase transition at approximately 27-30 °C, which is 1-4 °C lower than that of pure PNIPAM. A plastizer effect of PLina and PLinl in graft copolymers was observed, indicating a lower glass transition temperature than that of pure PNIPAM. © 2010 AOCS Daha fazlası Daha az

Polymeric linoleic acid-polyolefin conjugates: Cell adhesion and biocompatibility

Çakmaklı, Birten | Hazer, Baki | Tekin, İshak Özel | Açıkgöz, Şerefden | Can, Murat

Article | 2007 | JAOCS, Journal of the American Oil Chemists' Society84 ( 1 ) , pp.73 - 81

To diversify edible-oil polymer composite, polymeric linoleic acid (PLina) peroxide was obtained by the auto-oxidation of linoleic acid in a simple way for use as a macroinitiator in free radical polymerization of vinyl monomers. Peroxidation, epoxidation, and/or perepoxidation reactions of linoleic acid under air at room temperature resulted in PLina, having soluble fraction more than 91 weight percent (wt%), with molecular weight ranging from 1,644 to 2,763 Da, and containing up to 1.0 wt% of peroxide. PLina initiated the free radical polymerization of ether styrene (S), methyl methacrylate (MMA), or n-butyl methacrylate (nBMA) to . . . give PLina-g-polystyrene (PS), PLina-g-poly-MMA (PMMA), and PLina-g-poly- nBMA (PnBMA) graft copolymers. The polymers obtained were characterized by proton nuclear magnetic resonance (1H NMR), thermal gravimetric analysis (TGA), differential scanning calorimetry (DSC), and gel permeation chromatography (GPC) techniques. Microstructure of the graft copolymers was observed by using scanning electron microscope (SEM). Graft copolymers obtained contained polymeric linoleic acid in a range between 8.5 and 19.3 mol percent (mol%). PLina-g-PS, PLina-g-PMMA and PLina-g-PnBMA graft copolymer samples were also used in cell culture studies. Fibroblast and macrophage cells were strongly adhered and spread on the copolymer film surfaces. These newly synthesized copolymers were tested for their effects on human blood protein adsorption compared with PMMA graft copolymers containing polymeric soybean oil and polymeric linseed oil; interestingly we observed a dramatic decrease in the protein adsorption on the linoleic acid graft copolymer, which is important in tissue engineering. © AOCS 2007 Daha fazlası Daha az

Biodegradable poly(ε-caprolactone)-based graft copolymers via poly(linoleic acid): In vitro enzymatic evaluation

Allı, Sema | Tığlı-Aydın, Rahime Seda | Allı, Abdülkadir | Hazer, Baki

Article | 2015 | JAOCS, Journal of the American Oil Chemists' Society92 ( 3 ) , pp.449 - 458

Well-defined graft copolymers based on poly(?-caprolactone) (PCL) via poly(linoleic acid) (PLina), are derived from soybean oil. Poly(linoleic acid)-g-poly(?-caprolactone) (PLina-g-PCL) and poly(linoleic acid)-g-poly(styrene)-g-poly(?-caprolactone) (PLina-g-PSt-g-PCL) were synthesized by ring-opening polymerization of ?-caprolactone initiated by PLina and one-pot synthesis of graft copolymers, and by ring-opening polymerization and free radical polymerization by using PLina, respectively. PLina-g-PCL, PLina-g-PSt-g-PCL3, and PLina-g-PSt-g-PCL4 copolymers containing 96.97, 75.04 and 80.34 mol% CL, respectively, have been investigated . . . regarding their enzymatic degradation properties in the presence of Pseudomonas lipase. In terms of weight loss, after 1 month, 51.5% of PLina-g-PCL, 18.8% of PLina-g-PSt-g-PCL3, and 38.4% of PLina-g-PSt-g-PCL4 were degraded, leaving remaining copolymers with molecular weights of 16,140, 83,220 and 70,600 Da, respectively. Introducing the PLina unit into the copolymers greatly decreased the degradation rate. The molar ratio of [CL]/[Lina] dramatically decreased, from 21.3 to 8.4, after 30 days of incubation. Moreover, reduced PCL content in PLina-g-PSt-g-PCL copolymers decreased the degradation rate, probably due to the PSt enrichment within the structure, which blocks lipase contact with PCL units. Thus, copolymerization of PCL with PLina and PSt units leads to a controllable degradation profile, which encourages the use of these polymers as promising biomaterials for tissue engineering applications. © AOCS 2015 Daha fazlası Daha az

Efficiency of gold nano particles on the autoxidized soybean oil polymer: fractionation and structural analysis

Hazer, Baki | Akyol, Elvan

Article | 2016 | JAOCS, Journal of the American Oil Chemists' Society93 ( 2 ) , pp.201 - 213

Polyunsaturated plant oils have gained great interest as monomers to produce biodegradable polymers obtained from renewable resources due to the limited existing sources of petroleum oil and environmental issues. Soybean oil was autoxidized by exposure to atomospheric oxygen at room temperature with or without the presence of gold nanoparticles (Au NPs) 5-41 days. When the autoxidation process was catalyzed with Au NPs, the molecular weight of the oxidized oil was increased in 5 days. In contrast to this, without Au NPs, the oxidized oil was still a fluidized liquid. Autoxidized soybean oil polymer in toluene solution with gold NP s . . .howed a surface plasmon resonance at ?max = 540 nm in a UV-VIS spectrometer and a fluorescence emission spectrum at ?max = 450 nm, when it was irradiated at ?max = 390 nm. The higher molecular weight of the polymeric oils was successively fractionated by the extraction from the solvent-non-solvent mixture CHCl3/petroleum ether with the volume ratio of 5:15. Three polymeric oils fractions with different molecular weight (ca 1000, 4000, and 40,000 g/mol) were obtained. GC-MS analysis, 1H-NMR and GPC techniques were used in the structural analysis of the fractionated polymeric oils. © 2015 AOCS Daha fazlası Daha az

Influence of Soybean Oil Blending with Polylactic Acid (PLA) Films: In Vitro and In Vivo Evaluation

Aydın, R. Seda Tığlı | Akyol, Elvan | Hazer, Baki

Article | 2017 | JAOCS, Journal of the American Oil Chemists' Society94 ( 3 ) , pp.413 - 424

Due to the great interest in oil-based polymers, which are prepared from renewable resources, different forms and amounts of soybean oil-based PLA films were prepared and evaluated for their potential usage as a medical biomaterial. Soybean oil, epoxidized soybean oil and auto-oxidized soybean oil were blended with PLA and PLA/oil films with appropriate oil amounts [2, 7, 14 and 20% (w/w)] were obtained by solvent casting. Thermal stability and plasticization effect were determined by adjusting oil amounts and type. Epoxidized soybean oil blended films showed the smallest increase in elongation breaks (13–20%) and the highest decrea . . .se in thermal decomposition temperatures (364–327 °C) compared to other oil blended films. In vitro quantitative and qualitative cytotoxicity results showed no reactivity (grade 0) for the L929 cells treated with 14% (w/w) oil blended PLA films. In vivo irritation and implantation tests concluded that 14% (w/w) oil blended PLA films were non-irritant. No erythema, no oedema reactions, no traumatic necrosis and foreign debris were observed. Thus, along with superior biocompatibility, PLA/oil films can replace petroleum-based products for several biomedical uses. © 2017, AOCS Daha fazlası Daha az

Ecofriendly autoxidation of castor oil/ricinoleic acid. Multifunctional macroperoxide initiators for multi block/graft copolymers

Hazer, Baki | Eren, Melike

Article | 2019 | JAOCS, Journal of the American Oil Chemists' Society96 ( 4 ) , pp.421 - 432

Ecofriendly autoxidation is a reaction of air oxygen with unsaturated organic molecules at room temperature. Castor oil and ricinoleic acid were ecofriendly autoxidized for 5 months to obtain castor oil macroperoxide with a Mn of 1935 g mol -1 (Pcast5m) and the ricinoleic acid macroperoxide initiator (Prici5m) with a Mn of 1169 g mol -1 . Peroxide groups thermally initiated the free radical polymerization of methyl methacrylate (MMA), n-butyl methacrylate (nBMA), and styrene (S). Peroxide formation in the oxidized castor oil and ricinoleic acid was confirmed using iodometric analysis, elemental analysis, and differential scanning ca . . .lorimetry technique. Peroxide decomposition in both macroperoxide initiators was observed at 166 °C for Prici5m and 170 °C for Pcast5m. Hydroxyl groups of Pcast5m were reacted with methacryloyl chloride to obtain methacrylated castor oil macroperoxide (PcastMA). The polymerization rates of the obtained macroinitiators were compared. The polymerization rate order is Pcast5m > Prici5m > PcastMA. Polymerization of styrene by PcastMA resulted in an increase in molar masses and an increase in the polymerization time while those of the styrene polymerization by Pcast5m and Prici5m remained constant. Carboxylic acid groups were reacted with amine-terminated polyethylene glycol (PEG), polydimethyl siloxane (PDMS), and polytetrahydrofuran (PTHF) while the hydroxyl functionality initiated the ring-opening polymerization of ?-caprolactone (CL). Prici-PEG-PMMA, Prici-PS-PDMS, Prici-PS-PTHF, Pcast-PS-PCL, Pcast-PCL-PMMA, and Pcast-PS-PnBMA multiblock copolymers were prepared and characterized using spectrometric, thermal, and stress–strain measurement techniques. © 2019 AOC Daha fazlası Daha az

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