Free radical crosslinking of unsaturated bacterial polyesters obtained from soybean oily acids

Hazer, Baki; Demirel, Songun I.; Borcaklı, Mehlika; Eroğlu, Mehmet S.; Çakmak, Mükerrem; Erman, Burak

doi:10.1007/s002890170047

Cited by 50 publications

(29 citation statements)

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“…[7][8][9][10] The presence of functionalities, especially olefins, in PHAs provides sites for chemical modifications, which can affect the physical properties of the polymer and, due to their biodegradability, assure their use in various areas such as medical applications and the packing industry. In this manner, chlorination, 8 epoxidation, 9 and crosslinking 10,11 of the olefinic groups in the PHA have been reported in detail. Edible oily acids such as soybean, hazelnut, sesame, fish, and linseed oils are suitable substrates to obtain PHAs containing olefinic groups on the pendant side chains.…”

Section: Introductionmentioning

confidence: 95%

Hydroxylation of pendant vinyl groups of poly(3‐hydroxy undec‐10‐enoate) in high yield

Eroğlu

Hazer

Öztürk

et al. 2005

J of Applied Polymer Sci

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Poly(3-hydroxy undec-10-enoate) (PHU) was synthesized by feeding Pseudomonas oleovarans with 10-undecenoic acid and nearly 100% hydroxylation of double bonds of PHU was achieved by hydroboration-oxidation reaction using 9-borobicyclononane. The disappearance of vinyl signals of PHU in proton and 13 C NMR spectra was observed. Acetylation of hydroxylated PHU was conducted for molecular weight measurements. Molecular weight and polydispersity of hydroxylated PHU were found to be 10,000 and 1.23, respectively, while that of the originals was 32,000 and 2.42. Decomposition temperatures of original and hydroxylated PHU were 280 and 200°C, respectively.

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Section: Introductionmentioning

confidence: 95%

Hydroxylation of pendant vinyl groups of poly(3‐hydroxy undec‐10‐enoate) in high yield

Eroğlu

Hazer

Öztürk

et al. 2005

J of Applied Polymer Sci

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“…Some useful bioplastics have also been prepared from tung [6] and linseed oil [7] by thermal copolymerization. Crosslinked biological polyesters have been obtained by the free radical polymerization of soybean oil acids [8] and linseed oil [9]. These natural oil materials have a very bright future with exploring their new uses in various industrial applications.…”

Section: Introductionmentioning

confidence: 99%

A comparative study of the reactivity of three plant oil methyl esters with divinylbenzene by FTIR spectroscopy

et al. 2012

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Poly(divinylbenzene) microspheres were prepared by seed swelling polymerization of divinylbenzene in the presence of tung oil methyl esters, linseed oil methyl esters and soybean oil methyl esters, respectively. FTIR spectroscopy was used to characterize the polymers for investigating the reactivity of the three plant oil methyl esters. Results showed that tung oil methyl esters had strongest reactivity with divinylbenzene, and soybean oil methyl esters had weakest reactivity of the three oil methyl esters in the polymerization. These results were related with the fatty acid compositions of the oils.

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“…The melting point temperature is only about 60°C (1,18,29,69). It has been described in the literature that PHO, in particular PHO containing small fractions of unsaturated medium-chain-length hydroxyalkanoic acids, can be cross-linked by reactive chemicals or by irradiation yielding materials with interesting properties resembling natural rubber or even more vulcanized rubber (25,38,69). Therefore, many different applications have been described for PHO and structurally related polyesters (68).…”

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confidence: 99%

Large-Scale Production of Poly(3-Hydroxyoctanoic Acid) by Pseudomonas putida GPo1 and a Simplified Downstream Process

Elbahloul

Steinbüchel

2009

Appl Environ Microbiol

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The suitability of Pseudomonas putida GPo1 for large-scale cultivation and production of poly(3-hydroxyoctanoate) (PHO) was investigated in this study. Three fed-batch cultivations of P. putida GPo1 at the 350-or 400-liter scale in a bioreactor with a capacity of 650 liters were done in mineral salts medium containing initially 20 mM sodium octanoate as the carbon source. The feeding solution included ammonium octanoate, which was fed at a relatively low concentration to promote PHO accumulation under nitrogen-limited conditions. During cultivation, the pH was regulated by addition of NaOH, NH 4 OH, or octanoic acid, which was used as an additional carbon source. Partial O 2 pressure (pO 2 ) was adjusted to 20 to 40% by controlling the airflow and stirrer speed. Under the optimized conditions, P. putida GPo1 was able to grow to cell densities as high as 18, 37, and 53 g cells (dry mass) (CDM) per liter containing 49, 55, and 60% (wt/wt) of PHO, respectively. The resulting 40 kg CDM from these three cultivations was used directly for extraction of PHO. Three different methods of extraction of PHO were applied. From these, only acetone extraction showed better performance and resulted in 94% recovery of the PHO contents of cells. A novel mixture of precipitation solvents composed of 70% (vol/vol) methanol and 70% (vol/vol) ethanol was identified in this study. The ratio of PHO concentrate to the mixture was 0.2:1 (vol/vol) and allowed complete precipitation of PHO as white flakes. However, at a ratio of 1:1 (vol/vol) of the solvent mixture to PHO concentrate, a highly purified PHO was obtained. Precipitation yielded a dough-like polymeric material which was cast into thin layers and then shredded into small strips to allow evaporation of the remaining solvents. Gas chromatographic analysis revealed a purity of about 99% ؎ 0.2% (wt/wt) of the polymer, which consisted mainly of 3-hydroxyoctanoic acid (96 mol%).

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Free radical crosslinking of unsaturated bacterial polyesters obtained from soybean oily acids

Cited by 50 publications

References 0 publications

Hydroxylation of pendant vinyl groups of poly(3‐hydroxy undec‐10‐enoate) in high yield

Hydroxylation of pendant vinyl groups of poly(3‐hydroxy undec‐10‐enoate) in high yield

A comparative study of the reactivity of three plant oil methyl esters with divinylbenzene by FTIR spectroscopy

Large-Scale Production of Poly(3-Hydroxyoctanoic Acid) by Pseudomonas putida GPo1 and a Simplified Downstream Process

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