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Aliphatic Long-Chain Polypyrophosphates as Biodegradable Polyethylene Mimics.

ABSTRACT: Biodegradable polyethylene mimics have been synthesized by the introduction of pyrophosphate groups into the polymer backbone, allowing not only hydrolysis of the backbone but also further degradation by microorganisms. Because of cost, low weight, and good mechanical properties, the use of polyolefins has increased significantly in the past decades and has created many challenges in terms of disposal and their environmental impact. The durability and resistance to degradation make polyethylene difficult or impossible for nature to assimilate, thus making the degradability of polyolefins an essential topic of research. The biodegradable polypyrophosphate was prepared via acyclic diene metathesis polymerization of a diene monomer. The monomer is accessible via a three-step synthesis, in which the pyrophosphate was formed in the last step by DCC coupling of two phosphoric acid derivatives. This is the first report of a pyrophosphate group localized in an organic polymer backbone. The polypyrophosphate was characterized in detail by NMR spectroscopy, size exclusion chromatography, FTIR spectroscopy, differential scanning calorimetry, and thermogravimetry. X-ray diffraction was used to compare the crystallization structure in comparison to analogous polyphosphates showing poly(ethylene)-like structures. In spite of their hydrophobicity and water insolubility, the pyrophosphate groups exhibited fast hydrolysis, resulting in polymer degradation when films were immersed in water. Additionally, the hydrolyzed fragments were further biodegraded by microorganisms, rendering these PE mimics potential candidates for fast release of hydrophobic cargo, for example, in drug delivery applications.

SUBMITTER: Tee HT

PROVIDER: S-EPMC6728087 | biostudies-literature | 2019 Feb

REPOSITORIES: biostudies-literature

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Aliphatic Long-Chain Polypyrophosphates as Biodegradable Polyethylene Mimics.

Tee Hisaschi T HT Lieberwirth Ingo I Wurm Frederik R FR

Macromolecules 20190129 3

Biodegradable polyethylene mimics have been synthesized by the introduction of pyrophosphate groups into the polymer backbone, allowing not only hydrolysis of the backbone but also further degradation by microorganisms. Because of cost, low weight, and good mechanical properties, the use of polyolefins has increased significantly in the past decades and has created many challenges in terms of disposal and their environmental impact. The durability and resistance to degradation make polyethylene ...[more]

PMID: 31496542

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Project description:The main goal of this paper was to study the optical, electrical, and thermal properties of hybrid composites based on biodegradable polymers (L,D-poly(lactic acid), polycaprolactone or Ecoflex®), single walled carbon nanotubes (SWCN), and 4'-pentyl-4-biphenylcarbonitrile (5CB). The biodegradable polymers' binary and ternary compositions were analyzed in detail by ultraviolet and visible (UV-Vis) spectroscopy taking into consideration their chemical structure and interactions with 5CB and SWCN. Differential scanning calorimetry (DSC) studies of the created hybrid layers showed thermal stability and changes in glass transition temperature and melting point in comparison to neat polymers, depending on the chemical structure of the polymer used and the type of composition. Morphology of the created layers were investigated by atomic force and polarizing microscopy. The static contact angle measurements of a water drop showed that all of the neat polymer layers were hydrophobic with angle values ranging from 108° to 115°. In addition, in the case of the Ecoflex layers, both with and without additives, a rapid sorption of the deposited water drop was observed. Finally, a simple device with poly(ethylene terephthalate) (PET)/indium tin oxide (ITO)/poly(3,4-ethylenedioxythiophene):poly(styrenesulfonate) (PEDOT:PSS)/poly [[4,8-bis[(2-ethylhexyl)oxy]benzo[1,2-b:4,5-b']dithiophene-2,6-diyl][3-fluoro-2-[(2-ethylhexyl)carbonyl]thieno[3,4-b]thiophenediyl ]] (PTB7) : [6,6]-phenyl-C71-butyric acid methyl ester (PC70BM)/Ag/biodegradable polymer:SWCN architecture was constructed and tested using an infrared (IR) thermographic camera to investigate the surface defects on the created hybrid layers. Increasing the SWCN admixture from 0.01 to 0.5% significantly improved the conductivity only in the case of L,D-poly(lactic acid):SWCN (10:0.5), for which above 5 V, a current with a resistance of 3030.7 ? could be measured. In order to use the created layers as flexible electrodes, the first experiments were carried out with an admixture of SWCN and poly(3,4-ethylenedioxythiophene):poly(styrenesulfonate) as conductive compounds.

Dataset Information

Aliphatic Long-Chain Polypyrophosphates as Biodegradable Polyethylene Mimics.

Publications

Aliphatic Long-Chain Polypyrophosphates as Biodegradable Polyethylene Mimics.

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