Abstract
Completely bio-based poly(limonene carbonate) is a thermoplastic polymer, which can be synthesized by copolymerization of limonene oxide (derived from limonene, which is found in orange peel) and CO2. Poly(limonene carbonate) has one double bond per repeating unit that can be exploited for further chemical modifications. These chemical modifications allow the tuning of the properties of the aliphatic polycarbonate in nearly any direction. Here we show synthetic routes to demonstrate that poly(limonene carbonate) is the perfect green platform polymer, from which many functional materials can be derived. The relevant examples presented in this study are the transformation from an engineering thermoplastic into a rubber, addition of permanent antibacterial activity, hydrophilization and even pH-dependent water solubility of the polycarbonate. Finally, we show a synthetic route to yield the completely saturated counterpart that exhibits improved heat processability due to lower reactivity.
Highlights
Bio-based poly(limonene carbonate) is a thermoplastic polymer, which can be synthesized by copolymerization of limonene oxide and CO2
When butyl-3mercaptopropionate (B3MP) is used, an enormous change in mechanical properties is achieved. This leads to a transformation of the high-Tg thermoplastic into rubbery poly(limonene carbonate) (PLimC)-B3MP with a nearly three orders of magnitude decreased Young’s modulus
The antibacterial activity of PLimC-NQ was successfully tested against Escherichia coli bacteria
Summary
Bio-based poly(limonene carbonate) is a thermoplastic polymer, which can be synthesized by copolymerization of limonene oxide (derived from limonene, which is found in orange peel) and CO2. There is a natural limitation of petroleum resources, which eventually leads to a running out of oil and natural gas within this century[3] To overcome these limitations, efforts are directed towards the development of degradable polymers[4,5] and the use of bio-based monomers[6,7,8], respectively. Even for a material that is assigned to both classes—as for poly(lactic acid)—the origin of the bio-based monomers is questionable, as lactic acid is derived from glucose, which is again derived from corn starch The latter is an important food resource and, as such, in competition with the use as precursor for the conversion into plastics. O O n changes in the property profile of the engineering thermoplastic PLimC, including a transformation into a rubbery material, antibacterial activity, increased hydrophilicity or even water solubility and, last but not least, improved melt processability
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