Rigid biobased polycarbonates with good processability based on a spirocyclic diol derived from citric acid

Bonjour, Olivier; Liblikas, Ilme; Pehk, Tõnis; Truong, Khai‐Nghi; Vares, Lauri; Jannasch, Patric

doi:10.1039/d0gc00849d

Cited by 16 publications

(14 citation statements)

References 41 publications

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“…The previously reported diol tB was found to degrade slightly faster under these conditions (∼95% after 24 h). 14 Somewhat surprisingly, the glycerol diol gB was found to be very sensitive to trace amounts of HCl and water present in the undried and nonstabilized CDCl 3 , and signs of ketal cleavage were observed by 1 H NMR analysis already after a few hours in this solvent. For that reason, all NMR analyses of gB were conducted in either DMSO- d 6 or CD 3 CN.…”

Section: Resultsmentioning

confidence: 98%

Chemically Recyclable Poly(β-thioether ester)s Based on Rigid Spirocyclic Ketal Diols Derived from Citric Acid

et al. 2022

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Incorporating rigid cyclic acetal and ketal units into polymer structures is an important strategy toward recyclable high-performance materials from renewable resources. In the present work, citric acid, a widely used platform chemical derived from biomass, has been efficiently converted into di- and tricyclic diketones. Ketalization with glycerol or trimethylolpropane afforded rigid spirodiols, which were obtained as complex mixtures of isomers. After a comprehensive NMR analysis, the spirodiols were converted into the respective di(meth)acrylates and utilized in thiol–ene polymerizations in combination with different dithiols. The resulting poly(β-thioether ester ketal)s were thermally stable up to 300 °C and showed glass-transition temperatures in a range of −7 to 40 °C, depending on monomer composition. The polymers were stable in aqueous acids and bases, but in a mixture of 1 M aqueous HCl and acetone, the ketal functional groups were cleanly hydrolyzed, opening the pathway for potential chemical recycling of these materials. We envision that these novel bioderived spirodiols have a great potential to become valuable and versatile bio-based building blocks for several different kinds of polymer materials.

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Section: Resultsmentioning

confidence: 98%

Chemically Recyclable Poly(β-thioether ester)s Based on Rigid Spirocyclic Ketal Diols Derived from Citric Acid

et al. 2022

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“…When the decomposition temperature range is less than 210 °C, the L‐(‐)‐carnitine‐based ILs do not show significant changes on the thermal stability. [ 40,41 ] In addition, the melting temperature ( T m ) or glass transition temperature ( T g ) of all the variants is within the range of −50 to 50 °C. Differential scanning calorimetry analysis reveals that T g increases in the order of 1:4 < 1:3 < 1:2 < 1:1 (Figure S12b and S13h as well as Table S2, Supporting Information).…”

Section: Resultsmentioning

confidence: 99%

Enhancing the Solubility and Transdermal Delivery of Drugs Using Ionic Liquid‐In‐Oil Microemulsions

Lü

et al. 2021

Adv Funct Materials

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The development of hydrophobic drug and protein delivery carriers remains a challenge. To synthesize L‐(‐)‐carnitine‐based ionic liquid (IL), this study applies the density functional theory to investigate the hydrogen bonds and van der Waals force that govern L‐(‐)‐carnitine‐based IL formation. An ionic liquid‐in‐oil microemulsion (IL/O ME) is then developed to facilitate the transdermal delivery of proteins and increase the solubility of drugs. IL/O ME is prepared using isopropyl myristate (IPM), Tween 80/Span 20, and L‐(‐)‐carnitine‐based IL. The skin permeation studies conducted using mouse skin show that the insulin permeation percentage of the developed IL/O ME is 3.55 folds higher than that of phosphate‐buffered saline and 2.91 folds better than that of a hydrophilic L‐(‐)‐carnitine‐based IL. In addition, the solubility of two drug molecules, that is, rosiglitazone and bezafibrate, in IL/O ME is at least 49.28 folds higher than their solubility in water or IPM. Therefore, IL/O ME can significantly improve the solubility of drugs and increase the permeability of proteins (e.g., insulin), thus demonstrating a promising potential as a delivery carrier.

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“…The T d-95% value typically determined the maximum melt processing temperature of the polymer. 64 The T d-95% values of all the PIC specimens were above 390 °C, indicating that the thermal stability of PIC was high enough for melt processing and general applications in the plastics industry. 65 Polymers begin to soften and lose their mechanical rigidity at T g , so this value is usually used to set the This journal is © The Royal Society of Chemistry 2022 maximum temperature for a given application.…”

Section: Thermal Propertiesmentioning

confidence: 89%

Acylamido-based anion-functionalized ionic liquids for efficient synthesis of poly(isosorbide carbonate)

Fang

Zhang

et al. 2022

Catal. Sci. Technol.

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Rigid biobased polycarbonates with good processability based on a spirocyclic diol derived from citric acid

Abstract: A bicylic diketone is derived from citric acid and readily ketalized with trimethylolpropane to produce a spirodiol monomer for rigid, high-molecular weight, melt processable biobased polycarbonates.

Cited by 16 publications

References 41 publications

Chemically Recyclable Poly(β-thioether ester)s Based on Rigid Spirocyclic Ketal Diols Derived from Citric Acid

Chemically Recyclable Poly(β-thioether ester)s Based on Rigid Spirocyclic Ketal Diols Derived from Citric Acid

Enhancing the Solubility and Transdermal Delivery of Drugs Using Ionic Liquid‐In‐Oil Microemulsions

Acylamido-based anion-functionalized ionic liquids for efficient synthesis of poly(isosorbide carbonate)

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