Bio-Degradable Polyesters with Rigid Cyclic Diester from Camphor and Tartaric Acid

Kang, Ju Hui; Sim, Su Ji; Lee, Joon Hyuk; Lee, Sangkug; Suh, Dong Hack

doi:10.1007/s10924-022-02439-9

Cited by 4 publications

(12 citation statements)

References 41 publications

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“…However, when the replaced units have highly rigid structures, such as gludioxol units with bicyclic rings located in the main chains, the T g values were increased as the incorporated ratio was increased. We also observed that, when the incorporated ratio of the Ct diesters increased, the T g values were decreased . However, it is noted that the Ct-diester-based copolyesters showed a relatively small decreasing trend in T g in comparison to the tartrate and camphor acid-based copolyesters due to the relatively high rigidity of the Ct diester units (Figure S8b).…”

Section: Resultsmentioning

confidence: 69%

“…Due to solubility issue of T in chloroform, T′ was dissolved in chloroform for NMR analysis for comparison of C in the same solvent. Also 13 C NMR analysis can be utilized for clear characterizations of the synthesized compounds …”

Section: Methodsmentioning

confidence: 99%

“…Previously we reported the synthesis of PET-based copolyesters with variation of the incorporated contents of the bioderived monomers of camphor dimethyl dl -tartrate (Ct diester); tartaric acid − coupled with camphor by acetalizations was utilized to introduce ester linkages in polymeric backbones to increase chain stiffness by spiro-rings and hydrolysis reactivity by pH control . Tartaric acid has the advantage of being low cost, easily obtained from grapes, bananas, tamarinds, and citrus fruits .…”

Section: Introductionmentioning

confidence: 99%

“…Also 13 C NMR analysis can be utilized for clear characterizations of the synthesized compounds. 33 2.2.2. Melt Polymerization.…”

Section: Introductionmentioning

confidence: 99%

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Thermally Stable Biodegradable Polyesters with Camphor and Tartaric Acid Coupled Cyclic Diester Monomers for Controlled Hydrolytic Degradations

Kang

Lee

et al. 2023

ACS Appl. Polym. Mater.

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The development of biodegradable engineering plastics is challenging, because increases in biodegradability mostly degrade other material properties, such as mechanical and thermal properties of polymers. Here, we use bioderivatives of diester monomers, dimethyl (1S,4R)-1,7,7-trimethylspiro[bicyclo[2.2.1]heptane-2,2′-[1,3]dioxolane]-4′,5′-dicarboxylate (camphor dimethyl DL-tartrate, Ct diester), for the synthesis of phthalatebased copolyesters to enhance degradability without a notable loss of thermal stability. Ct diester synthesized by acetalization of tartaric acid and camphor contains a bridged type of rigid bicycling ring with high thermal stability and controlled degradation via hydrolysis of acetal groups within the spiro-ring structure. Various alkyl-length diols of ethylene, butylene, and hexylene are copolymerized with mixtures of dimethyl phthalate (DMT) and Ct diester in a 9:1 molar ratio. The glass transition temperature and degradation temperature of the copolyesters are comparable to those of DMT-based homopolyesters. Due to decreases in crystallinity, copolyesters exhibit slight decreases in melting temperature of 10 to 20 °C, which can be advantageous for reducing processing temperatures. Notably, the copolyesters demonstrate enhanced hydrolytic degradation of 9.3 to 26.2% in pH 2 environment for 18 days, as measured by the degree of molecular weight reductions. These values are between 1.7 and 3.5 times higher than the degradation rates of their control samples of DMT-based homopolyesters under the same degradation conditions.

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Section: Resultsmentioning

confidence: 69%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…Also 13 C NMR analysis can be utilized for clear characterizations of the synthesized compounds. 33 2.2.2. Melt Polymerization.…”

Section: Introductionmentioning

confidence: 99%

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Thermally Stable Biodegradable Polyesters with Camphor and Tartaric Acid Coupled Cyclic Diester Monomers for Controlled Hydrolytic Degradations

Kang

Lee

et al. 2023

ACS Appl. Polym. Mater.

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“…Biopolymers are promising routes toward closing the loop on global waste generation [1][2][3][4][5]. One of the most successive biopolymers is polylactic acid, yet relatively low glass transition temperature (T g ), brittle nature, and slow degradation pro le impede its wide applications [6][7][8][9][10].…”

Section: Introductionmentioning

confidence: 99%

Ultrafast Biodegradation Pathway of Polyimides Using Aromatic Diamine with Two Spiro Moieties Derived from Camphor

Sim

Kang²,

Lee³

et al. 2022

J Polym Environ

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As a key structural element, polyimides (PIs) are garnering attention as high-functional polymers in the microelectronics and optical elds. Recently, their structural behaviour renders PIs as promising candidates for the formation of charge-transfer complex (CTC). However, unfortunate drawbacks of PIbased CTCs are in their insolubility and low degradability. The endeavour to overcome the aforementioned issue is aimed at designing biodegradable PIs with high solubility. A novel organic diamine monomer bridges this gap. Based on these fundamental phenomena, we demonstrate an environmentally-friendly camphor aromatic diamine (CAD diamine). The efforts described herein shows excellent solubility and thermal stability by introducing two spiro moieties. Ultrafast degradable PIs were further prepared from CAD diamine, which not only prevented the polymer deterioration but also reported ultrafast degradability in a su cient manner.

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Effect of hybridization on camphor soot-embedded palmyra fiber-reinforced nylon nanocomposites

Raghavendra,

C A,

Shilpa

et al. 2023

Funct. Compos. Struct.

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In the present study camphor soot filled palmyra fiber reinforced nylon 6 hybrid nano composites (CPFNnC) were prepared using a twin -screw extruder with different wt. % (0, 3, 6, 9). These composites were characterized to study the thermal, mechanical, and rheological properties. Thermo gravimetric Analysis (TGA) showed marginal increase in thermal stability with 6wt. % CPFNnC. Differential Scanning Calorimetry (DSC) curves showed a slight increment in the melting point in CPFNnC while degradation temperature decreased with fiber contents. Dynamic Mechanical Analysis (DMA) indicated with maximum storage modulus for 6wt. % CPFNnC at 803 MPa compared with fiber free nylon-6 (696 MPa at 25 °C). Tan δ for 3 wt. % CPFNnC showed better damping effect due to the existence of palmyra fibers. Creep results indicated that, CPFNnC contains 6 wt.% fibers has minimum depth impression of 0.124 mm compared to fiber free nylon with 0.146 mm. Scanning Electron Microscope (SEM) revealed uniform distribution of modified palmyra fibers in the matrix and brittle fracture was observed in the CPFNnC. Compared to fiber free nylon-6, the tensile strength, flexural strength and density of the CPFNnC increased with increase in fiber content, however the impact strength and a lower Melt Flow Index (MFI) properties were found declined.

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Bio-Degradable Polyesters with Rigid Cyclic Diester from Camphor and Tartaric Acid

Cited by 4 publications

References 41 publications

Thermally Stable Biodegradable Polyesters with Camphor and Tartaric Acid Coupled Cyclic Diester Monomers for Controlled Hydrolytic Degradations

Thermally Stable Biodegradable Polyesters with Camphor and Tartaric Acid Coupled Cyclic Diester Monomers for Controlled Hydrolytic Degradations

Ultrafast Biodegradation Pathway of Polyimides Using Aromatic Diamine with Two Spiro Moieties Derived from Camphor

Effect of hybridization on camphor soot-embedded palmyra fiber-reinforced nylon nanocomposites

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