Piperidine-conjugated polyfunctional star-shaped PLLA as a novel bio-based antioxidant additive for bioplastics

Haema, Kamonwon; Piroonpan, Thananchai; Taechutrakul, Saowaluk; Kempanichkul, Anan; Pasanphan, Wanvimol

doi:10.1016/j.polymdegradstab.2017.07.001

Cited by 14 publications

(8 citation statements)

References 40 publications

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“…The influence of the sugar core molecule, monomer, temperature and reaction time on the suPLA production was studied. As in previous reports, a temperature of 130 °C is generally used for the laboratory scale synthesis of the star-shaped PLA using ROP. , For the pilot-scale reactor in this study, the reaction temperatures varied from 130 °C down to 120, 110, and 100 °C. It was found that the synthesized suPLA product could not be obtained at 130 or 120 °C because the sample changed to a black burned liquid (data not shown).…”

Section: Resultsmentioning

confidence: 99%

“…The PDI of suPLA corresponded to the PDIs of other types of multibranched PLA in the literature (ca. 1.1–1.5). ,, By optimizing the reaction parameters for ROP of the L-LA in the presence of the table sugar-core molecule, it was suggested that the sugar: L-LA molar ratio of 1:160 offered the highest suPLA production yield (∼80%) with the highest M w and M n of 1376 and 982 Da with a PDI of 1.40. Although it is difficult to clarify the polymerization variation occurring on each branch of the sugar-core molecule because of different levels of reactivity in the −OH groups on sucrose, the increase of the M n , M w , and DP n with an increase of the sugar: L-LA molar ratio suggests successful progressive polymerization due to feeding the L-LA monomer.…”

Section: Resultsmentioning

confidence: 99%

“…To be reviewed, the multibranched PLA have been prepared using different core molecules having varieties of the hydroxyl groups or polyol, such as succinic acid (SA), malic acid (MA), and citric acid (CA), 18 carbohydrate derivatives, 22 glycerol, xylitol, sorbitol, erythritol, 23 and pentaerythritol (PETH). 12,19 While examples of multibranched PLA have been proposed, most of them were synthesized from synthetic core-molecules. Table sugar, granulated sugar, and regular sugar generally refer to sucrose, a disaccharide composed of glucose and fructose.…”

Section: ■ Introductionmentioning

confidence: 99%

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Sugar-Core Synthesized Multibranched Polylactic Acid and Its Diacrylate Blends as a UV LED-Curable Coating with Enhanced Toughness and Performance

Piroonpan

Booncharoen

Pasanphan

2022

ACS Sustainable Chem. Eng.

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Exploring the application of biodegradable/bioplastic coating material for eco-friendly and sustainable packaging is one of the global challenges being tackled. In this context, we propose (i) the synthesis of multibranched polylactic acid (PLA) using table sugar mainly composed of sucrose as a core initiator, and (ii) a model formula for sugar-based PLA (suPLA) and its diacrylate blends as a UV LED-curable coating. The synthesis of suPLA through ring-opening polymerization (ROP) was optimized by sugar: l-lactide (L-LA) molar ratio, temperature, and reaction time. suPLA, with a M w of ∼1000 g/mol, was obtained with a maximum yield of around 80%. To establish a model UV LED-curable bioplastic-based coating, the suPLA with different content was formulated in tripropylene glycol diacrylate (TPGDA) as a diluent monomer. The influence of curing time (0–60 s) on double bond conversion for turning the liquid coating to a solid film of the suPLA/TPGDA blending system was assessed. Aiming to validate the influence of the curing degree, changes in the chemical function, thermal stability, glass transition temperature, crystallization temperature, and enthalpy were also characterized. By increasing the suPLA content, the tensile tests on the UV LED-cured suPLA-TPGDA films showed significant improvement in terms of toughness. The coating surface morphologies and optical properties (i.e., gloss value, color difference, yellowness, and whiteness indexes) were also determined. It is worth noting that the sugar molecule and multibranched structure play an important role in moisture absorption. The biodegradation test demonstrated that the UV LED-cured suPLA-TPGDA film exhibited biodegradation phenomena, as analyzed from CO2 production, physical appearance, changes of mass, chemical functions, and thermal stability. The current study showed that the suPLA and its diacrylate blends are promising biobased, printable, and UV LED-curable coating prototypes to create a tough film for a sustainable packaging approach in the future.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

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Sugar-Core Synthesized Multibranched Polylactic Acid and Its Diacrylate Blends as a UV LED-Curable Coating with Enhanced Toughness and Performance

Piroonpan

Booncharoen

Pasanphan

2022

ACS Sustainable Chem. Eng.

Self Cite

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“…In particular, due to different hydrophilicity and crystalline performance, changing the chemical structure of PLA is possible to make porous fibres via a simple solvent method in wet conditions. The molecular morphology of PLA can be divided into two types: linear and branching [ 24 , 25 ]. The linear PLA has poor hydrophilicity and high crystallization ability.…”

Section: Introductionmentioning

confidence: 99%

Effect on electrospun fibres by synthesis of high branching polylactic acid

Shen

Zhang

et al. 2018

R. Soc. open sci.

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Polylactic electrospun porous fibres have been widely used in tissue engineering scaffolds. However, the application of linear polylactic is limited due to its poor hydrophilicity, which leads to phase separation and has been seldom used in porous fibre preparation. Instead, branching polylactic acts as a new effective method to prepare porous fibres because it can increase polylactic polar property and make it easy to be formulated in the following application. In the current study, we prepared an ultra-high molecular weight of high branching polylactic with glycerol as the initiator by controlling the ring-opening polymerization time, adding amount of catalyst and glycerol. The structure, molecular weight and thermal properties of copolymers were tested subsequently. The result showed that the surface of the high branching polylactic films is smooth, hydrophilic and porous. This branching polylactic formed electrospun porous fibres and possessed a strong adsorption of silver ion. Our study provided a simple and efficient way to synthesize branching polylactic polymer and prepare electrospun porous fibres, which may provide potential applications in the field of biomaterials for tissue engineering or antibacterial dressing compared with the application of linear polylactic and 3-arm polylactic materials.

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“…Multibranched‐chain PLA is a special structure of PLA that has more hydroxyl terminal groups. It is reported that the multibranched‐chain PLA can improve PLA properties . In the multibranched‐chain PLA, the hydroxyl groups as the terminal groups repel each other, so the molecular chain has larger spatial extensibility and hydrophilicity, making it easier to adsorb ions with positive charges.…”

Section: Introductionmentioning

confidence: 99%

Research on electrospinning three‐branched‐chain PLA porous microspheres and adsorption for silver ions

Shen

Zhang

et al. 2018

J of Applied Polymer Sci

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The objective of the present study was to prepare poly(lactic acid) (PLA) porous microspheres. Special attention was paid to the effects of improving the surface hydrophilicity of the microspheres on the adsorption of silver ions. The linear PLA and the three‐branched‐chain PLA microspheres with pores or without pores were obtained by electrospinning. The morphology, hydrophilicity, and silver ion adsorption of the microspheres were investigated, and the antibacterial properties of microspheres with adsorbed silver ions were studied. The research showed that the three‐branched‐chain PLA porous microspheres had good hydrophilicity and strong adsorption ability of silver ions. Using X‐ray photoelectron spectroscopy and scanning electron microscopy, it is found that the microspheres can adsorb more silver ions with an increase in holes. However, the multihydroxyl structure of the three‐branched‐chain PLA has strong hydrophilicity. It has a better phase separation ability to obtain the porous structures easily. In aqueous solution, these microspheres are more likely to adsorb drugs with positive charge, and the size of the microspheres is controlled in the solvent with different dielectric constants. © 2018 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2018, 135, 46735.

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Piperidine-conjugated polyfunctional star-shaped PLLA as a novel bio-based antioxidant additive for bioplastics

Cited by 14 publications

References 40 publications

Sugar-Core Synthesized Multibranched Polylactic Acid and Its Diacrylate Blends as a UV LED-Curable Coating with Enhanced Toughness and Performance

Sugar-Core Synthesized Multibranched Polylactic Acid and Its Diacrylate Blends as a UV LED-Curable Coating with Enhanced Toughness and Performance

Effect on electrospun fibres by synthesis of high branching polylactic acid

Research on electrospinning three‐branched‐chain PLA porous microspheres and adsorption for silver ions

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