Synthesis of poly(glycolic acids) via solution polycondensation and investigation of their thermal degradation behaviors

Ayyoob, Muhammad; Lee, Doo Hyun; Kim, Ji Heung; Nam, Sung Woo; Kim, Young Jun

doi:10.1007/s12221-017-6889-1

Cited by 36 publications

(41 citation statements)

References 32 publications

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“…For this reason hexafluoroisopropanol- d 2 (HFIP) was used. 41 Unfortunately, since (deuterated) HFIP is an expensive and harmful solvent, its general use in several analytical techniques is limited. Therefore, chloroform- d was used as solvent for the remaining samples.…”

Section: Resultsmentioning

confidence: 99%

PLGA Barrier Materials from CO₂. The influence of Lactide Co-monomer on Glycolic Acid Polyesters

Valderrama

Putten

Gruter

2020

ACS Appl. Polym. Mater.

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The combination of the predicted polymer market growth and the emergence of renewable feedstocks creates a fantastic opportunity for sustainable polymers. To replace fossil-based feedstock, there are only three alternative sustainable carbon sources: biomass, CO 2 , and existing plastics (via mechanical and/or chemical recycling). The ultimate circular feedstock would be CO 2 : it can be electrochemically reduced to formic acid derivatives that subsequently can be converted into useful monomers such as glycolic acid. This work is part of the European Horizon 2020 project “Ocean” in which the steps from CO 2 to glycolic acid are developed. Polyglycolic acid (PGA) and poly(lactide- co -glycolide) (PLGA) copolyesters with high lactic acid (LA) content are well-known. PGA is very difficult to handle due to its high crystallinity. On the other hand, PLGAs with high LA content lack good oxygen and moisture barriers. The aim of this work is to understand the structure–property relationships for the mostly unexplored glycolic acid rich PLGA copolymer series and to assess their suitability as barrier materials. Thus, PLGA copolymers with between 50 and 91 mol % glycolic acid were synthesized and their properties were evaluated. Increased thermal stability was observed with increasing glycolic acid content. Only those containing 87 and 91 mol % glycolic acid were semicrystalline. A crystallization study under non-isothermal conditions revealed that copolymerization reduces the crystallization rate for PLGA compared to polylactic acid (PLA) and PGA. While PGA homopolymer crystallizes completely when cooled at 10 °C·min –1 , the copolymers with 9 and 13% lactic acid show almost 10 times slower crystallization, which is a huge advantage vis-à-vis PGA for processing. The kinetics of this process, modeled with the Jeziorny-modified Avrami method, confirmed those observations. Barrier property assessment revealed great potential for these copolymers for application in barrier films. Increasing glycolic acid content in PLGA copolymers enhances the barrier to both oxygen and water vapor. At room temperature and a relative humidity below 70% the PLGA copolymers with high glycolic acid content outperform the barrier properties of polyethylene terephthalate.

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Section: Resultsmentioning

confidence: 99%

PLGA Barrier Materials from CO₂. The influence of Lactide Co-monomer on Glycolic Acid Polyesters

Valderrama

Putten

Gruter

2020

ACS Appl. Polym. Mater.

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“…Polyglycolic acid (PGA) is one of the first synthetic polymers, and it is studied for biomedical applications. PGA exhibits good tensile properties but poor thermal stability, as well as a very low solubility because of its high crystallinity (45–65%) [4,5,6,7]. Initially, the first biodegradable synthetic suture that was developed with PGA and was approved by the FDA (Food and Drug Administration USA) and marketed as DEXON ® .…”

Section: Introductionmentioning

confidence: 99%

Effect of Chemical Composition Variant and Oxygen Plasma Treatments on the Wettability of PLGA Thin Films, Synthesized by Direct Copolycondensation

Ayyoob

Kim

2018

Polymers

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The synthesis of high molecular weight poly (lactic-co-glycolic) acid (PLGA) copolymers via direct condensation copolymerization is itself a challenging task. Moreover, some of the characteristic properties of polylactide (PLA)-based biomaterials, such as brittleness, hydrophobicity, and longer degradation time, are not suitable for certain biomedical applications. However, such properties can be altered by the copolymerization of PLA with other biodegradable monomers, such as glycolic acid. A series of high molecular weight PLGAs were synthesized through the direct condensation copolymerization of lactic and glycolic acids, starting from 0 to 50 mol% of glycolic acid, and the wettability of its films was monitored as a function of the feed molar ratio. Copolymerization was performed in the presence of a bi-catalytic system using stannous chloride dihydrate and methanesulfonic acid (MSA). The viscosity average molecular weight of the resulting PLGA was in the range of 80k to 135k g/mol. The PLGA films were prepared using the solvent casting technique, and were treated with oxygen plasma for 2 min. The water contact angle of the PLGA films was determined before and after the oxygen plasma treatments, and it was observed that the wettability increased with an increase in the glycolic acid contents, however, the manifolds increased after 2 min of oxygen plasma treatments.

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“…The thermal stabilities of PP/PGA blends with different contents of hybrid compatibilizer evaluated by the TGA method are given in Figure . The initial decomposition temperature (weight loss of 5%) of PGA was around 304°C, which was much lower than that of pure PP . A two‐step decomposition process ascribed to PGA and PP respectively was observed obviously in the TGA curve of PP/PGA blends without compatibilizer, and the initial decomposition temperature of PGA was increased to nearly 326°C, revealing that PP could delay the thermal decomposition of PGA.…”

Section: Resultsmentioning

confidence: 99%

Compatibilization of polypropylene/poly(glycolic acid) blend with maleated poe/attapulgite hybrid compatibilizer: Evaluation of mechanical, thermal, rheological, and morphological characteristics

Cai

Liu

Cao

et al. 2020

Journal of Polymer Science

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In this work, the compatibilization effects of hybrid maleated POE/attapulgite hybrid compatibilizer (M‐POE/ATP) on the immiscible polypropylene/poly(glycolic acid) (PP/PGA) blends was investigated. The hybrid compatibilizer integrating strengthening, toughening and compatibilization functions was prepared via one‐step reactive extrusion using peroxidated ATP as the initiator. Then, the effects of compatibilizer dosage on the mechanical, thermal, rheological and morphological characteristics of blends were evaluated in detail. It was found that the hybrid compatibilizer resulted in the significantly enhanced compatibility and mechanical performance. Increased amount of compatibilizer content fractionated and almost wholly suppressed the crystallization process of PGA. The compatibilized blends showed higher thermal stability than pure PGA, and lower storage modulus and complex viscosity at higher shearing frequency. PGA in the blends presented a much lower degradation rate, which lead to the higher strength retention of 81% for the blend with 4 wt% of compatibilizer in buffer solution after 35 days.

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Synthesis of poly(glycolic acids) via solution polycondensation and investigation of their thermal degradation behaviors

Cited by 36 publications

References 32 publications

PLGA Barrier Materials from CO₂. The influence of Lactide Co-monomer on Glycolic Acid Polyesters

PLGA Barrier Materials from CO₂. The influence of Lactide Co-monomer on Glycolic Acid Polyesters

Effect of Chemical Composition Variant and Oxygen Plasma Treatments on the Wettability of PLGA Thin Films, Synthesized by Direct Copolycondensation

Compatibilization of polypropylene/poly(glycolic acid) blend with maleated poe/attapulgite hybrid compatibilizer: Evaluation of mechanical, thermal, rheological, and morphological characteristics

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Synthesis of poly(glycolic acids) via solution polycondensation and investigation of their thermal degradation behaviors

Cited by 36 publications

References 32 publications

PLGA Barrier Materials from CO2. The influence of Lactide Co-monomer on Glycolic Acid Polyesters

PLGA Barrier Materials from CO2. The influence of Lactide Co-monomer on Glycolic Acid Polyesters

Effect of Chemical Composition Variant and Oxygen Plasma Treatments on the Wettability of PLGA Thin Films, Synthesized by Direct Copolycondensation

Compatibilization of polypropylene/poly(glycolic acid) blend with maleated poe/attapulgite hybrid compatibilizer: Evaluation of mechanical, thermal, rheological, and morphological characteristics

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PLGA Barrier Materials from CO₂. The influence of Lactide Co-monomer on Glycolic Acid Polyesters

PLGA Barrier Materials from CO₂. The influence of Lactide Co-monomer on Glycolic Acid Polyesters