Biobased poly(glycerol citrate) synthesis optimization via design of experiments

Gadomska‐Gajadhur, Agnieszka; Bandzerewicz, Aleksandra; Wrzecionek, Michał; Ruśkowski, Paweł

doi:10.1002/pat.5498

Cited by 10 publications

(9 citation statements)

References 57 publications

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“…Based on the reaction conditions designated for the condensation of glycerol with other dicarboxylic acids, poly(glycerol citraconate) can be synthesized. A wide range of products with different properties, structures, and molecular weights is possible in various reaction conditions. ,− By now, many of the glycerol polyesters are already well known. One of the most widely used is a poly(glycerol sebacate) used, for example, in heart tissue engineering, ,− nerve tissue engineering, , and vascular tissue engineering. , Poly(glycerol succinate) is also a well-studied glycerol polyester. − Materials based on it can be used in orthopedic and ophthalmic surgeries .…”

Section: Introductionmentioning

confidence: 99%

“…Various methods of glycerol esterification have been described, leading to products ranging from linear to dendritic structures. − Aliphatic polyesters are one of the most common biodegradable polymers used in medicine. Extensive research has been carried out in the past on their potential applications. − All polyesters are biodegradable by hydrolysis of the ester bond . Based on the reaction conditions designated for the condensation of glycerol with other dicarboxylic acids, poly(glycerol citraconate) can be synthesized.…”

Section: Introductionmentioning

confidence: 99%

“… 4 − 7 All polyesters are biodegradable by hydrolysis of the ester bond. 8 Based on the reaction conditions designated for the condensation of glycerol with other dicarboxylic acids, poly(glycerol citraconate) can be synthesized. A wide range of products with different properties, structures, and molecular weights is possible in various reaction conditions.…”

Section: Introductionmentioning

confidence: 99%

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Optimization of the Poly(glycerol citraconate) Synthesis Using the Box–Behnken Design

Kolankowski,

Rżewska,

Ruśkowski

et al. 2023

ACS Omega

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This work aimed to obtain poly(glycerol citraconate) (PGCitrn) for biomedical applications, analyze the obtained polyester by spectroscopic methods, and optimize its preparation. Polycondensation reactions of glycerol and citraconic anhydride were carried out. It was provided that the results in the reaction are oligomers of poly(glycerol citraconate). Optimization studies were carried out based on the Box−Behnken design. The input variables in this plan were the ratio of functional groups, temperature, and time and occurrence in coded form: −1, 0, or 1. Three output variables were optimized: the degree of esterification, the percentage of Z-mers, and the degree of carboxyl group conversion; they were determined by titration and spectroscopic methods. The optimization criterion was to maximize the values of output variables. A mathematical model and an equation describing it were determined for each output variable. The models predicted the experimental results well. An experiment was conducted under determined optimal conditions. The experimental results were very close to the calculated values. Poly(glycerol citraconate) oligomers with an esterification degree of 55.2%, a Z-mer content of 79.0%, and a degree of rearrangement of carboxyl groups of 88.6% were obtained. The obtained PGCitrn can serve as a component of an injectable implant. The obtained material can be used to produce nonwoven fabrics (with the addition of PLLA, for example), which can be subjected to a cytotoxicity test which can then serve as a dressing material.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Optimization of the Poly(glycerol citraconate) Synthesis Using the Box–Behnken Design

Kolankowski,

Rżewska,

Ruśkowski

et al. 2023

ACS Omega

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“…Glycerol polymers, which can be synthesized through the polycondensation reaction of glycerol with various di-or triacids, such as succinic, citric, sebacic acid, can be potentially used as chain extenders since they can result in prepolymers with controllable molecular weight and functionality [15][16][17][18]. Glycerol-based polymers have hydroxyl and carboxylic end groups that can react with the end groups of PET chains [19].…”

Section: Introductionmentioning

confidence: 99%

Influence of the addition of glycerol-derived polymers on the properties of post-consumer recycled PET

Seixas

Figueiredo²,

Santos³

et al. 2023

Preprint

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In the present work, the influence of glycerol prepolymers, as potential chain extenders in the reactive mixture with post-consumer recycled PET (PET-PCR), was studied, namely: poly(glycerol citrate) (PGC), poly(glycerol succinate) (PGSu) and poly(glycerol citrate-co-succinate) (PGCSu). Mixture of recycled PET with 2wt% of glycerol prepolymers or Joncryl ADR®4638, commercial chain extender, were processed in an internal mixer at 265°C for 6min and 60rpm. The compositions were characterized by viscosimetry, carboxylic end groups (CEG) through the Pohl method, crosslinking degree as the percentage of insoluble gel, Fourier transform infrared spectroscopy (FTIR), thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). The addition of glycerol prepolymers increased the fluidity in the post-consumer PET resin, consequently, decreasing its viscosity by 33% for PETPCR/PGC, 24% for PET-PCR/PGSu, 44% for PET-PCR/PGCSu and 17% PET-PCR/Joncryl; the molecular weight in the order of 42% for PET-PCR/PGC, 31% for PET-PCR/PGSu, 55% for PETPCR/PGCSu and 23% for PET-PCR/Joncryl and increasing the number of carboxylic end groups. Although they did not show extensive chain crosslinking, the samples were fragile and brittle, thus making the tensile test unfeasible. Thermogravimetry showed that the polyesters were thermally stable up to approximately 350°C and the sample that presented the lowest thermal stability was the PETPCR/PGCSu corroborating to the highest reduction in the molecular weight recorded. The DSC results showed na almost constant melting and glass transition temperature among the samples, a decrease of 8°C in the crystallization temperature and an increase in the degree of crystallinity relative to neat PET-PCR, which corroborates to the intrinsic viscosity results. These results indicated that at the concentration and processing conditions used, the potential additives to chain extenders had an opposite effect to the desired one, that is, they reduced the molecular weight of recycled PET and the same effect occurred for the commercial chain extender. However, the additive that showed the greatest potential for use as chain extender was PGSu, which presented results similar to the commercial extender Joncryl ADR®4638, composed of multifunctional epoxy groups.

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“…The thermal curing strategy was mostly applied method to prepare crosslinked polyester elastomers. [26][27][28] Shin and co-workers prepared thermosetting elastomers including plant-based poly(carvomenthide) (PCM) and poly(lactide) (PLA) blocks from dicarboxy-terminated triblock polyester precursors via a subsequent thermal curing process. 29 These thermosetting elastomers had tunable mechanical strength (7.9-16.0 MPa), strain at break (1100%-860%)…”

Section: Introductionmentioning

confidence: 99%

Preparation of degradable aliphatic polyester elastomers with tunable strength and elasticity via photo‐crosslinking

Kang

Yang

Wang

et al. 2022

Polymers for Advanced Techs

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Degradable polyester elastomers are highly desirable for biomedical applications.Here, highly transparent and degradable aliphatic polyester elastomers were prepared using the ring-opening copolymerization (ROCP) of commercial monomers, followed by a photo-crosslinking process. A series of the semi-crystalline copolyester (PMBL-co-PBL-co-PCL) precursors with different molecular weights and pendent vinyl contents were synthesized by one-pot ROCP of α-methylene-γ-butyrolactone (MBL), ε-caprolactone (ε-CL) and γ-butyrolactone (γ-BL). Then, UV irradiation was applied to photo-crosslink the precursors to obtain several elastomers. The obtained aliphatic polyester elastomers (CPEs) displayed excellent mechanical properties with high tensile strength (11.3 MPa), high elongation at break (1300%) and high elastic recovery (about 99% after 10 hysteresis cycles). In addition, the elastomer showed much better stability than uncrosslinked (co)polyesters, but maintained degradability in the basic aqueous solution, with $30% of the mass loss in 1 M NaOH solution after 30 days. Through efficient ROCP, we demonstrated a strategy to prepare degradable CPEs bearing high strength, good elasticity, excellent resilience and degradation capability, which can serve as sustainable elastomers for various applications.

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Biobased poly(glycerol citrate) synthesis optimization via design of experiments

Cited by 10 publications

References 57 publications

Optimization of the Poly(glycerol citraconate) Synthesis Using the Box–Behnken Design

Optimization of the Poly(glycerol citraconate) Synthesis Using the Box–Behnken Design

Influence of the addition of glycerol-derived polymers on the properties of post-consumer recycled PET

Preparation of degradable aliphatic polyester elastomers with tunable strength and elasticity via photo‐crosslinking

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