Synthesis of Poly(glycerol butenedioate)─PGB─Unsaturated Polyester toward Biomedical Applications

Wrzecionek, Michał; Kolankowski, Krzysztof; Gadomska‐Gajadhur, Agnieszka

doi:10.1021/acsomega.2c01934

Cited by 5 publications

(6 citation statements)

References 71 publications

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“…An excess of glycerol results in greater anhydride conversion which results in a lower acid number which results in a higher degree of esterification. As the temperature increases, the degree of isomerization of the Z to E mers increases, which is consistent with our earlier studies Figure shows how strong the effect of the ratio of OH/COOH groups is in comparison to reaction time.…”

Section: Resultsmentioning

confidence: 99%

“…As the temperature increases, the degree of isomerization of the Z to E mers increases, which is consistent with our earlier studies. 41 Figure 10 shows how strong the effect of the ratio of OH/COOH groups is in comparison to reaction time. It is impossible to get a higher degree of anhydride conversion by running the reactions longer without changing the ratio of groups in favor of glycerol.…”

Section: Resultsmentioning

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: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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

Kolankowski,

Rżewska,

Ruśkowski

et al. 2023

ACS Omega

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“…Therefore, it is unfeasible to dye polyester fibers after extrusion. [24][25][26][27] Plasma curing of textile fibers has been described as an eco-friendly technique to stimulate the fabric topmost layer to improve its colorimetric properties. [28][29][30][31] The preparation of multifunctional luminescent polyester textile materials has not been described yet.…”

Section: Introductionmentioning

confidence: 99%

An anticounterfeiting strategy based on photochromic nonwoven polyester fabric by plasma‐assisting spray coating with ultraviolet‐responsive silica@strontium aluminate nanoparticles

Al‐Ahmed

Alzahrani

AlJohani

et al. 2023

Applied Organom Chemis

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Photochromism is an interesting method to enhance the anticounterfeiting activity of commercial products. Polyester fibers have been significant polymers for a variety of applications; however, they have been known to resist staining due to the absence of reactive dyeing site on their fibrous surface. Herein, we present recycled nonwoven polyester immobilized with rare‐earth activated aluminate nanoparticles for anticounterfeiting applications. Using the heterogeneous precipitation method, the lanthanide‐doped aluminate pigment was firstly coated with silica to give phosphor‐encapsulated within silica nanoparticles (Silica@Phosphor). The produced Silica@Phosphor particles were mixed with an adhesive binder in an aqueous medium, which was then spray‐coated directly onto plasma‐pretreated nonwoven polyester fabric. The fibrous composite demonstrated ultraviolet‐induced photochromism. Both phosphor and Silica@Phosphor morphologies demonstrated particle diameter of 4–12 and 90–105 nm, respectively. Various techniques were utilized to examine both morphologies and compositions of the photochromic nonwoven fabrics. The antibacterial activity, cytotoxicity, comfortability, colorfastness, and ultraviolet shielding of the prepared polyesters immobilized with Silica@Phosphor were also reported. The luminescent fabrics demonstrated two emission wavelengths at 435 and 514 nm (green) upon excitation at 369 nm (colorless). The nonwoven fabrics showed an enhanced superhydrophobicity as an improved contact angle up to 129.9° was detected upon increasing the Silica@Phosphor ratio.

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“…PGS has received notable attention from the scientific community, and many studies as well as some reviews have been published on the matter. 6−15 There are other poly(glycerol-co-diacids) described in the literature, 1,2,4,5,16,17 but they received much less interest than PGS. It is the case of poly(glycerol succinate) (PGSu), which has the potential to gain importance in the near future but, so far, only a few scientific publications have focused on reporting its synthesis.…”

Section: ■ Introductionmentioning

confidence: 99%

“…There are other poly(glycerol- co -diacids) described in the literature, ,,,,, but they received much less interest than PGS. It is the case of poly(glycerol succinate) (PGSu), which has the potential to gain importance in the near future but, so far, only a few scientific publications have focused on reporting its synthesis.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Prepolymers of Poly(glycerol-co-diacids) Based on Sebacic and Succinic Acid Mixtures

et al. 2023

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In this study, poly(glycerol- co -diacids) prepolymers were produced using different ratios of glycerol (G), sebacic acid (S), and succinic acid (Su) (molar ratios: GS 1:1, GSSu 1:0.9:0.1, GSSu 1:0.8:0.2, GSSu 1:0.5:0.5, GSSu 1:0.2:0.8, GSSu 1:0.1:0.9, GSu 1:1). All polycondensation reactions were performed at 150 °C until reaching a degree of polymerization of ≈55%, inferred by the water volume collected from a reactor. We concluded that the reaction time is correlated with the ratio of diacids used, that is, the increase in succinic acid is proportional to a decrease in the duration of the reaction. In fact, the reaction of poly(glycerol sebacate) (PGS 1:1) is twice as slow as the reaction of poly(glycerol succinate) (PGSu 1:1). The obtained prepolymers were analyzed by electrospray ionization mass spectrometry (ESI-MS) and 1 H and 13 C nuclear magnetic resonance (NMR). Besides its catalytic influence in poly(glycerol)/ether bond formation, the presence of succinic acid also contributes to a mass growth of ester oligomers, the formation of cyclic structures, a greater number of oligomers detected, and a difference in mass distribution. When compared with PGS (1:1), and even at lower ratios, the prepolymers produced with succinic acid presented mass peak characteristics of oligomer species with a glycerol unit as its end group in higher abundance. Generally, the most abundant oligomers have molecular weights between 400 and 800 g/mol.

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Synthesis of Poly(glycerol butenedioate)─PGB─Unsaturated Polyester toward Biomedical Applications

Cited by 5 publications

References 71 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

An anticounterfeiting strategy based on photochromic nonwoven polyester fabric by plasma‐assisting spray coating with ultraviolet‐responsive silica@strontium aluminate nanoparticles

Synthesis of Prepolymers of Poly(glycerol-co-diacids) Based on Sebacic and Succinic Acid Mixtures

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