Novel poly(3-hydroxy butyrate) macro RAFT agent. Synthesis and characterization of thermoresponsive block copolymers

Hazer, Baki̇; Eren, Melike; Senemoğlu, Yetkin; Modjinou, Tina; Renard, Estelle; Langlois, Valérie

doi:10.1007/s10965-020-02133-1

Cited by 16 publications

(7 citation statements)

References 41 publications

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“…Compared to the commonly used aromatic polyesters like PET, PHAs are usually inferior in their thermal and mechanical properties and thus need chemical modifications. [16][17][18][19][20][21][22][23][24][25][26][27][28] Such chemical modifications may also alter their, solubility, processability and hydrophobicity to facilitate their applications. Salicylic acid (2-hydroxybenzoic acid) is prevalent in willow leaves, as well as in poplar and birch trees; It is widely used in the manufacture of aspirin as an analgesic.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Biobased Block Copolymers Using A Novel Methacrylated Methyl Salicylate and Poly(3‐Hydroxybutyrate)

2021

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A novel biobased vinyl monomer was synthesized by the reaction of methyl salicylate with methacrylic anhydride. The resulting salicylate based monomer was polymerized by reversible addition fragmentation transfer (RAFT) polymerizations using two or three trithiocarbonate functionalized poly(3‐hydroxybutyrate) macro agents. The molecular structures of the obtained polymers were confirmed by NMR spectroscopy and GPC analysis. The resulting block copolymers showed glass transition temperature (Tg) at 5 °C and melting temperature (Tm) at 160 °C according to DSC results. Compared to PHB, the obtained block copolymers displayed enhanced thermal stability according to TGA results. The overall rate constants of the RAFT polymerization using tri‐functionalized PHB macro agent were determined as 2.58 ×10−4, 1.17×10−4, and 0.50×10−4 L mol−1s−1 for 70, 80 and 90 °C, respectively. The activation energy was found to be 18.6 kcal K−1mol−1. The overall rate constant of the homopolymerization of the obtained monomer was determined as 1.14×10−4 Lmol−1s−1.

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Section: Introductionmentioning

confidence: 99%

Synthesis of Biobased Block Copolymers Using A Novel Methacrylated Methyl Salicylate and Poly(3‐Hydroxybutyrate)

2021

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“…To generate hydroxylated PHB with three hydroxyl endings, DEA was capped with the carboxylic end of PHB. Tri-hydroxylated PHB (PHB-DEA) was generated many times as a precursor in previous investigations. , The FTIR and 1 H NMR techniques were used to structurally characterize the resulting PHB-DEA. Characteristic PHB-DEA FTIR signals (Figure ) were found at 1563, 3315, and 1736 cm –1 , which corresponded to amide carbonyl, DEA primary hydroxyl groups, and PHB ester carbonyl, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…The structure of PHB-DEA-CafA was also confirmed by the 1 H NMR (Figure b), where the chemical shifts at 1.3 ppm for −CH 3 , 2.4–2.6 ppm for CH 2 –COO–, 3.0 ppm for −N–CH 2 –, 3.5–3.8 ppm for −CH 2 –OH, 4.1 ppm for −CH–OH, 5.1–5.3 ppm for −CH–O–, 7.086 ppm for −CH, and 7.4–7.55 ppm for cyclic–C–H were observed. The hydroxyl groups of PHB were previously substituted by N -isopropyl acryl amide (NIPAM), forming a thermoresponsive block copolymer for biomedical applications . Similarly, Erol et al studied PHB-DEA reaction with 2,3,5-tri-iodobenzoic acid and 4-iodobenzoic acid, generating tri-novel radiopaque iodinated PHB with X-ray visibility for medical diagnosis .…”

Section: Resultsmentioning

confidence: 99%

“…The hydroxyl groups of PHB were previously substituted by N -isopropyl acryl amide (NIPAM), forming a thermoresponsive block copolymer for biomedical applications. 25 Similarly, Erol et al studied PHB-DEA reaction with 2,3,5-tri-iodobenzoic acid and 4-iodobenzoic acid, generating tri-novel radiopaque iodinated PHB with X-ray visibility for medical diagnosis. 36 The previously mentioned studies were proposed with the aim of enhancing the biomedical functionality of PHB.…”

Section: Resultsmentioning

confidence: 99%

“…24 Chain-End Functionalization of PHB-DEA by CafA. Using the esterification process described by Hazer et al, 25 PHB-DEA and CafA reacted to generate PHB-DEA-CafA. PHB-DEA (3.5 g) was dissolved in dichloromethane (DCM) (30 mL).…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

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Novel Biodegradable Nanoparticulate Chain-End Functionalized Polyhydroxybutyrate–Caffeic Acid with Multifunctionalities for Active Food Coatings

Abdelmalek

Rofeal

Pietrasik

et al. 2023

ACS Sustainable Chem. Eng.

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The bioactivities of polyhydroxyalkanoates have been curtailed owing to the lack of bioactive functional groups in their backbones. In this regard, polyhydroxybutyrate (PHB) produced from new locally isolated Bacillus nealsonii ICRI16 was chemically modified for enhancing its functionality, stability as well as solubility. First, PHB was transformed to PHB-diethanolamine (PHB-DEA) by transamination. Subsequently, for the first time, the chain ends of the polymer were substituted by caffeic acid molecules (CafA), generating novel PHB-DEA-CafA. The chemical structure of such a polymer was confirmed by Fourier-transform infrared (FTIR) spectroscopy and proton nuclear magnetic resonance ( 1 H NMR). The modified polyester demonstrated improved thermal behavior compared to PHB-DEA as was shown by thermogravimetric analysis, derivative thermogravimetry, and differential scanning calorimetry analyses. Interestingly, 65% of PHB-DEA-CafA was biodegraded in a clay soil environment after 60 days at 25 °C, while 50% of PHB was degraded within the same period. On another avenue, PHB-DEA-CafA nanoparticles (NPs) were successfully prepared with an impressive mean particle size of 223 ± 0.12 nm and high colloidal stability. The nanoparticulate polyester had powerful antioxidant capacity with an IC 50 of 32.2 mg/mL, which was the result of CafA loading in the polymer chain. More importantly, the NPs had a considerable effect on the bacterial behavior of four food pathogens, inhibiting 98 ± 0.12% of Listeria monocytogenes DSM 19094 after 48 h of exposure. Finally, the raw polish sausage coated with NPs had a significantly lower bacterial count of 2.11 ± 0.21 log cfu/g in comparison to other groups. When all these positive features are recognized, the polyester described herein could be considered as a good candidate for commercial active food coatings.

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Synthesis and characterization of block copolymer: thermal and morphological properties of SiO2-filled block copolymer nanocomposites

2022

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Novel poly(3-hydroxy butyrate) macro RAFT agent. Synthesis and characterization of thermoresponsive block copolymers

Cited by 16 publications

References 41 publications

Synthesis of Biobased Block Copolymers Using A Novel Methacrylated Methyl Salicylate and Poly(3‐Hydroxybutyrate)

Synthesis of Biobased Block Copolymers Using A Novel Methacrylated Methyl Salicylate and Poly(3‐Hydroxybutyrate)

Novel Biodegradable Nanoparticulate Chain-End Functionalized Polyhydroxybutyrate–Caffeic Acid with Multifunctionalities for Active Food Coatings

Synthesis and characterization of block copolymer: thermal and morphological properties of SiO2-filled block copolymer nanocomposites

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