Biobased Pyrazine-Containing Polyesters

Würdemann, Martien A.; Bernaerts, Katrien V.

doi:10.1021/acssuschemeng.0c03159

Cited by 9 publications

(10 citation statements)

References 26 publications

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“…This indicates that the materials no longer crystallize on the DSC measurement time scale. At higher levels of oxidation, the T g of the DMDPP-C6 polymer also increased from 4 °C for the nascent material to 31 °C upon complete di-oxidation.…”

Section: Resultsmentioning

confidence: 98%

“…This is, however, taking 5% weight loss as the cutoff for degradation. The DMDPP-C6 polymer already degrades below this cutoff via intramolecular nucleophilic attack of the pyrazine nitrogen to the ester bond . Oxidation may block this reaction pathway but also changes the electronic character.…”

Section: Resultsmentioning

confidence: 99%

“…On the other hand, nitrogen-rich biomass receives, as of now, relatively little attention as a source of biogenic carbon for the synthesis of advance polymers . Our group recently developed a number of pyrazine-containing polyesters from nitrogen-rich biomass . More specific, biobased pyrazine diacids are dimethyldipropionic and dipropionic acid pyrazine ( DMDPP and DPP , respectively) (see Figure ).…”

Section: Introductionmentioning

confidence: 99%

“…5 Our group recently developed a number of pyrazine-containing polyesters from nitrogen-rich biomass. 6 More specific, biobased pyrazine diacids are dimethyldipropionic and dipropionic acid pyrazine (DMDPP and DPP, respectively) (see Figure 1). Both are prepared using a straightforward process from simple amino acids (glutamic-and δ-amino-levulinic acid) and were employed to access our polyesters.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Monomers Me 2 DMDPP and Me 2 DPP and polymers DMDPP-C6 and DPP-C6 were synthesized according to the literature. 6 Trimethyloxonium tetrafluoroborate and trifluoroacetic acid were supplied by TCI at >95% purity; 3-chloroperbenzoic acid (meta-chloroperbenzoic acid, mCPBA) at 77 wt % purity, sodium thiosulphate, and sodium bicarbonate were supplied by Sigma-Aldrich, and all were used as received. Silica gel (Davisil 60A) was supplied by Grace.…”

Section: ■ Introductionmentioning

confidence: 99%

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Post-Modification of Biobased Pyrazines and Their Polyesters

et al. 2021

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Monomers and polymers from biobased pyrazine underwent post-modification reactions to synthesize a series of novel tailored polyesters with a tunable structure and adjustable physico-chemical properties. Modification by alkylation had limited success. However, controlled oxidative post-modification is possible, without loss of molecular weight. The degree of oxidation has a large effect on the thermal properties of the polyesters. One of the polyesters shows loss of crystallinity combined with an increase in the glass-transition temperature at increasing degrees of oxidation. For the other polyester, oxidation results in an elevated melting point. Weak hydrogen bonds are responsible for the latter observation as demonstrated by infrared spectroscopy. The surface modification of a polymer film results in different wetting behaviors. Our biobased pyrazine building blocks and their ability to be post-modified offer interesting opportunities in added functionality materials of the future.

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Section: Resultsmentioning

confidence: 98%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

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Post-Modification of Biobased Pyrazines and Their Polyesters

et al. 2021

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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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