Synthesis of polyesters mimicking polyethylene terephthalate and their thermal and mechanical properties

Kurt, Gülşah; Göktürk, Ersen

doi:10.1007/s10965-020-02285-0

Cited by 4 publications

(7 citation statements)

References 20 publications

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“…In addition, phenols, such as the one in methyl ferulate, have a lower reactivity compared to primary alcohols, especially in CALB-catalyzed transesterification [24,45]. For all these reasons, ferulic acid is often modified before polymerization [28,29,31]. This allows at the same time to fine-tune the properties of the monomer and those of the resulting polymer, especially of the chain rigidity.…”

Section: Polyesters Based On Ferulic Diestersmentioning

confidence: 99%

“…Recently, Kurt et al [31] used hydrogenated derivatives of ferulic acid for the synthesis of aromatic polyesters catalyzed by zinc acetate and obtained M n up to 8000 g•mol −1 . Moreover, because of its therapeutic as well as anti-UV properties, native unmodified ferulic acid also allows the synthesis of material with innovative properties.…”

Section: Introductionmentioning

confidence: 99%

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Ferulic Acid as Building Block for the Lipase-Catalyzed Synthesis of Biobased Aromatic Polyesters

2021

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Enzymatic synthesis of aromatic biobased polyesters is a recent and rapidly expanding research field. However, the direct lipase-catalyzed synthesis of polyesters from ferulic acid has not yet been reported. In this work, various ferulic-based monomers were considered for their capability to undergo CALB-catalyzed polymerization. After conversion into diesters of different lengths, the CALB-catalyzed polymerization of these monomers with 1,4-butanediol resulted in short oligomers with a DPn up to 5. Hydrogenation of the double bond resulted in monomers allowing obtaining polyesters of higher molar masses with DPn up to 58 and Mw up to 33,100 g·mol−1. These polyesters presented good thermal resistance up to 350 °C and Tg up to 7 °C. Reduction of the ferulic-based diesters into diols allowed preserving the double bond and synthesizing polyesters with a DPn up to 19 and Mw up to 15,500 g·mol−1 and higher Tg (up to 21 °C). Thus, this study has shown that the monomer hydrogenation strategy proved to be the most promising route to achieve ferulic-based polyester chains of high DPn. This study also demonstrates for the first time that ferulic-based diols allow the synthesis of high Tg polyesters. Therefore, this is an important first step toward the synthesis of competitive biobased aromatic polyesters by enzymatic catalysis.

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Section: Polyesters Based On Ferulic Diestersmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Ferulic Acid as Building Block for the Lipase-Catalyzed Synthesis of Biobased Aromatic Polyesters

2021

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“…202,203,[211][212][213] For example, the polymer obtained with dimethyl succinate (Scheme 4 ( 7)) exhibited a T g similar to PET (68 °C) and a storage modulus of 5.1 GPa. 202 Scheme 4 Representative multitude of vanillin-(1, 197 2, 198 3 & 4, 199 5, 200 6, 201 7, 202 8 203 ), vanillic acid-(9, 204-206 10, 204,207 11, 208 12, 205,209 13, 209 14, 210 15, 211,212 16, 213 17, 208 18 214 ), and ferulic acid-(19, 215 20, 216 21, 217 22, 218 Mankar et al designed a spiro-diol vanillin-based monomer, whose synthesis remarkably produced lower GHG emissions than biobased 1,3-propanediol and afforded a transparent material after polymerization (Scheme 4 ( 8)). 203 Finally, it is noteworthy that polymer 16 from Scheme 4 exhibited better mechanical properties than PET.…”

Section: Lignin-based Thermoplastic Polymersmentioning

confidence: 99%

“…Scheme 4 Representative multitude of vanillin-(1,197 2, 198 3 & 4,199 5,200 6,201 7,202 8 203 ), vanillic acid-(9, 204-206 10, 204,207 11,208 12, 205,209 13,209 14,210 15, 211,212 16,213 17,208 18214 ), and ferulic acid-(19,215 20,216 21,217 22,218 23 209 ) based thermoplastic polyesters.…”

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confidence: 99%

Recommendations for replacing PET on packaging, fiber, and film materials with biobased counterparts

et al. 2021

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“…43 In addition, because of the insolubility of highmolecular-weight polymers, it is also difficult to measure the molecular weight distribution using general gas permeation chromatography (GPC) analysis, which makes it hard for characterization and verification. 44 Second, the output average molecular weight is a range value because of the property constraints, and it shows the tolerance of the design values to the experimental values in the polymer synthesis. In other words, the wider the range of average molecular weight, the easier is the synthesis of polymers to meet the design requirements.…”

Section: Improved Computer-aided Polymer Designmentioning

confidence: 99%

Polymer Product Design: Considering Detailed Polymer Attributes and Production Guidelines

Yang

Wei-xuan

et al. 2021

Ind. Eng. Chem. Res.

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Because polymer properties are influenced by numerous complex structural factors, repeat unit structures provided by previous polymer designs are not sufficient for the production guidelines. In addition, neither the phase state nor the working temperature is considered when determining product attributes in previous studies. Considering these deficiencies, an improved polymer product design framework is proposed. Target polymer repeat unit structures with an average molecular weight range and difficulty of synthesis are provided under target properties, working temperatures, and phase states. First, the molecular weight and temperature-dependent properties are classified; then, limiting properties determined using the group contribution method are introduced to describe molecular weightproperty relationship. Finally, van der Waals volume is introduced to predict molar volume at a certain working temperature so that temperature-dependent properties can be determined. Advantages of the proposed framework are discussed and compared with the traditional polymer design, and a practical binder design example for coating is presented to demonstrate the applicability.

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Synthesis of polyesters mimicking polyethylene terephthalate and their thermal and mechanical properties

Cited by 4 publications

References 20 publications

Ferulic Acid as Building Block for the Lipase-Catalyzed Synthesis of Biobased Aromatic Polyesters

Ferulic Acid as Building Block for the Lipase-Catalyzed Synthesis of Biobased Aromatic Polyesters

Recommendations for replacing PET on packaging, fiber, and film materials with biobased counterparts

Polymer Product Design: Considering Detailed Polymer Attributes and Production Guidelines

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