Naphthalene engineering of chemically recyclable polyesters with enhanced thermal and mechanical properties

Wang, Xuemei; Huang, Hsien‐Cheng; Tu, Yi-Min; Cai, Zhongzheng; Zhu, Jianbo

doi:10.1039/d3py00275f

Cited by 10 publications

(3 citation statements)

References 57 publications

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“…Subsequently, the same group targeted a series of BDPO-based monomers with differing benzene ring substitution, including the introduction of methoxy, bromo, and naphthalene groups, with the goal of tailoring the properties of the resultant semiaromatic polyesters (Scheme ). These monomers retained high polymerization activity with a TBD catalyst and led to high M n (up to 297 kg mol –1 ) semiaromatic polyesters. Introducing a bromo substituent to BDPO-2 led to the monomer BDPO-7, and the resultant polyester exhibited a slight improvement in T g , increasing from 49 to 75 °C compared to the nonsubstituted PBDPO-2.…”

Section: Emerging Aromatic and Aromatic–aliphatic Polyestersmentioning

confidence: 99%

Recyclable and (Bio)degradable Polyesters in a Circular Plastics Economy

Shi,

Quinn,

Diment

et al. 2024

Chem. Rev.

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Polyesters carrying polar main-chain ester linkages exhibit distinct material properties for diverse applications and thus play an important role in today's plastics economy. It is anticipated that they will play an even greater role in tomorrow's circular plastics economy that focuses on sustainability, thanks to the abundant availability of their biosourced building blocks and the presence of the main-chain ester bonds that can be chemically or biologically cleaved on demand by multiple methods and thus bring about more desired end-of-life plastic waste management options. Because of this potential and promise, there have been intense research activities directed at addressing recycling, upcycling or biodegradation of existing legacy polyesters, designing their biorenewable alternatives, and redesigning future polyesters with intrinsic chemical recyclability and tailored performance that can rival today's commodity plastics that are either petroleum based and/or hard to recycle. This review captures these exciting recent developments and outlines future challenges and opportunities. Case studies on the legacy polyesters, poly(lactic acid), poly(3-hydroxyalkanoate)s, poly(ethylene terephthalate), poly(butylene succinate), and poly(butylene-adipate terephthalate), are presented, and emerging chemically recyclable polyesters are comprehensively reviewed.

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Section: Emerging Aromatic and Aromatic–aliphatic Polyestersmentioning

confidence: 99%

Recyclable and (Bio)degradable Polyesters in a Circular Plastics Economy

Shi,

Quinn,

Diment

et al. 2024

Chem. Rev.

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“…Developing a circular plastics economy presents the most promising solution to this issue . For the past few years, the preparation of chemically recyclable polymers with desirable properties has made tremendous progress, especially in the synthesis of chemically recyclable aliphatic polyesters via ROP of cyclic ester monomers. − Nevertheless, due to its complicated synthesis steps accompanied by low yields, and limited functional diversity of cyclic lactones, the application range of ROP for preparing aromatic recyclable polyesters is restricted. − Therefore, it is imperative to develop a new polymerization approach that enables efficient polymerization of inexpensive and easily obtainable biobased aromatic monomers and prepares high-performance recyclable aromatic polyesters with both theoretical and practical significance (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Direct Coupling of Biobased Bifunctional Hydroxy-Aldehyde Monomers to Chemically Recyclable Alipharomatic Polyesters via Dehydrogenative Polycondensation

Xu,

Deng,

Zeng

et al. 2024

Macromolecules

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A series of biobased alipharomatic polyesters using vanillin-derived bifunctional hydroxy-aldehyde monomers (M1)s as the starting materials are synthesized through direct dehydrogenative polycondensation with commercially available Milstein catalyst. The thermal properties of the resulting P(M1)s can be precisely tuned by altering the alkylene length of the monomers, with a maximum T g value reaching 37.9 °C. Compared to the reported vanillic acid-based polyesters, the synthesis of M1 is less labor-intensive, and the polymerization conditions are milder than those of conventional polycondensation. Additionally, experimental results and mechanism elucidations revealed four different types of ester linkages in the P(M1) chain. The ruthenium dihydride complex has been identified as the true active species required for promoting the polymerization of hydroxy-aldehyde monomers into polyesters. Moreover, this catalytic system also exhibits depolymerization capability toward resulting polyester back into vanillin-derived diol (M2), which can then be repolymerized into a polyester P(M2) with an identical structure to that of P(M1), thus demonstrating a rare example where two different monomers yield the same polymer product. This study presents a green and economical approach to the preparation and recycling of widely used alipharomatic polyesters.

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“…[23,24] The introduction of benzo-fused structures to ɛ-caprolactone contributed to enhance its depolymerizability, manifesting the feasibility of chemical recycling to monomer. Representative examples including DHB-(2,3-dihydro-5H-1,4benzodioxepin), [23,[25][26][27][28] BDXO-(3,4-dihydro-2H-benzo[b]- [1,4]dioxepin-2-one), [29] and BDPO-(5H-1,4-benzodioxepin-3(2H)-one) [30,31] based monomers and salicylic methyl glycolide (SMG) [32,33] were reported to accomplish completely reversible polymerization and depolymerization process via the manipulation of the reaction conditions. Meanwhile, these benzo-fused polyester products with diverse function-ality and tacticity were disclosed to perform distinct thermal and mechanical properties.…”

mentioning

confidence: 99%

Torsional Strain Enabled Ring‐Opening Polymerization towards Axially Chiral Semiaromatic Polyesters with Chemical Recyclability

Cao,

Tu,

Fan

et al. 2024

Angewandte Chemie

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The development of new chemically recyclable polymers via monomer design would provide a transformative strategy to address the energy crisis and plastic pollution problem. Biaryl‐fused cyclic esters were targeted to generate axially chiral polymers, which would impart new material performance. To overcome the non‐polymerizability of the biaryl‐fused monomer DBO, a cyclic ester Me‐DBO installed with dimethyl substitution was prepared to enable its polymerizability via enhancing torsional strain. Impressively, Me‐DBO readily went through well‐controlled ring‐opening polymerization, producing polymer P(Me‐DBO) with high glass transition temperature (Tg >100 °C). Intriguingly, mixing these complementary enantiopure polymers containing axial chirality promoted a transformation from amorphous to crystalline material, affording a semicrystalline stereocomplex with a melting transition temperature more than 300 °C. P(Me‐DBO) were capable of depolymerizing back to Me‐DBO in high efficiency, highlighting an excellent recyclability.

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Naphthalene engineering of chemically recyclable polyesters with enhanced thermal and mechanical properties

Abstract: Developing new chemically recyclable polymers is highly demanded for establishing a circular plastics economy. The superior aliphatic-aromatic 5H-1,4-benzodioxepin-3(2H)-one (BDPO) system combined the high reactivity of aliphatic esters with the beneficial...

Cited by 10 publications

References 57 publications

Recyclable and (Bio)degradable Polyesters in a Circular Plastics Economy

Recyclable and (Bio)degradable Polyesters in a Circular Plastics Economy

Direct Coupling of Biobased Bifunctional Hydroxy-Aldehyde Monomers to Chemically Recyclable Alipharomatic Polyesters via Dehydrogenative Polycondensation

Torsional Strain Enabled Ring‐Opening Polymerization towards Axially Chiral Semiaromatic Polyesters with Chemical Recyclability

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