Cyclic Monomers: Epoxides, Lactide, Lactones, Lactams, Cyclic Silicon-Containing Monomers, Cyclic Carbonates, and Others

Carlotti, Stéphane; Peruch, Frédéric

doi:10.1007/978-4-431-54186-8_5

Cited by 11 publications

(9 citation statements)

References 770 publications

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“…According to the references, , alkoxides as the strong base can not only launch a nucleophilic attack of the lactone monomer (Scheme (i) pathway A) but also turn into an enolate anion initiator through a proton abstraction of lactone monomer (Scheme (i) pathway B). Thus, the ROP of γ-BL only using KOMe or NaOMe should undergo the mechanism mentioned above, which is proved by MALDI-TOF MS (Figure ).…”

Section: Results and Discussionmentioning

confidence: 99%

Nonstrained γ-Butyrolactone to High-Molecular-Weight Poly(γ-butyrolactone): Facile Bulk Polymerization Using Economical Ureas/Alkoxides

et al. 2018

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We disclose an efficient catalyst system of commercial ureas/alkoxides for the challenging ring-opening polymerization (ROP) of bioderived "nonpolymerizable" γbutyrolactone (γ-BL). This effective polymerization can not only be performed under mild conditions like bulk polymerization, higher monomer ratio, and elevated temperature (−20 °C comparing to −40 °C), but also obtains high-molecular-weight poly(γ-butyrolactone) (PγBL) (M n up to 68.2 kg/mol). To our knowledge, this is a big progress in the research area of ROP of γ-BL, which provides a promising prospect for the industrial-scale methodology of PγBL production. Structural analysis including NMR and MALDI-TOF, along with mechanistic computational studies based on DFT calculations, show that urea anion acts as a bifunctional catalyst, which activates the alcohol initiator and γ-BL before obeying an anionic polymerization. Furthermore, the catalytic activities of ureas/alkoxides systems have been optimized using the ureas with electron-donating groups which are proved to have lower activation barrier by computational calculation.

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Section: Results and Discussionmentioning

confidence: 99%

Nonstrained γ-Butyrolactone to High-Molecular-Weight Poly(γ-butyrolactone): Facile Bulk Polymerization Using Economical Ureas/Alkoxides

et al. 2018

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“…Organocatalytic polymerization following a nucleophilic/anionic mechanism is a powerful pathway for the synthesis of metal-free polymers with different macromolecular architectures. Since the first report of nucleophilic organocatalyzed ROP of lactide [79] or cyclic monomers [80], several reviews focusing on this subject have been published [4,7,69,[81][82][83][84][85][86][87][88], including on initiating/catalytic systems for the polymerization of γBL and derivatives.…”

Section: Organic Base-catalyzed Rop/rocp Of γ-Lactonesmentioning

confidence: 99%

Ring-opening polymerization of γ-lactones and copolymerization with other cyclic monomers

Song

Pascouau

Zhao

et al. 2020

Progress in Polymer Science

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Triggered by raised environmental awareness and the rising requirements for sustainable polymers such as degradable or recyclable polymers, studies on ring-opening (co)polymerization (ROP/ROCP) of (bio-based) cyclic monomers (e.g., cyclic esters, lactides, epoxides etc.) have been booming in recent years. Renewable five-membered γ-butyrolactone (γBL) and derivatives would thus be a desirable feedstock to produce poly(γ-butyrolactone) (PγBL) and different (bio-based) functional polyesters. Their copolymerization with other cyclic monomers could also afford an alternative to tune the properties of the resulting materials.Although γBL was traditionally regarded "non-polymerizable", some progresses were made recently concerning the ROP/ROCP of γBL and derivatives. More importantly, some polyesters could be totally depolymerized back to their monomers by thermal or chemical treatment. This review is specially focused on ROP of γ-lactones and their copolymerization with other cyclic monomers by different catalytic/initiating systems, including Lewis/Brønsted acids, organic bases and alkali metal compounds, organometallic compounds, and cooperative bicomponent catalytic systems. The depolymerization process of some obtained polyesters is also discussed.

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“…Since the description in 2001 of the first nucleophilic organocatalyzed ROP of lactide 39 , lots of organocatalytic systems have been studied for the ROP of cyclic esters. 40 The phosphazene base, cases. ROCP of γBL with εCL and δVL following the same approach was also successful.…”

Section: Organic Bases and Acid-base Pairs As Initiators/catalystsmentioning

confidence: 99%

Ring-opening (co)polymerization of γ-butyrolactone: a review

Song

Zhao

Zhang

et al. 2019

Polym J

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With increased environment concerns and the rising demands for sustainable polymers, e.g. degradable polymers and chemically recyclable polymers, studies on ring-opening polymerization (ROP) of cycle esters have been developed during last decades. Biorenewable five-membered γ-butyrolactone (γBL) could be a desirable feedstock for the chemical synthesis of poly(γ-butyrolactone) (PγBL) or for the incorporation of γBL units into polyester chains in order to modify their properties. Although γBL is traditionally considered to be "nonpolymerizable", some progresses were recently made in ROP of γBL. This mini-review is thus specially focused on the ROP of γBL and its copolymerization with other cyclic esters.

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Cyclic Monomers: Epoxides, Lactide, Lactones, Lactams, Cyclic Silicon-Containing Monomers, Cyclic Carbonates, and Others

Cited by 11 publications

References 770 publications

Nonstrained γ-Butyrolactone to High-Molecular-Weight Poly(γ-butyrolactone): Facile Bulk Polymerization Using Economical Ureas/Alkoxides

Nonstrained γ-Butyrolactone to High-Molecular-Weight Poly(γ-butyrolactone): Facile Bulk Polymerization Using Economical Ureas/Alkoxides

Ring-opening polymerization of γ-lactones and copolymerization with other cyclic monomers

Ring-opening (co)polymerization of γ-butyrolactone: a review

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