Ring-Opening Copolymerization of Epoxides and Cyclic Anhydrides with Discrete Metal Complexes: Structure–Property Relationships

Longo, Julie M.; Sanford, Maria J.; Coates, Geoffrey W.

doi:10.1021/acs.chemrev.6b00553

Cited by 436 publications

(533 citation statements)

References 87 publications

(387 reference statements)

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“…In addition to conventional syntheses, ring opening polymerizations have also emerged. These are characterized by the use of milder reaction conditions and they allow shorter reaction times, while they are not concomitant with byproduct formation . However, due to the limited availability of cyclic derivatives, only a few semi‐aromatic polyesters have been synthesized to date by ring opening polymerizations.…”

Section: Introductionmentioning

confidence: 99%

Single‐step solution polymerization of poly(alkylene terephthalate)s: synthesis parameters and polymer characterization

Giol

Brande

Mele

et al. 2018

Polymer International

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Poly(alkylene terephthalate)s represent one of the most frequently used polymer classes worldwide. Well‐known examples include poly(ethylene terephthalate) (n = 2) and poly(butylene terephthalate) (n = 4). The conventional synthesis method for these polymers is based on melt polycondensation, a two‐stage process performed under harsh conditions that includes the synthesis of an intermediate prepolymer and the presence of a catalyst, which may induce toxicity issues. The present work reports on a straightforward single‐step solution polycondensation method performed under mild conditions and in the absence of a catalyst. A homologous series of poly(alkylene terephthalate)s (n = 5 − 10) of molar masses up to 20 000 g mol−1 and dispersity <2.4 was synthesized and characterized thoroughly. Great attention was given to the thermal properties assessment by using state‐of‐the‐art techniques and a highly sensitive prototype technique called rapid heat − cool DSC. Similar to melt‐synthesized polyesters, a particular odd − even trend of the thermal properties versus the number of methylene groups within the monomer unit was revealed. To the best of our knowledge, this is the first report covering a single‐step solution‐based polycondensation performed in the absence of a catalyst that results in highly reproducible polyesters possessing unaltered thermal properties compared to polyesters synthesized through industrially applied conventional routes. © 2017 Society of Chemical Industry

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Section: Introductionmentioning

confidence: 99%

Single‐step solution polymerization of poly(alkylene terephthalate)s: synthesis parameters and polymer characterization

Giol

Brande

Mele

et al. 2018

Polymer International

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“…ROCOP is a controlled and atom‐economical approach to produce PEs with the advantage of less energy intensive process compared to condensation polymerization approach . In addition, the ROCOP process can easily be adapted for the preparation of a wide range of PEs by taking advantage of the variety of epoxides and anhydrides available both from petrochemicals and renewable resources …”

Section: Introductionmentioning

confidence: 99%

Synthesis of high molecular weight aromatic polyesters via integrated alternating ring‐opening copolymerization and chain extension methods

Cheng

Rabnawaz

Khan

et al. 2018

J of Applied Polymer Sci

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Due to their good mechanical properties, high molecular weight polyesters (PEs) are highly desirable for a wide range of applications especially in the packaging industry. However, the synthesis of high molecular weight polymers by energy efficient methods is difficult. In this study, a series of semi‐aromatic PEs were synthesized via the alternating ring‐opening copolymerization (ROCOP) of phthalic anhydride (PA) and cyclohexene oxide (CHO) using a salen chromium(III) complex as a catalyst and 4‐(dimethylamino)pyridine as a cocatalyst. By varying the molar ratios between CHO and PA, PEs of different molecular weights were obtained. Hexamethylene diisocyanate was used as a chain extender that further increased the molecular weights of these PEs. These chain extended aromatic polyesters (PE‐Xs) showed significant improvement in the glass transition temperature (Tg) values. Thus, integration of ROCOP with the chain extension method can be used as an effective strategy to prepare high molecular weight PEs with improved thermal stabilities and enhanced mechanical properties. © 2018 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2019, 136, 47200.

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“…[8] It has been used to make afew hydrophilic polyesters but such processes require complex monomer syntheses,h ydrophile protection/deprotection strategies,a nd may be hampered by low polymerizability. [10] Here,n ew amphiphilic block polyesters are prepared by e-caprolactone (e-CL) ROP,f ollowed by ROCOP of succinic anhydride (SA) and 2-((2-(2-(2-methoxyethoxy)ethoxy)ethoxy)methyl)oxirane (ME 3 MO;F igure 1a;s ee Figure S2 in the Supporting Information). [10] Here,n ew amphiphilic block polyesters are prepared by e-caprolactone (e-CL) ROP,f ollowed by ROCOP of succinic anhydride (SA) and 2-((2-(2-(2-methoxyethoxy)ethoxy)ethoxy)methyl)oxirane (ME 3 MO;F igure 1a;s ee Figure S2 in the Supporting Information).…”

mentioning

confidence: 99%

Metabolically Active, Fully Hydrolysable Polymersomes

et al. 2019

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The synthesis and aqueous self‐assembly of a new class of amphiphilic aliphatic polyesters are presented. These AB block polyesters comprise polycaprolactone (hydrophobe) and an alternating polyester from succinic acid and an ether‐substituted epoxide (hydrophile). They self‐assemble into biodegradable polymersomes capable of entering cells. Their degradation products are bioactive, giving rise to differentiated cellular responses inducing stromal cell proliferation and macrophage apoptosis. Both effects emerge only when the copolymers enter cells as polymersomes and their magnitudes are size dependent.

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Ring-Opening Copolymerization of Epoxides and Cyclic Anhydrides with Discrete Metal Complexes: Structure–Property Relationships

Cited by 436 publications

References 87 publications

Single‐step solution polymerization of poly(alkylene terephthalate)s: synthesis parameters and polymer characterization

Single‐step solution polymerization of poly(alkylene terephthalate)s: synthesis parameters and polymer characterization

Synthesis of high molecular weight aromatic polyesters via integrated alternating ring‐opening copolymerization and chain extension methods

Metabolically Active, Fully Hydrolysable Polymersomes

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