Preparation of Chemically Recyclable Poly(ether-<italic style="font-style: italic">alt</italic>-ester) by the Ring Opening Polymerization of Cyclic Monomers Synthesized by Coupling Glycolide and Epoxides

Feng Ren; Zhuang-Zhuang Liang; Ming-Xin Niu; Chen-Yang Hu; Xuan Pang

doi:10.1007/s10118-023-3040-1

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Preparation of Chemically Recyclable Poly(ether-alt-ester) by the Ring Opening Polymerization of Cyclic Monomers Synthesized by Coupling Glycolide and Epoxides

RESEARCH ARTICLE | Updated：2024-01-12

- Preparation of Chemically Recyclable Poly(ether-alt-ester) by the Ring Opening Polymerization of Cyclic Monomers Synthesized by Coupling Glycolide and Epoxides
- Chinese Journal of Polymer Science Vol. 42, Issue 2, Pages: 168-175(2024)
- Affiliations：
  
  a.Key Laboratory of Polymer Ecomaterials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China
  b.School of Applied Chemistry and Engineering, University of Science and Technology of China, Hefei 230026, China
- Author bio：
  
  cyhu@ciac.ac.cn (C.Y.H.)
  xpang@ciac.ac.cn (X.P.)
- Funds：
- DOI：10.1007/s10118-023-3040-1
  CLC：
- Received：07 July 2023，
  
  Revised：2023-7-27，
  
  Accepted：27 July 2023，
  
  Online First：15 November 2023，
  
  Published：01 February 2024
- Accepted：
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Ren, F.; Liang, Z. Z.; Niu, M. X.; Hu, C. Y.; Pang, X. Preparation of chemically recyclable poly(ether-alt-ester) by the ring opening polymerization of cyclic monomers synthesized by coupling glycolide and epoxides. Chinese J. Polym. Sci. 2024, 42, 168–175

Feng Ren, Zhuang-Zhuang Liang, Ming-Xin Niu, et al. Preparation of Chemically Recyclable Poly(ether-alt-ester) by the Ring Opening Polymerization of Cyclic Monomers Synthesized by Coupling Glycolide and Epoxides[J]. Chinese Journal of Polymer Science, 2024, 42(2): 168-175. DOI: 10.1007/s10118-023-3040-1.
Ren, F.; Liang, Z. Z.; Niu, M. X.; Hu, C. Y.; Pang, X. Preparation of chemically recyclable poly(ether-alt-ester) by the ring opening polymerization of cyclic monomers synthesized by coupling glycolide and epoxides. Chinese J. Polym. Sci. 2024, 42, 168–175 DOI： 10.1007/s10118-023-3040-1.

Feng Ren, Zhuang-Zhuang Liang, Ming-Xin Niu, et al. Preparation of Chemically Recyclable Poly(ether-alt-ester) by the Ring Opening Polymerization of Cyclic Monomers Synthesized by Coupling Glycolide and Epoxides[J]. Chinese Journal of Polymer Science, 2024, 42(2): 168-175. DOI: 10.1007/s10118-023-3040-1. DOI：

摘要

Here

we reported that 1

4-dioxan-2-one with different substituents was successfully synthesized by coupling glycolide with epoxide using Salen-Cr(Ⅲ)/PPNCl as catalyst. The monomers underwent ROP to form poly(ester-alt-ether)s with alternating glycolic acid and epoxides using thiourea/base. The poly(ester-alt-ether)s showed low

and chemical recyclability to monomers in the presence of catalysts.

Abstract

Polyester and polyether are two key oxygenated polymers

and completely alternative sequence of poly(ester-

alt

-ether) could efficiently combine the advantages (including flexibility

degradability

etc

.) of both segments. Currently

despite their copolymers could be synthesized from one-pot mixture of cyclic esters and epoxides

perfectly alternative microstructure is very challenging to realize and typically restricted to certain monomer pairs. Moving forward

synthesizing poly(ester-

alt

-ether) from commercially available and largescale monomers would be a significant advance. For example

successfully commercialized poly(glycolic acid) (PGA)

which is not easily soluble in polymers due to its high crystallinity and is brittle and difficult to control the degradation cycle

would encounter a new paradigm if engineered into poly(ester-

alt

-ether). In this work

starting from the design of monomer with hybrid structures

we successfully synthesized a series of 1

4-dioxan-2-one containing different substituents based on glycolide (GA) and epoxides using commercially available Salen-Cr(III) and PPNCl catalytic systems. The new monomers underwent ring-opening polymerization (ROP) to form a series of poly(ester

-alt-

ether) with perfectly alternating glycolic acid and propylene glycol repeat units under catalytic system of thiourea/base. The poly(ester-

alt

-ether) have significantly lower glass-transition temperature than PGA. Additionally

the poly(ester-

alt

-ether) can be chemically recovered to monomer using Sn(Oct)

or 1

8-diazabicyclo[5.4.0]undecane-7-ene (DBU) as a catalyst in solution

thus establishing a closed-loop life cycle. From monomers derived from GA and epoxides

this work furnishes a novel strategy for the synthesis of poly(ester-

alt

-ether) with chemical recyclability.

关键词

Keywords

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⁰

Preparation of Chemically Recyclable Poly(ether-alt-ester) by the Ring Opening Polymerization of Cyclic Monomers Synthesized by Coupling Glycolide and Epoxides

DOI：10.1007/s10118-023-3040-1

摘要

Abstract

关键词

Keywords

references