Synthesis and chemoselective crosslinking of functionalized polyesters from bio-based epoxides and cyclic anhydrides

Marcell N.D. Haslewood; Thomas J. Farmer; Michael North

doi:10.1002/pol.20220552

Synthesis and chemoselective crosslinking of functionalized polyesters from bio-based epoxides and cyclic anhydrides

Marcell N.D. Haslewood, Thomas J. Farmer^*, Michael North

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

Biomass derivable epichlorohydrin undergoes ring-opening copolymerization with either succinic or itaconic anhydride (both biosourcable) under standard laboratory conditions using metal-based or an entirely organic initiator to form highly functionalized, low molecular weight polyesters. The linear polyesters obtained from epichlorohydrin and itaconic anhydride contain both alkyl chlorides and α,β-unsaturated esters and can be crosslinked to form insoluble resins by treatment with di- to tetra-functional amines and thiols. Crosslinking with amines predominately occurs through the alkyl chlorides whilst crosslinking with thiols occurs through the α,β-unsaturated esters allowing the synthesis of insoluble polyester derived resins with complementary and controllable functionalities.

Original language	English
Number of pages	12
Journal	Journal of Polymer Science
Early online date	24 Oct 2022
DOIs	https://doi.org/10.1002/pol.20220552
Publication status	E-pub ahead of print - 24 Oct 2022

Bibliographical note

Keywords

anhydride
bio-derivable
cross-link
epoxide
ring-opening copolymerization

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Journal of Polymer Science - 2022 - Haslewood - Synthesis and chemoselective crosslinking of functionalized polyesters from
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title = "Synthesis and chemoselective crosslinking of functionalized polyesters from bio-based epoxides and cyclic anhydrides",

abstract = "Biomass derivable epichlorohydrin undergoes ring-opening copolymerization with either succinic or itaconic anhydride (both biosourcable) under standard laboratory conditions using metal-based or an entirely organic initiator to form highly functionalized, low molecular weight polyesters. The linear polyesters obtained from epichlorohydrin and itaconic anhydride contain both alkyl chlorides and α,β-unsaturated esters and can be crosslinked to form insoluble resins by treatment with di- to tetra-functional amines and thiols. Crosslinking with amines predominately occurs through the alkyl chlorides whilst crosslinking with thiols occurs through the α,β-unsaturated esters allowing the synthesis of insoluble polyester derived resins with complementary and controllable functionalities.",

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author = "Haslewood, {Marcell N.D.} and Farmer, {Thomas J.} and Michael North",

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doi = "10.1002/pol.20220552",

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T1 - Synthesis and chemoselective crosslinking of functionalized polyesters from bio-based epoxides and cyclic anhydrides

AU - Haslewood, Marcell N.D.

AU - Farmer, Thomas J.

AU - North, Michael

PY - 2022/10/24

Y1 - 2022/10/24

N2 - Biomass derivable epichlorohydrin undergoes ring-opening copolymerization with either succinic or itaconic anhydride (both biosourcable) under standard laboratory conditions using metal-based or an entirely organic initiator to form highly functionalized, low molecular weight polyesters. The linear polyesters obtained from epichlorohydrin and itaconic anhydride contain both alkyl chlorides and α,β-unsaturated esters and can be crosslinked to form insoluble resins by treatment with di- to tetra-functional amines and thiols. Crosslinking with amines predominately occurs through the alkyl chlorides whilst crosslinking with thiols occurs through the α,β-unsaturated esters allowing the synthesis of insoluble polyester derived resins with complementary and controllable functionalities.

AB - Biomass derivable epichlorohydrin undergoes ring-opening copolymerization with either succinic or itaconic anhydride (both biosourcable) under standard laboratory conditions using metal-based or an entirely organic initiator to form highly functionalized, low molecular weight polyesters. The linear polyesters obtained from epichlorohydrin and itaconic anhydride contain both alkyl chlorides and α,β-unsaturated esters and can be crosslinked to form insoluble resins by treatment with di- to tetra-functional amines and thiols. Crosslinking with amines predominately occurs through the alkyl chlorides whilst crosslinking with thiols occurs through the α,β-unsaturated esters allowing the synthesis of insoluble polyester derived resins with complementary and controllable functionalities.

KW - anhydride

KW - bio-derivable

KW - cross-link

KW - epoxide

KW - ring-opening copolymerization

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U2 - 10.1002/pol.20220552

DO - 10.1002/pol.20220552

M3 - Article

AN - SCOPUS:85140413975

SN - 2642-4150

JO - Journal of Polymer Science

JF - Journal of Polymer Science

ER -

Synthesis and chemoselective crosslinking of functionalized polyesters from bio-based epoxides and cyclic anhydrides

Abstract

Bibliographical note

Keywords

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