Anionic Copolymerization of o-Phthalaldehyde with Epoxides: Facile Access to Degradable Polyacetals and Their Copolymers under Ambient Conditions

Naganath Patil; Yves Gnanou; Xiaoshuang Feng

doi:10.1021/acs.macromol.2c01363

Anionic Copolymerization of o-Phthalaldehyde with Epoxides: Facile Access to Degradable Polyacetals and Their Copolymers under Ambient Conditions

Naganath Patil, Yves Gnanou^*, Xiaoshuang Feng^*

^*Corresponding author for this work

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

13 Scopus citations

Abstract

Traditionally o-phthalaldehyde (OPA) has to be homopolymerized or copolymerized with other monomers at low temperature due to its very low ceiling temperature (T_c= -36 °C). In the presence of a Lewis acid such as triethylborane (TEB) the anionic copolymerization of OPA with various epoxides including ethylene oxide, propylene oxide, 1-butene oxide, 1-octene oxide, allyl glycidyl ether, phenyl glycidyl ether, and styrene oxide could be successfully carried out under ambient conditions, resulting in the formation of a host of polyacetals. The role and effect of TEB, its amount, and also the feeding ratio of OPA to epoxides during their copolymerizations were respectively investigated. The successful "living" OPA/epoxides copolymerization was further extended to the synthesis of polyether-b-polyacetal block copolymers with different structure and properties.

Original language	English (US)
Pages (from-to)	7817-7826
Number of pages	10
Journal	Macromolecules
Volume	55
Issue number	17
DOIs	https://doi.org/10.1021/acs.macromol.2c01363
State	Published - Sep 13 2022

Bibliographical note

Funding Information:
This research work is supported by KAUST under baseline funding (BAS/1/1374-01-01).

Publisher Copyright:
© 2022 American Chemical Society. All rights reserved.

ASJC Scopus subject areas

Organic Chemistry
Polymers and Plastics
Inorganic Chemistry
Materials Chemistry

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10.1021/acs.macromol.2c01363

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title = "Anionic Copolymerization of o-Phthalaldehyde with Epoxides: Facile Access to Degradable Polyacetals and Their Copolymers under Ambient Conditions",

abstract = "Traditionally o-phthalaldehyde (OPA) has to be homopolymerized or copolymerized with other monomers at low temperature due to its very low ceiling temperature (Tc= -36 °C). In the presence of a Lewis acid such as triethylborane (TEB) the anionic copolymerization of OPA with various epoxides including ethylene oxide, propylene oxide, 1-butene oxide, 1-octene oxide, allyl glycidyl ether, phenyl glycidyl ether, and styrene oxide could be successfully carried out under ambient conditions, resulting in the formation of a host of polyacetals. The role and effect of TEB, its amount, and also the feeding ratio of OPA to epoxides during their copolymerizations were respectively investigated. The successful {"}living{"} OPA/epoxides copolymerization was further extended to the synthesis of polyether-b-polyacetal block copolymers with different structure and properties.",

author = "Naganath Patil and Yves Gnanou and Xiaoshuang Feng",

note = "Funding Information: This research work is supported by KAUST under baseline funding (BAS/1/1374-01-01). Publisher Copyright: {\textcopyright} 2022 American Chemical Society. All rights reserved.",

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AU - Patil, Naganath

AU - Gnanou, Yves

AU - Feng, Xiaoshuang

PY - 2022/9/13

Y1 - 2022/9/13

N2 - Traditionally o-phthalaldehyde (OPA) has to be homopolymerized or copolymerized with other monomers at low temperature due to its very low ceiling temperature (Tc= -36 °C). In the presence of a Lewis acid such as triethylborane (TEB) the anionic copolymerization of OPA with various epoxides including ethylene oxide, propylene oxide, 1-butene oxide, 1-octene oxide, allyl glycidyl ether, phenyl glycidyl ether, and styrene oxide could be successfully carried out under ambient conditions, resulting in the formation of a host of polyacetals. The role and effect of TEB, its amount, and also the feeding ratio of OPA to epoxides during their copolymerizations were respectively investigated. The successful "living" OPA/epoxides copolymerization was further extended to the synthesis of polyether-b-polyacetal block copolymers with different structure and properties.

AB - Traditionally o-phthalaldehyde (OPA) has to be homopolymerized or copolymerized with other monomers at low temperature due to its very low ceiling temperature (Tc= -36 °C). In the presence of a Lewis acid such as triethylborane (TEB) the anionic copolymerization of OPA with various epoxides including ethylene oxide, propylene oxide, 1-butene oxide, 1-octene oxide, allyl glycidyl ether, phenyl glycidyl ether, and styrene oxide could be successfully carried out under ambient conditions, resulting in the formation of a host of polyacetals. The role and effect of TEB, its amount, and also the feeding ratio of OPA to epoxides during their copolymerizations were respectively investigated. The successful "living" OPA/epoxides copolymerization was further extended to the synthesis of polyether-b-polyacetal block copolymers with different structure and properties.

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DO - 10.1021/acs.macromol.2c01363

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Anionic Copolymerization of o-Phthalaldehyde with Epoxides: Facile Access to Degradable Polyacetals and Their Copolymers under Ambient Conditions

Abstract

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ASJC Scopus subject areas

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