Amino functional poly(ethylene glycol) copolymers via protected amino glycidol

Boris Obermeier; Frederik Wurm; Holger Frey

doi:10.1021/ma902245d

Amino functional poly(ethylene glycol) copolymers via protected amino glycidol

Boris Obermeier, Frederik Wurm, Holger Frey^*

^*Corresponding author for this work

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

80 Citations (Scopus)

Abstract

The synthesis of poly (ethylene glycol) (PEG) copolymers with multiple amino functionalities within the chain is described, relying on an epoxide comonomer bearing a protected amino group. N,Ndibenzyl amino glycidol (DBAG) and ethylene oxide (EO) were copolymerized via anionic polymerization, leading to well-defined polymers with varied comonomer content and low polydispersities (M_w/M_n in the range of 1.1 to 1.2). Subsequent hydrogenolysis with Pearlman's catalyst afforded polyethylene glycol-coamino glycerols (PEG-coPAG) with a precisely adjusted number of randomly incorporated amino groups in the range of 2-15%. For the first time, the kinetics of an. EO copolymerizations have has been directly monitored by ¹H NMR spectroscopy in real time. Monomer consumption and compositional drift in monomer feed have been studied for various reaction temperatures, revealing a slightly tapered yet random DBAG distribution in the copolymers. The random structure of the copolymers was confirmed by detailed ¹³C NMR characterization of EO- and DBAG-centered triad sequence distribution and DSC measurements.

Original language	English
Pages (from-to)	2244-2251
Number of pages	8
Journal	Macromolecules
Volume	43
Issue number	5
DOIs	https://doi.org/10.1021/ma902245d
Publication status	Published - 9 Mar 2010
Externally published	Yes

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title = "Amino functional poly(ethylene glycol) copolymers via protected amino glycidol",

abstract = "The synthesis of poly (ethylene glycol) (PEG) copolymers with multiple amino functionalities within the chain is described, relying on an epoxide comonomer bearing a protected amino group. N,Ndibenzyl amino glycidol (DBAG) and ethylene oxide (EO) were copolymerized via anionic polymerization, leading to well-defined polymers with varied comonomer content and low polydispersities (Mw/Mn in the range of 1.1 to 1.2). Subsequent hydrogenolysis with Pearlman's catalyst afforded polyethylene glycol-coamino glycerols (PEG-coPAG) with a precisely adjusted number of randomly incorporated amino groups in the range of 2-15%. For the first time, the kinetics of an. EO copolymerizations have has been directly monitored by 1H NMR spectroscopy in real time. Monomer consumption and compositional drift in monomer feed have been studied for various reaction temperatures, revealing a slightly tapered yet random DBAG distribution in the copolymers. The random structure of the copolymers was confirmed by detailed 13C NMR characterization of EO- and DBAG-centered triad sequence distribution and DSC measurements.",

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year = "2010",

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T1 - Amino functional poly(ethylene glycol) copolymers via protected amino glycidol

AU - Obermeier, Boris

AU - Wurm, Frederik

AU - Frey, Holger

PY - 2010/3/9

Y1 - 2010/3/9

N2 - The synthesis of poly (ethylene glycol) (PEG) copolymers with multiple amino functionalities within the chain is described, relying on an epoxide comonomer bearing a protected amino group. N,Ndibenzyl amino glycidol (DBAG) and ethylene oxide (EO) were copolymerized via anionic polymerization, leading to well-defined polymers with varied comonomer content and low polydispersities (Mw/Mn in the range of 1.1 to 1.2). Subsequent hydrogenolysis with Pearlman's catalyst afforded polyethylene glycol-coamino glycerols (PEG-coPAG) with a precisely adjusted number of randomly incorporated amino groups in the range of 2-15%. For the first time, the kinetics of an. EO copolymerizations have has been directly monitored by 1H NMR spectroscopy in real time. Monomer consumption and compositional drift in monomer feed have been studied for various reaction temperatures, revealing a slightly tapered yet random DBAG distribution in the copolymers. The random structure of the copolymers was confirmed by detailed 13C NMR characterization of EO- and DBAG-centered triad sequence distribution and DSC measurements.

AB - The synthesis of poly (ethylene glycol) (PEG) copolymers with multiple amino functionalities within the chain is described, relying on an epoxide comonomer bearing a protected amino group. N,Ndibenzyl amino glycidol (DBAG) and ethylene oxide (EO) were copolymerized via anionic polymerization, leading to well-defined polymers with varied comonomer content and low polydispersities (Mw/Mn in the range of 1.1 to 1.2). Subsequent hydrogenolysis with Pearlman's catalyst afforded polyethylene glycol-coamino glycerols (PEG-coPAG) with a precisely adjusted number of randomly incorporated amino groups in the range of 2-15%. For the first time, the kinetics of an. EO copolymerizations have has been directly monitored by 1H NMR spectroscopy in real time. Monomer consumption and compositional drift in monomer feed have been studied for various reaction temperatures, revealing a slightly tapered yet random DBAG distribution in the copolymers. The random structure of the copolymers was confirmed by detailed 13C NMR characterization of EO- and DBAG-centered triad sequence distribution and DSC measurements.

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DO - 10.1021/ma902245d

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JO - Macromolecules

JF - Macromolecules

SN - 0024-9297

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ER -

Amino functional poly(ethylene glycol) copolymers via protected amino glycidol

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