Synthesis and Characterization of Block Copolymers of Styrene-maleic Acid with Acrylamide and N,N-dimethylacrylamide

Thidarat Khaojanta; Wichaya Kalaithong; Runglawan Somsunan; Patchara Punyamoonwongsa; Anisa Mahomed; Paul D. Topham; Brian J. Tighe; Robert Molloy

doi:10.1002/pen.25986

Synthesis and Characterization of Block Copolymers of Styrene-maleic Acid with Acrylamide and N,N-dimethylacrylamide

Thidarat Khaojanta, Wichaya Kalaithong, Runglawan Somsunan, Patchara Punyamoonwongsa, Anisa Mahomed, Paul D. Topham, Brian J. Tighe, Robert Molloy^*

^*Corresponding author for this work

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

Abstract

Styrene-maleic acid (SMA) block copolymers with either acrylamide (AM) or N,N-dimethylacrylamide (DMA) have been synthesized via a 3-step process comprising: (1) photopolymerization of styrene and maleic anhydride in solution to yield an alternating styrene maleic anhydride (SMAnh) copolymer, (2) copolymerization of SMAnh with either AM or DMA to yield SMAnh-b-AM and SMAnh-b-DMA block copolymers and (3) hydrolysis of the anhydride groups to yield water-soluble SMA-b-AM and SMA-b-DMA block copolymers as the final products. With a view to their intended application in membrane protein solubilization, molecular weights are controlled to below 10,000 by the synthesis conditions employed in step (1), including using carbon tetrabromide (CBr4) as a chain transfer agent. The CBr4 also plays an important role in step (2). By terminating the SMAnh chain radicals from step (1) with C-Br bonds that are photolytically active, SMAnh chain radicals can be regenerated to act as macroinitiators for the polymerization of AM or DMA in step (2). Finally, following step (3) and due to the pH-dependency of the SMA chain conformation in solution, a pH of 7-8 is found to be optimal for enabling the final products to be precipitated in a solid form that is completely soluble in water.

Original language	English
Pages (from-to)	2031-2046
Number of pages	16
Journal	Polymer Engineering and Science
Volume	62
Issue number	6
Early online date	9 Apr 2022
DOIs	https://doi.org/10.1002/pen.25986
Publication status	Published - Jun 2022

Bibliographical note

© 2022 Society of Plastics Engineers. This is the peer reviewed version of the following article: 'Khaojanta, T., Kalaithong, W., Punyamoonwongsa, P., Mahomed, A. et al (2022) "Synthesis and Characterization of Block Copolymers of Styrene-maleic Acid with Acrylamide and N,N-dimethylacrylamide" Polymer Engineering and Science,' which has been published in final form at [Link to final article using the DOI here once published]. This article may be used for non-commercial purposes in accordance With Wiley Terms and Conditions for self-archiving. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited.

This research was supported by the Program Management Unit for Human Resources & Institutional Development, Research and Innovation; Office of National Higher Education, Science Research and Innovation Policy Council (NXPO) [Grant Number B16F640001] and the Center of Excellence in Materials Science and Technology, Chiang Mai University. The research also received support from the European Union’s Horizon 2020 research and innovation programme under the Marie Sklodowska-Curie grant agreement No. 871650 (MEDIPOL).

Keywords

N,N-dimethylacrylamide
acrylamide
block copolymers
membrane protein solubilization
styrene-maleic acid
styrene-maleic anhydride

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SMA Revised Manuscript (Accepted)
© 2022 Society of Plastics Engineers. This is the peer reviewed version of the following article: 'Khaojanta, T., Kalaithong, W., Punyamoonwongsa, P., Mahomed, A. et al (2022) "Synthesis and Characterization of Block Copolymers of Styrene-Maleic Acid with Acrylamide and N,N-dimethylacrylamide" Polymer Engineering and Science,' which has been published in final form at [Link to final article using the DOI here once published]. This article may be used for non-commercial purposes in accordance With Wiley Terms and Conditions for self-archiving.
Accepted author manuscript, 1.16 MBLicence: CC BY-NC-ND 4.0

Cite this

@article{d4ed3d5dbe0e4ed18e23b4391bcd0248,

title = "Synthesis and Characterization of Block Copolymers of Styrene-maleic Acid with Acrylamide and N,N-dimethylacrylamide",

abstract = "Styrene-maleic acid (SMA) block copolymers with either acrylamide (AM) or N,N-dimethylacrylamide (DMA) have been synthesized via a 3-step process comprising: (1) photopolymerization of styrene and maleic anhydride in solution to yield an alternating styrene maleic anhydride (SMAnh) copolymer, (2) copolymerization of SMAnh with either AM or DMA to yield SMAnh-b-AM and SMAnh-b-DMA block copolymers and (3) hydrolysis of the anhydride groups to yield water-soluble SMA-b-AM and SMA-b-DMA block copolymers as the final products. With a view to their intended application in membrane protein solubilization, molecular weights are controlled to below 10,000 by the synthesis conditions employed in step (1), including using carbon tetrabromide (CBr4) as a chain transfer agent. The CBr4 also plays an important role in step (2). By terminating the SMAnh chain radicals from step (1) with C-Br bonds that are photolytically active, SMAnh chain radicals can be regenerated to act as macroinitiators for the polymerization of AM or DMA in step (2). Finally, following step (3) and due to the pH-dependency of the SMA chain conformation in solution, a pH of 7-8 is found to be optimal for enabling the final products to be precipitated in a solid form that is completely soluble in water.",

keywords = "N,N-dimethylacrylamide, acrylamide, block copolymers, membrane protein solubilization, styrene-maleic acid, styrene-maleic anhydride",

author = "Thidarat Khaojanta and Wichaya Kalaithong and Runglawan Somsunan and Patchara Punyamoonwongsa and Anisa Mahomed and Topham, {Paul D.} and Tighe, {Brian J.} and Robert Molloy",

note = "{\textcopyright} 2022 Society of Plastics Engineers. This is the peer reviewed version of the following article: 'Khaojanta, T., Kalaithong, W., Punyamoonwongsa, P., Mahomed, A. et al (2022) {"}Synthesis and Characterization of Block Copolymers of Styrene-maleic Acid with Acrylamide and N,N-dimethylacrylamide{"} Polymer Engineering and Science,' which has been published in final form at [Link to final article using the DOI here once published]. This article may be used for non-commercial purposes in accordance With Wiley Terms and Conditions for self-archiving. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley{\textquoteright}s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited. This research was supported by the Program Management Unit for Human Resources & Institutional Development, Research and Innovation; Office of National Higher Education, Science Research and Innovation Policy Council (NXPO) [Grant Number B16F640001] and the Center of Excellence in Materials Science and Technology, Chiang Mai University. The research also received support from the European Union{\textquoteright}s Horizon 2020 research and innovation programme under the Marie Sklodowska-Curie grant agreement No. 871650 (MEDIPOL). ",

year = "2022",

month = jun,

doi = "10.1002/pen.25986",

language = "English",

volume = "62",

pages = "2031--2046",

number = "6",

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TY - JOUR

T1 - Synthesis and Characterization of Block Copolymers of Styrene-maleic Acid with Acrylamide and N,N-dimethylacrylamide

AU - Khaojanta, Thidarat

AU - Kalaithong, Wichaya

AU - Somsunan, Runglawan

AU - Punyamoonwongsa, Patchara

AU - Mahomed, Anisa

AU - Topham, Paul D.

AU - Tighe, Brian J.

AU - Molloy, Robert

N1 - © 2022 Society of Plastics Engineers. This is the peer reviewed version of the following article: 'Khaojanta, T., Kalaithong, W., Punyamoonwongsa, P., Mahomed, A. et al (2022) "Synthesis and Characterization of Block Copolymers of Styrene-maleic Acid with Acrylamide and N,N-dimethylacrylamide" Polymer Engineering and Science,' which has been published in final form at [Link to final article using the DOI here once published]. This article may be used for non-commercial purposes in accordance With Wiley Terms and Conditions for self-archiving. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited. This research was supported by the Program Management Unit for Human Resources & Institutional Development, Research and Innovation; Office of National Higher Education, Science Research and Innovation Policy Council (NXPO) [Grant Number B16F640001] and the Center of Excellence in Materials Science and Technology, Chiang Mai University. The research also received support from the European Union’s Horizon 2020 research and innovation programme under the Marie Sklodowska-Curie grant agreement No. 871650 (MEDIPOL).

PY - 2022/6

Y1 - 2022/6

N2 - Styrene-maleic acid (SMA) block copolymers with either acrylamide (AM) or N,N-dimethylacrylamide (DMA) have been synthesized via a 3-step process comprising: (1) photopolymerization of styrene and maleic anhydride in solution to yield an alternating styrene maleic anhydride (SMAnh) copolymer, (2) copolymerization of SMAnh with either AM or DMA to yield SMAnh-b-AM and SMAnh-b-DMA block copolymers and (3) hydrolysis of the anhydride groups to yield water-soluble SMA-b-AM and SMA-b-DMA block copolymers as the final products. With a view to their intended application in membrane protein solubilization, molecular weights are controlled to below 10,000 by the synthesis conditions employed in step (1), including using carbon tetrabromide (CBr4) as a chain transfer agent. The CBr4 also plays an important role in step (2). By terminating the SMAnh chain radicals from step (1) with C-Br bonds that are photolytically active, SMAnh chain radicals can be regenerated to act as macroinitiators for the polymerization of AM or DMA in step (2). Finally, following step (3) and due to the pH-dependency of the SMA chain conformation in solution, a pH of 7-8 is found to be optimal for enabling the final products to be precipitated in a solid form that is completely soluble in water.

AB - Styrene-maleic acid (SMA) block copolymers with either acrylamide (AM) or N,N-dimethylacrylamide (DMA) have been synthesized via a 3-step process comprising: (1) photopolymerization of styrene and maleic anhydride in solution to yield an alternating styrene maleic anhydride (SMAnh) copolymer, (2) copolymerization of SMAnh with either AM or DMA to yield SMAnh-b-AM and SMAnh-b-DMA block copolymers and (3) hydrolysis of the anhydride groups to yield water-soluble SMA-b-AM and SMA-b-DMA block copolymers as the final products. With a view to their intended application in membrane protein solubilization, molecular weights are controlled to below 10,000 by the synthesis conditions employed in step (1), including using carbon tetrabromide (CBr4) as a chain transfer agent. The CBr4 also plays an important role in step (2). By terminating the SMAnh chain radicals from step (1) with C-Br bonds that are photolytically active, SMAnh chain radicals can be regenerated to act as macroinitiators for the polymerization of AM or DMA in step (2). Finally, following step (3) and due to the pH-dependency of the SMA chain conformation in solution, a pH of 7-8 is found to be optimal for enabling the final products to be precipitated in a solid form that is completely soluble in water.

KW - N,N-dimethylacrylamide

KW - acrylamide

KW - block copolymers

KW - membrane protein solubilization

KW - styrene-maleic acid

KW - styrene-maleic anhydride

UR - https://onlinelibrary.wiley.com/doi/10.1002/pen.25986

UR - http://www.scopus.com/inward/record.url?scp=85127621880&partnerID=8YFLogxK

U2 - 10.1002/pen.25986

DO - 10.1002/pen.25986

M3 - Article

SN - 0032-3888

VL - 62

SP - 2031

EP - 2046

JO - Polymer Engineering and Science

JF - Polymer Engineering and Science

IS - 6

ER -

Synthesis and Characterization of Block Copolymers of Styrene-maleic Acid with Acrylamide and N,N-dimethylacrylamide

Abstract

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