One‐step synthesis of polycarbonates bearing pendant carboxyl groups by lipase‐catalyzed ring‐opening polymerization
Abstract The ring‐opening polymerization of a monomer containing a free carboxylic acid group is reported for the first time. The monomer, 5‐methyl‐5‐carboxyl‐1,3‐dioxan‐2‐one (MCC), was copolymerized with trimethylene carbonate (TMC) in an enzymatic ring‐opening polymerization conducted in bulk at...
Published in: | Journal of Polymer Science Part A: Polymer Chemistry |
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crwiley:10.1002/pola.10212 2024-06-02T07:58:19+00:00 One‐step synthesis of polycarbonates bearing pendant carboxyl groups by lipase‐catalyzed ring‐opening polymerization Al‐Azemi, Talal F. Bisht, Kirpal S. 2002 http://dx.doi.org/10.1002/pola.10212 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fpola.10212 https://onlinelibrary.wiley.com/doi/pdf/10.1002/pola.10212 en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor Journal of Polymer Science Part A: Polymer Chemistry volume 40, issue 9, page 1267-1274 ISSN 0887-624X 1099-0518 journal-article 2002 crwiley https://doi.org/10.1002/pola.10212 2024-05-03T11:13:39Z Abstract The ring‐opening polymerization of a monomer containing a free carboxylic acid group is reported for the first time. The monomer, 5‐methyl‐5‐carboxyl‐1,3‐dioxan‐2‐one (MCC), was copolymerized with trimethylene carbonate (TMC) in an enzymatic ring‐opening polymerization conducted in bulk at 80 °C. The low‐melting TMC comonomer also solubilized the high‐melting MCC monomer, allowing for solvent‐free polymerizations. Six commercially available lipases were screened, and Candida antarctica lipase‐B (Novozym‐435) and Pseudomonas cepacia lipase were selected to catalyze the copolymerization because of their higher monomer conversions. Higher molecular weight polymers (weight‐average molecular weight = 7800–9200) were prepared when Novozym‐435 was used, with less MCC incorporated into the copolymer than used in the monomer feed. However, Pseudomonas cepacia lipase showed good agreement between the molar feed ratios and the molar composition, but the molecular weights (weight‐average molecular weight = 3600–4800) were lower than those obtained when Novozym‐435 was used. 13 C NMR spectral data were used for microstructural analysis, which suggested the formation of random, linear, and pendant carboxylic acid groups containing polycarbonates with hydroxyl groups at both chain ends. © 2002 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 40: 1267–1274, 2002 Article in Journal/Newspaper Antarc* Antarctica Wiley Online Library Journal of Polymer Science Part A: Polymer Chemistry 40 9 1267 1274 |
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Open Polar |
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Wiley Online Library |
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crwiley |
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English |
description |
Abstract The ring‐opening polymerization of a monomer containing a free carboxylic acid group is reported for the first time. The monomer, 5‐methyl‐5‐carboxyl‐1,3‐dioxan‐2‐one (MCC), was copolymerized with trimethylene carbonate (TMC) in an enzymatic ring‐opening polymerization conducted in bulk at 80 °C. The low‐melting TMC comonomer also solubilized the high‐melting MCC monomer, allowing for solvent‐free polymerizations. Six commercially available lipases were screened, and Candida antarctica lipase‐B (Novozym‐435) and Pseudomonas cepacia lipase were selected to catalyze the copolymerization because of their higher monomer conversions. Higher molecular weight polymers (weight‐average molecular weight = 7800–9200) were prepared when Novozym‐435 was used, with less MCC incorporated into the copolymer than used in the monomer feed. However, Pseudomonas cepacia lipase showed good agreement between the molar feed ratios and the molar composition, but the molecular weights (weight‐average molecular weight = 3600–4800) were lower than those obtained when Novozym‐435 was used. 13 C NMR spectral data were used for microstructural analysis, which suggested the formation of random, linear, and pendant carboxylic acid groups containing polycarbonates with hydroxyl groups at both chain ends. © 2002 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 40: 1267–1274, 2002 |
format |
Article in Journal/Newspaper |
author |
Al‐Azemi, Talal F. Bisht, Kirpal S. |
spellingShingle |
Al‐Azemi, Talal F. Bisht, Kirpal S. One‐step synthesis of polycarbonates bearing pendant carboxyl groups by lipase‐catalyzed ring‐opening polymerization |
author_facet |
Al‐Azemi, Talal F. Bisht, Kirpal S. |
author_sort |
Al‐Azemi, Talal F. |
title |
One‐step synthesis of polycarbonates bearing pendant carboxyl groups by lipase‐catalyzed ring‐opening polymerization |
title_short |
One‐step synthesis of polycarbonates bearing pendant carboxyl groups by lipase‐catalyzed ring‐opening polymerization |
title_full |
One‐step synthesis of polycarbonates bearing pendant carboxyl groups by lipase‐catalyzed ring‐opening polymerization |
title_fullStr |
One‐step synthesis of polycarbonates bearing pendant carboxyl groups by lipase‐catalyzed ring‐opening polymerization |
title_full_unstemmed |
One‐step synthesis of polycarbonates bearing pendant carboxyl groups by lipase‐catalyzed ring‐opening polymerization |
title_sort |
one‐step synthesis of polycarbonates bearing pendant carboxyl groups by lipase‐catalyzed ring‐opening polymerization |
publisher |
Wiley |
publishDate |
2002 |
url |
http://dx.doi.org/10.1002/pola.10212 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fpola.10212 https://onlinelibrary.wiley.com/doi/pdf/10.1002/pola.10212 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Journal of Polymer Science Part A: Polymer Chemistry volume 40, issue 9, page 1267-1274 ISSN 0887-624X 1099-0518 |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1002/pola.10212 |
container_title |
Journal of Polymer Science Part A: Polymer Chemistry |
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40 |
container_issue |
9 |
container_start_page |
1267 |
op_container_end_page |
1274 |
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1800741635541172224 |