Synthesis, characterization and enzymatic degradation of copolymers of ε-caprolactone and hydroxy-fatty acids
Abstract New copolymers of ε-caprolactone with three hydroxy-fatty acids, 12-hydroxy stearic acid, 16-hydroxyhexadecanoic acid and ricinoleic acid, were synthesized by catalytic polyesterification. The reactions were carried out in solvent-free systems and in organic solvents as well, using tin(II)...
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Walter de Gruyter GmbH
2016
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crdegruyter:10.1515/pac-2016-0920 2024-09-15T17:46:10+00:00 Synthesis, characterization and enzymatic degradation of copolymers of ε-caprolactone and hydroxy-fatty acids Aparaschivei, Diana Todea, Anamaria Păuşescu, Iulia Badea, Valentin Medeleanu, Mihai Şişu, Eugen Puiu, Maria Chiriţă-Emandi, Adela Peter, Francisc 2016 http://dx.doi.org/10.1515/pac-2016-0920 https://www.degruyter.com/view/journals/pac/88/12/article-p1191.xml https://www.degruyter.com/document/doi/10.1515/pac-2016-0920/xml https://www.degruyter.com/document/doi/10.1515/pac-2016-0920/pdf en eng Walter de Gruyter GmbH Pure and Applied Chemistry volume 88, issue 12, page 1191-1201 ISSN 1365-3075 0033-4545 journal-article 2016 crdegruyter https://doi.org/10.1515/pac-2016-0920 2024-07-15T04:11:27Z Abstract New copolymers of ε-caprolactone with three hydroxy-fatty acids, 12-hydroxy stearic acid, 16-hydroxyhexadecanoic acid and ricinoleic acid, were synthesized by catalytic polyesterification. The reactions were carried out in solvent-free systems and in organic solvents as well, using tin(II) 2-ethylhexanoate as catalyst, at different temperatures and molar ratios of the comonomers. Cyclic and linear polymeric products with medium molar weight of about 2000 Da have been synthesized and their chemical structures were confirmed by FT-IR, NMR and MALDI-TOF MS analysis. The synthesis parameters were optimized and the ε-caprolactone/hydroxy acid molar ratio was set as 5:1, according to mass spectrometry results. The biodegradability of the newly synthesized polymers was studied in the presence of Candida antarctica B lipase in phosphate buffer solutions (pH=7.4), at 37°C. The weight-loss profile emphasized the degradation of the 16-hydroxyhexadecanoic acid based polymer samples at more than 50% of their initial weight in 18 days of incubation in the presence of the lipase. The composition of the degradation products was assessed using the GC-MS technique and displayed residues of the comonomers moieties. Article in Journal/Newspaper Antarc* Antarctica De Gruyter Pure and Applied Chemistry 88 12 1191 1201 |
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English |
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Abstract New copolymers of ε-caprolactone with three hydroxy-fatty acids, 12-hydroxy stearic acid, 16-hydroxyhexadecanoic acid and ricinoleic acid, were synthesized by catalytic polyesterification. The reactions were carried out in solvent-free systems and in organic solvents as well, using tin(II) 2-ethylhexanoate as catalyst, at different temperatures and molar ratios of the comonomers. Cyclic and linear polymeric products with medium molar weight of about 2000 Da have been synthesized and their chemical structures were confirmed by FT-IR, NMR and MALDI-TOF MS analysis. The synthesis parameters were optimized and the ε-caprolactone/hydroxy acid molar ratio was set as 5:1, according to mass spectrometry results. The biodegradability of the newly synthesized polymers was studied in the presence of Candida antarctica B lipase in phosphate buffer solutions (pH=7.4), at 37°C. The weight-loss profile emphasized the degradation of the 16-hydroxyhexadecanoic acid based polymer samples at more than 50% of their initial weight in 18 days of incubation in the presence of the lipase. The composition of the degradation products was assessed using the GC-MS technique and displayed residues of the comonomers moieties. |
format |
Article in Journal/Newspaper |
author |
Aparaschivei, Diana Todea, Anamaria Păuşescu, Iulia Badea, Valentin Medeleanu, Mihai Şişu, Eugen Puiu, Maria Chiriţă-Emandi, Adela Peter, Francisc |
spellingShingle |
Aparaschivei, Diana Todea, Anamaria Păuşescu, Iulia Badea, Valentin Medeleanu, Mihai Şişu, Eugen Puiu, Maria Chiriţă-Emandi, Adela Peter, Francisc Synthesis, characterization and enzymatic degradation of copolymers of ε-caprolactone and hydroxy-fatty acids |
author_facet |
Aparaschivei, Diana Todea, Anamaria Păuşescu, Iulia Badea, Valentin Medeleanu, Mihai Şişu, Eugen Puiu, Maria Chiriţă-Emandi, Adela Peter, Francisc |
author_sort |
Aparaschivei, Diana |
title |
Synthesis, characterization and enzymatic degradation of copolymers of ε-caprolactone and hydroxy-fatty acids |
title_short |
Synthesis, characterization and enzymatic degradation of copolymers of ε-caprolactone and hydroxy-fatty acids |
title_full |
Synthesis, characterization and enzymatic degradation of copolymers of ε-caprolactone and hydroxy-fatty acids |
title_fullStr |
Synthesis, characterization and enzymatic degradation of copolymers of ε-caprolactone and hydroxy-fatty acids |
title_full_unstemmed |
Synthesis, characterization and enzymatic degradation of copolymers of ε-caprolactone and hydroxy-fatty acids |
title_sort |
synthesis, characterization and enzymatic degradation of copolymers of ε-caprolactone and hydroxy-fatty acids |
publisher |
Walter de Gruyter GmbH |
publishDate |
2016 |
url |
http://dx.doi.org/10.1515/pac-2016-0920 https://www.degruyter.com/view/journals/pac/88/12/article-p1191.xml https://www.degruyter.com/document/doi/10.1515/pac-2016-0920/xml https://www.degruyter.com/document/doi/10.1515/pac-2016-0920/pdf |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Pure and Applied Chemistry volume 88, issue 12, page 1191-1201 ISSN 1365-3075 0033-4545 |
op_doi |
https://doi.org/10.1515/pac-2016-0920 |
container_title |
Pure and Applied Chemistry |
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88 |
container_issue |
12 |
container_start_page |
1191 |
op_container_end_page |
1201 |
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1810494149193891840 |