Intrinsically Flame‐Retardant Polyamide 6 by Anionic Ring‐Opening Copolymerization with a Phosphorous‐Containing Comonomer
Abstract A three‐step synthetic route is established for the synthesis of a phosphorus‐containing ε‐caprolactam derivative, starting from cyclohex‐2‐enone and diphenylphosphinous chloride, followed by a Beckmann rearrangement. 2D NMR spectroscopy reveals that the phosphorus moiety is selectively loc...
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| Format: | Article |
| Language: | English |
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Wiley-VCH
2025-01-01
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| Series: | Macromolecular Materials and Engineering |
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| Online Access: | https://doi.org/10.1002/mame.202400253 |
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| author | Carlo Pani Hagen J. Altmann Patrick Probst Iris Elser Mark Steinmann Simon König Philipp Kreis Lisa Kuske Dominik Weidich Anke Gähr Jonas Groos Julian Kappler Janis Musso Dongren Wang Michael R. Buchmeiser |
| author_facet | Carlo Pani Hagen J. Altmann Patrick Probst Iris Elser Mark Steinmann Simon König Philipp Kreis Lisa Kuske Dominik Weidich Anke Gähr Jonas Groos Julian Kappler Janis Musso Dongren Wang Michael R. Buchmeiser |
| author_sort | Carlo Pani |
| collection | DOAJ |
| description | Abstract A three‐step synthetic route is established for the synthesis of a phosphorus‐containing ε‐caprolactam derivative, starting from cyclohex‐2‐enone and diphenylphosphinous chloride, followed by a Beckmann rearrangement. 2D NMR spectroscopy reveals that the phosphorus moiety is selectively localized at the 4‐position of the caprolactam ring. Different amounts of the phosphorus‐containing comonomer are systematically incorporated into polyamide 6 by anionic ring‐opening copolymerization with ε‐caprolactam at elevated temperatures. Polymerization reactions are initiated by a latent, CO2 protected N‐heterocyclic carbene in the presence of N‐acetyl caprolactam and MgCl2. The phosphorus content is determined by inductively‐coupled plasma‐optical emission spectroscopy (ICP‐OES) analysis. Limiting oxygen indices up to 23.5 are found for polymers containing ≈1 wt.‐% of phosphorus. The thermal properties of the copolymers are determined and compared to those of polyamide 6. |
| format | Article |
| id | doaj-art-a972409842b14bc899110c3a2a7354af |
| institution | Kabale University |
| issn | 1438-7492 1439-2054 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Wiley-VCH |
| record_format | Article |
| series | Macromolecular Materials and Engineering |
| spelling | doaj-art-a972409842b14bc899110c3a2a7354af2025-01-13T15:24:25ZengWiley-VCHMacromolecular Materials and Engineering1438-74921439-20542025-01-013101n/an/a10.1002/mame.202400253Intrinsically Flame‐Retardant Polyamide 6 by Anionic Ring‐Opening Copolymerization with a Phosphorous‐Containing ComonomerCarlo Pani0Hagen J. Altmann1Patrick Probst2Iris Elser3Mark Steinmann4Simon König5Philipp Kreis6Lisa Kuske7Dominik Weidich8Anke Gähr9Jonas Groos10Julian Kappler11Janis Musso12Dongren Wang13Michael R. Buchmeiser14Institute of Polymer Chemistry University of Stuttgart Pfaffenwaldring 55 70569 Stuttgart GermanyInstitute of Polymer Chemistry University of Stuttgart Pfaffenwaldring 55 70569 Stuttgart GermanyInstitute of Polymer Chemistry University of Stuttgart Pfaffenwaldring 55 70569 Stuttgart GermanyGerman Institutes of Textile and Fiber Research Denkendorf Körschtalstraße 26 73770 Denkendorf GermanyGerman Institutes of Textile and Fiber Research Denkendorf Körschtalstraße 26 73770 Denkendorf GermanyGerman Institutes of Textile and Fiber Research Denkendorf Körschtalstraße 26 73770 Denkendorf GermanyGerman Institutes of Textile and Fiber Research Denkendorf Körschtalstraße 26 73770 Denkendorf GermanyGerman Institutes of Textile and Fiber Research Denkendorf Körschtalstraße 26 73770 Denkendorf GermanyGerman Institutes of Textile and Fiber Research Denkendorf Körschtalstraße 26 73770 Denkendorf GermanyGerman Institutes of Textile and Fiber Research Denkendorf Körschtalstraße 26 73770 Denkendorf GermanyInstitute of Polymer Chemistry University of Stuttgart Pfaffenwaldring 55 70569 Stuttgart GermanyInstitute of Polymer Chemistry University of Stuttgart Pfaffenwaldring 55 70569 Stuttgart GermanyInstitute of Polymer Chemistry University of Stuttgart Pfaffenwaldring 55 70569 Stuttgart GermanyInstitute of Polymer Chemistry University of Stuttgart Pfaffenwaldring 55 70569 Stuttgart GermanyInstitute of Polymer Chemistry University of Stuttgart Pfaffenwaldring 55 70569 Stuttgart GermanyAbstract A three‐step synthetic route is established for the synthesis of a phosphorus‐containing ε‐caprolactam derivative, starting from cyclohex‐2‐enone and diphenylphosphinous chloride, followed by a Beckmann rearrangement. 2D NMR spectroscopy reveals that the phosphorus moiety is selectively localized at the 4‐position of the caprolactam ring. Different amounts of the phosphorus‐containing comonomer are systematically incorporated into polyamide 6 by anionic ring‐opening copolymerization with ε‐caprolactam at elevated temperatures. Polymerization reactions are initiated by a latent, CO2 protected N‐heterocyclic carbene in the presence of N‐acetyl caprolactam and MgCl2. The phosphorus content is determined by inductively‐coupled plasma‐optical emission spectroscopy (ICP‐OES) analysis. Limiting oxygen indices up to 23.5 are found for polymers containing ≈1 wt.‐% of phosphorus. The thermal properties of the copolymers are determined and compared to those of polyamide 6.https://doi.org/10.1002/mame.202400253cast polyamide 6flame retardantlatent |
| spellingShingle | Carlo Pani Hagen J. Altmann Patrick Probst Iris Elser Mark Steinmann Simon König Philipp Kreis Lisa Kuske Dominik Weidich Anke Gähr Jonas Groos Julian Kappler Janis Musso Dongren Wang Michael R. Buchmeiser Intrinsically Flame‐Retardant Polyamide 6 by Anionic Ring‐Opening Copolymerization with a Phosphorous‐Containing Comonomer Macromolecular Materials and Engineering cast polyamide 6 flame retardant latent |
| title | Intrinsically Flame‐Retardant Polyamide 6 by Anionic Ring‐Opening Copolymerization with a Phosphorous‐Containing Comonomer |
| title_full | Intrinsically Flame‐Retardant Polyamide 6 by Anionic Ring‐Opening Copolymerization with a Phosphorous‐Containing Comonomer |
| title_fullStr | Intrinsically Flame‐Retardant Polyamide 6 by Anionic Ring‐Opening Copolymerization with a Phosphorous‐Containing Comonomer |
| title_full_unstemmed | Intrinsically Flame‐Retardant Polyamide 6 by Anionic Ring‐Opening Copolymerization with a Phosphorous‐Containing Comonomer |
| title_short | Intrinsically Flame‐Retardant Polyamide 6 by Anionic Ring‐Opening Copolymerization with a Phosphorous‐Containing Comonomer |
| title_sort | intrinsically flame retardant polyamide 6 by anionic ring opening copolymerization with a phosphorous containing comonomer |
| topic | cast polyamide 6 flame retardant latent |
| url | https://doi.org/10.1002/mame.202400253 |
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