Experimental and computational investigations on ring-opening polymerization mechanisms of amide-functional benzoxazines

We observed an unusual low polymerization temperature for the ortho-amide benzoxazine in comparison with its para-isomer. Density functional theory (DFT) calculations suggested that the intramolecular hydrogen bond between the oxazine ring and the adjacent amide softens the C–O bond, resulting in a...
Ausführliche Beschreibung

Gespeichert in:

Autor*in:	Zhao, Wenqian [verfasserIn] Yang, Richie Yang, Shengfu Zhang, Kan

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2023

Schlagwörter:	Benzoxazine Amide Hydrogen bonding Polybenzoxazine Polymerization kinetics

Anmerkung:	© The Author(s), under exclusive licence to The Polymer Society of Korea 2023. Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Übergeordnetes Werk:	Enthalten in: Macromolecular research - Heidelberg : Springer, 2010, 31(2023), 1 vom: Jan., Seite 45-52
Übergeordnetes Werk:	volume:31 ; year:2023 ; number:1 ; month:01 ; pages:45-52

Links:	Volltext

DOI / URN:	10.1007/s13233-022-00105-6

Katalog-ID:	SPR051487713

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520			\|a We observed an unusual low polymerization temperature for the ortho-amide benzoxazine in comparison with its para-isomer. Density functional theory (DFT) calculations suggested that the intramolecular hydrogen bond between the oxazine ring and the adjacent amide softens the C–O bond, resulting in a reduced activation energy and thus a low ring-opening polymerization temperature. In addition, the polymerization kinetics of both para- and ortho-amide functional benzoxazines were investigated using the Starink method, which confirmed a relatively lower activation energy for the ortho-amide functional benzoxazine compared with its para-isomer. Our work suggests that softening chemical bonds by intramolecular hydrogen bonding may become a new strategy for the design of high-performance polybenzoxazine thermosets with low processing temperatures. Graphical abstract
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allfields	10.1007/s13233-022-00105-6 doi (DE-627)SPR051487713 (SPR)s13233-022-00105-6-e DE-627 ger DE-627 rakwb eng Zhao, Wenqian verfasserin aut Experimental and computational investigations on ring-opening polymerization mechanisms of amide-functional benzoxazines 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © The Author(s), under exclusive licence to The Polymer Society of Korea 2023. Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law. We observed an unusual low polymerization temperature for the ortho-amide benzoxazine in comparison with its para-isomer. Density functional theory (DFT) calculations suggested that the intramolecular hydrogen bond between the oxazine ring and the adjacent amide softens the C–O bond, resulting in a reduced activation energy and thus a low ring-opening polymerization temperature. In addition, the polymerization kinetics of both para- and ortho-amide functional benzoxazines were investigated using the Starink method, which confirmed a relatively lower activation energy for the ortho-amide functional benzoxazine compared with its para-isomer. Our work suggests that softening chemical bonds by intramolecular hydrogen bonding may become a new strategy for the design of high-performance polybenzoxazine thermosets with low processing temperatures. Graphical abstract Benzoxazine (dpeaa)DE-He213 Amide (dpeaa)DE-He213 Hydrogen bonding (dpeaa)DE-He213 Polybenzoxazine (dpeaa)DE-He213 Polymerization kinetics (dpeaa)DE-He213 Yang, Richie aut Yang, Shengfu aut Zhang, Kan (orcid)0000-0003-4628-2704 aut Enthalten in Macromolecular research Heidelberg : Springer, 2010 31(2023), 1 vom: Jan., Seite 45-52 (DE-627)618327576 (DE-600)2537708-5 2092-7673 nnns volume:31 year:2023 number:1 month:01 pages:45-52 https://dx.doi.org/10.1007/s13233-022-00105-6 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4328 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 31 2023 1 01 45-52
spelling	10.1007/s13233-022-00105-6 doi (DE-627)SPR051487713 (SPR)s13233-022-00105-6-e DE-627 ger DE-627 rakwb eng Zhao, Wenqian verfasserin aut Experimental and computational investigations on ring-opening polymerization mechanisms of amide-functional benzoxazines 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © The Author(s), under exclusive licence to The Polymer Society of Korea 2023. Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law. We observed an unusual low polymerization temperature for the ortho-amide benzoxazine in comparison with its para-isomer. Density functional theory (DFT) calculations suggested that the intramolecular hydrogen bond between the oxazine ring and the adjacent amide softens the C–O bond, resulting in a reduced activation energy and thus a low ring-opening polymerization temperature. In addition, the polymerization kinetics of both para- and ortho-amide functional benzoxazines were investigated using the Starink method, which confirmed a relatively lower activation energy for the ortho-amide functional benzoxazine compared with its para-isomer. Our work suggests that softening chemical bonds by intramolecular hydrogen bonding may become a new strategy for the design of high-performance polybenzoxazine thermosets with low processing temperatures. Graphical abstract Benzoxazine (dpeaa)DE-He213 Amide (dpeaa)DE-He213 Hydrogen bonding (dpeaa)DE-He213 Polybenzoxazine (dpeaa)DE-He213 Polymerization kinetics (dpeaa)DE-He213 Yang, Richie aut Yang, Shengfu aut Zhang, Kan (orcid)0000-0003-4628-2704 aut Enthalten in Macromolecular research Heidelberg : Springer, 2010 31(2023), 1 vom: Jan., Seite 45-52 (DE-627)618327576 (DE-600)2537708-5 2092-7673 nnns volume:31 year:2023 number:1 month:01 pages:45-52 https://dx.doi.org/10.1007/s13233-022-00105-6 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4328 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 31 2023 1 01 45-52
allfields_unstemmed	10.1007/s13233-022-00105-6 doi (DE-627)SPR051487713 (SPR)s13233-022-00105-6-e DE-627 ger DE-627 rakwb eng Zhao, Wenqian verfasserin aut Experimental and computational investigations on ring-opening polymerization mechanisms of amide-functional benzoxazines 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © The Author(s), under exclusive licence to The Polymer Society of Korea 2023. Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law. We observed an unusual low polymerization temperature for the ortho-amide benzoxazine in comparison with its para-isomer. Density functional theory (DFT) calculations suggested that the intramolecular hydrogen bond between the oxazine ring and the adjacent amide softens the C–O bond, resulting in a reduced activation energy and thus a low ring-opening polymerization temperature. In addition, the polymerization kinetics of both para- and ortho-amide functional benzoxazines were investigated using the Starink method, which confirmed a relatively lower activation energy for the ortho-amide functional benzoxazine compared with its para-isomer. Our work suggests that softening chemical bonds by intramolecular hydrogen bonding may become a new strategy for the design of high-performance polybenzoxazine thermosets with low processing temperatures. Graphical abstract Benzoxazine (dpeaa)DE-He213 Amide (dpeaa)DE-He213 Hydrogen bonding (dpeaa)DE-He213 Polybenzoxazine (dpeaa)DE-He213 Polymerization kinetics (dpeaa)DE-He213 Yang, Richie aut Yang, Shengfu aut Zhang, Kan (orcid)0000-0003-4628-2704 aut Enthalten in Macromolecular research Heidelberg : Springer, 2010 31(2023), 1 vom: Jan., Seite 45-52 (DE-627)618327576 (DE-600)2537708-5 2092-7673 nnns volume:31 year:2023 number:1 month:01 pages:45-52 https://dx.doi.org/10.1007/s13233-022-00105-6 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4328 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 31 2023 1 01 45-52
allfieldsGer	10.1007/s13233-022-00105-6 doi (DE-627)SPR051487713 (SPR)s13233-022-00105-6-e DE-627 ger DE-627 rakwb eng Zhao, Wenqian verfasserin aut Experimental and computational investigations on ring-opening polymerization mechanisms of amide-functional benzoxazines 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © The Author(s), under exclusive licence to The Polymer Society of Korea 2023. Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law. We observed an unusual low polymerization temperature for the ortho-amide benzoxazine in comparison with its para-isomer. Density functional theory (DFT) calculations suggested that the intramolecular hydrogen bond between the oxazine ring and the adjacent amide softens the C–O bond, resulting in a reduced activation energy and thus a low ring-opening polymerization temperature. In addition, the polymerization kinetics of both para- and ortho-amide functional benzoxazines were investigated using the Starink method, which confirmed a relatively lower activation energy for the ortho-amide functional benzoxazine compared with its para-isomer. Our work suggests that softening chemical bonds by intramolecular hydrogen bonding may become a new strategy for the design of high-performance polybenzoxazine thermosets with low processing temperatures. Graphical abstract Benzoxazine (dpeaa)DE-He213 Amide (dpeaa)DE-He213 Hydrogen bonding (dpeaa)DE-He213 Polybenzoxazine (dpeaa)DE-He213 Polymerization kinetics (dpeaa)DE-He213 Yang, Richie aut Yang, Shengfu aut Zhang, Kan (orcid)0000-0003-4628-2704 aut Enthalten in Macromolecular research Heidelberg : Springer, 2010 31(2023), 1 vom: Jan., Seite 45-52 (DE-627)618327576 (DE-600)2537708-5 2092-7673 nnns volume:31 year:2023 number:1 month:01 pages:45-52 https://dx.doi.org/10.1007/s13233-022-00105-6 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4328 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 31 2023 1 01 45-52
allfieldsSound	10.1007/s13233-022-00105-6 doi (DE-627)SPR051487713 (SPR)s13233-022-00105-6-e DE-627 ger DE-627 rakwb eng Zhao, Wenqian verfasserin aut Experimental and computational investigations on ring-opening polymerization mechanisms of amide-functional benzoxazines 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © The Author(s), under exclusive licence to The Polymer Society of Korea 2023. Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law. We observed an unusual low polymerization temperature for the ortho-amide benzoxazine in comparison with its para-isomer. Density functional theory (DFT) calculations suggested that the intramolecular hydrogen bond between the oxazine ring and the adjacent amide softens the C–O bond, resulting in a reduced activation energy and thus a low ring-opening polymerization temperature. In addition, the polymerization kinetics of both para- and ortho-amide functional benzoxazines were investigated using the Starink method, which confirmed a relatively lower activation energy for the ortho-amide functional benzoxazine compared with its para-isomer. Our work suggests that softening chemical bonds by intramolecular hydrogen bonding may become a new strategy for the design of high-performance polybenzoxazine thermosets with low processing temperatures. Graphical abstract Benzoxazine (dpeaa)DE-He213 Amide (dpeaa)DE-He213 Hydrogen bonding (dpeaa)DE-He213 Polybenzoxazine (dpeaa)DE-He213 Polymerization kinetics (dpeaa)DE-He213 Yang, Richie aut Yang, Shengfu aut Zhang, Kan (orcid)0000-0003-4628-2704 aut Enthalten in Macromolecular research Heidelberg : Springer, 2010 31(2023), 1 vom: Jan., Seite 45-52 (DE-627)618327576 (DE-600)2537708-5 2092-7673 nnns volume:31 year:2023 number:1 month:01 pages:45-52 https://dx.doi.org/10.1007/s13233-022-00105-6 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4328 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 31 2023 1 01 45-52
language	English
source	Enthalten in Macromolecular research 31(2023), 1 vom: Jan., Seite 45-52 volume:31 year:2023 number:1 month:01 pages:45-52
sourceStr	Enthalten in Macromolecular research 31(2023), 1 vom: Jan., Seite 45-52 volume:31 year:2023 number:1 month:01 pages:45-52
format_phy_str_mv	Article
institution	findex.gbv.de
topic_facet	Benzoxazine Amide Hydrogen bonding Polybenzoxazine Polymerization kinetics
isfreeaccess_bool	false
container_title	Macromolecular research
authorswithroles_txt_mv	Zhao, Wenqian @@aut@@ Yang, Richie @@aut@@ Yang, Shengfu @@aut@@ Zhang, Kan @@aut@@
publishDateDaySort_date	2023-01-01T00:00:00Z
hierarchy_top_id	618327576
id	SPR051487713
language_de	englisch
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Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.</subfield></datafield><datafield tag="520" ind1=" " ind2=" "><subfield code="a">We observed an unusual low polymerization temperature for the ortho-amide benzoxazine in comparison with its para-isomer. Density functional theory (DFT) calculations suggested that the intramolecular hydrogen bond between the oxazine ring and the adjacent amide softens the C–O bond, resulting in a reduced activation energy and thus a low ring-opening polymerization temperature. In addition, the polymerization kinetics of both para- and ortho-amide functional benzoxazines were investigated using the Starink method, which confirmed a relatively lower activation energy for the ortho-amide functional benzoxazine compared with its para-isomer. Our work suggests that softening chemical bonds by intramolecular hydrogen bonding may become a new strategy for the design of high-performance polybenzoxazine thermosets with low processing temperatures. 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author	Zhao, Wenqian
spellingShingle	Zhao, Wenqian misc Benzoxazine misc Amide misc Hydrogen bonding misc Polybenzoxazine misc Polymerization kinetics Experimental and computational investigations on ring-opening polymerization mechanisms of amide-functional benzoxazines
authorStr	Zhao, Wenqian
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topic_title	Experimental and computational investigations on ring-opening polymerization mechanisms of amide-functional benzoxazines Benzoxazine (dpeaa)DE-He213 Amide (dpeaa)DE-He213 Hydrogen bonding (dpeaa)DE-He213 Polybenzoxazine (dpeaa)DE-He213 Polymerization kinetics (dpeaa)DE-He213
topic	misc Benzoxazine misc Amide misc Hydrogen bonding misc Polybenzoxazine misc Polymerization kinetics
topic_unstemmed	misc Benzoxazine misc Amide misc Hydrogen bonding misc Polybenzoxazine misc Polymerization kinetics
topic_browse	misc Benzoxazine misc Amide misc Hydrogen bonding misc Polybenzoxazine misc Polymerization kinetics
format_facet	Elektronische Aufsätze Aufsätze Elektronische Ressource
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title	Experimental and computational investigations on ring-opening polymerization mechanisms of amide-functional benzoxazines
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title_full	Experimental and computational investigations on ring-opening polymerization mechanisms of amide-functional benzoxazines
author_sort	Zhao, Wenqian
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author_browse	Zhao, Wenqian Yang, Richie Yang, Shengfu Zhang, Kan
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author-letter	Zhao, Wenqian
doi_str_mv	10.1007/s13233-022-00105-6
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title_sort	experimental and computational investigations on ring-opening polymerization mechanisms of amide-functional benzoxazines
title_auth	Experimental and computational investigations on ring-opening polymerization mechanisms of amide-functional benzoxazines
abstract	We observed an unusual low polymerization temperature for the ortho-amide benzoxazine in comparison with its para-isomer. Density functional theory (DFT) calculations suggested that the intramolecular hydrogen bond between the oxazine ring and the adjacent amide softens the C–O bond, resulting in a reduced activation energy and thus a low ring-opening polymerization temperature. In addition, the polymerization kinetics of both para- and ortho-amide functional benzoxazines were investigated using the Starink method, which confirmed a relatively lower activation energy for the ortho-amide functional benzoxazine compared with its para-isomer. Our work suggests that softening chemical bonds by intramolecular hydrogen bonding may become a new strategy for the design of high-performance polybenzoxazine thermosets with low processing temperatures. Graphical abstract © The Author(s), under exclusive licence to The Polymer Society of Korea 2023. Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
abstractGer	We observed an unusual low polymerization temperature for the ortho-amide benzoxazine in comparison with its para-isomer. Density functional theory (DFT) calculations suggested that the intramolecular hydrogen bond between the oxazine ring and the adjacent amide softens the C–O bond, resulting in a reduced activation energy and thus a low ring-opening polymerization temperature. In addition, the polymerization kinetics of both para- and ortho-amide functional benzoxazines were investigated using the Starink method, which confirmed a relatively lower activation energy for the ortho-amide functional benzoxazine compared with its para-isomer. Our work suggests that softening chemical bonds by intramolecular hydrogen bonding may become a new strategy for the design of high-performance polybenzoxazine thermosets with low processing temperatures. Graphical abstract © The Author(s), under exclusive licence to The Polymer Society of Korea 2023. Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
abstract_unstemmed	We observed an unusual low polymerization temperature for the ortho-amide benzoxazine in comparison with its para-isomer. Density functional theory (DFT) calculations suggested that the intramolecular hydrogen bond between the oxazine ring and the adjacent amide softens the C–O bond, resulting in a reduced activation energy and thus a low ring-opening polymerization temperature. In addition, the polymerization kinetics of both para- and ortho-amide functional benzoxazines were investigated using the Starink method, which confirmed a relatively lower activation energy for the ortho-amide functional benzoxazine compared with its para-isomer. Our work suggests that softening chemical bonds by intramolecular hydrogen bonding may become a new strategy for the design of high-performance polybenzoxazine thermosets with low processing temperatures. Graphical abstract © The Author(s), under exclusive licence to The Polymer Society of Korea 2023. Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
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title_short	Experimental and computational investigations on ring-opening polymerization mechanisms of amide-functional benzoxazines
url	https://dx.doi.org/10.1007/s13233-022-00105-6
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author2	Yang, Richie Yang, Shengfu Zhang, Kan
author2Str	Yang, Richie Yang, Shengfu Zhang, Kan
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doi_str	10.1007/s13233-022-00105-6
up_date	2024-07-03T22:06:16.632Z
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Experimental and computational investigations on ring-opening polymerization mechanisms of amide-functional benzoxazines

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