Synthesis and characterization of new methacrylate copolymers having pendant chloroacetophenon; monomer reactivity ratio, thermal degradation kinetics and biological activity
In this work, 2-(4-acetyl-2,6-dichloroanilino)-2-oxoethyl-2-methylprop-2-enoate (CFAOMA) monomer was synthesized and characterized. Then, copolymers of this monomer with glycidyl methacrylate (GMA) were synthesized by the free radical polymerization method at 65 °C in the 1,4-dioxane solvent. Struct...
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| Veröffentlicht in: | Polymer bulletin (Berlin, Germany) Germany), 2022-10, Vol.79 (10), p.8717-8742 |
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| creator | Erol, Ibrahim Hoşsöz, M. Onur Gurler, Zeki |
| description | In this work, 2-(4-acetyl-2,6-dichloroanilino)-2-oxoethyl-2-methylprop-2-enoate (CFAOMA) monomer was synthesized and characterized. Then, copolymers of this monomer with glycidyl methacrylate (GMA) were synthesized by the free radical polymerization method at 65 °C in the 1,4-dioxane solvent. Structural characterizations of all compounds were carried out using FTIR,
1
H- and
13
C-NMR techniques. The composition of the copolymers was determined by elemental analysis. The monomer reactivity ratios were by calculated Finemann-Ross(FR) and Kelen-Tudos(KT) method. Average monomer reactivity ratio values determined by both methods were found as 0.26 for CFAOMA and 0.36 for GMA. The glass transition temperature (Tg) value of polymers was determined by differential scanning calorimetry (DSC). According to the thermogravimetric analysis (TGA) data, the thermal stability of the poly(CFAOMA) was higher than copolymers. The molecular weights (Mw and Mn) and polydispersity index of the polymers were determined by gel permeation chromatography (GPC). The thermal decomposition activation energy (Ea) values of polymers were determined using the Ozawa and Kissinger methods. The Ea values of the copolymer were found between 111.03 and 134.71 kJ/ mol by the Ozawa method and 134.51–109.24 kJ/mol by the Kissinger method. Besides, the photo-stability of the copolymers was investigated. Finally, the biological activity of polymers was investigated against different types of bacteria and fungi. |
| doi_str_mv | 10.1007/s00289-021-03934-0 |
| format | Article |
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1
H- and
13
C-NMR techniques. The composition of the copolymers was determined by elemental analysis. The monomer reactivity ratios were by calculated Finemann-Ross(FR) and Kelen-Tudos(KT) method. Average monomer reactivity ratio values determined by both methods were found as 0.26 for CFAOMA and 0.36 for GMA. The glass transition temperature (Tg) value of polymers was determined by differential scanning calorimetry (DSC). According to the thermogravimetric analysis (TGA) data, the thermal stability of the poly(CFAOMA) was higher than copolymers. The molecular weights (Mw and Mn) and polydispersity index of the polymers were determined by gel permeation chromatography (GPC). The thermal decomposition activation energy (Ea) values of polymers were determined using the Ozawa and Kissinger methods. The Ea values of the copolymer were found between 111.03 and 134.71 kJ/ mol by the Ozawa method and 134.51–109.24 kJ/mol by the Kissinger method. Besides, the photo-stability of the copolymers was investigated. Finally, the biological activity of polymers was investigated against different types of bacteria and fungi.</description><identifier>ISSN: 0170-0839</identifier><identifier>EISSN: 1436-2449</identifier><identifier>DOI: 10.1007/s00289-021-03934-0</identifier><language>eng</language><publisher>Berlin/Heidelberg: Springer Berlin Heidelberg</publisher><subject>Antimicrobial agents ; Biological activity ; Characterization and Evaluation of Materials ; Chemical analysis ; Chemical synthesis ; Chemistry ; Chemistry and Materials Science ; Chlorine ; Complex Fluids and Microfluidics ; Copolymers ; Ethanol ; Free radical polymerization ; Free radicals ; Gel chromatography ; Glass transition temperature ; Heat resistance ; Monomers ; Nitrogen ; NMR ; Nuclear magnetic resonance ; Organic Chemistry ; Original Paper ; Physical Chemistry ; Physical properties ; Polydispersity ; Polymer Sciences ; Polymerization ; Polymers ; Polymethyl methacrylate ; Polyvinyl chloride ; Potash ; Potassium ; Reactivity ; Soft and Granular Matter ; Solvents ; Stability analysis ; Temperature ; Thermal decomposition ; Thermal degradation ; Thermal stability ; Thermogravimetric analysis</subject><ispartof>Polymer bulletin (Berlin, Germany), 2022-10, Vol.79 (10), p.8717-8742</ispartof><rights>The Author(s), under exclusive licence to Springer-Verlag GmbH Germany, part of Springer Nature 2021</rights><rights>The Author(s), under exclusive licence to Springer-Verlag GmbH Germany, part of Springer Nature 2021.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c319t-e24265a95f8771aa491d251e77df3f5861e16cbd9119de26d0cd6f61117db4cd3</citedby><cites>FETCH-LOGICAL-c319t-e24265a95f8771aa491d251e77df3f5861e16cbd9119de26d0cd6f61117db4cd3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s00289-021-03934-0$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://www.proquest.com/docview/2918136487?pq-origsite=primo$$EHTML$$P50$$Gproquest$$H</linktohtml><link.rule.ids>314,780,784,21388,27924,27925,33744,41488,42557,43805,51319,64385,64389,72469</link.rule.ids></links><search><creatorcontrib>Erol, Ibrahim</creatorcontrib><creatorcontrib>Hoşsöz, M. Onur</creatorcontrib><creatorcontrib>Gurler, Zeki</creatorcontrib><title>Synthesis and characterization of new methacrylate copolymers having pendant chloroacetophenon; monomer reactivity ratio, thermal degradation kinetics and biological activity</title><title>Polymer bulletin (Berlin, Germany)</title><addtitle>Polym. Bull</addtitle><description>In this work, 2-(4-acetyl-2,6-dichloroanilino)-2-oxoethyl-2-methylprop-2-enoate (CFAOMA) monomer was synthesized and characterized. Then, copolymers of this monomer with glycidyl methacrylate (GMA) were synthesized by the free radical polymerization method at 65 °C in the 1,4-dioxane solvent. Structural characterizations of all compounds were carried out using FTIR,
1
H- and
13
C-NMR techniques. The composition of the copolymers was determined by elemental analysis. The monomer reactivity ratios were by calculated Finemann-Ross(FR) and Kelen-Tudos(KT) method. Average monomer reactivity ratio values determined by both methods were found as 0.26 for CFAOMA and 0.36 for GMA. The glass transition temperature (Tg) value of polymers was determined by differential scanning calorimetry (DSC). According to the thermogravimetric analysis (TGA) data, the thermal stability of the poly(CFAOMA) was higher than copolymers. The molecular weights (Mw and Mn) and polydispersity index of the polymers were determined by gel permeation chromatography (GPC). The thermal decomposition activation energy (Ea) values of polymers were determined using the Ozawa and Kissinger methods. The Ea values of the copolymer were found between 111.03 and 134.71 kJ/ mol by the Ozawa method and 134.51–109.24 kJ/mol by the Kissinger method. Besides, the photo-stability of the copolymers was investigated. Finally, the biological activity of polymers was investigated against different types of bacteria and fungi.</description><subject>Antimicrobial agents</subject><subject>Biological activity</subject><subject>Characterization and Evaluation of Materials</subject><subject>Chemical analysis</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chlorine</subject><subject>Complex Fluids and Microfluidics</subject><subject>Copolymers</subject><subject>Ethanol</subject><subject>Free radical polymerization</subject><subject>Free radicals</subject><subject>Gel chromatography</subject><subject>Glass transition temperature</subject><subject>Heat resistance</subject><subject>Monomers</subject><subject>Nitrogen</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Organic Chemistry</subject><subject>Original Paper</subject><subject>Physical Chemistry</subject><subject>Physical properties</subject><subject>Polydispersity</subject><subject>Polymer Sciences</subject><subject>Polymerization</subject><subject>Polymers</subject><subject>Polymethyl methacrylate</subject><subject>Polyvinyl chloride</subject><subject>Potash</subject><subject>Potassium</subject><subject>Reactivity</subject><subject>Soft and Granular Matter</subject><subject>Solvents</subject><subject>Stability analysis</subject><subject>Temperature</subject><subject>Thermal decomposition</subject><subject>Thermal degradation</subject><subject>Thermal stability</subject><subject>Thermogravimetric analysis</subject><issn>0170-0839</issn><issn>1436-2449</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><sourceid>AFKRA</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><recordid>eNp9kUFr3DAQhUVpoNtt_kBPgl7rRCN5ZYueSmibQKCHJmejlcZrpbbkSkqC86P6G6PEKbn1MsPA994beIR8BHYCjDWniTHeqopxqJhQoq7YG7KBWsiK17V6SzYMGlaxVqh35H1KN6zcUsKG_P21-Dxgcolqb6kZdNQmY3QPOrvgaeipx3s6YR60icuoM1IT5jAuE8ZEB33n_IHO6K32ucjHEIM2mMM8oA_-C52CDwWlEYuvu3N5ofHJ-jMtsXHSI7V4iNqucb-dx-zM-szehTEcnCnMP-0HctTrMeHxy96S6-_frs7Oq8ufPy7Ovl5WRoDKFfKay51Wu75tGtC6VmD5DrBpbC_6XSsBQZq9VQDKIpeWGSt7CQCN3dfGii35tPrOMfy5xZS7m3AbfYnsuIIWhKzbplB8pUwMKUXsuzm6ScelA9Y99dKtvXSll-65lzK3RKyiVGB_wPhq_R_VI3Vrlm0</recordid><startdate>20221001</startdate><enddate>20221001</enddate><creator>Erol, Ibrahim</creator><creator>Hoşsöz, M. Onur</creator><creator>Gurler, Zeki</creator><general>Springer Berlin Heidelberg</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><scope>8FE</scope><scope>8FG</scope><scope>ABJCF</scope><scope>AFKRA</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>HCIFZ</scope><scope>KB.</scope><scope>PDBOC</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope></search><sort><creationdate>20221001</creationdate><title>Synthesis and characterization of new methacrylate copolymers having pendant chloroacetophenon; monomer reactivity ratio, thermal degradation kinetics and biological activity</title><author>Erol, Ibrahim ; Hoşsöz, M. Onur ; Gurler, Zeki</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c319t-e24265a95f8771aa491d251e77df3f5861e16cbd9119de26d0cd6f61117db4cd3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Antimicrobial agents</topic><topic>Biological activity</topic><topic>Characterization and Evaluation of Materials</topic><topic>Chemical analysis</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chlorine</topic><topic>Complex Fluids and Microfluidics</topic><topic>Copolymers</topic><topic>Ethanol</topic><topic>Free radical polymerization</topic><topic>Free radicals</topic><topic>Gel chromatography</topic><topic>Glass transition temperature</topic><topic>Heat resistance</topic><topic>Monomers</topic><topic>Nitrogen</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Organic Chemistry</topic><topic>Original Paper</topic><topic>Physical Chemistry</topic><topic>Physical properties</topic><topic>Polydispersity</topic><topic>Polymer Sciences</topic><topic>Polymerization</topic><topic>Polymers</topic><topic>Polymethyl methacrylate</topic><topic>Polyvinyl chloride</topic><topic>Potash</topic><topic>Potassium</topic><topic>Reactivity</topic><topic>Soft and Granular Matter</topic><topic>Solvents</topic><topic>Stability analysis</topic><topic>Temperature</topic><topic>Thermal decomposition</topic><topic>Thermal degradation</topic><topic>Thermal stability</topic><topic>Thermogravimetric analysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Erol, Ibrahim</creatorcontrib><creatorcontrib>Hoşsöz, M. Onur</creatorcontrib><creatorcontrib>Gurler, Zeki</creatorcontrib><collection>CrossRef</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central</collection><collection>Technology Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central Korea</collection><collection>SciTech Premium Collection</collection><collection>Materials Science Database</collection><collection>Materials Science Collection</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><jtitle>Polymer bulletin (Berlin, Germany)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Erol, Ibrahim</au><au>Hoşsöz, M. Onur</au><au>Gurler, Zeki</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and characterization of new methacrylate copolymers having pendant chloroacetophenon; monomer reactivity ratio, thermal degradation kinetics and biological activity</atitle><jtitle>Polymer bulletin (Berlin, Germany)</jtitle><stitle>Polym. Bull</stitle><date>2022-10-01</date><risdate>2022</risdate><volume>79</volume><issue>10</issue><spage>8717</spage><epage>8742</epage><pages>8717-8742</pages><issn>0170-0839</issn><eissn>1436-2449</eissn><abstract>In this work, 2-(4-acetyl-2,6-dichloroanilino)-2-oxoethyl-2-methylprop-2-enoate (CFAOMA) monomer was synthesized and characterized. Then, copolymers of this monomer with glycidyl methacrylate (GMA) were synthesized by the free radical polymerization method at 65 °C in the 1,4-dioxane solvent. Structural characterizations of all compounds were carried out using FTIR,
1
H- and
13
C-NMR techniques. The composition of the copolymers was determined by elemental analysis. The monomer reactivity ratios were by calculated Finemann-Ross(FR) and Kelen-Tudos(KT) method. Average monomer reactivity ratio values determined by both methods were found as 0.26 for CFAOMA and 0.36 for GMA. The glass transition temperature (Tg) value of polymers was determined by differential scanning calorimetry (DSC). According to the thermogravimetric analysis (TGA) data, the thermal stability of the poly(CFAOMA) was higher than copolymers. The molecular weights (Mw and Mn) and polydispersity index of the polymers were determined by gel permeation chromatography (GPC). The thermal decomposition activation energy (Ea) values of polymers were determined using the Ozawa and Kissinger methods. The Ea values of the copolymer were found between 111.03 and 134.71 kJ/ mol by the Ozawa method and 134.51–109.24 kJ/mol by the Kissinger method. Besides, the photo-stability of the copolymers was investigated. Finally, the biological activity of polymers was investigated against different types of bacteria and fungi.</abstract><cop>Berlin/Heidelberg</cop><pub>Springer Berlin Heidelberg</pub><doi>10.1007/s00289-021-03934-0</doi><tpages>26</tpages></addata></record> |
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| subjects | Antimicrobial agents Biological activity Characterization and Evaluation of Materials Chemical analysis Chemical synthesis Chemistry Chemistry and Materials Science Chlorine Complex Fluids and Microfluidics Copolymers Ethanol Free radical polymerization Free radicals Gel chromatography Glass transition temperature Heat resistance Monomers Nitrogen NMR Nuclear magnetic resonance Organic Chemistry Original Paper Physical Chemistry Physical properties Polydispersity Polymer Sciences Polymerization Polymers Polymethyl methacrylate Polyvinyl chloride Potash Potassium Reactivity Soft and Granular Matter Solvents Stability analysis Temperature Thermal decomposition Thermal degradation Thermal stability Thermogravimetric analysis |
| title | Synthesis and characterization of new methacrylate copolymers having pendant chloroacetophenon; monomer reactivity ratio, thermal degradation kinetics and biological activity |
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