Cationic polyesters with antibacterial properties: Facile and controllable synthesis and antibacterial study

[Display omitted] •The synthesis reaction of cationic polyester is simple and controllable.•The ionic content on the surface and chain length affect the antibacterial properties of cationic polyester.•When the alkyl chain length of is 12, it has good antibacterial activity. In this work, biodegradab...

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Veröffentlicht in:European polymer journal 2019-01, Vol.110, p.41-48
Hauptverfasser: Yan, Jia, Zheng, Liuchun, Hu, Kun, Li, Luhai, Li, Chuncheng, Zhu, Li, Wang, Hengliang, Xiao, Yaonan, Wu, Shaohua, Liu, Jiajian, Zhang, Bo, Zhang, Fan
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container_end_page 48
container_issue
container_start_page 41
container_title European polymer journal
container_volume 110
creator Yan, Jia
Zheng, Liuchun
Hu, Kun
Li, Luhai
Li, Chuncheng
Zhu, Li
Wang, Hengliang
Xiao, Yaonan
Wu, Shaohua
Liu, Jiajian
Zhang, Bo
Zhang, Fan
description [Display omitted] •The synthesis reaction of cationic polyester is simple and controllable.•The ionic content on the surface and chain length affect the antibacterial properties of cationic polyester.•When the alkyl chain length of is 12, it has good antibacterial activity. In this work, biodegradable antimicrobial cationic copolyesters were prepared via a simple two-step process. Firstly, brominated poly(butylene succinate) (BPBS) was prepared by addition of bromine to carbon–carbon double bonds on the backbone of poly(butylene succinate-co-butylene fumarate) (PBSF). Then, the quaternization of BPBS with series of N,N-dimethyl alkylamines afforded poly(butylene succinate) containing quaternary ammonium cations (QPBS) with various ion contents and alkyl chain lengths. The structures of BPBS and QPBS were systematically characterized by NMR, ATR-FTIR, GPC and XPS. The hydrophilicity and the antibacterial activity have been studied by water contact angle (WCA), inhibition zone method, optical density method and scanning electron microscope (SEM). WCA test indicates that the hydrophilicity of polyester is greatly improved after the introduction of quaternary ammonium cations. The antibacterial study reveals that cationic copolyesters exhibited excellent antibacterial performance for both S. aureus and E. coli when the alkyl chain length was greater than 8, as compared with the ion content and alkyl chain length is a more important factor for the antibacterial performance. Considering the biodegradation, good antibacterial activities and simple process, this kind of material may have great potential to be applied as biomaterials.
doi_str_mv 10.1016/j.eurpolymj.2018.11.009
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In this work, biodegradable antimicrobial cationic copolyesters were prepared via a simple two-step process. Firstly, brominated poly(butylene succinate) (BPBS) was prepared by addition of bromine to carbon–carbon double bonds on the backbone of poly(butylene succinate-co-butylene fumarate) (PBSF). Then, the quaternization of BPBS with series of N,N-dimethyl alkylamines afforded poly(butylene succinate) containing quaternary ammonium cations (QPBS) with various ion contents and alkyl chain lengths. The structures of BPBS and QPBS were systematically characterized by NMR, ATR-FTIR, GPC and XPS. The hydrophilicity and the antibacterial activity have been studied by water contact angle (WCA), inhibition zone method, optical density method and scanning electron microscope (SEM). WCA test indicates that the hydrophilicity of polyester is greatly improved after the introduction of quaternary ammonium cations. The antibacterial study reveals that cationic copolyesters exhibited excellent antibacterial performance for both S. aureus and E. coli when the alkyl chain length was greater than 8, as compared with the ion content and alkyl chain length is a more important factor for the antibacterial performance. Considering the biodegradation, good antibacterial activities and simple process, this kind of material may have great potential to be applied as biomaterials.</description><identifier>ISSN: 0014-3057</identifier><identifier>EISSN: 1873-1945</identifier><identifier>DOI: 10.1016/j.eurpolymj.2018.11.009</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Alkylamines ; Antibacterial ; Biodegradability ; Biodegradable ; Biodegradation ; Biomedical materials ; Bromination ; Bromine ; Carbon ; Cationic ; Cations ; Chains ; Contact angle ; E coli ; Hydrophilicity ; NMR ; Nuclear magnetic resonance ; Optical density ; Poly(butylene succinate) ; Polyester resins ; Polyesters ; Quaternization ; Scanning electron microscopy ; X ray photoelectron spectroscopy</subject><ispartof>European polymer journal, 2019-01, Vol.110, p.41-48</ispartof><rights>2018 Elsevier Ltd</rights><rights>Copyright Elsevier BV Jan 2019</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c380t-51d0f2b1f6e3109d14fd3c59de50ce0a72433d795edbabaaaca83510058539723</citedby><cites>FETCH-LOGICAL-c380t-51d0f2b1f6e3109d14fd3c59de50ce0a72433d795edbabaaaca83510058539723</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.eurpolymj.2018.11.009$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids></links><search><creatorcontrib>Yan, Jia</creatorcontrib><creatorcontrib>Zheng, Liuchun</creatorcontrib><creatorcontrib>Hu, Kun</creatorcontrib><creatorcontrib>Li, Luhai</creatorcontrib><creatorcontrib>Li, Chuncheng</creatorcontrib><creatorcontrib>Zhu, Li</creatorcontrib><creatorcontrib>Wang, Hengliang</creatorcontrib><creatorcontrib>Xiao, Yaonan</creatorcontrib><creatorcontrib>Wu, Shaohua</creatorcontrib><creatorcontrib>Liu, Jiajian</creatorcontrib><creatorcontrib>Zhang, Bo</creatorcontrib><creatorcontrib>Zhang, Fan</creatorcontrib><title>Cationic polyesters with antibacterial properties: Facile and controllable synthesis and antibacterial study</title><title>European polymer journal</title><description>[Display omitted] •The synthesis reaction of cationic polyester is simple and controllable.•The ionic content on the surface and chain length affect the antibacterial properties of cationic polyester.•When the alkyl chain length of is 12, it has good antibacterial activity. In this work, biodegradable antimicrobial cationic copolyesters were prepared via a simple two-step process. Firstly, brominated poly(butylene succinate) (BPBS) was prepared by addition of bromine to carbon–carbon double bonds on the backbone of poly(butylene succinate-co-butylene fumarate) (PBSF). Then, the quaternization of BPBS with series of N,N-dimethyl alkylamines afforded poly(butylene succinate) containing quaternary ammonium cations (QPBS) with various ion contents and alkyl chain lengths. The structures of BPBS and QPBS were systematically characterized by NMR, ATR-FTIR, GPC and XPS. The hydrophilicity and the antibacterial activity have been studied by water contact angle (WCA), inhibition zone method, optical density method and scanning electron microscope (SEM). WCA test indicates that the hydrophilicity of polyester is greatly improved after the introduction of quaternary ammonium cations. The antibacterial study reveals that cationic copolyesters exhibited excellent antibacterial performance for both S. aureus and E. coli when the alkyl chain length was greater than 8, as compared with the ion content and alkyl chain length is a more important factor for the antibacterial performance. Considering the biodegradation, good antibacterial activities and simple process, this kind of material may have great potential to be applied as biomaterials.</description><subject>Alkylamines</subject><subject>Antibacterial</subject><subject>Biodegradability</subject><subject>Biodegradable</subject><subject>Biodegradation</subject><subject>Biomedical materials</subject><subject>Bromination</subject><subject>Bromine</subject><subject>Carbon</subject><subject>Cationic</subject><subject>Cations</subject><subject>Chains</subject><subject>Contact angle</subject><subject>E coli</subject><subject>Hydrophilicity</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Optical density</subject><subject>Poly(butylene succinate)</subject><subject>Polyester resins</subject><subject>Polyesters</subject><subject>Quaternization</subject><subject>Scanning electron microscopy</subject><subject>X ray photoelectron spectroscopy</subject><issn>0014-3057</issn><issn>1873-1945</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNqFUMtOwzAQtBBIlMI3EIlzwm5c1wm3quIlVeICZ8uxN6qjNCm2C-rf41KExInTSrMzszvD2DVCgYDz266gnd-O_X7TFSVgVSAWAPUJm2AleY71TJyyCQDOcg5CnrOLEDoAkHzOJ6xf6ujGwZnsYEEhkg_Zp4vrTA_RNdokwOk-2_pxSz46CnfZgzaup0SwmRmH6Me-100Cwn6IawoufK_-6kPc2f0lO2t1H-jqZ07Z28P96_IpX708Pi8Xq9zwCmIu0EJbNtjOiSPUFmet5UbUlgQYAi3LGedW1oJsoxuttdEVFwggKsFrWfIpuzn6pq_fdymU6sadH9JJVaKshOT1HBJLHlnGjyF4atXWu432e4WgDtWqTv1Wqw7VKkSVqk3KxVFJKcSHI6-CcTQYss6TicqO7l-PL6tcib0</recordid><startdate>201901</startdate><enddate>201901</enddate><creator>Yan, Jia</creator><creator>Zheng, Liuchun</creator><creator>Hu, Kun</creator><creator>Li, Luhai</creator><creator>Li, Chuncheng</creator><creator>Zhu, Li</creator><creator>Wang, Hengliang</creator><creator>Xiao, Yaonan</creator><creator>Wu, Shaohua</creator><creator>Liu, Jiajian</creator><creator>Zhang, Bo</creator><creator>Zhang, Fan</creator><general>Elsevier Ltd</general><general>Elsevier BV</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>201901</creationdate><title>Cationic polyesters with antibacterial properties: Facile and controllable synthesis and antibacterial study</title><author>Yan, Jia ; Zheng, Liuchun ; Hu, Kun ; Li, Luhai ; Li, Chuncheng ; Zhu, Li ; Wang, Hengliang ; Xiao, Yaonan ; Wu, Shaohua ; Liu, Jiajian ; Zhang, Bo ; Zhang, Fan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c380t-51d0f2b1f6e3109d14fd3c59de50ce0a72433d795edbabaaaca83510058539723</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Alkylamines</topic><topic>Antibacterial</topic><topic>Biodegradability</topic><topic>Biodegradable</topic><topic>Biodegradation</topic><topic>Biomedical materials</topic><topic>Bromination</topic><topic>Bromine</topic><topic>Carbon</topic><topic>Cationic</topic><topic>Cations</topic><topic>Chains</topic><topic>Contact angle</topic><topic>E coli</topic><topic>Hydrophilicity</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Optical density</topic><topic>Poly(butylene succinate)</topic><topic>Polyester resins</topic><topic>Polyesters</topic><topic>Quaternization</topic><topic>Scanning electron microscopy</topic><topic>X ray photoelectron spectroscopy</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yan, Jia</creatorcontrib><creatorcontrib>Zheng, Liuchun</creatorcontrib><creatorcontrib>Hu, Kun</creatorcontrib><creatorcontrib>Li, Luhai</creatorcontrib><creatorcontrib>Li, Chuncheng</creatorcontrib><creatorcontrib>Zhu, Li</creatorcontrib><creatorcontrib>Wang, Hengliang</creatorcontrib><creatorcontrib>Xiao, Yaonan</creatorcontrib><creatorcontrib>Wu, Shaohua</creatorcontrib><creatorcontrib>Liu, Jiajian</creatorcontrib><creatorcontrib>Zhang, Bo</creatorcontrib><creatorcontrib>Zhang, Fan</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>European polymer journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yan, Jia</au><au>Zheng, Liuchun</au><au>Hu, Kun</au><au>Li, Luhai</au><au>Li, Chuncheng</au><au>Zhu, Li</au><au>Wang, Hengliang</au><au>Xiao, Yaonan</au><au>Wu, Shaohua</au><au>Liu, Jiajian</au><au>Zhang, Bo</au><au>Zhang, Fan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cationic polyesters with antibacterial properties: Facile and controllable synthesis and antibacterial study</atitle><jtitle>European polymer journal</jtitle><date>2019-01</date><risdate>2019</risdate><volume>110</volume><spage>41</spage><epage>48</epage><pages>41-48</pages><issn>0014-3057</issn><eissn>1873-1945</eissn><abstract>[Display omitted] •The synthesis reaction of cationic polyester is simple and controllable.•The ionic content on the surface and chain length affect the antibacterial properties of cationic polyester.•When the alkyl chain length of is 12, it has good antibacterial activity. In this work, biodegradable antimicrobial cationic copolyesters were prepared via a simple two-step process. Firstly, brominated poly(butylene succinate) (BPBS) was prepared by addition of bromine to carbon–carbon double bonds on the backbone of poly(butylene succinate-co-butylene fumarate) (PBSF). Then, the quaternization of BPBS with series of N,N-dimethyl alkylamines afforded poly(butylene succinate) containing quaternary ammonium cations (QPBS) with various ion contents and alkyl chain lengths. The structures of BPBS and QPBS were systematically characterized by NMR, ATR-FTIR, GPC and XPS. The hydrophilicity and the antibacterial activity have been studied by water contact angle (WCA), inhibition zone method, optical density method and scanning electron microscope (SEM). WCA test indicates that the hydrophilicity of polyester is greatly improved after the introduction of quaternary ammonium cations. The antibacterial study reveals that cationic copolyesters exhibited excellent antibacterial performance for both S. aureus and E. coli when the alkyl chain length was greater than 8, as compared with the ion content and alkyl chain length is a more important factor for the antibacterial performance. Considering the biodegradation, good antibacterial activities and simple process, this kind of material may have great potential to be applied as biomaterials.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><doi>10.1016/j.eurpolymj.2018.11.009</doi><tpages>8</tpages></addata></record>
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subjects Alkylamines
Antibacterial
Biodegradability
Biodegradable
Biodegradation
Biomedical materials
Bromination
Bromine
Carbon
Cationic
Cations
Chains
Contact angle
E coli
Hydrophilicity
NMR
Nuclear magnetic resonance
Optical density
Poly(butylene succinate)
Polyester resins
Polyesters
Quaternization
Scanning electron microscopy
X ray photoelectron spectroscopy
title Cationic polyesters with antibacterial properties: Facile and controllable synthesis and antibacterial study
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