An efficient and facile method of grafting Allyl groups to chemically resistant polyketone membranes
Polyketone is a thermoplastic polymer known for its strong mechanical properties and chemical resistance. Such superiorities make it difficult to process and chemically modify for further functionalizations and applications. In this work, we introduce a novel method for functionalizing the alpha car...
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Veröffentlicht in: | Polymer (Guilford) 2018-04, Vol.141, p.102-108 |
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description | Polyketone is a thermoplastic polymer known for its strong mechanical properties and chemical resistance. Such superiorities make it difficult to process and chemically modify for further functionalizations and applications. In this work, we introduce a novel method for functionalizing the alpha carbon of polyketone. We succeeded to attach allyl groups to the backbone of polyketone by a heterogeneous reaction between polyketone enolate and allyl bromide. Allylated polyketone is not soluble in common solvents. Since we started with a membrane of polyketone, there is no need to cast again. Further functionalization is possible through pending allyl groups via alkene addition reactions and ionic or radicalic polymerization. FTIR, elemental analysis, solid NMR, FT-Raman, SEM and XPS methods were employed to confirm the elemental composition, molecular structure and morphology. In addition, X-ray diffractometer (XRD), UV–Visible spectroscopy and thermal analysis were used to investigate the crystal structure, physical and electronic properties.
Grafting pending allyl groups onto polyketone polymer chain. [Display omitted]
•First chemical grafting method for heavy-molecular-weight polyketone (PK) polymers.•Carbonyl groups not interfered and only aliphatic part is mainly used for substitution.•Heterogenous reaction allowed a membrane of allylated polyketone (PK-allyl).•Further functionalization of PK-allyl polymer is possible via addition and polymerization.•Flexibility weakens, but membranes preserve thermal and apparent mechanical strength. |
doi_str_mv | 10.1016/j.polymer.2018.03.007 |
format | Article |
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Grafting pending allyl groups onto polyketone polymer chain. [Display omitted]
•First chemical grafting method for heavy-molecular-weight polyketone (PK) polymers.•Carbonyl groups not interfered and only aliphatic part is mainly used for substitution.•Heterogenous reaction allowed a membrane of allylated polyketone (PK-allyl).•Further functionalization of PK-allyl polymer is possible via addition and polymerization.•Flexibility weakens, but membranes preserve thermal and apparent mechanical strength.</description><identifier>ISSN: 0032-3861</identifier><identifier>EISSN: 1873-2291</identifier><identifier>DOI: 10.1016/j.polymer.2018.03.007</identifier><language>eng</language><publisher>Kidlington: Elsevier Ltd</publisher><subject>Addition polymerization ; Alkenes ; Allyl bromide ; Chemical composition ; Crystal structure ; Electronic properties ; Enolization ; Grafting ; Mechanical properties ; Membranes ; Molecular chains ; Molecular structure ; Morphology ; NMR ; Nuclear magnetic resonance ; Organic chemistry ; Polyketone ; Polymerization ; Polymers ; Potassium ; Potassium tert-butoxide ; Spectroscopy ; Thermal analysis ; Thermoplastic composites ; Thermoplastics ; X ray photoelectron spectroscopy ; X-ray diffraction</subject><ispartof>Polymer (Guilford), 2018-04, Vol.141, p.102-108</ispartof><rights>2018 Elsevier Ltd</rights><rights>Copyright Elsevier BV Apr 11, 2018</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c403t-7895ea94ab5c3265566940812cabe559d759bce5a85be4ed71005252e154e78f3</citedby><cites>FETCH-LOGICAL-c403t-7895ea94ab5c3265566940812cabe559d759bce5a85be4ed71005252e154e78f3</cites><orcidid>0000-0003-2488-1167 ; 0000-0002-5462-6039</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0032386118302052$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids></links><search><creatorcontrib>Jung, Youn Seo</creatorcontrib><creatorcontrib>Canlier, Ali</creatorcontrib><creatorcontrib>Hwang, Taek Sung</creatorcontrib><title>An efficient and facile method of grafting Allyl groups to chemically resistant polyketone membranes</title><title>Polymer (Guilford)</title><description>Polyketone is a thermoplastic polymer known for its strong mechanical properties and chemical resistance. Such superiorities make it difficult to process and chemically modify for further functionalizations and applications. In this work, we introduce a novel method for functionalizing the alpha carbon of polyketone. We succeeded to attach allyl groups to the backbone of polyketone by a heterogeneous reaction between polyketone enolate and allyl bromide. Allylated polyketone is not soluble in common solvents. Since we started with a membrane of polyketone, there is no need to cast again. Further functionalization is possible through pending allyl groups via alkene addition reactions and ionic or radicalic polymerization. FTIR, elemental analysis, solid NMR, FT-Raman, SEM and XPS methods were employed to confirm the elemental composition, molecular structure and morphology. In addition, X-ray diffractometer (XRD), UV–Visible spectroscopy and thermal analysis were used to investigate the crystal structure, physical and electronic properties.
Grafting pending allyl groups onto polyketone polymer chain. [Display omitted]
•First chemical grafting method for heavy-molecular-weight polyketone (PK) polymers.•Carbonyl groups not interfered and only aliphatic part is mainly used for substitution.•Heterogenous reaction allowed a membrane of allylated polyketone (PK-allyl).•Further functionalization of PK-allyl polymer is possible via addition and polymerization.•Flexibility weakens, but membranes preserve thermal and apparent mechanical strength.</description><subject>Addition polymerization</subject><subject>Alkenes</subject><subject>Allyl bromide</subject><subject>Chemical composition</subject><subject>Crystal structure</subject><subject>Electronic properties</subject><subject>Enolization</subject><subject>Grafting</subject><subject>Mechanical properties</subject><subject>Membranes</subject><subject>Molecular chains</subject><subject>Molecular structure</subject><subject>Morphology</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Organic chemistry</subject><subject>Polyketone</subject><subject>Polymerization</subject><subject>Polymers</subject><subject>Potassium</subject><subject>Potassium tert-butoxide</subject><subject>Spectroscopy</subject><subject>Thermal analysis</subject><subject>Thermoplastic composites</subject><subject>Thermoplastics</subject><subject>X ray photoelectron spectroscopy</subject><subject>X-ray diffraction</subject><issn>0032-3861</issn><issn>1873-2291</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNqFkE1LxDAQhoMouH78BCHguXWSNG16kkX8AsGLnkOaTjVr26xJVth_b8p69zTM1zvzPoRcMSgZsPpmU279uJ8wlByYKkGUAM0RWTHViILzlh2TFYDghVA1OyVnMW4AgEterUi_nikOg7MO50TN3NPBWDcinTB9-p76gX4EMyQ3f9D1OO7HnPrdNtLkqf3EyVmTqzRgdDGZLLG88oXJz4vE1AUzY7wgJ4MZI17-xXPy_nD_dvdUvLw-Pt-tXwpbgUhFo1qJpq1MJ63gtZR13VagGLemQynbvpFtZ1EaJTussG8YgMw2kMkKGzWIc3J90N0G_73DmPTG78KcT2oOUvFaCWjzlDxM2eBjDDjobXCTCXvNQC9A9Ub_AdULUA1CZ6B57_awh9nCj8vduFCz2LuANuneu38UfgFESIKM</recordid><startdate>20180411</startdate><enddate>20180411</enddate><creator>Jung, Youn Seo</creator><creator>Canlier, Ali</creator><creator>Hwang, Taek Sung</creator><general>Elsevier Ltd</general><general>Elsevier BV</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7QF</scope><scope>7QO</scope><scope>7QQ</scope><scope>7SC</scope><scope>7SE</scope><scope>7SP</scope><scope>7SR</scope><scope>7T7</scope><scope>7TA</scope><scope>7TB</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>C1K</scope><scope>F28</scope><scope>FR3</scope><scope>H8D</scope><scope>H8G</scope><scope>JG9</scope><scope>JQ2</scope><scope>KR7</scope><scope>L7M</scope><scope>L~C</scope><scope>L~D</scope><scope>P64</scope><orcidid>https://orcid.org/0000-0003-2488-1167</orcidid><orcidid>https://orcid.org/0000-0002-5462-6039</orcidid></search><sort><creationdate>20180411</creationdate><title>An efficient and facile method of grafting Allyl groups to chemically resistant polyketone membranes</title><author>Jung, Youn Seo ; Canlier, Ali ; Hwang, Taek Sung</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c403t-7895ea94ab5c3265566940812cabe559d759bce5a85be4ed71005252e154e78f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Addition polymerization</topic><topic>Alkenes</topic><topic>Allyl bromide</topic><topic>Chemical composition</topic><topic>Crystal structure</topic><topic>Electronic properties</topic><topic>Enolization</topic><topic>Grafting</topic><topic>Mechanical properties</topic><topic>Membranes</topic><topic>Molecular chains</topic><topic>Molecular structure</topic><topic>Morphology</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Organic chemistry</topic><topic>Polyketone</topic><topic>Polymerization</topic><topic>Polymers</topic><topic>Potassium</topic><topic>Potassium tert-butoxide</topic><topic>Spectroscopy</topic><topic>Thermal analysis</topic><topic>Thermoplastic composites</topic><topic>Thermoplastics</topic><topic>X ray photoelectron spectroscopy</topic><topic>X-ray diffraction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jung, Youn Seo</creatorcontrib><creatorcontrib>Canlier, Ali</creatorcontrib><creatorcontrib>Hwang, Taek Sung</creatorcontrib><collection>CrossRef</collection><collection>Aluminium Industry Abstracts</collection><collection>Biotechnology Research Abstracts</collection><collection>Ceramic Abstracts</collection><collection>Computer and Information Systems Abstracts</collection><collection>Corrosion Abstracts</collection><collection>Electronics & Communications Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Materials Business File</collection><collection>Mechanical & Transportation Engineering Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ANTE: Abstracts in New Technology & Engineering</collection><collection>Engineering Research Database</collection><collection>Aerospace Database</collection><collection>Copper Technical Reference Library</collection><collection>Materials Research Database</collection><collection>ProQuest Computer Science Collection</collection><collection>Civil Engineering Abstracts</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>Computer and Information Systems Abstracts Academic</collection><collection>Computer and Information Systems Abstracts Professional</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Polymer (Guilford)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Jung, Youn Seo</au><au>Canlier, Ali</au><au>Hwang, Taek Sung</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>An efficient and facile method of grafting Allyl groups to chemically resistant polyketone membranes</atitle><jtitle>Polymer (Guilford)</jtitle><date>2018-04-11</date><risdate>2018</risdate><volume>141</volume><spage>102</spage><epage>108</epage><pages>102-108</pages><issn>0032-3861</issn><eissn>1873-2291</eissn><abstract>Polyketone is a thermoplastic polymer known for its strong mechanical properties and chemical resistance. Such superiorities make it difficult to process and chemically modify for further functionalizations and applications. In this work, we introduce a novel method for functionalizing the alpha carbon of polyketone. We succeeded to attach allyl groups to the backbone of polyketone by a heterogeneous reaction between polyketone enolate and allyl bromide. Allylated polyketone is not soluble in common solvents. Since we started with a membrane of polyketone, there is no need to cast again. Further functionalization is possible through pending allyl groups via alkene addition reactions and ionic or radicalic polymerization. FTIR, elemental analysis, solid NMR, FT-Raman, SEM and XPS methods were employed to confirm the elemental composition, molecular structure and morphology. In addition, X-ray diffractometer (XRD), UV–Visible spectroscopy and thermal analysis were used to investigate the crystal structure, physical and electronic properties.
Grafting pending allyl groups onto polyketone polymer chain. [Display omitted]
•First chemical grafting method for heavy-molecular-weight polyketone (PK) polymers.•Carbonyl groups not interfered and only aliphatic part is mainly used for substitution.•Heterogenous reaction allowed a membrane of allylated polyketone (PK-allyl).•Further functionalization of PK-allyl polymer is possible via addition and polymerization.•Flexibility weakens, but membranes preserve thermal and apparent mechanical strength.</abstract><cop>Kidlington</cop><pub>Elsevier Ltd</pub><doi>10.1016/j.polymer.2018.03.007</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0003-2488-1167</orcidid><orcidid>https://orcid.org/0000-0002-5462-6039</orcidid></addata></record> |
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subjects | Addition polymerization Alkenes Allyl bromide Chemical composition Crystal structure Electronic properties Enolization Grafting Mechanical properties Membranes Molecular chains Molecular structure Morphology NMR Nuclear magnetic resonance Organic chemistry Polyketone Polymerization Polymers Potassium Potassium tert-butoxide Spectroscopy Thermal analysis Thermoplastic composites Thermoplastics X ray photoelectron spectroscopy X-ray diffraction |
title | An efficient and facile method of grafting Allyl groups to chemically resistant polyketone membranes |
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