Anomalous crystallinity in a semi-fluorinated perfluorocyclobutyl (PFCB) polymer containing the hexafluoro- i-propylidene (6F) linkage
The thermal cyclopolymerization of 2,2-bis(4-trifluorovinyloxyphenyl)-1,1,1,3,3,3-hexafluoropropane affords the first example of a semi-crystalline perfluorocyclobutyl (PFCB) polymer and an anomalous feature for a polymer containing the hexafluoroisopropylidene (6F) linkage. Fluoroalkylation of 2,2-...
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| Veröffentlicht in: | Polymer (Guilford) 2004-08, Vol.45 (17), p.5755-5760 |
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| creator | Smith, Dennis W. Jin, Jianyong Shah, Hiren V. Xie, Yuan DesMarteau, Darryl D. |
| description | The thermal cyclopolymerization of 2,2-bis(4-trifluorovinyloxyphenyl)-1,1,1,3,3,3-hexafluoropropane affords the first example of a semi-crystalline perfluorocyclobutyl (PFCB) polymer and an anomalous feature for a polymer containing the hexafluoroisopropylidene (6F) linkage. Fluoroalkylation of 2,2-bis(hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropane (6F bisphenol A) with 1,2-dibromotetrafluoroethane, followed by zinc mediated elimination affords the bis(trifluorovinyloxyphenyl) monomer in good yield. High molecular weight polymer (
M
w=66,700) with molecular weight distribution approaching 2 was obtained by heating neat monomer at 180 °C for 24 h and 220 °C for 8 h. The stereo-random polymer (ca. 48 to 52
cis- to
trans-1,2-disubstituted perfluorocyclobutyl groups) is easily crystallized from the melt despite the presence of the 6F group and a substantial increased fluorocarbon content per repeat unit compared to traditional PFCB polymers. A melting temperature approaching 200 °C was measured by DSC and the crystallinity was characterized by WAXD. Remarkably, the high melting semi-crystalline polymer could be easily dissolved in common solvents in greater than 50
wt% solutions. |
| doi_str_mv | 10.1016/j.polymer.2004.06.011 |
| format | Article |
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M
w=66,700) with molecular weight distribution approaching 2 was obtained by heating neat monomer at 180 °C for 24 h and 220 °C for 8 h. The stereo-random polymer (ca. 48 to 52
cis- to
trans-1,2-disubstituted perfluorocyclobutyl groups) is easily crystallized from the melt despite the presence of the 6F group and a substantial increased fluorocarbon content per repeat unit compared to traditional PFCB polymers. A melting temperature approaching 200 °C was measured by DSC and the crystallinity was characterized by WAXD. Remarkably, the high melting semi-crystalline polymer could be easily dissolved in common solvents in greater than 50
wt% solutions.</description><identifier>ISSN: 0032-3861</identifier><identifier>EISSN: 1873-2291</identifier><identifier>DOI: 10.1016/j.polymer.2004.06.011</identifier><identifier>CODEN: POLMAG</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Applied sciences ; Exact sciences and technology ; Hexafluoroisopropylidene ; Organic polymers ; Perfluorocyclobutyl polymer ; Physicochemistry of polymers ; Polymer crystallization ; Polymerization ; Preparation, kinetics, thermodynamics, mechanism and catalysts</subject><ispartof>Polymer (Guilford), 2004-08, Vol.45 (17), p.5755-5760</ispartof><rights>2004</rights><rights>2004 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c368t-af7e1fe0623742726fc3fee6f280a807ec209ce2a6155915a3e9ded97f5faf0d3</citedby><cites>FETCH-LOGICAL-c368t-af7e1fe0623742726fc3fee6f280a807ec209ce2a6155915a3e9ded97f5faf0d3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.polymer.2004.06.011$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=15984436$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Smith, Dennis W.</creatorcontrib><creatorcontrib>Jin, Jianyong</creatorcontrib><creatorcontrib>Shah, Hiren V.</creatorcontrib><creatorcontrib>Xie, Yuan</creatorcontrib><creatorcontrib>DesMarteau, Darryl D.</creatorcontrib><title>Anomalous crystallinity in a semi-fluorinated perfluorocyclobutyl (PFCB) polymer containing the hexafluoro- i-propylidene (6F) linkage</title><title>Polymer (Guilford)</title><description>The thermal cyclopolymerization of 2,2-bis(4-trifluorovinyloxyphenyl)-1,1,1,3,3,3-hexafluoropropane affords the first example of a semi-crystalline perfluorocyclobutyl (PFCB) polymer and an anomalous feature for a polymer containing the hexafluoroisopropylidene (6F) linkage. Fluoroalkylation of 2,2-bis(hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropane (6F bisphenol A) with 1,2-dibromotetrafluoroethane, followed by zinc mediated elimination affords the bis(trifluorovinyloxyphenyl) monomer in good yield. High molecular weight polymer (
M
w=66,700) with molecular weight distribution approaching 2 was obtained by heating neat monomer at 180 °C for 24 h and 220 °C for 8 h. The stereo-random polymer (ca. 48 to 52
cis- to
trans-1,2-disubstituted perfluorocyclobutyl groups) is easily crystallized from the melt despite the presence of the 6F group and a substantial increased fluorocarbon content per repeat unit compared to traditional PFCB polymers. A melting temperature approaching 200 °C was measured by DSC and the crystallinity was characterized by WAXD. Remarkably, the high melting semi-crystalline polymer could be easily dissolved in common solvents in greater than 50
wt% solutions.</description><subject>Applied sciences</subject><subject>Exact sciences and technology</subject><subject>Hexafluoroisopropylidene</subject><subject>Organic polymers</subject><subject>Perfluorocyclobutyl polymer</subject><subject>Physicochemistry of polymers</subject><subject>Polymer crystallization</subject><subject>Polymerization</subject><subject>Preparation, kinetics, thermodynamics, mechanism and catalysts</subject><issn>0032-3861</issn><issn>1873-2291</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><recordid>eNqFUM1u1DAQjhBILC2PgOQLqD0kHduJk5xQu2IBqRI9lLNlnHHrxbGD7UXkBXhuXHYljpxGI33_VfWGQkOBiqt9swS3zhgbBtA2IBqg9Fm1oUPPa8ZG-rzaAHBW80HQl9WrlPYAwDrWbqrf1z7MyoVDIjquKSvnrLd5JdYTRRLOtjbuEKL1KuNEFox_36BX7cK3Q14dubjbbW8uySkD0cFnVTT8A8mPSB7xlzpSamLrJYZldXZCj-RC7C5JcfuuHvC8emGUS_j6dM-qr7sP99tP9e2Xj5-317e15mLItTI9UoMgGO9b1jNhNDeIwrAB1AA9agajRqYE7bqRdorjOOE09qYzysDEz6p3R90S5McBU5azTRqdUx7LBpINbBC8ZQXYHYE6hpQiGrlEO6u4SgryaXW5l6fG8ml1CUKW1Qvv7clAJa2cicprm_6Ru3FoWy4K7v0Rh6XtT1tUkrboNU42os5yCvY_Tn8AspSeVA</recordid><startdate>20040805</startdate><enddate>20040805</enddate><creator>Smith, Dennis W.</creator><creator>Jin, Jianyong</creator><creator>Shah, Hiren V.</creator><creator>Xie, Yuan</creator><creator>DesMarteau, Darryl D.</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20040805</creationdate><title>Anomalous crystallinity in a semi-fluorinated perfluorocyclobutyl (PFCB) polymer containing the hexafluoro- i-propylidene (6F) linkage</title><author>Smith, Dennis W. ; Jin, Jianyong ; Shah, Hiren V. ; Xie, Yuan ; DesMarteau, Darryl D.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c368t-af7e1fe0623742726fc3fee6f280a807ec209ce2a6155915a3e9ded97f5faf0d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Applied sciences</topic><topic>Exact sciences and technology</topic><topic>Hexafluoroisopropylidene</topic><topic>Organic polymers</topic><topic>Perfluorocyclobutyl polymer</topic><topic>Physicochemistry of polymers</topic><topic>Polymer crystallization</topic><topic>Polymerization</topic><topic>Preparation, kinetics, thermodynamics, mechanism and catalysts</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Smith, Dennis W.</creatorcontrib><creatorcontrib>Jin, Jianyong</creatorcontrib><creatorcontrib>Shah, Hiren V.</creatorcontrib><creatorcontrib>Xie, Yuan</creatorcontrib><creatorcontrib>DesMarteau, Darryl D.</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Polymer (Guilford)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Smith, Dennis W.</au><au>Jin, Jianyong</au><au>Shah, Hiren V.</au><au>Xie, Yuan</au><au>DesMarteau, Darryl D.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Anomalous crystallinity in a semi-fluorinated perfluorocyclobutyl (PFCB) polymer containing the hexafluoro- i-propylidene (6F) linkage</atitle><jtitle>Polymer (Guilford)</jtitle><date>2004-08-05</date><risdate>2004</risdate><volume>45</volume><issue>17</issue><spage>5755</spage><epage>5760</epage><pages>5755-5760</pages><issn>0032-3861</issn><eissn>1873-2291</eissn><coden>POLMAG</coden><abstract>The thermal cyclopolymerization of 2,2-bis(4-trifluorovinyloxyphenyl)-1,1,1,3,3,3-hexafluoropropane affords the first example of a semi-crystalline perfluorocyclobutyl (PFCB) polymer and an anomalous feature for a polymer containing the hexafluoroisopropylidene (6F) linkage. Fluoroalkylation of 2,2-bis(hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropane (6F bisphenol A) with 1,2-dibromotetrafluoroethane, followed by zinc mediated elimination affords the bis(trifluorovinyloxyphenyl) monomer in good yield. High molecular weight polymer (
M
w=66,700) with molecular weight distribution approaching 2 was obtained by heating neat monomer at 180 °C for 24 h and 220 °C for 8 h. The stereo-random polymer (ca. 48 to 52
cis- to
trans-1,2-disubstituted perfluorocyclobutyl groups) is easily crystallized from the melt despite the presence of the 6F group and a substantial increased fluorocarbon content per repeat unit compared to traditional PFCB polymers. A melting temperature approaching 200 °C was measured by DSC and the crystallinity was characterized by WAXD. Remarkably, the high melting semi-crystalline polymer could be easily dissolved in common solvents in greater than 50
wt% solutions.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><doi>10.1016/j.polymer.2004.06.011</doi><tpages>6</tpages></addata></record> |
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| subjects | Applied sciences Exact sciences and technology Hexafluoroisopropylidene Organic polymers Perfluorocyclobutyl polymer Physicochemistry of polymers Polymer crystallization Polymerization Preparation, kinetics, thermodynamics, mechanism and catalysts |
| title | Anomalous crystallinity in a semi-fluorinated perfluorocyclobutyl (PFCB) polymer containing the hexafluoro- i-propylidene (6F) linkage |
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