Flexible oligomeric silicon‐containing poly(ether‐azomethine)s obtained from epoxide derivatives. Synthesis and characterization
ABSTRACT Three new diamines derived from epoxide compounds were synthesized. The preparation of diamine monomers implied the reaction between a phenoxyalkyloxirane (alkyl: H, methyl, isopropyl) and bisphenol A, obtaining the respective aliphatic diols, which produced the corresponding dinitro deriva...
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| Veröffentlicht in: | Journal of applied polymer science 2019-11, Vol.136 (42), p.n/a |
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| creator | Tundidor‐Camba, Alain Araya, Nélida González‐Henríquez, Carmen M. Tagle, Luis H. Hauyon, René A. Sobarzo, Patricio A. Rodríguez‐González, Fidel E. Jessop, Ignacio A. Recabarren‐Gajardo, Gonzalo Terraza, Claudio A. |
| description | ABSTRACT
Three new diamines derived from epoxide compounds were synthesized. The preparation of diamine monomers implied the reaction between a phenoxyalkyloxirane (alkyl: H, methyl, isopropyl) and bisphenol A, obtaining the respective aliphatic diols, which produced the corresponding dinitro derivatives. Finally, these derivatives were reduced by using palladium/carbon activated as catalyst and hydrazine as a hydrogen source. Then, six oligomeric poly(ether‐azomethine)s (PEAzMs) were obtained from a polycondensation reaction between the new diamines and bis(4‐formylbiphenyl‐4‐yl)dialkylsilane (alkyl: methyl, phenyl) with 84–93% yields. The structural characterization of the diamines and PEAzMs was performed by elemental analysis, infrared spectroscopy, and nuclear magnetic resonance spectroscopy (1H, 13C, and 29Si). Furthermore, polymers were analyzed by solubility tests, gel permeation chromatography, ultraviolet–visible (UV–vis) spectroscopy, thermogravimetry, and differential scanning calorimetry analysis. The results showed PEAzMs with 2–11 repetitive units, where the design of the monomers allowed to obtain improved solution processability in comparison with previously reported silylated poly(azomethine)s and good thermal stability. Additionally, all samples showed high transparency in the UV–vis region. © 2019 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2019, 136, 48055. |
| doi_str_mv | 10.1002/app.48055 |
| format | Article |
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Three new diamines derived from epoxide compounds were synthesized. The preparation of diamine monomers implied the reaction between a phenoxyalkyloxirane (alkyl: H, methyl, isopropyl) and bisphenol A, obtaining the respective aliphatic diols, which produced the corresponding dinitro derivatives. Finally, these derivatives were reduced by using palladium/carbon activated as catalyst and hydrazine as a hydrogen source. Then, six oligomeric poly(ether‐azomethine)s (PEAzMs) were obtained from a polycondensation reaction between the new diamines and bis(4‐formylbiphenyl‐4‐yl)dialkylsilane (alkyl: methyl, phenyl) with 84–93% yields. The structural characterization of the diamines and PEAzMs was performed by elemental analysis, infrared spectroscopy, and nuclear magnetic resonance spectroscopy (1H, 13C, and 29Si). Furthermore, polymers were analyzed by solubility tests, gel permeation chromatography, ultraviolet–visible (UV–vis) spectroscopy, thermogravimetry, and differential scanning calorimetry analysis. The results showed PEAzMs with 2–11 repetitive units, where the design of the monomers allowed to obtain improved solution processability in comparison with previously reported silylated poly(azomethine)s and good thermal stability. Additionally, all samples showed high transparency in the UV–vis region. © 2019 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2019, 136, 48055.</description><identifier>ISSN: 0021-8995</identifier><identifier>EISSN: 1097-4628</identifier><identifier>DOI: 10.1002/app.48055</identifier><language>eng</language><publisher>Hoboken, USA: John Wiley & Sons, Inc</publisher><subject>Activated carbon ; Aliphatic compounds ; Bisphenol A ; Derivatives ; Diamines ; Differential scanning calorimetry ; Diols ; flexibility ; Hydrazines ; Infrared analysis ; Liquid chromatography ; Materials science ; Monomers ; NMR ; Nuclear magnetic resonance ; Palladium ; Polyazomethines ; Polycondensation reactions ; Polymers ; silylated poly(ether‐azomethine)s ; Spectroscopic analysis ; Spectrum analysis ; Structural analysis ; Thermal stability ; thermal/optical properties ; Thermogravimetry</subject><ispartof>Journal of applied polymer science, 2019-11, Vol.136 (42), p.n/a</ispartof><rights>2019 Wiley Periodicals, Inc.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3345-974b44613b093825f7af26ed8c42c4e6548a9129ada9f6a2c6113aa618045f293</citedby><cites>FETCH-LOGICAL-c3345-974b44613b093825f7af26ed8c42c4e6548a9129ada9f6a2c6113aa618045f293</cites><orcidid>0000-0002-6326-8771</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fapp.48055$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fapp.48055$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>315,782,786,1419,27933,27934,45583,45584</link.rule.ids></links><search><creatorcontrib>Tundidor‐Camba, Alain</creatorcontrib><creatorcontrib>Araya, Nélida</creatorcontrib><creatorcontrib>González‐Henríquez, Carmen M.</creatorcontrib><creatorcontrib>Tagle, Luis H.</creatorcontrib><creatorcontrib>Hauyon, René A.</creatorcontrib><creatorcontrib>Sobarzo, Patricio A.</creatorcontrib><creatorcontrib>Rodríguez‐González, Fidel E.</creatorcontrib><creatorcontrib>Jessop, Ignacio A.</creatorcontrib><creatorcontrib>Recabarren‐Gajardo, Gonzalo</creatorcontrib><creatorcontrib>Terraza, Claudio A.</creatorcontrib><title>Flexible oligomeric silicon‐containing poly(ether‐azomethine)s obtained from epoxide derivatives. Synthesis and characterization</title><title>Journal of applied polymer science</title><description>ABSTRACT
Three new diamines derived from epoxide compounds were synthesized. The preparation of diamine monomers implied the reaction between a phenoxyalkyloxirane (alkyl: H, methyl, isopropyl) and bisphenol A, obtaining the respective aliphatic diols, which produced the corresponding dinitro derivatives. Finally, these derivatives were reduced by using palladium/carbon activated as catalyst and hydrazine as a hydrogen source. Then, six oligomeric poly(ether‐azomethine)s (PEAzMs) were obtained from a polycondensation reaction between the new diamines and bis(4‐formylbiphenyl‐4‐yl)dialkylsilane (alkyl: methyl, phenyl) with 84–93% yields. The structural characterization of the diamines and PEAzMs was performed by elemental analysis, infrared spectroscopy, and nuclear magnetic resonance spectroscopy (1H, 13C, and 29Si). Furthermore, polymers were analyzed by solubility tests, gel permeation chromatography, ultraviolet–visible (UV–vis) spectroscopy, thermogravimetry, and differential scanning calorimetry analysis. The results showed PEAzMs with 2–11 repetitive units, where the design of the monomers allowed to obtain improved solution processability in comparison with previously reported silylated poly(azomethine)s and good thermal stability. Additionally, all samples showed high transparency in the UV–vis region. © 2019 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2019, 136, 48055.</description><subject>Activated carbon</subject><subject>Aliphatic compounds</subject><subject>Bisphenol A</subject><subject>Derivatives</subject><subject>Diamines</subject><subject>Differential scanning calorimetry</subject><subject>Diols</subject><subject>flexibility</subject><subject>Hydrazines</subject><subject>Infrared analysis</subject><subject>Liquid chromatography</subject><subject>Materials science</subject><subject>Monomers</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Palladium</subject><subject>Polyazomethines</subject><subject>Polycondensation reactions</subject><subject>Polymers</subject><subject>silylated poly(ether‐azomethine)s</subject><subject>Spectroscopic analysis</subject><subject>Spectrum analysis</subject><subject>Structural analysis</subject><subject>Thermal stability</subject><subject>thermal/optical properties</subject><subject>Thermogravimetry</subject><issn>0021-8995</issn><issn>1097-4628</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp10L1OwzAQB3ALgUQpDLyBJRY6pPVX3HisKgpIlagEzJHjOK2rNA52WppODDwAz8iT4BJWlrN0_t2d9AfgGqMhRoiMZF0PWYLi-AT0MBLjiHGSnIJe-MNRIkR8Di68XyOEcYx4D3zOSr03WamhLc3SbrQzCnpTGmWr74-vUBtpKlMtYW3L9lY3K-1CXx4CbVam0gMPbXY0OoeFsxuoa7s3uYZ5WLWTjdlpP4TPbRUmvfFQVjlUK-mkagI4BGCrS3BWyNLrq7-3D15ndy_Th2j-dP84ncwjRSmLIzFmGWMc0wwJmpC4GMuCcJ0nihHFNI9ZIgUmQuZSFFwSxTGmUnKcIBYXRNA-uOn21s6-bbVv0rXduiqcTAnhnFBEaRLUoFPKWe-dLtLamY10bYpRegw5DSGnvyEHO-rsuyl1-z9MJ4tFN_EDeamCpQ</recordid><startdate>20191110</startdate><enddate>20191110</enddate><creator>Tundidor‐Camba, Alain</creator><creator>Araya, Nélida</creator><creator>González‐Henríquez, Carmen M.</creator><creator>Tagle, Luis H.</creator><creator>Hauyon, René A.</creator><creator>Sobarzo, Patricio A.</creator><creator>Rodríguez‐González, Fidel E.</creator><creator>Jessop, Ignacio A.</creator><creator>Recabarren‐Gajardo, Gonzalo</creator><creator>Terraza, Claudio A.</creator><general>John Wiley & Sons, Inc</general><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8FD</scope><scope>JG9</scope><orcidid>https://orcid.org/0000-0002-6326-8771</orcidid></search><sort><creationdate>20191110</creationdate><title>Flexible oligomeric silicon‐containing poly(ether‐azomethine)s obtained from epoxide derivatives. Synthesis and characterization</title><author>Tundidor‐Camba, Alain ; Araya, Nélida ; González‐Henríquez, Carmen M. ; Tagle, Luis H. ; Hauyon, René A. ; Sobarzo, Patricio A. ; Rodríguez‐González, Fidel E. ; Jessop, Ignacio A. ; Recabarren‐Gajardo, Gonzalo ; Terraza, Claudio A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3345-974b44613b093825f7af26ed8c42c4e6548a9129ada9f6a2c6113aa618045f293</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Activated carbon</topic><topic>Aliphatic compounds</topic><topic>Bisphenol A</topic><topic>Derivatives</topic><topic>Diamines</topic><topic>Differential scanning calorimetry</topic><topic>Diols</topic><topic>flexibility</topic><topic>Hydrazines</topic><topic>Infrared analysis</topic><topic>Liquid chromatography</topic><topic>Materials science</topic><topic>Monomers</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Palladium</topic><topic>Polyazomethines</topic><topic>Polycondensation reactions</topic><topic>Polymers</topic><topic>silylated poly(ether‐azomethine)s</topic><topic>Spectroscopic analysis</topic><topic>Spectrum analysis</topic><topic>Structural analysis</topic><topic>Thermal stability</topic><topic>thermal/optical properties</topic><topic>Thermogravimetry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tundidor‐Camba, Alain</creatorcontrib><creatorcontrib>Araya, Nélida</creatorcontrib><creatorcontrib>González‐Henríquez, Carmen M.</creatorcontrib><creatorcontrib>Tagle, Luis H.</creatorcontrib><creatorcontrib>Hauyon, René A.</creatorcontrib><creatorcontrib>Sobarzo, Patricio A.</creatorcontrib><creatorcontrib>Rodríguez‐González, Fidel E.</creatorcontrib><creatorcontrib>Jessop, Ignacio A.</creatorcontrib><creatorcontrib>Recabarren‐Gajardo, Gonzalo</creatorcontrib><creatorcontrib>Terraza, Claudio A.</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Journal of applied polymer science</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tundidor‐Camba, Alain</au><au>Araya, Nélida</au><au>González‐Henríquez, Carmen M.</au><au>Tagle, Luis H.</au><au>Hauyon, René A.</au><au>Sobarzo, Patricio A.</au><au>Rodríguez‐González, Fidel E.</au><au>Jessop, Ignacio A.</au><au>Recabarren‐Gajardo, Gonzalo</au><au>Terraza, Claudio A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Flexible oligomeric silicon‐containing poly(ether‐azomethine)s obtained from epoxide derivatives. Synthesis and characterization</atitle><jtitle>Journal of applied polymer science</jtitle><date>2019-11-10</date><risdate>2019</risdate><volume>136</volume><issue>42</issue><epage>n/a</epage><issn>0021-8995</issn><eissn>1097-4628</eissn><abstract>ABSTRACT
Three new diamines derived from epoxide compounds were synthesized. The preparation of diamine monomers implied the reaction between a phenoxyalkyloxirane (alkyl: H, methyl, isopropyl) and bisphenol A, obtaining the respective aliphatic diols, which produced the corresponding dinitro derivatives. Finally, these derivatives were reduced by using palladium/carbon activated as catalyst and hydrazine as a hydrogen source. Then, six oligomeric poly(ether‐azomethine)s (PEAzMs) were obtained from a polycondensation reaction between the new diamines and bis(4‐formylbiphenyl‐4‐yl)dialkylsilane (alkyl: methyl, phenyl) with 84–93% yields. The structural characterization of the diamines and PEAzMs was performed by elemental analysis, infrared spectroscopy, and nuclear magnetic resonance spectroscopy (1H, 13C, and 29Si). Furthermore, polymers were analyzed by solubility tests, gel permeation chromatography, ultraviolet–visible (UV–vis) spectroscopy, thermogravimetry, and differential scanning calorimetry analysis. The results showed PEAzMs with 2–11 repetitive units, where the design of the monomers allowed to obtain improved solution processability in comparison with previously reported silylated poly(azomethine)s and good thermal stability. Additionally, all samples showed high transparency in the UV–vis region. © 2019 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2019, 136, 48055.</abstract><cop>Hoboken, USA</cop><pub>John Wiley & Sons, Inc</pub><doi>10.1002/app.48055</doi><tpages>14</tpages><orcidid>https://orcid.org/0000-0002-6326-8771</orcidid></addata></record> |
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| subjects | Activated carbon Aliphatic compounds Bisphenol A Derivatives Diamines Differential scanning calorimetry Diols flexibility Hydrazines Infrared analysis Liquid chromatography Materials science Monomers NMR Nuclear magnetic resonance Palladium Polyazomethines Polycondensation reactions Polymers silylated poly(ether‐azomethine)s Spectroscopic analysis Spectrum analysis Structural analysis Thermal stability thermal/optical properties Thermogravimetry |
| title | Flexible oligomeric silicon‐containing poly(ether‐azomethine)s obtained from epoxide derivatives. Synthesis and characterization |
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