Polyurethanes derived from carbohydrates and cystine-based monomers
ABSTRACT Linear [m,n]‐type polyurethanes (PUs) fully based on renewable materials are synthesized by interfacial polycondensation reaction of diamines derived from the amino‐acid cystine with (bis)chloroformates derived from alditols having L‐arabino or xylo configuration. The degradability of the n...
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| Veröffentlicht in: | Journal of applied polymer science 2015-01, Vol.132 (3), p.n/a |
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| container_title | Journal of applied polymer science |
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| creator | Begines, Belén Zamora, Francisca de Paz, M. Violante Hakkou, Khalid Galbis, Juan A. |
| description | ABSTRACT
Linear [m,n]‐type polyurethanes (PUs) fully based on renewable materials are synthesized by interfacial polycondensation reaction of diamines derived from the amino‐acid cystine with (bis)chloroformates derived from alditols having L‐arabino or xylo configuration. The degradability of the new PUs has been enhanced by the introduction of disulfide linkages into the polymer backbone leading to a new group of stimulus‐responsive sugar‐based polyurethanes able to be degraded by glutathione under physiological conditions. All these polyurethanes are stable up to around 245°C, decomposing at higher temperatures through a one‐stage mechanism. The new materials display high chemical homogeneity and degradability in both hydrolytic and reductive environments, with reductions of above 90% in Mw. © 2014 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2015, 132, 41304. |
| doi_str_mv | 10.1002/app.41304 |
| format | Article |
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Linear [m,n]‐type polyurethanes (PUs) fully based on renewable materials are synthesized by interfacial polycondensation reaction of diamines derived from the amino‐acid cystine with (bis)chloroformates derived from alditols having L‐arabino or xylo configuration. The degradability of the new PUs has been enhanced by the introduction of disulfide linkages into the polymer backbone leading to a new group of stimulus‐responsive sugar‐based polyurethanes able to be degraded by glutathione under physiological conditions. All these polyurethanes are stable up to around 245°C, decomposing at higher temperatures through a one‐stage mechanism. The new materials display high chemical homogeneity and degradability in both hydrolytic and reductive environments, with reductions of above 90% in Mw. © 2014 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2015, 132, 41304.</description><identifier>ISSN: 0021-8995</identifier><identifier>EISSN: 1097-4628</identifier><identifier>DOI: 10.1002/app.41304</identifier><identifier>CODEN: JAPNAB</identifier><language>eng</language><publisher>Hoboken: Blackwell Publishing Ltd</publisher><subject>biodegradable ; Carbohydrates ; Cystine ; Degradation ; Diamines ; Homogeneity ; Materials science ; Monomers ; polycondensation ; Polycondensation reactions ; Polymers ; Polyurethane resins ; polyurethanes ; thermal properties ; thermogravimetric analysis (TGA)</subject><ispartof>Journal of applied polymer science, 2015-01, Vol.132 (3), p.n/a</ispartof><rights>2014 Wiley Periodicals, Inc.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4424-9ec4b97b5ad5e5e9dd0bd391be386c6168e9911da684a87e7eef4a03c2383ce83</citedby><cites>FETCH-LOGICAL-c4424-9ec4b97b5ad5e5e9dd0bd391be386c6168e9911da684a87e7eef4a03c2383ce83</cites></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.41304$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fapp.41304$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids></links><search><creatorcontrib>Begines, Belén</creatorcontrib><creatorcontrib>Zamora, Francisca</creatorcontrib><creatorcontrib>de Paz, M. Violante</creatorcontrib><creatorcontrib>Hakkou, Khalid</creatorcontrib><creatorcontrib>Galbis, Juan A.</creatorcontrib><title>Polyurethanes derived from carbohydrates and cystine-based monomers</title><title>Journal of applied polymer science</title><addtitle>J. Appl. Polym. Sci</addtitle><description>ABSTRACT
Linear [m,n]‐type polyurethanes (PUs) fully based on renewable materials are synthesized by interfacial polycondensation reaction of diamines derived from the amino‐acid cystine with (bis)chloroformates derived from alditols having L‐arabino or xylo configuration. The degradability of the new PUs has been enhanced by the introduction of disulfide linkages into the polymer backbone leading to a new group of stimulus‐responsive sugar‐based polyurethanes able to be degraded by glutathione under physiological conditions. All these polyurethanes are stable up to around 245°C, decomposing at higher temperatures through a one‐stage mechanism. The new materials display high chemical homogeneity and degradability in both hydrolytic and reductive environments, with reductions of above 90% in Mw. © 2014 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2015, 132, 41304.</description><subject>biodegradable</subject><subject>Carbohydrates</subject><subject>Cystine</subject><subject>Degradation</subject><subject>Diamines</subject><subject>Homogeneity</subject><subject>Materials science</subject><subject>Monomers</subject><subject>polycondensation</subject><subject>Polycondensation reactions</subject><subject>Polymers</subject><subject>Polyurethane resins</subject><subject>polyurethanes</subject><subject>thermal properties</subject><subject>thermogravimetric analysis (TGA)</subject><issn>0021-8995</issn><issn>1097-4628</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNqF0E1P3DAQBmCrAqnL0kP_wUq9lEPAYzuOfUTLt4BupX4cLceeFaFJvNhZIP--hi09ICFOPszzjsYvIZ-B7gOl7MCuVvsCOBUfyASorgohmdoikzyDQmldfiQ7Kd1SClBSOSHzRWjHdcThxvaYZh5jc49-toyhmzkb63Az-miHPLK9n7kxDU2PRW1TRl3oQ4cx7ZLtpW0Tfvr3TsnPk-Mf87Pi8tvp-fzwsnBCMFFodKLWVV1aX2KJ2ntae66hRq6kkyAVag3grVTCqgorxKWwlDvGFXeo-JR83exdxXC3xjSYrkkO2zafHtbJQCVEBZwBe59KpnkJDGSmX17R27COff5IVsAUlyrbKdnbKBdDShGXZhWbzsbRADVPzZvcvHluPtuDjX1oWhzfhuZwsXhJFJtEkwZ8_J-w8Y-RFa9K8_v61LBfR4uL73BlTvhfDUKTag</recordid><startdate>20150115</startdate><enddate>20150115</enddate><creator>Begines, Belén</creator><creator>Zamora, Francisca</creator><creator>de Paz, M. Violante</creator><creator>Hakkou, Khalid</creator><creator>Galbis, Juan A.</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20150115</creationdate><title>Polyurethanes derived from carbohydrates and cystine-based monomers</title><author>Begines, Belén ; Zamora, Francisca ; de Paz, M. Violante ; Hakkou, Khalid ; Galbis, Juan A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4424-9ec4b97b5ad5e5e9dd0bd391be386c6168e9911da684a87e7eef4a03c2383ce83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>biodegradable</topic><topic>Carbohydrates</topic><topic>Cystine</topic><topic>Degradation</topic><topic>Diamines</topic><topic>Homogeneity</topic><topic>Materials science</topic><topic>Monomers</topic><topic>polycondensation</topic><topic>Polycondensation reactions</topic><topic>Polymers</topic><topic>Polyurethane resins</topic><topic>polyurethanes</topic><topic>thermal properties</topic><topic>thermogravimetric analysis (TGA)</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Begines, Belén</creatorcontrib><creatorcontrib>Zamora, Francisca</creatorcontrib><creatorcontrib>de Paz, M. Violante</creatorcontrib><creatorcontrib>Hakkou, Khalid</creatorcontrib><creatorcontrib>Galbis, Juan A.</creatorcontrib><collection>Istex</collection><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>Begines, Belén</au><au>Zamora, Francisca</au><au>de Paz, M. Violante</au><au>Hakkou, Khalid</au><au>Galbis, Juan A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Polyurethanes derived from carbohydrates and cystine-based monomers</atitle><jtitle>Journal of applied polymer science</jtitle><addtitle>J. Appl. Polym. Sci</addtitle><date>2015-01-15</date><risdate>2015</risdate><volume>132</volume><issue>3</issue><epage>n/a</epage><issn>0021-8995</issn><eissn>1097-4628</eissn><coden>JAPNAB</coden><abstract>ABSTRACT
Linear [m,n]‐type polyurethanes (PUs) fully based on renewable materials are synthesized by interfacial polycondensation reaction of diamines derived from the amino‐acid cystine with (bis)chloroformates derived from alditols having L‐arabino or xylo configuration. The degradability of the new PUs has been enhanced by the introduction of disulfide linkages into the polymer backbone leading to a new group of stimulus‐responsive sugar‐based polyurethanes able to be degraded by glutathione under physiological conditions. All these polyurethanes are stable up to around 245°C, decomposing at higher temperatures through a one‐stage mechanism. The new materials display high chemical homogeneity and degradability in both hydrolytic and reductive environments, with reductions of above 90% in Mw. © 2014 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2015, 132, 41304.</abstract><cop>Hoboken</cop><pub>Blackwell Publishing Ltd</pub><doi>10.1002/app.41304</doi><tpages>8</tpages></addata></record> |
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| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | biodegradable Carbohydrates Cystine Degradation Diamines Homogeneity Materials science Monomers polycondensation Polycondensation reactions Polymers Polyurethane resins polyurethanes thermal properties thermogravimetric analysis (TGA) |
| title | Polyurethanes derived from carbohydrates and cystine-based monomers |
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