Influence of Peripheral Hydrogen Bonding on the Mechanical Properties of Photo-Cross-Linked Star-Shaped Poly(d,l-lactide) Networks
Four-arm, star-shaped poly(d,l-lactide) (PDLLA) oligomers of controlled molar mass and narrow molar mass distribution were successfully synthesized by use of an ethoxylated pentaerythritol initiator. Derivatization of the terminal hydroxyl groups with either methacrylic anhydride (MAAH) or 2-isocyan...
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| Veröffentlicht in: | Biomacromolecules 2005-09, Vol.6 (5), p.2866-2874 |
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| creator | Karikari, Afia S Edwards, Wesleigh F Mecham, Jeffrey B Long, Timothy E |
| description | Four-arm, star-shaped poly(d,l-lactide) (PDLLA) oligomers of controlled molar mass and narrow molar mass distribution were successfully synthesized by use of an ethoxylated pentaerythritol initiator. Derivatization of the terminal hydroxyl groups with either methacrylic anhydride (MAAH) or 2-isocyanatoethyl methacrylate (IEM) to yield PDLLA-M (M = methacrylate end group) and PDLLA-UM (UM = urethane methacrylate end group), respectively, was monitored by in situ Fourier transform infrared (FTIR) spectroscopy. Photo-cross-linking of the functional oligomers yielded networks with high gel contents (>95%). The glass transition temperature (T g) of these networks was strongly dependent on prepolymer molar mass, and networks based on low molar mass precursors were more rigid than the networks obtained from higher molar mass oligomers. The tensile strength (TS) and Young's modulus of the PDLLA-M samples, approximately 7 and 17 MPa, respectively, were significantly lower than the values of 19 MPa (TS) and 113−354 MPa (Young's modulus) for the PDLLA-UM samples. The introduction of terminal hydrogen-bonding sites that were adjacent to the photo-cross-linking site resulted in higher performance poly(lactide)-based bioadhesives. |
| doi_str_mv | 10.1021/bm050375i |
| format | Article |
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Derivatization of the terminal hydroxyl groups with either methacrylic anhydride (MAAH) or 2-isocyanatoethyl methacrylate (IEM) to yield PDLLA-M (M = methacrylate end group) and PDLLA-UM (UM = urethane methacrylate end group), respectively, was monitored by in situ Fourier transform infrared (FTIR) spectroscopy. Photo-cross-linking of the functional oligomers yielded networks with high gel contents (>95%). The glass transition temperature (T g) of these networks was strongly dependent on prepolymer molar mass, and networks based on low molar mass precursors were more rigid than the networks obtained from higher molar mass oligomers. The tensile strength (TS) and Young's modulus of the PDLLA-M samples, approximately 7 and 17 MPa, respectively, were significantly lower than the values of 19 MPa (TS) and 113−354 MPa (Young's modulus) for the PDLLA-UM samples. The introduction of terminal hydrogen-bonding sites that were adjacent to the photo-cross-linking site resulted in higher performance poly(lactide)-based bioadhesives.</description><identifier>ISSN: 1525-7797</identifier><identifier>EISSN: 1526-4602</identifier><identifier>DOI: 10.1021/bm050375i</identifier><identifier>PMID: 16153129</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Applied sciences ; Calorimetry, Differential Scanning ; Chromatography ; Cross-Linking Reagents - pharmacology ; Exact sciences and technology ; Glass ; Hot Temperature ; Hydrogen Bonding ; Isocyanates - chemistry ; Magnetic Resonance Spectroscopy ; Methacrylates - chemistry ; Models, Chemical ; Organic polymers ; Physicochemistry of polymers ; Polyesters - chemistry ; Polymerization ; Polymethacrylic Acids - chemistry ; Preparation, kinetics, thermodynamics, mechanism and catalysts ; Spectroscopy, Fourier Transform Infrared ; Stress, Mechanical ; Temperature ; Tensile Strength ; Tissue Adhesions ; Urethane - chemistry</subject><ispartof>Biomacromolecules, 2005-09, Vol.6 (5), p.2866-2874</ispartof><rights>Copyright © 2005 American Chemical Society</rights><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a343t-7475222874ca519389b0f84011249db82b8bd8f98becc49642257ecaeceb361b3</citedby><cites>FETCH-LOGICAL-a343t-7475222874ca519389b0f84011249db82b8bd8f98becc49642257ecaeceb361b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/bm050375i$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/bm050375i$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17137531$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16153129$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Karikari, Afia S</creatorcontrib><creatorcontrib>Edwards, Wesleigh F</creatorcontrib><creatorcontrib>Mecham, Jeffrey B</creatorcontrib><creatorcontrib>Long, Timothy E</creatorcontrib><title>Influence of Peripheral Hydrogen Bonding on the Mechanical Properties of Photo-Cross-Linked Star-Shaped Poly(d,l-lactide) Networks</title><title>Biomacromolecules</title><addtitle>Biomacromolecules</addtitle><description>Four-arm, star-shaped poly(d,l-lactide) (PDLLA) oligomers of controlled molar mass and narrow molar mass distribution were successfully synthesized by use of an ethoxylated pentaerythritol initiator. Derivatization of the terminal hydroxyl groups with either methacrylic anhydride (MAAH) or 2-isocyanatoethyl methacrylate (IEM) to yield PDLLA-M (M = methacrylate end group) and PDLLA-UM (UM = urethane methacrylate end group), respectively, was monitored by in situ Fourier transform infrared (FTIR) spectroscopy. Photo-cross-linking of the functional oligomers yielded networks with high gel contents (>95%). The glass transition temperature (T g) of these networks was strongly dependent on prepolymer molar mass, and networks based on low molar mass precursors were more rigid than the networks obtained from higher molar mass oligomers. The tensile strength (TS) and Young's modulus of the PDLLA-M samples, approximately 7 and 17 MPa, respectively, were significantly lower than the values of 19 MPa (TS) and 113−354 MPa (Young's modulus) for the PDLLA-UM samples. The introduction of terminal hydrogen-bonding sites that were adjacent to the photo-cross-linking site resulted in higher performance poly(lactide)-based bioadhesives.</description><subject>Applied sciences</subject><subject>Calorimetry, Differential Scanning</subject><subject>Chromatography</subject><subject>Cross-Linking Reagents - pharmacology</subject><subject>Exact sciences and technology</subject><subject>Glass</subject><subject>Hot Temperature</subject><subject>Hydrogen Bonding</subject><subject>Isocyanates - chemistry</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Methacrylates - chemistry</subject><subject>Models, Chemical</subject><subject>Organic polymers</subject><subject>Physicochemistry of polymers</subject><subject>Polyesters - chemistry</subject><subject>Polymerization</subject><subject>Polymethacrylic Acids - chemistry</subject><subject>Preparation, kinetics, thermodynamics, mechanism and catalysts</subject><subject>Spectroscopy, Fourier Transform Infrared</subject><subject>Stress, Mechanical</subject><subject>Temperature</subject><subject>Tensile Strength</subject><subject>Tissue Adhesions</subject><subject>Urethane - chemistry</subject><issn>1525-7797</issn><issn>1526-4602</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkEtP3DAURq2qqMC0i_6ByptKHQm3fsbJko54SUM7Eu06sp0bYsjYkZ0Rmi2_nAAjZsPqfotzXwehr4z-ZJSzX3ZNFRVa-Q_oiCleEFlQ_vElK6J1pQ_Rcc53lNJKSPUJHbKCKcF4dYQer0LbbyA4wLHFK0h-6CCZHl9umxRvIeDfMTQ-3OIY8NgBvgbXmeDdhKxSHCCNHvJLbxfHSBYp5kyWPtxDg29Gk8hNZ4Ypr2K__dGc9KQ3bvQNzPEfGB9ius-f0UFr-gxfdnWG_p-f_VtckuXfi6vF6ZIYIcVItNSKc15q6YxilSgrS9tSUsa4rBpbclvapmyr0oJzsiok50qDM-DAioJZMUPz17nu-cYEbT0kvzZpWzNaP3us3zxO7LdXdtjYNTR7ciduAr7vAJMnF20ywfm85zSb5gi254zL9V3cpDC9-M7CJ4jvhwI</recordid><startdate>20050901</startdate><enddate>20050901</enddate><creator>Karikari, Afia S</creator><creator>Edwards, Wesleigh F</creator><creator>Mecham, Jeffrey B</creator><creator>Long, Timothy E</creator><general>American Chemical Society</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20050901</creationdate><title>Influence of Peripheral Hydrogen Bonding on the Mechanical Properties of Photo-Cross-Linked Star-Shaped Poly(d,l-lactide) Networks</title><author>Karikari, Afia S ; Edwards, Wesleigh F ; Mecham, Jeffrey B ; Long, Timothy E</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a343t-7475222874ca519389b0f84011249db82b8bd8f98becc49642257ecaeceb361b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Applied sciences</topic><topic>Calorimetry, Differential Scanning</topic><topic>Chromatography</topic><topic>Cross-Linking Reagents - pharmacology</topic><topic>Exact sciences and technology</topic><topic>Glass</topic><topic>Hot Temperature</topic><topic>Hydrogen Bonding</topic><topic>Isocyanates - chemistry</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Methacrylates - chemistry</topic><topic>Models, Chemical</topic><topic>Organic polymers</topic><topic>Physicochemistry of polymers</topic><topic>Polyesters - chemistry</topic><topic>Polymerization</topic><topic>Polymethacrylic Acids - chemistry</topic><topic>Preparation, kinetics, thermodynamics, mechanism and catalysts</topic><topic>Spectroscopy, Fourier Transform Infrared</topic><topic>Stress, Mechanical</topic><topic>Temperature</topic><topic>Tensile Strength</topic><topic>Tissue Adhesions</topic><topic>Urethane - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Karikari, Afia S</creatorcontrib><creatorcontrib>Edwards, Wesleigh F</creatorcontrib><creatorcontrib>Mecham, Jeffrey B</creatorcontrib><creatorcontrib>Long, Timothy E</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><jtitle>Biomacromolecules</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Karikari, Afia S</au><au>Edwards, Wesleigh F</au><au>Mecham, Jeffrey B</au><au>Long, Timothy E</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Influence of Peripheral Hydrogen Bonding on the Mechanical Properties of Photo-Cross-Linked Star-Shaped Poly(d,l-lactide) Networks</atitle><jtitle>Biomacromolecules</jtitle><addtitle>Biomacromolecules</addtitle><date>2005-09-01</date><risdate>2005</risdate><volume>6</volume><issue>5</issue><spage>2866</spage><epage>2874</epage><pages>2866-2874</pages><issn>1525-7797</issn><eissn>1526-4602</eissn><abstract>Four-arm, star-shaped poly(d,l-lactide) (PDLLA) oligomers of controlled molar mass and narrow molar mass distribution were successfully synthesized by use of an ethoxylated pentaerythritol initiator. Derivatization of the terminal hydroxyl groups with either methacrylic anhydride (MAAH) or 2-isocyanatoethyl methacrylate (IEM) to yield PDLLA-M (M = methacrylate end group) and PDLLA-UM (UM = urethane methacrylate end group), respectively, was monitored by in situ Fourier transform infrared (FTIR) spectroscopy. Photo-cross-linking of the functional oligomers yielded networks with high gel contents (>95%). The glass transition temperature (T g) of these networks was strongly dependent on prepolymer molar mass, and networks based on low molar mass precursors were more rigid than the networks obtained from higher molar mass oligomers. The tensile strength (TS) and Young's modulus of the PDLLA-M samples, approximately 7 and 17 MPa, respectively, were significantly lower than the values of 19 MPa (TS) and 113−354 MPa (Young's modulus) for the PDLLA-UM samples. The introduction of terminal hydrogen-bonding sites that were adjacent to the photo-cross-linking site resulted in higher performance poly(lactide)-based bioadhesives.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>16153129</pmid><doi>10.1021/bm050375i</doi><tpages>9</tpages></addata></record> |
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| subjects | Applied sciences Calorimetry, Differential Scanning Chromatography Cross-Linking Reagents - pharmacology Exact sciences and technology Glass Hot Temperature Hydrogen Bonding Isocyanates - chemistry Magnetic Resonance Spectroscopy Methacrylates - chemistry Models, Chemical Organic polymers Physicochemistry of polymers Polyesters - chemistry Polymerization Polymethacrylic Acids - chemistry Preparation, kinetics, thermodynamics, mechanism and catalysts Spectroscopy, Fourier Transform Infrared Stress, Mechanical Temperature Tensile Strength Tissue Adhesions Urethane - chemistry |
| title | Influence of Peripheral Hydrogen Bonding on the Mechanical Properties of Photo-Cross-Linked Star-Shaped Poly(d,l-lactide) Networks |
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