Bio-based epoxy resin from itaconic acid and its thermosets cured with anhydride and comonomers
A novel itaconic acid (IA) based epoxy resin with curable double bonds (EIA) was synthesized by the esterification reaction between IA and epichlorohydrin (ECH). Its chemical structure was confirmed in detail by FT-IR, 1 H-NMR and ESI-ION TRAP MS before being cured by methyl hexahydrophthalic anhydr...
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| Veröffentlicht in: | Green chemistry : an international journal and green chemistry resource : GC 2013-01, Vol.15 (1), p.245-254 |
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| creator | Ma, Songqi Liu, Xiaoqing Jiang, Yanhua Tang, Zhaobin Zhang, Chuanzhi Zhu, Jin |
| description | A novel itaconic acid (IA) based epoxy resin with curable double bonds (EIA) was synthesized by the esterification reaction between IA and epichlorohydrin (ECH). Its chemical structure was confirmed in detail by FT-IR,
1
H-NMR and ESI-ION TRAP MS before being cured by methyl hexahydrophthalic anhydride (MHHPA). In order to manipulate the properties of the cured resin, divinyl benzene (DVB) and acrylated epoxidized soybean oil (AESO) were employed here to act as comonomers. The results demonstrated that EIA showed a higher epoxy value of 0.625 and higher curing reactivity toward MHHPA compared with the commonly used diglycidyl ether of bisphenol A (DGEBA). The glass transition temperature, tensile strength, flexural strength and modulus of the cured EIA without comonomers were 130.4 °C, 87.5 MPa, 152.4 MPa and 3400 MPa, respectively, which were comparable or better than those of DGEBA cured by the same curing agent. After being copolymerized with DVB or AESO, the properties of the cured EIA could be regulated further. The results indicated that EIA has great potential to replace the petroleum-based thermosetting resin, such as DGEBA.
An itaconic acid based epoxy resin with curable double bonds, which exhibited high and adjustable performance, was synthesized. |
| doi_str_mv | 10.1039/c2gc36715g |
| format | Article |
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1
H-NMR and ESI-ION TRAP MS before being cured by methyl hexahydrophthalic anhydride (MHHPA). In order to manipulate the properties of the cured resin, divinyl benzene (DVB) and acrylated epoxidized soybean oil (AESO) were employed here to act as comonomers. The results demonstrated that EIA showed a higher epoxy value of 0.625 and higher curing reactivity toward MHHPA compared with the commonly used diglycidyl ether of bisphenol A (DGEBA). The glass transition temperature, tensile strength, flexural strength and modulus of the cured EIA without comonomers were 130.4 °C, 87.5 MPa, 152.4 MPa and 3400 MPa, respectively, which were comparable or better than those of DGEBA cured by the same curing agent. After being copolymerized with DVB or AESO, the properties of the cured EIA could be regulated further. The results indicated that EIA has great potential to replace the petroleum-based thermosetting resin, such as DGEBA.
An itaconic acid based epoxy resin with curable double bonds, which exhibited high and adjustable performance, was synthesized.</description><identifier>ISSN: 1463-9262</identifier><identifier>EISSN: 1463-9270</identifier><identifier>DOI: 10.1039/c2gc36715g</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Anhydrides ; Applied sciences ; Biological and medical sciences ; Bisphenol A ; Carcinogenesis, carcinogens and anticarcinogens ; Chemical agents ; Chemical reactivity ; Chemistry ; Crude oil, natural gas and petroleum products ; Curing ; Energy ; Epoxy resins ; Ethers ; Exact sciences and technology ; Fuels ; Itaconic acid ; Medical sciences ; Modulus of rupture in bending ; Noncondensed benzenic compounds ; Organic chemistry ; Preparations and properties ; Prospecting and production of crude oil, natural gas, oil shales and tar sands ; Reactivity and mechanisms ; Thermosetting resins ; Tumors</subject><ispartof>Green chemistry : an international journal and green chemistry resource : GC, 2013-01, Vol.15 (1), p.245-254</ispartof><rights>2014 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c375t-fd69c058a612d2cb7ecdab1218efa2ad2f2c01093886c50a72020220699839003</citedby><cites>FETCH-LOGICAL-c375t-fd69c058a612d2cb7ecdab1218efa2ad2f2c01093886c50a72020220699839003</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,4024,27923,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=27158400$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Ma, Songqi</creatorcontrib><creatorcontrib>Liu, Xiaoqing</creatorcontrib><creatorcontrib>Jiang, Yanhua</creatorcontrib><creatorcontrib>Tang, Zhaobin</creatorcontrib><creatorcontrib>Zhang, Chuanzhi</creatorcontrib><creatorcontrib>Zhu, Jin</creatorcontrib><title>Bio-based epoxy resin from itaconic acid and its thermosets cured with anhydride and comonomers</title><title>Green chemistry : an international journal and green chemistry resource : GC</title><description>A novel itaconic acid (IA) based epoxy resin with curable double bonds (EIA) was synthesized by the esterification reaction between IA and epichlorohydrin (ECH). Its chemical structure was confirmed in detail by FT-IR,
1
H-NMR and ESI-ION TRAP MS before being cured by methyl hexahydrophthalic anhydride (MHHPA). In order to manipulate the properties of the cured resin, divinyl benzene (DVB) and acrylated epoxidized soybean oil (AESO) were employed here to act as comonomers. The results demonstrated that EIA showed a higher epoxy value of 0.625 and higher curing reactivity toward MHHPA compared with the commonly used diglycidyl ether of bisphenol A (DGEBA). The glass transition temperature, tensile strength, flexural strength and modulus of the cured EIA without comonomers were 130.4 °C, 87.5 MPa, 152.4 MPa and 3400 MPa, respectively, which were comparable or better than those of DGEBA cured by the same curing agent. After being copolymerized with DVB or AESO, the properties of the cured EIA could be regulated further. The results indicated that EIA has great potential to replace the petroleum-based thermosetting resin, such as DGEBA.
An itaconic acid based epoxy resin with curable double bonds, which exhibited high and adjustable performance, was synthesized.</description><subject>Anhydrides</subject><subject>Applied sciences</subject><subject>Biological and medical sciences</subject><subject>Bisphenol A</subject><subject>Carcinogenesis, carcinogens and anticarcinogens</subject><subject>Chemical agents</subject><subject>Chemical reactivity</subject><subject>Chemistry</subject><subject>Crude oil, natural gas and petroleum products</subject><subject>Curing</subject><subject>Energy</subject><subject>Epoxy resins</subject><subject>Ethers</subject><subject>Exact sciences and technology</subject><subject>Fuels</subject><subject>Itaconic acid</subject><subject>Medical sciences</subject><subject>Modulus of rupture in bending</subject><subject>Noncondensed benzenic compounds</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Prospecting and production of crude oil, natural gas, oil shales and tar sands</subject><subject>Reactivity and mechanisms</subject><subject>Thermosetting resins</subject><subject>Tumors</subject><issn>1463-9262</issn><issn>1463-9270</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNqNkU1LAzEQhoMoqNWLd2E9CCKs5mM32T3qolUoeNFzSCdJG9nd1GSL9t8b21JvInOYYeaZl-EdhM4IviGY1bdAZ8C4IOVsDx2RgrO8pgLv72pOD9FxjO8YEyJ4cYTkvfP5VEWjM7PwX6ssmOj6zAbfZW5Q4HsHmQKnM9Xr1InZMDeh89GkEpYh7X26YZ6m85UOTps1B77zve9MiCfowKo2mtNtHqG3x4fX5imfvIyfm7tJDkyUQ241rwGXleKEagpTYUCrKaGkMlZRpamlgAmuWVVxKLESFKegmNd1xWqM2QhdbXQXwX8sTRxk5yKYtlW98csoSTKlIJyJf6BUUEE4KYuEXm9QCD7GYKxcBNepsJIEyx_DZUPHzdrwcYIvt7oqgmptUD24uNtImmVVrE-92HAhwm76-zi50DYx538x7Bv5LJSR</recordid><startdate>20130101</startdate><enddate>20130101</enddate><creator>Ma, Songqi</creator><creator>Liu, Xiaoqing</creator><creator>Jiang, Yanhua</creator><creator>Tang, Zhaobin</creator><creator>Zhang, Chuanzhi</creator><creator>Zhu, Jin</creator><general>Royal Society of Chemistry</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20130101</creationdate><title>Bio-based epoxy resin from itaconic acid and its thermosets cured with anhydride and comonomers</title><author>Ma, Songqi ; Liu, Xiaoqing ; Jiang, Yanhua ; Tang, Zhaobin ; Zhang, Chuanzhi ; Zhu, Jin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c375t-fd69c058a612d2cb7ecdab1218efa2ad2f2c01093886c50a72020220699839003</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Anhydrides</topic><topic>Applied sciences</topic><topic>Biological and medical sciences</topic><topic>Bisphenol A</topic><topic>Carcinogenesis, carcinogens and anticarcinogens</topic><topic>Chemical agents</topic><topic>Chemical reactivity</topic><topic>Chemistry</topic><topic>Crude oil, natural gas and petroleum products</topic><topic>Curing</topic><topic>Energy</topic><topic>Epoxy resins</topic><topic>Ethers</topic><topic>Exact sciences and technology</topic><topic>Fuels</topic><topic>Itaconic acid</topic><topic>Medical sciences</topic><topic>Modulus of rupture in bending</topic><topic>Noncondensed benzenic compounds</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Prospecting and production of crude oil, natural gas, oil shales and tar sands</topic><topic>Reactivity and mechanisms</topic><topic>Thermosetting resins</topic><topic>Tumors</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ma, Songqi</creatorcontrib><creatorcontrib>Liu, Xiaoqing</creatorcontrib><creatorcontrib>Jiang, Yanhua</creatorcontrib><creatorcontrib>Tang, Zhaobin</creatorcontrib><creatorcontrib>Zhang, Chuanzhi</creatorcontrib><creatorcontrib>Zhu, Jin</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ma, Songqi</au><au>Liu, Xiaoqing</au><au>Jiang, Yanhua</au><au>Tang, Zhaobin</au><au>Zhang, Chuanzhi</au><au>Zhu, Jin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Bio-based epoxy resin from itaconic acid and its thermosets cured with anhydride and comonomers</atitle><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle><date>2013-01-01</date><risdate>2013</risdate><volume>15</volume><issue>1</issue><spage>245</spage><epage>254</epage><pages>245-254</pages><issn>1463-9262</issn><eissn>1463-9270</eissn><abstract>A novel itaconic acid (IA) based epoxy resin with curable double bonds (EIA) was synthesized by the esterification reaction between IA and epichlorohydrin (ECH). Its chemical structure was confirmed in detail by FT-IR,
1
H-NMR and ESI-ION TRAP MS before being cured by methyl hexahydrophthalic anhydride (MHHPA). In order to manipulate the properties of the cured resin, divinyl benzene (DVB) and acrylated epoxidized soybean oil (AESO) were employed here to act as comonomers. The results demonstrated that EIA showed a higher epoxy value of 0.625 and higher curing reactivity toward MHHPA compared with the commonly used diglycidyl ether of bisphenol A (DGEBA). The glass transition temperature, tensile strength, flexural strength and modulus of the cured EIA without comonomers were 130.4 °C, 87.5 MPa, 152.4 MPa and 3400 MPa, respectively, which were comparable or better than those of DGEBA cured by the same curing agent. After being copolymerized with DVB or AESO, the properties of the cured EIA could be regulated further. The results indicated that EIA has great potential to replace the petroleum-based thermosetting resin, such as DGEBA.
An itaconic acid based epoxy resin with curable double bonds, which exhibited high and adjustable performance, was synthesized.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/c2gc36715g</doi><tpages>1</tpages></addata></record> |
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| ispartof | Green chemistry : an international journal and green chemistry resource : GC, 2013-01, Vol.15 (1), p.245-254 |
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| source | Royal Society Of Chemistry Journals; Alma/SFX Local Collection |
| subjects | Anhydrides Applied sciences Biological and medical sciences Bisphenol A Carcinogenesis, carcinogens and anticarcinogens Chemical agents Chemical reactivity Chemistry Crude oil, natural gas and petroleum products Curing Energy Epoxy resins Ethers Exact sciences and technology Fuels Itaconic acid Medical sciences Modulus of rupture in bending Noncondensed benzenic compounds Organic chemistry Preparations and properties Prospecting and production of crude oil, natural gas, oil shales and tar sands Reactivity and mechanisms Thermosetting resins Tumors |
| title | Bio-based epoxy resin from itaconic acid and its thermosets cured with anhydride and comonomers |
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