Synthesis of tetraallylated cystamine and the study of its performance as a curing agent for the epoxy/thiol-ene photopolymerization of biobased nopol epoxy resins
This article reports the synthesis of a bio-inspired curing agent, the tetraallyl cystamine (TAC) and the evaluation of its performance to photocure two epoxy resins derived from the terpenoid nopol, by using the epoxy/thiol-ene photopolymerization technique. The curing agent was prepared in two sta...
Gespeichert in:
| Veröffentlicht in: | Journal of polymer research 2021-10, Vol.28 (10), Article 366 |
|---|---|
| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | |
|---|---|
| container_issue | 10 |
| container_start_page | |
| container_title | Journal of polymer research |
| container_volume | 28 |
| creator | Acosta Ortiz, Ricardo Hernández Jiménez, Alan Isaac García Valdez, Aida Esmeralda |
| description | This article reports the synthesis of a bio-inspired curing agent, the tetraallyl cystamine (TAC) and the evaluation of its performance to photocure two epoxy resins derived from the terpenoid nopol, by using the epoxy/thiol-ene photopolymerization technique. The curing agent was prepared in two stages: a) reaction of the diallylamine with ethylene disulfide, through a mercaptoethylation reaction and b) oxidation of the obtained thiol to disulfide, using dimethylsulfoxide as an oxidizing agent. To the epoxy resins was added the curing agent TAC, pentaerythritol tetrakis (3-mercaptopropionate) and dimethoxyphenylacetophenone, to obtain cross-linked co-networks of the polyether-polythioether type. A trifunctional nopol epoxycycloaliphatic epoxy resin and an epoxycycloaliphatic-glycidyl nopol epoxy resin were evaluated, with the former displaying higher reactivity, higher modulus and higher thermal stability. |
| doi_str_mv | 10.1007/s10965-021-02725-5 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2569394520</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2569394520</sourcerecordid><originalsourceid>FETCH-LOGICAL-c319t-8207d5462e7d49b1a9b50b63fda7b08f0382639e042c0043fae0a4cbb77241223</originalsourceid><addsrcrecordid>eNp9kc1KxDAUhYsoOP68gKuA6zo3SdM0Sxn8A8GFug5pm85k6CQ1yYD1dXxR06ngzkW4gfudcy_3ZNkVhhsMwJcBgyhZDgSnxwnL2VG2wIyTvBKUHac_EJILXsJpdhbCFoAxXlaL7Pt1tHGjgwnIdSjq6JXq-7FXUbeoGUNUO2M1UrZFCUMh7ttxIk0MaNC-c36nbJOAgBRq9t7YNVJrbSNKrYNED-5zXMaNcX2uk9WwcdENrh932psvFY2zk2FtXK1CGmqn5qxCPi1mw0V20qk-6Mvfep6939-9rR7z55eHp9Xtc95QLGJeEeAtK0qieVuIGitRM6hL2rWK11B1QCtSUqGhIA1AQTulQRVNXXNOCkwIPc-uZ9_Bu4-9DlFu3d7bNFISVgoqCkYgUWSmGu9C8LqTgzc75UeJQU5hyDkMmcKQhzAkSyI6i8IwnUj7P-t_VD8w_JCB</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2569394520</pqid></control><display><type>article</type><title>Synthesis of tetraallylated cystamine and the study of its performance as a curing agent for the epoxy/thiol-ene photopolymerization of biobased nopol epoxy resins</title><source>SpringerLink Journals - AutoHoldings</source><creator>Acosta Ortiz, Ricardo ; Hernández Jiménez, Alan Isaac ; García Valdez, Aida Esmeralda</creator><creatorcontrib>Acosta Ortiz, Ricardo ; Hernández Jiménez, Alan Isaac ; García Valdez, Aida Esmeralda</creatorcontrib><description>This article reports the synthesis of a bio-inspired curing agent, the tetraallyl cystamine (TAC) and the evaluation of its performance to photocure two epoxy resins derived from the terpenoid nopol, by using the epoxy/thiol-ene photopolymerization technique. The curing agent was prepared in two stages: a) reaction of the diallylamine with ethylene disulfide, through a mercaptoethylation reaction and b) oxidation of the obtained thiol to disulfide, using dimethylsulfoxide as an oxidizing agent. To the epoxy resins was added the curing agent TAC, pentaerythritol tetrakis (3-mercaptopropionate) and dimethoxyphenylacetophenone, to obtain cross-linked co-networks of the polyether-polythioether type. A trifunctional nopol epoxycycloaliphatic epoxy resin and an epoxycycloaliphatic-glycidyl nopol epoxy resin were evaluated, with the former displaying higher reactivity, higher modulus and higher thermal stability.</description><identifier>ISSN: 1022-9760</identifier><identifier>EISSN: 1572-8935</identifier><identifier>DOI: 10.1007/s10965-021-02725-5</identifier><language>eng</language><publisher>Dordrecht: Springer Netherlands</publisher><subject>Characterization and Evaluation of Materials ; Chemistry ; Chemistry and Materials Science ; Curing ; Curing agents ; Epoxy resins ; Industrial Chemistry/Chemical Engineering ; Original Paper ; Oxidation ; Oxidizing agents ; Performance evaluation ; Photopolymerization ; Polymer Sciences ; Rapid prototyping ; Synthesis ; Thermal stability</subject><ispartof>Journal of polymer research, 2021-10, Vol.28 (10), Article 366</ispartof><rights>The Polymer Society, Taipei 2021</rights><rights>The Polymer Society, Taipei 2021.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c319t-8207d5462e7d49b1a9b50b63fda7b08f0382639e042c0043fae0a4cbb77241223</citedby><cites>FETCH-LOGICAL-c319t-8207d5462e7d49b1a9b50b63fda7b08f0382639e042c0043fae0a4cbb77241223</cites><orcidid>0000-0003-4824-9625 ; 0000-0002-3730-7765</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s10965-021-02725-5$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s10965-021-02725-5$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,778,782,27907,27908,41471,42540,51302</link.rule.ids></links><search><creatorcontrib>Acosta Ortiz, Ricardo</creatorcontrib><creatorcontrib>Hernández Jiménez, Alan Isaac</creatorcontrib><creatorcontrib>García Valdez, Aida Esmeralda</creatorcontrib><title>Synthesis of tetraallylated cystamine and the study of its performance as a curing agent for the epoxy/thiol-ene photopolymerization of biobased nopol epoxy resins</title><title>Journal of polymer research</title><addtitle>J Polym Res</addtitle><description>This article reports the synthesis of a bio-inspired curing agent, the tetraallyl cystamine (TAC) and the evaluation of its performance to photocure two epoxy resins derived from the terpenoid nopol, by using the epoxy/thiol-ene photopolymerization technique. The curing agent was prepared in two stages: a) reaction of the diallylamine with ethylene disulfide, through a mercaptoethylation reaction and b) oxidation of the obtained thiol to disulfide, using dimethylsulfoxide as an oxidizing agent. To the epoxy resins was added the curing agent TAC, pentaerythritol tetrakis (3-mercaptopropionate) and dimethoxyphenylacetophenone, to obtain cross-linked co-networks of the polyether-polythioether type. A trifunctional nopol epoxycycloaliphatic epoxy resin and an epoxycycloaliphatic-glycidyl nopol epoxy resin were evaluated, with the former displaying higher reactivity, higher modulus and higher thermal stability.</description><subject>Characterization and Evaluation of Materials</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Curing</subject><subject>Curing agents</subject><subject>Epoxy resins</subject><subject>Industrial Chemistry/Chemical Engineering</subject><subject>Original Paper</subject><subject>Oxidation</subject><subject>Oxidizing agents</subject><subject>Performance evaluation</subject><subject>Photopolymerization</subject><subject>Polymer Sciences</subject><subject>Rapid prototyping</subject><subject>Synthesis</subject><subject>Thermal stability</subject><issn>1022-9760</issn><issn>1572-8935</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNp9kc1KxDAUhYsoOP68gKuA6zo3SdM0Sxn8A8GFug5pm85k6CQ1yYD1dXxR06ngzkW4gfudcy_3ZNkVhhsMwJcBgyhZDgSnxwnL2VG2wIyTvBKUHac_EJILXsJpdhbCFoAxXlaL7Pt1tHGjgwnIdSjq6JXq-7FXUbeoGUNUO2M1UrZFCUMh7ttxIk0MaNC-c36nbJOAgBRq9t7YNVJrbSNKrYNED-5zXMaNcX2uk9WwcdENrh932psvFY2zk2FtXK1CGmqn5qxCPi1mw0V20qk-6Mvfep6939-9rR7z55eHp9Xtc95QLGJeEeAtK0qieVuIGitRM6hL2rWK11B1QCtSUqGhIA1AQTulQRVNXXNOCkwIPc-uZ9_Bu4-9DlFu3d7bNFISVgoqCkYgUWSmGu9C8LqTgzc75UeJQU5hyDkMmcKQhzAkSyI6i8IwnUj7P-t_VD8w_JCB</recordid><startdate>20211001</startdate><enddate>20211001</enddate><creator>Acosta Ortiz, Ricardo</creator><creator>Hernández Jiménez, Alan Isaac</creator><creator>García Valdez, Aida Esmeralda</creator><general>Springer Netherlands</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8FD</scope><scope>JG9</scope><orcidid>https://orcid.org/0000-0003-4824-9625</orcidid><orcidid>https://orcid.org/0000-0002-3730-7765</orcidid></search><sort><creationdate>20211001</creationdate><title>Synthesis of tetraallylated cystamine and the study of its performance as a curing agent for the epoxy/thiol-ene photopolymerization of biobased nopol epoxy resins</title><author>Acosta Ortiz, Ricardo ; Hernández Jiménez, Alan Isaac ; García Valdez, Aida Esmeralda</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c319t-8207d5462e7d49b1a9b50b63fda7b08f0382639e042c0043fae0a4cbb77241223</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Characterization and Evaluation of Materials</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Curing</topic><topic>Curing agents</topic><topic>Epoxy resins</topic><topic>Industrial Chemistry/Chemical Engineering</topic><topic>Original Paper</topic><topic>Oxidation</topic><topic>Oxidizing agents</topic><topic>Performance evaluation</topic><topic>Photopolymerization</topic><topic>Polymer Sciences</topic><topic>Rapid prototyping</topic><topic>Synthesis</topic><topic>Thermal stability</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Acosta Ortiz, Ricardo</creatorcontrib><creatorcontrib>Hernández Jiménez, Alan Isaac</creatorcontrib><creatorcontrib>García Valdez, Aida Esmeralda</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Journal of polymer research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Acosta Ortiz, Ricardo</au><au>Hernández Jiménez, Alan Isaac</au><au>García Valdez, Aida Esmeralda</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of tetraallylated cystamine and the study of its performance as a curing agent for the epoxy/thiol-ene photopolymerization of biobased nopol epoxy resins</atitle><jtitle>Journal of polymer research</jtitle><stitle>J Polym Res</stitle><date>2021-10-01</date><risdate>2021</risdate><volume>28</volume><issue>10</issue><artnum>366</artnum><issn>1022-9760</issn><eissn>1572-8935</eissn><abstract>This article reports the synthesis of a bio-inspired curing agent, the tetraallyl cystamine (TAC) and the evaluation of its performance to photocure two epoxy resins derived from the terpenoid nopol, by using the epoxy/thiol-ene photopolymerization technique. The curing agent was prepared in two stages: a) reaction of the diallylamine with ethylene disulfide, through a mercaptoethylation reaction and b) oxidation of the obtained thiol to disulfide, using dimethylsulfoxide as an oxidizing agent. To the epoxy resins was added the curing agent TAC, pentaerythritol tetrakis (3-mercaptopropionate) and dimethoxyphenylacetophenone, to obtain cross-linked co-networks of the polyether-polythioether type. A trifunctional nopol epoxycycloaliphatic epoxy resin and an epoxycycloaliphatic-glycidyl nopol epoxy resin were evaluated, with the former displaying higher reactivity, higher modulus and higher thermal stability.</abstract><cop>Dordrecht</cop><pub>Springer Netherlands</pub><doi>10.1007/s10965-021-02725-5</doi><orcidid>https://orcid.org/0000-0003-4824-9625</orcidid><orcidid>https://orcid.org/0000-0002-3730-7765</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1022-9760 |
| ispartof | Journal of polymer research, 2021-10, Vol.28 (10), Article 366 |
| issn | 1022-9760 1572-8935 |
| language | eng |
| recordid | cdi_proquest_journals_2569394520 |
| source | SpringerLink Journals - AutoHoldings |
| subjects | Characterization and Evaluation of Materials Chemistry Chemistry and Materials Science Curing Curing agents Epoxy resins Industrial Chemistry/Chemical Engineering Original Paper Oxidation Oxidizing agents Performance evaluation Photopolymerization Polymer Sciences Rapid prototyping Synthesis Thermal stability |
| title | Synthesis of tetraallylated cystamine and the study of its performance as a curing agent for the epoxy/thiol-ene photopolymerization of biobased nopol epoxy resins |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-17T02%3A03%3A17IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis%20of%20tetraallylated%20cystamine%20and%20the%20study%20of%20its%20performance%20as%20a%20curing%20agent%20for%20the%20epoxy/thiol-ene%20photopolymerization%20of%20biobased%20nopol%20epoxy%20resins&rft.jtitle=Journal%20of%20polymer%20research&rft.au=Acosta%20Ortiz,%20Ricardo&rft.date=2021-10-01&rft.volume=28&rft.issue=10&rft.artnum=366&rft.issn=1022-9760&rft.eissn=1572-8935&rft_id=info:doi/10.1007/s10965-021-02725-5&rft_dat=%3Cproquest_cross%3E2569394520%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2569394520&rft_id=info:pmid/&rfr_iscdi=true |