Synthesis of Novel Benzoxazines Containing Sulfur and Their Application in Rubber Compounds
This work reports the synthesis and successful use of novel benzoxazines as reinforcing resins in polyisoprene rubber compounds. For this purpose, three new dibenzoxazines containing one (4DTP-fa) or two heteroatoms of sulfur (3DPDS-fa and 4DPDS-fa) were synthesized following a Mannich condensation...
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| Veröffentlicht in: | Polymers 2021-04, Vol.13 (8), p.1262 |
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| creator | Trejo-Machin, Acerina Cosas Fernandes, João Paulo Puchot, Laura Balko, Suzanne Wirtz, Marcel Weydert, Marc Verge, Pierre |
| description | This work reports the synthesis and successful use of novel benzoxazines as reinforcing resins in polyisoprene rubber compounds. For this purpose, three new dibenzoxazines containing one (4DTP-fa) or two heteroatoms of sulfur (3DPDS-fa and 4DPDS-fa) were synthesized following a Mannich condensation reaction. The structural features of each benzoxazine precursor were characterized by
H and
C nuclear magnetic resonance (NMR), Fourier transform infrared (FTIR) and Raman. The new precursors showed well suited reactivity as characterized by differential scanning calorimetry (DSC) and rheology and were incorporated in rubber compounds. After the mixing, the curing profiles, morphologies and mechanical properties of the materials were tested. These results show that the structural feature of each isomer was significantly affecting its behavior during the curing of the rubber compounds. Among the tested benzoxazines, 3DPDS-fa exhibited the best ability to reinforce the rubber compound even compared to common phenolic resin. These results prove the feasibility to reinforce rubber compounds with benzoxazine resins as a possible alternative to replace conventional phenolic resins. This paper provides the first guide to use benzoxazines as reinforcing resins for rubber applications, based on their curing kinetics. |
| doi_str_mv | 10.3390/polym13081262 |
| format | Article |
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H and
C nuclear magnetic resonance (NMR), Fourier transform infrared (FTIR) and Raman. The new precursors showed well suited reactivity as characterized by differential scanning calorimetry (DSC) and rheology and were incorporated in rubber compounds. After the mixing, the curing profiles, morphologies and mechanical properties of the materials were tested. These results show that the structural feature of each isomer was significantly affecting its behavior during the curing of the rubber compounds. Among the tested benzoxazines, 3DPDS-fa exhibited the best ability to reinforce the rubber compound even compared to common phenolic resin. These results prove the feasibility to reinforce rubber compounds with benzoxazine resins as a possible alternative to replace conventional phenolic resins. This paper provides the first guide to use benzoxazines as reinforcing resins for rubber applications, based on their curing kinetics.</description><identifier>ISSN: 2073-4360</identifier><identifier>EISSN: 2073-4360</identifier><identifier>DOI: 10.3390/polym13081262</identifier><identifier>PMID: 33924584</identifier><language>eng</language><publisher>Switzerland: MDPI AG</publisher><subject>Benzoxazines ; Bisphenol A ; Carbon ; Curing ; Fourier transforms ; Heat conductivity ; Mechanical properties ; Morphology ; Nitrogen ; NMR ; Nuclear magnetic resonance ; Phenolic resins ; Phenols ; Polymerization ; Precursors ; Resins ; Rheological properties ; Rheology ; Rubber ; Sulfur</subject><ispartof>Polymers, 2021-04, Vol.13 (8), p.1262</ispartof><rights>2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><rights>2021 by the authors. 2021</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c415t-cce9e00c4bb04be45ea0dd3fe4fc1ce8675a2725099e4655f60a5254c2fad5ae3</citedby><cites>FETCH-LOGICAL-c415t-cce9e00c4bb04be45ea0dd3fe4fc1ce8675a2725099e4655f60a5254c2fad5ae3</cites><orcidid>0000-0002-6131-9926 ; 0000-0001-6704-6909 ; 0000-0002-9713-3349 ; 0000-0001-9844-0394</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC8069091/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC8069091/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,881,27901,27902,53766,53768</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33924584$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Trejo-Machin, Acerina</creatorcontrib><creatorcontrib>Cosas Fernandes, João Paulo</creatorcontrib><creatorcontrib>Puchot, Laura</creatorcontrib><creatorcontrib>Balko, Suzanne</creatorcontrib><creatorcontrib>Wirtz, Marcel</creatorcontrib><creatorcontrib>Weydert, Marc</creatorcontrib><creatorcontrib>Verge, Pierre</creatorcontrib><title>Synthesis of Novel Benzoxazines Containing Sulfur and Their Application in Rubber Compounds</title><title>Polymers</title><addtitle>Polymers (Basel)</addtitle><description>This work reports the synthesis and successful use of novel benzoxazines as reinforcing resins in polyisoprene rubber compounds. For this purpose, three new dibenzoxazines containing one (4DTP-fa) or two heteroatoms of sulfur (3DPDS-fa and 4DPDS-fa) were synthesized following a Mannich condensation reaction. The structural features of each benzoxazine precursor were characterized by
H and
C nuclear magnetic resonance (NMR), Fourier transform infrared (FTIR) and Raman. The new precursors showed well suited reactivity as characterized by differential scanning calorimetry (DSC) and rheology and were incorporated in rubber compounds. After the mixing, the curing profiles, morphologies and mechanical properties of the materials were tested. These results show that the structural feature of each isomer was significantly affecting its behavior during the curing of the rubber compounds. Among the tested benzoxazines, 3DPDS-fa exhibited the best ability to reinforce the rubber compound even compared to common phenolic resin. These results prove the feasibility to reinforce rubber compounds with benzoxazine resins as a possible alternative to replace conventional phenolic resins. This paper provides the first guide to use benzoxazines as reinforcing resins for rubber applications, based on their curing kinetics.</description><subject>Benzoxazines</subject><subject>Bisphenol A</subject><subject>Carbon</subject><subject>Curing</subject><subject>Fourier transforms</subject><subject>Heat conductivity</subject><subject>Mechanical properties</subject><subject>Morphology</subject><subject>Nitrogen</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Phenolic resins</subject><subject>Phenols</subject><subject>Polymerization</subject><subject>Precursors</subject><subject>Resins</subject><subject>Rheological properties</subject><subject>Rheology</subject><subject>Rubber</subject><subject>Sulfur</subject><issn>2073-4360</issn><issn>2073-4360</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>BENPR</sourceid><recordid>eNpdkUFP3DAQha2qVRcBx14rS730Ejp2bCe5VIIVBSQEEtBTD5bjTFijxA52glh-fbNaitjOZUaab57m6RHyhcFRnlfwYwjdumc5lIwr_oHscSjyTOQKPr6bF-QwpQeYS0ilWPGZLOZjLmQp9sif27UfV5hcoqGlV-EJO3qC_iU8mxfnMdFl8KNx3vl7ejt17RSp8Q29W6GL9HgYOmfN6IKnztObqa4xzhf9ECbfpAPyqTVdwsPXvk9-_zq9W55nl9dnF8vjy8wKJsfMWqwQwIq6BlGjkGigafIWRWuZxVIV0vCCS6gqFErKVoGRXArLW9NIg_k--bnVHaa6x8aiH6Pp9BBdb-JaB-P07sa7lb4PT7oEVUHFZoHvrwIxPE6YRt27ZLHrjMcwJc0lh1IpUMWMfvsPfQhT9LO9mZLAJeNiQ2VbysaQUsT27RkGepOc3klu5r--d_BG_8sp_wuXKZas</recordid><startdate>20210413</startdate><enddate>20210413</enddate><creator>Trejo-Machin, Acerina</creator><creator>Cosas Fernandes, João Paulo</creator><creator>Puchot, Laura</creator><creator>Balko, Suzanne</creator><creator>Wirtz, Marcel</creator><creator>Weydert, Marc</creator><creator>Verge, Pierre</creator><general>MDPI AG</general><general>MDPI</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8FD</scope><scope>8FE</scope><scope>8FG</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>HCIFZ</scope><scope>JG9</scope><scope>KB.</scope><scope>PDBOC</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-6131-9926</orcidid><orcidid>https://orcid.org/0000-0001-6704-6909</orcidid><orcidid>https://orcid.org/0000-0002-9713-3349</orcidid><orcidid>https://orcid.org/0000-0001-9844-0394</orcidid></search><sort><creationdate>20210413</creationdate><title>Synthesis of Novel Benzoxazines Containing Sulfur and Their Application in Rubber Compounds</title><author>Trejo-Machin, Acerina ; Cosas Fernandes, João Paulo ; Puchot, Laura ; Balko, Suzanne ; Wirtz, Marcel ; Weydert, Marc ; Verge, Pierre</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c415t-cce9e00c4bb04be45ea0dd3fe4fc1ce8675a2725099e4655f60a5254c2fad5ae3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Benzoxazines</topic><topic>Bisphenol A</topic><topic>Carbon</topic><topic>Curing</topic><topic>Fourier transforms</topic><topic>Heat conductivity</topic><topic>Mechanical properties</topic><topic>Morphology</topic><topic>Nitrogen</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Phenolic resins</topic><topic>Phenols</topic><topic>Polymerization</topic><topic>Precursors</topic><topic>Resins</topic><topic>Rheological properties</topic><topic>Rheology</topic><topic>Rubber</topic><topic>Sulfur</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Trejo-Machin, Acerina</creatorcontrib><creatorcontrib>Cosas Fernandes, João Paulo</creatorcontrib><creatorcontrib>Puchot, Laura</creatorcontrib><creatorcontrib>Balko, Suzanne</creatorcontrib><creatorcontrib>Wirtz, Marcel</creatorcontrib><creatorcontrib>Weydert, Marc</creatorcontrib><creatorcontrib>Verge, Pierre</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Technology Research Database</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>Technology Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central Korea</collection><collection>SciTech Premium Collection</collection><collection>Materials Research Database</collection><collection>Materials Science Database</collection><collection>Materials Science Collection</collection><collection>Publicly Available Content Database</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Polymers</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Trejo-Machin, Acerina</au><au>Cosas Fernandes, João Paulo</au><au>Puchot, Laura</au><au>Balko, Suzanne</au><au>Wirtz, Marcel</au><au>Weydert, Marc</au><au>Verge, Pierre</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Novel Benzoxazines Containing Sulfur and Their Application in Rubber Compounds</atitle><jtitle>Polymers</jtitle><addtitle>Polymers (Basel)</addtitle><date>2021-04-13</date><risdate>2021</risdate><volume>13</volume><issue>8</issue><spage>1262</spage><pages>1262-</pages><issn>2073-4360</issn><eissn>2073-4360</eissn><abstract>This work reports the synthesis and successful use of novel benzoxazines as reinforcing resins in polyisoprene rubber compounds. For this purpose, three new dibenzoxazines containing one (4DTP-fa) or two heteroatoms of sulfur (3DPDS-fa and 4DPDS-fa) were synthesized following a Mannich condensation reaction. The structural features of each benzoxazine precursor were characterized by
H and
C nuclear magnetic resonance (NMR), Fourier transform infrared (FTIR) and Raman. The new precursors showed well suited reactivity as characterized by differential scanning calorimetry (DSC) and rheology and were incorporated in rubber compounds. After the mixing, the curing profiles, morphologies and mechanical properties of the materials were tested. These results show that the structural feature of each isomer was significantly affecting its behavior during the curing of the rubber compounds. Among the tested benzoxazines, 3DPDS-fa exhibited the best ability to reinforce the rubber compound even compared to common phenolic resin. These results prove the feasibility to reinforce rubber compounds with benzoxazine resins as a possible alternative to replace conventional phenolic resins. This paper provides the first guide to use benzoxazines as reinforcing resins for rubber applications, based on their curing kinetics.</abstract><cop>Switzerland</cop><pub>MDPI AG</pub><pmid>33924584</pmid><doi>10.3390/polym13081262</doi><orcidid>https://orcid.org/0000-0002-6131-9926</orcidid><orcidid>https://orcid.org/0000-0001-6704-6909</orcidid><orcidid>https://orcid.org/0000-0002-9713-3349</orcidid><orcidid>https://orcid.org/0000-0001-9844-0394</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Benzoxazines Bisphenol A Carbon Curing Fourier transforms Heat conductivity Mechanical properties Morphology Nitrogen NMR Nuclear magnetic resonance Phenolic resins Phenols Polymerization Precursors Resins Rheological properties Rheology Rubber Sulfur |
| title | Synthesis of Novel Benzoxazines Containing Sulfur and Their Application in Rubber Compounds |
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