The crystalline behavior of poly(L‐lactide) induced by nucleating agents with amide structure: The effect of benzamide molecule symmetry
Amide nucleating agents have been reported to be effective in promoting poly(L‐lactide) (PLLA) crystallization, while few research efforts have focused on the structure–activity relationship of the nucleating agents which is one basic issue to develop new agents. In this work, three amide nucleating...
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| Veröffentlicht in: | Journal of polymer science (2020) 2023-01, Vol.61 (1), p.67-82 |
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| container_title | Journal of polymer science (2020) |
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| creator | He, Zejian Shao, Haifeng Zhang, Nannan Li, Jie Xiao, Hai Weng, Tianhang Zhou, Mi Wen, Bianying Chen, Yulong |
| description | Amide nucleating agents have been reported to be effective in promoting poly(L‐lactide) (PLLA) crystallization, while few research efforts have focused on the structure–activity relationship of the nucleating agents which is one basic issue to develop new agents. In this work, three amide nucleating agents with different symmetry were designed and synthesized to investigate the effect of the symmetry of benzamide nucleating agents on PLLA crystallization. It is found that the C3 symmetric amide structure of N, N′, N″‐tricyclohexyl‐1,3,5‐benzenetriamine (BTCA) agent can form a highly oriented structure by a triple hydrogen bond of π–π bond and benzene ring and can act as efficient nucleation sites. In addition, the strong intramolecular hydrogen bond with PLLA would further promote the crystallization of PLLA. In general, it is the self‐assembled ability and intramolecular hydrogen bonding with PLLA affects the rate and degree of PLLA crystallinity, and we find the C3 symmetric amide structure exhibits the best performance. |
| doi_str_mv | 10.1002/pol.20220295 |
| format | Article |
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In this work, three amide nucleating agents with different symmetry were designed and synthesized to investigate the effect of the symmetry of benzamide nucleating agents on PLLA crystallization. It is found that the C3 symmetric amide structure of N, N′, N″‐tricyclohexyl‐1,3,5‐benzenetriamine (BTCA) agent can form a highly oriented structure by a triple hydrogen bond of π–π bond and benzene ring and can act as efficient nucleation sites. In addition, the strong intramolecular hydrogen bond with PLLA would further promote the crystallization of PLLA. In general, it is the self‐assembled ability and intramolecular hydrogen bonding with PLLA affects the rate and degree of PLLA crystallinity, and we find the C3 symmetric amide structure exhibits the best performance.</description><identifier>ISSN: 2642-4150</identifier><identifier>EISSN: 2642-4169</identifier><identifier>DOI: 10.1002/pol.20220295</identifier><language>eng</language><publisher>Hoboken, USA: John Wiley & Sons, Inc</publisher><subject>amide nucleating agents ; Benzamide ; Benzene ; Covalent bonds ; Crystallization ; Hydrogen bonding ; Hydrogen bonds ; Molecular structure ; Nucleation ; poly(L‐lactide) ; Symmetry</subject><ispartof>Journal of polymer science (2020), 2023-01, Vol.61 (1), p.67-82</ispartof><rights>2022 Wiley Periodicals LLC.</rights><rights>2023 Wiley Periodicals LLC.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3073-80f04307b995235ba10ddbb19fc4a1a4a163f32a9acf1888b51b272b4725616e3</citedby><cites>FETCH-LOGICAL-c3073-80f04307b995235ba10ddbb19fc4a1a4a163f32a9acf1888b51b272b4725616e3</cites><orcidid>0000-0001-8588-878X ; 0000-0001-6310-1384</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fpol.20220295$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fpol.20220295$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>315,781,785,1418,27928,27929,45578,45579</link.rule.ids></links><search><creatorcontrib>He, Zejian</creatorcontrib><creatorcontrib>Shao, Haifeng</creatorcontrib><creatorcontrib>Zhang, Nannan</creatorcontrib><creatorcontrib>Li, Jie</creatorcontrib><creatorcontrib>Xiao, Hai</creatorcontrib><creatorcontrib>Weng, Tianhang</creatorcontrib><creatorcontrib>Zhou, Mi</creatorcontrib><creatorcontrib>Wen, Bianying</creatorcontrib><creatorcontrib>Chen, Yulong</creatorcontrib><title>The crystalline behavior of poly(L‐lactide) induced by nucleating agents with amide structure: The effect of benzamide molecule symmetry</title><title>Journal of polymer science (2020)</title><description>Amide nucleating agents have been reported to be effective in promoting poly(L‐lactide) (PLLA) crystallization, while few research efforts have focused on the structure–activity relationship of the nucleating agents which is one basic issue to develop new agents. In this work, three amide nucleating agents with different symmetry were designed and synthesized to investigate the effect of the symmetry of benzamide nucleating agents on PLLA crystallization. It is found that the C3 symmetric amide structure of N, N′, N″‐tricyclohexyl‐1,3,5‐benzenetriamine (BTCA) agent can form a highly oriented structure by a triple hydrogen bond of π–π bond and benzene ring and can act as efficient nucleation sites. In addition, the strong intramolecular hydrogen bond with PLLA would further promote the crystallization of PLLA. In general, it is the self‐assembled ability and intramolecular hydrogen bonding with PLLA affects the rate and degree of PLLA crystallinity, and we find the C3 symmetric amide structure exhibits the best performance.</description><subject>amide nucleating agents</subject><subject>Benzamide</subject><subject>Benzene</subject><subject>Covalent bonds</subject><subject>Crystallization</subject><subject>Hydrogen bonding</subject><subject>Hydrogen bonds</subject><subject>Molecular structure</subject><subject>Nucleation</subject><subject>poly(L‐lactide)</subject><subject>Symmetry</subject><issn>2642-4150</issn><issn>2642-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNp90MtKAzEUBuBBFCzanQ8QcKPg1Fzm6q4Ub1Coi7oeksxJOyUzU5OMZVy5duUz-iSmjLoUEnIWH_8hfxCcETwhGNPrbasnFFN_8vggGNEkomFEkvzwb47xcTC2doM9Z3ES4WQUfCzXgKTpreNaVw0gAWv-WrUGtQr5yP5i_vX-qbl0VQmXqGrKTkKJRI-aTmrgrmpWiK-gcRbtKrdGvPYQWWc66ToDN2i_AJQC6faRApq3gdStBtlpb_u6Bmf60-BIcW1h_POeBM93t8vZQzhf3D_OpvNQMpyyMMMKR34SeR77bwhOcFkKQXIlI064vwlTjPKcS0WyLBMxETSlIkppnJAE2ElwPuRuTfvSgXXFpu1M41cWNI3zLCMJiby6GpQ0rbUGVLE1Vc1NXxBc7AsvfDvFb-Ges4HvKg39v7Z4WsynDEcZY9-iPYVU</recordid><startdate>20230101</startdate><enddate>20230101</enddate><creator>He, Zejian</creator><creator>Shao, Haifeng</creator><creator>Zhang, Nannan</creator><creator>Li, Jie</creator><creator>Xiao, Hai</creator><creator>Weng, Tianhang</creator><creator>Zhou, Mi</creator><creator>Wen, Bianying</creator><creator>Chen, Yulong</creator><general>John Wiley & Sons, Inc</general><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0001-8588-878X</orcidid><orcidid>https://orcid.org/0000-0001-6310-1384</orcidid></search><sort><creationdate>20230101</creationdate><title>The crystalline behavior of poly(L‐lactide) induced by nucleating agents with amide structure: The effect of benzamide molecule symmetry</title><author>He, Zejian ; Shao, Haifeng ; Zhang, Nannan ; Li, Jie ; Xiao, Hai ; Weng, Tianhang ; Zhou, Mi ; Wen, Bianying ; Chen, Yulong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3073-80f04307b995235ba10ddbb19fc4a1a4a163f32a9acf1888b51b272b4725616e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>amide nucleating agents</topic><topic>Benzamide</topic><topic>Benzene</topic><topic>Covalent bonds</topic><topic>Crystallization</topic><topic>Hydrogen bonding</topic><topic>Hydrogen bonds</topic><topic>Molecular structure</topic><topic>Nucleation</topic><topic>poly(L‐lactide)</topic><topic>Symmetry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>He, Zejian</creatorcontrib><creatorcontrib>Shao, Haifeng</creatorcontrib><creatorcontrib>Zhang, Nannan</creatorcontrib><creatorcontrib>Li, Jie</creatorcontrib><creatorcontrib>Xiao, Hai</creatorcontrib><creatorcontrib>Weng, Tianhang</creatorcontrib><creatorcontrib>Zhou, Mi</creatorcontrib><creatorcontrib>Wen, Bianying</creatorcontrib><creatorcontrib>Chen, Yulong</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Journal of polymer science (2020)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>He, Zejian</au><au>Shao, Haifeng</au><au>Zhang, Nannan</au><au>Li, Jie</au><au>Xiao, Hai</au><au>Weng, Tianhang</au><au>Zhou, Mi</au><au>Wen, Bianying</au><au>Chen, Yulong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The crystalline behavior of poly(L‐lactide) induced by nucleating agents with amide structure: The effect of benzamide molecule symmetry</atitle><jtitle>Journal of polymer science (2020)</jtitle><date>2023-01-01</date><risdate>2023</risdate><volume>61</volume><issue>1</issue><spage>67</spage><epage>82</epage><pages>67-82</pages><issn>2642-4150</issn><eissn>2642-4169</eissn><abstract>Amide nucleating agents have been reported to be effective in promoting poly(L‐lactide) (PLLA) crystallization, while few research efforts have focused on the structure–activity relationship of the nucleating agents which is one basic issue to develop new agents. In this work, three amide nucleating agents with different symmetry were designed and synthesized to investigate the effect of the symmetry of benzamide nucleating agents on PLLA crystallization. It is found that the C3 symmetric amide structure of N, N′, N″‐tricyclohexyl‐1,3,5‐benzenetriamine (BTCA) agent can form a highly oriented structure by a triple hydrogen bond of π–π bond and benzene ring and can act as efficient nucleation sites. In addition, the strong intramolecular hydrogen bond with PLLA would further promote the crystallization of PLLA. In general, it is the self‐assembled ability and intramolecular hydrogen bonding with PLLA affects the rate and degree of PLLA crystallinity, and we find the C3 symmetric amide structure exhibits the best performance.</abstract><cop>Hoboken, USA</cop><pub>John Wiley & Sons, Inc</pub><doi>10.1002/pol.20220295</doi><tpages>16</tpages><orcidid>https://orcid.org/0000-0001-8588-878X</orcidid><orcidid>https://orcid.org/0000-0001-6310-1384</orcidid></addata></record> |
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| subjects | amide nucleating agents Benzamide Benzene Covalent bonds Crystallization Hydrogen bonding Hydrogen bonds Molecular structure Nucleation poly(L‐lactide) Symmetry |
| title | The crystalline behavior of poly(L‐lactide) induced by nucleating agents with amide structure: The effect of benzamide molecule symmetry |
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