Synthesis of α,β-unsaturated esters of perfluoropolyalkylethers (PFPAEs) based on hexafluoropropylene oxide units for photopolymerization
α,β-unsaturated esters are usually synthesized for polymer applications. However, the addition of maleate ( cis- configuration) to a fluorinated moiety is challenging due to its potential isomerization during esterification. Various synthetic routes were attempted and led to very low conversion or s...
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| Veröffentlicht in: | RSC advances 2018-09, Vol.8 (57), p.32664-32671 |
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| creator | Bonneaud, Céline Decostanzi, Mélanie Burgess, Julia Trusiano, Giuseppe Burgess, Trevor Bongiovanni, Roberta Joly-Duhamel, Christine Friesen, Chadron M |
| description | α,β-unsaturated esters are usually synthesized for polymer applications. However, the addition of maleate (
cis-
configuration) to a fluorinated moiety is challenging due to its potential isomerization during esterification. Various synthetic routes were attempted and led to very low conversion or side-products. The immiscibility of both reagents combined with an easy isomerization or attack on the double bond were potential explanations. In this paper, the synthesis of maleates oligo(hexafluoropropylene oxide) is reported by Steglich esterification and the reaction conditions are discussed depending on the molecular weight of the fluorinated moieties. After UV-curing, hydrophobic polymers were obtained by copolymerization with vinyl ethers by electron acceptor-donor systems.
Hydrophobic macromonomers synthesized by Steglich esterification to generate UV-curable materials. |
| doi_str_mv | 10.1039/c8ra06354k |
| format | Article |
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cis-
configuration) to a fluorinated moiety is challenging due to its potential isomerization during esterification. Various synthetic routes were attempted and led to very low conversion or side-products. The immiscibility of both reagents combined with an easy isomerization or attack on the double bond were potential explanations. In this paper, the synthesis of maleates oligo(hexafluoropropylene oxide) is reported by Steglich esterification and the reaction conditions are discussed depending on the molecular weight of the fluorinated moieties. After UV-curing, hydrophobic polymers were obtained by copolymerization with vinyl ethers by electron acceptor-donor systems.
Hydrophobic macromonomers synthesized by Steglich esterification to generate UV-curable materials.</description><identifier>ISSN: 2046-2069</identifier><identifier>EISSN: 2046-2069</identifier><identifier>DOI: 10.1039/c8ra06354k</identifier><identifier>PMID: 35547709</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Addition polymerization ; Chemical Sciences ; Chemical synthesis ; Chemistry ; Copolymerization ; Esterification ; Esters ; Ethers ; Fluorination ; Infrared spectroscopy ; Isomerization ; Maleates ; Miscibility ; Molecular weight ; Photopolymerization ; Reaction kinetics ; Reagents ; Spectra ; Vinyl ethers</subject><ispartof>RSC advances, 2018-09, Vol.8 (57), p.32664-32671</ispartof><rights>This journal is © The Royal Society of Chemistry.</rights><rights>Copyright Royal Society of Chemistry 2018</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><rights>This journal is © The Royal Society of Chemistry 2018 The Royal Society of Chemistry</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c377k-d20c45c2c4678fd98cc42a76761ae8c1470152a2e1deda6c22896e004aa77863</citedby><cites>FETCH-LOGICAL-c377k-d20c45c2c4678fd98cc42a76761ae8c1470152a2e1deda6c22896e004aa77863</cites><orcidid>0000-0001-9955-5695 ; 0000-0002-5101-1223 ; 0000-0002-2607-9461</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/PMC9086334/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC9086334/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,860,881,27903,27904,53770,53772</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/35547709$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.umontpellier.fr/hal-01928700$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Bonneaud, Céline</creatorcontrib><creatorcontrib>Decostanzi, Mélanie</creatorcontrib><creatorcontrib>Burgess, Julia</creatorcontrib><creatorcontrib>Trusiano, Giuseppe</creatorcontrib><creatorcontrib>Burgess, Trevor</creatorcontrib><creatorcontrib>Bongiovanni, Roberta</creatorcontrib><creatorcontrib>Joly-Duhamel, Christine</creatorcontrib><creatorcontrib>Friesen, Chadron M</creatorcontrib><title>Synthesis of α,β-unsaturated esters of perfluoropolyalkylethers (PFPAEs) based on hexafluoropropylene oxide units for photopolymerization</title><title>RSC advances</title><addtitle>RSC Adv</addtitle><description>α,β-unsaturated esters are usually synthesized for polymer applications. However, the addition of maleate (
cis-
configuration) to a fluorinated moiety is challenging due to its potential isomerization during esterification. Various synthetic routes were attempted and led to very low conversion or side-products. The immiscibility of both reagents combined with an easy isomerization or attack on the double bond were potential explanations. In this paper, the synthesis of maleates oligo(hexafluoropropylene oxide) is reported by Steglich esterification and the reaction conditions are discussed depending on the molecular weight of the fluorinated moieties. After UV-curing, hydrophobic polymers were obtained by copolymerization with vinyl ethers by electron acceptor-donor systems.
Hydrophobic macromonomers synthesized by Steglich esterification to generate UV-curable materials.</description><subject>Addition polymerization</subject><subject>Chemical Sciences</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Copolymerization</subject><subject>Esterification</subject><subject>Esters</subject><subject>Ethers</subject><subject>Fluorination</subject><subject>Infrared spectroscopy</subject><subject>Isomerization</subject><subject>Maleates</subject><subject>Miscibility</subject><subject>Molecular weight</subject><subject>Photopolymerization</subject><subject>Reaction kinetics</subject><subject>Reagents</subject><subject>Spectra</subject><subject>Vinyl ethers</subject><issn>2046-2069</issn><issn>2046-2069</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNpdks1u1DAUhSNERau2G_YgS2xaRODacexkgzQatbTqSFTQveU6NySdjB3spOrwCjwNPEifCXdmGEotS7Z8vnP8d5PkJYX3FLLygym8BpHlfP4s2WPARcpAlM8fzXeTwxBuIDaRUyboi2Q3y3MuJZR7yc-vSzs0GNpAXE3uf727_52ONuhh9HrAimAY0K-0Hn3djc673nVL3c2XHUZj1I4uTy8nJ-GYXOsQHc6SBu_0ho09ghaJu2srJKNth0Bq50nfuGEVtUDf_tBD6-xBslPrLuDhZtxPrk5PrqZn6ezzp_PpZJaaTMp5WjEwPDfMcCGLuioLYzjTUkhBNRaGcgk0Z5ohrbDSwjBWlAIBuNZSFiLbTz6uY_vxeoGVQTt43anetwvtl8rpVv2v2LZR39ytKiG6Mx4DjtcBzRPb2WSmHtaAlqyQALc0skebzbz7PsbXVIs2GOw6bdGNQTEhuCw5A4jomyfojRu9jS-hGKUsh5JzFqm3a8p4F4LHensCCuqhItS0-DJZVcRFhF8_vuoW_fv_EXi1BnwwW_VfSWV_AOVNvys</recordid><startdate>20180921</startdate><enddate>20180921</enddate><creator>Bonneaud, Céline</creator><creator>Decostanzi, Mélanie</creator><creator>Burgess, Julia</creator><creator>Trusiano, Giuseppe</creator><creator>Burgess, Trevor</creator><creator>Bongiovanni, Roberta</creator><creator>Joly-Duhamel, Christine</creator><creator>Friesen, Chadron M</creator><general>Royal Society of Chemistry</general><general>The Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>1XC</scope><scope>VOOES</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0001-9955-5695</orcidid><orcidid>https://orcid.org/0000-0002-5101-1223</orcidid><orcidid>https://orcid.org/0000-0002-2607-9461</orcidid></search><sort><creationdate>20180921</creationdate><title>Synthesis of α,β-unsaturated esters of perfluoropolyalkylethers (PFPAEs) based on hexafluoropropylene oxide units for photopolymerization</title><author>Bonneaud, Céline ; Decostanzi, Mélanie ; Burgess, Julia ; Trusiano, Giuseppe ; Burgess, Trevor ; Bongiovanni, Roberta ; Joly-Duhamel, Christine ; Friesen, Chadron M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c377k-d20c45c2c4678fd98cc42a76761ae8c1470152a2e1deda6c22896e004aa77863</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Addition polymerization</topic><topic>Chemical Sciences</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Copolymerization</topic><topic>Esterification</topic><topic>Esters</topic><topic>Ethers</topic><topic>Fluorination</topic><topic>Infrared spectroscopy</topic><topic>Isomerization</topic><topic>Maleates</topic><topic>Miscibility</topic><topic>Molecular weight</topic><topic>Photopolymerization</topic><topic>Reaction kinetics</topic><topic>Reagents</topic><topic>Spectra</topic><topic>Vinyl ethers</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bonneaud, Céline</creatorcontrib><creatorcontrib>Decostanzi, Mélanie</creatorcontrib><creatorcontrib>Burgess, Julia</creatorcontrib><creatorcontrib>Trusiano, Giuseppe</creatorcontrib><creatorcontrib>Burgess, Trevor</creatorcontrib><creatorcontrib>Bongiovanni, Roberta</creatorcontrib><creatorcontrib>Joly-Duhamel, Christine</creatorcontrib><creatorcontrib>Friesen, Chadron M</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><collection>Hyper Article en Ligne (HAL)</collection><collection>Hyper Article en Ligne (HAL) (Open Access)</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>RSC advances</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bonneaud, Céline</au><au>Decostanzi, Mélanie</au><au>Burgess, Julia</au><au>Trusiano, Giuseppe</au><au>Burgess, Trevor</au><au>Bongiovanni, Roberta</au><au>Joly-Duhamel, Christine</au><au>Friesen, Chadron M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of α,β-unsaturated esters of perfluoropolyalkylethers (PFPAEs) based on hexafluoropropylene oxide units for photopolymerization</atitle><jtitle>RSC advances</jtitle><addtitle>RSC Adv</addtitle><date>2018-09-21</date><risdate>2018</risdate><volume>8</volume><issue>57</issue><spage>32664</spage><epage>32671</epage><pages>32664-32671</pages><issn>2046-2069</issn><eissn>2046-2069</eissn><abstract>α,β-unsaturated esters are usually synthesized for polymer applications. However, the addition of maleate (
cis-
configuration) to a fluorinated moiety is challenging due to its potential isomerization during esterification. Various synthetic routes were attempted and led to very low conversion or side-products. The immiscibility of both reagents combined with an easy isomerization or attack on the double bond were potential explanations. In this paper, the synthesis of maleates oligo(hexafluoropropylene oxide) is reported by Steglich esterification and the reaction conditions are discussed depending on the molecular weight of the fluorinated moieties. After UV-curing, hydrophobic polymers were obtained by copolymerization with vinyl ethers by electron acceptor-donor systems.
Hydrophobic macromonomers synthesized by Steglich esterification to generate UV-curable materials.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>35547709</pmid><doi>10.1039/c8ra06354k</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0001-9955-5695</orcidid><orcidid>https://orcid.org/0000-0002-5101-1223</orcidid><orcidid>https://orcid.org/0000-0002-2607-9461</orcidid><oa>free_for_read</oa></addata></record> |
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| source | DOAJ Directory of Open Access Journals; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; PubMed Central Open Access; PubMed Central |
| subjects | Addition polymerization Chemical Sciences Chemical synthesis Chemistry Copolymerization Esterification Esters Ethers Fluorination Infrared spectroscopy Isomerization Maleates Miscibility Molecular weight Photopolymerization Reaction kinetics Reagents Spectra Vinyl ethers |
| title | Synthesis of α,β-unsaturated esters of perfluoropolyalkylethers (PFPAEs) based on hexafluoropropylene oxide units for photopolymerization |
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