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Synthesis of new photocurable oligoisoprenes and kinetic studies of their radical photopolymerization
New photosensitive oligoisoprenes were synthesized by controlled degradation of high molecular weight cis‐1,4‐polyisoprene and successive chemical modification of the chain‐ends. Oligomers with diacrylate extremities were synthesized, characterized, and used in photocrosslinking reactions in differe...
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Published in: | Journal of applied polymer science 2013-01, Vol.127 (2), p.1359-1368 |
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container_title | Journal of applied polymer science |
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creator | Jellali, Rachid Campistron, Irène Laguerre, Albert Pasetto, Pamela Lecamp, Laurence Bunel, Claude Mouget, Jean-Luc Pilard, Jean-François |
description | New photosensitive oligoisoprenes were synthesized by controlled degradation of high molecular weight cis‐1,4‐polyisoprene and successive chemical modification of the chain‐ends. Oligomers with diacrylate extremities were synthesized, characterized, and used in photocrosslinking reactions in different conditions. The photoinitiated polymerization of the diacrylate oligoisoprenes was carried out using 2,2‐dimethyl‐2‐hydroxyacetophenone (Darocur 1173) as initiator and the reaction was monitored by photocalorimetry‐DSC and real time FTIR spectroscopy. The influence of oxygen, photoinitiator concentration, light intensity, diluting agent, and oligomers molecular weight on the reaction rate was investigated. It was found that the presence of oxygen does not influence the photopolymerization kinetics of the diacrylate oligoisoprenes. Maximum conversion was obtained for a photoinitiator concentration of 5% (w/w) and for a light intensity of 13.5 mW/cm2. Decreasing the formulation viscosity by addition of a diluent (1,6‐hexanediol diacrylate) raised the photopolymerization rate, by increasing the reactive species mobility. © 2012 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2013 |
doi_str_mv | 10.1002/app.37691 |
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Oligomers with diacrylate extremities were synthesized, characterized, and used in photocrosslinking reactions in different conditions. The photoinitiated polymerization of the diacrylate oligoisoprenes was carried out using 2,2‐dimethyl‐2‐hydroxyacetophenone (Darocur 1173) as initiator and the reaction was monitored by photocalorimetry‐DSC and real time FTIR spectroscopy. The influence of oxygen, photoinitiator concentration, light intensity, diluting agent, and oligomers molecular weight on the reaction rate was investigated. It was found that the presence of oxygen does not influence the photopolymerization kinetics of the diacrylate oligoisoprenes. Maximum conversion was obtained for a photoinitiator concentration of 5% (w/w) and for a light intensity of 13.5 mW/cm2. Decreasing the formulation viscosity by addition of a diluent (1,6‐hexanediol diacrylate) raised the photopolymerization rate, by increasing the reactive species mobility. © 2012 Wiley Periodicals, Inc. J. Appl. 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Sci., 2013</description><identifier>ISSN: 0021-8995</identifier><identifier>EISSN: 1097-4628</identifier><identifier>DOI: 10.1002/app.37691</identifier><identifier>CODEN: JAPNAB</identifier><language>eng</language><publisher>Hoboken: Wiley Subscription Services, Inc., A Wiley Company</publisher><subject>antifouling coating ; Applied sciences ; Chemical Sciences ; Degradation ; Exact sciences and technology ; Materials science ; Molecular weight ; Oligomers ; Photoinitiators ; Photopolymerization ; Physicochemistry of polymers ; polyisoprene ; Polymerization ; Polymers ; Polymers and radiations ; radical photopolymerization ; Reaction kinetics ; Reproduction ; telechelic oligomers</subject><ispartof>Journal of applied polymer science, 2013-01, Vol.127 (2), p.1359-1368</ispartof><rights>Copyright © 2012 Wiley Periodicals, Inc.</rights><rights>2014 INIST-CNRS</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4671-abd9646789eac6554e5ab12a4583d6cbb10f61726088dade1d6967017e98bef13</citedby><cites>FETCH-LOGICAL-c4671-abd9646789eac6554e5ab12a4583d6cbb10f61726088dade1d6967017e98bef13</cites><orcidid>0000-0002-5535-1022 ; 0000-0002-5682-5410 ; 0000-0003-2209-8080 ; 0000-0003-0154-7289</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,780,784,885,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=26915974$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-00782895$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Jellali, Rachid</creatorcontrib><creatorcontrib>Campistron, Irène</creatorcontrib><creatorcontrib>Laguerre, Albert</creatorcontrib><creatorcontrib>Pasetto, Pamela</creatorcontrib><creatorcontrib>Lecamp, Laurence</creatorcontrib><creatorcontrib>Bunel, Claude</creatorcontrib><creatorcontrib>Mouget, Jean-Luc</creatorcontrib><creatorcontrib>Pilard, Jean-François</creatorcontrib><title>Synthesis of new photocurable oligoisoprenes and kinetic studies of their radical photopolymerization</title><title>Journal of applied polymer science</title><addtitle>J. Appl. Polym. Sci</addtitle><description>New photosensitive oligoisoprenes were synthesized by controlled degradation of high molecular weight cis‐1,4‐polyisoprene and successive chemical modification of the chain‐ends. Oligomers with diacrylate extremities were synthesized, characterized, and used in photocrosslinking reactions in different conditions. The photoinitiated polymerization of the diacrylate oligoisoprenes was carried out using 2,2‐dimethyl‐2‐hydroxyacetophenone (Darocur 1173) as initiator and the reaction was monitored by photocalorimetry‐DSC and real time FTIR spectroscopy. The influence of oxygen, photoinitiator concentration, light intensity, diluting agent, and oligomers molecular weight on the reaction rate was investigated. It was found that the presence of oxygen does not influence the photopolymerization kinetics of the diacrylate oligoisoprenes. Maximum conversion was obtained for a photoinitiator concentration of 5% (w/w) and for a light intensity of 13.5 mW/cm2. Decreasing the formulation viscosity by addition of a diluent (1,6‐hexanediol diacrylate) raised the photopolymerization rate, by increasing the reactive species mobility. © 2012 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2013</description><subject>antifouling coating</subject><subject>Applied sciences</subject><subject>Chemical Sciences</subject><subject>Degradation</subject><subject>Exact sciences and technology</subject><subject>Materials science</subject><subject>Molecular weight</subject><subject>Oligomers</subject><subject>Photoinitiators</subject><subject>Photopolymerization</subject><subject>Physicochemistry of polymers</subject><subject>polyisoprene</subject><subject>Polymerization</subject><subject>Polymers</subject><subject>Polymers and radiations</subject><subject>radical photopolymerization</subject><subject>Reaction kinetics</subject><subject>Reproduction</subject><subject>telechelic oligomers</subject><issn>0021-8995</issn><issn>1097-4628</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNp1kV2L1DAUhosoOK5e-A8KIuhFd5M2n5fDojPioMuqCN6E0_TUyW6n6Sat6_jrzWzXEQSvEpLnfc5JTpY9p-SUElKewTCcVlJo-iBbUKJlwUSpHmaLdEcLpTV_nD2J8YoQSjkRiww_7ftxi9HF3Ld5j7f5sPWjt1OAusPcd-67d9EPAXuMOfRNfu16HJ3N4zg1Du9iSeBCHqBxFrpZMPhuv8PgfsHofP80e9RCF_HZ_XqSfXn75vP5uth8XL07X24Ky4SkBdSNFmmnNIIVnDPkUNMSGFdVI2xdU9IKKktBlGqgQdoILSShErWqsaXVSfZ69m6hM0NwOwh748GZ9XJjDmeESFUqzX8c2FczOwR_M2Eczc5Fi10HPfopGpo6Ypypskroi3_QKz-FPr3E0IpzQhlT1d_iNvgYA7bHDigxh-GYNBxzN5zEvrw3Qkx_1gborYvHQJkYriVL3NnM3boO9_8XmuXFxR9zMSdcHPHnMQHh2ghZSW6-fliZNbm8lN9W742ufgMusa0d</recordid><startdate>20130115</startdate><enddate>20130115</enddate><creator>Jellali, Rachid</creator><creator>Campistron, Irène</creator><creator>Laguerre, Albert</creator><creator>Pasetto, Pamela</creator><creator>Lecamp, Laurence</creator><creator>Bunel, Claude</creator><creator>Mouget, Jean-Luc</creator><creator>Pilard, Jean-François</creator><general>Wiley Subscription Services, Inc., A Wiley Company</general><general>Wiley</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8FD</scope><scope>JG9</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0002-5535-1022</orcidid><orcidid>https://orcid.org/0000-0002-5682-5410</orcidid><orcidid>https://orcid.org/0000-0003-2209-8080</orcidid><orcidid>https://orcid.org/0000-0003-0154-7289</orcidid></search><sort><creationdate>20130115</creationdate><title>Synthesis of new photocurable oligoisoprenes and kinetic studies of their radical photopolymerization</title><author>Jellali, Rachid ; Campistron, Irène ; Laguerre, Albert ; Pasetto, Pamela ; Lecamp, Laurence ; Bunel, Claude ; Mouget, Jean-Luc ; Pilard, Jean-François</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4671-abd9646789eac6554e5ab12a4583d6cbb10f61726088dade1d6967017e98bef13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>antifouling coating</topic><topic>Applied sciences</topic><topic>Chemical Sciences</topic><topic>Degradation</topic><topic>Exact sciences and technology</topic><topic>Materials science</topic><topic>Molecular weight</topic><topic>Oligomers</topic><topic>Photoinitiators</topic><topic>Photopolymerization</topic><topic>Physicochemistry of polymers</topic><topic>polyisoprene</topic><topic>Polymerization</topic><topic>Polymers</topic><topic>Polymers and radiations</topic><topic>radical photopolymerization</topic><topic>Reaction kinetics</topic><topic>Reproduction</topic><topic>telechelic oligomers</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jellali, Rachid</creatorcontrib><creatorcontrib>Campistron, Irène</creatorcontrib><creatorcontrib>Laguerre, Albert</creatorcontrib><creatorcontrib>Pasetto, Pamela</creatorcontrib><creatorcontrib>Lecamp, Laurence</creatorcontrib><creatorcontrib>Bunel, Claude</creatorcontrib><creatorcontrib>Mouget, Jean-Luc</creatorcontrib><creatorcontrib>Pilard, Jean-François</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Journal of applied polymer science</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Jellali, Rachid</au><au>Campistron, Irène</au><au>Laguerre, Albert</au><au>Pasetto, Pamela</au><au>Lecamp, Laurence</au><au>Bunel, Claude</au><au>Mouget, Jean-Luc</au><au>Pilard, Jean-François</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of new photocurable oligoisoprenes and kinetic studies of their radical photopolymerization</atitle><jtitle>Journal of applied polymer science</jtitle><addtitle>J. Appl. Polym. Sci</addtitle><date>2013-01-15</date><risdate>2013</risdate><volume>127</volume><issue>2</issue><spage>1359</spage><epage>1368</epage><pages>1359-1368</pages><issn>0021-8995</issn><eissn>1097-4628</eissn><coden>JAPNAB</coden><abstract>New photosensitive oligoisoprenes were synthesized by controlled degradation of high molecular weight cis‐1,4‐polyisoprene and successive chemical modification of the chain‐ends. Oligomers with diacrylate extremities were synthesized, characterized, and used in photocrosslinking reactions in different conditions. The photoinitiated polymerization of the diacrylate oligoisoprenes was carried out using 2,2‐dimethyl‐2‐hydroxyacetophenone (Darocur 1173) as initiator and the reaction was monitored by photocalorimetry‐DSC and real time FTIR spectroscopy. The influence of oxygen, photoinitiator concentration, light intensity, diluting agent, and oligomers molecular weight on the reaction rate was investigated. It was found that the presence of oxygen does not influence the photopolymerization kinetics of the diacrylate oligoisoprenes. Maximum conversion was obtained for a photoinitiator concentration of 5% (w/w) and for a light intensity of 13.5 mW/cm2. Decreasing the formulation viscosity by addition of a diluent (1,6‐hexanediol diacrylate) raised the photopolymerization rate, by increasing the reactive species mobility. © 2012 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2013</abstract><cop>Hoboken</cop><pub>Wiley Subscription Services, Inc., A Wiley Company</pub><doi>10.1002/app.37691</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0002-5535-1022</orcidid><orcidid>https://orcid.org/0000-0002-5682-5410</orcidid><orcidid>https://orcid.org/0000-0003-2209-8080</orcidid><orcidid>https://orcid.org/0000-0003-0154-7289</orcidid><oa>free_for_read</oa></addata></record> |
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subjects | antifouling coating Applied sciences Chemical Sciences Degradation Exact sciences and technology Materials science Molecular weight Oligomers Photoinitiators Photopolymerization Physicochemistry of polymers polyisoprene Polymerization Polymers Polymers and radiations radical photopolymerization Reaction kinetics Reproduction telechelic oligomers |
title | Synthesis of new photocurable oligoisoprenes and kinetic studies of their radical photopolymerization |
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