Curable, thermally stable poly(enaminonitriles)

Three new bis(1-chloro-2,2-dicyanovinyl) aromatic monomers have been synthesized. Vinylic nucleophilic substitution polymerization with 4,4'-diaminodiphenyl ether led to moderately high molecular weight poly(enaminonitriles) (0.39 < ( eta ) < 0.84 dL/g, measured in dimethylformamide at 25...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Macromolecules 1989-03, Vol.22 (3), p.1084-1092
Hauptverfasser: Moore, J. A, Robello, Douglas R
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 1092
container_issue 3
container_start_page 1084
container_title Macromolecules
container_volume 22
creator Moore, J. A
Robello, Douglas R
description Three new bis(1-chloro-2,2-dicyanovinyl) aromatic monomers have been synthesized. Vinylic nucleophilic substitution polymerization with 4,4'-diaminodiphenyl ether led to moderately high molecular weight poly(enaminonitriles) (0.39 < ( eta ) < 0.84 dL/g, measured in dimethylformamide at 25 deg C). The polymers exhibited excellent thermal stability, retaining 100% of their mass up to 400 deg C under nitrogen. Evidence is presented for an intramolecular cyclization reaction occurring > 300 deg C to form poly(4-aminoquinoline) repeat units. The cyclization reaction occurs without the emission of volatile byproducts, which is a drawback in the curing of polyimides. The dielectric constant of a representative polymer of this class was found to be approximately eight before heat treatment and five afterward. 21 ref.--AA
doi_str_mv 10.1021/ma00193a015
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_25161030</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>25161030</sourcerecordid><originalsourceid>FETCH-LOGICAL-a427t-cb4a29d5bbefefa92752023a50850758eb43f135abf4d9d49d020b5ad43c7b563</originalsourceid><addsrcrecordid>eNpt0EtLAzEQB_AgCtbqyS_Qg_hA1-bZNEetjwoVBSt4C5PdLG7N7tZkF-y3N2VL8eBpYOY3w_BH6Jjga4IpGZaAMVEMMBE7qEcExYkYM7GLehhTniiq5D46CGERGRGc9dBw0nowzl4Nmk_rS3BuNQjNujNY1m51bisoi6quisYXzoaLQ7SXgwv2aFP76P3hfj6ZJrOXx6fJzSwBTmWTpIYDVZkwxuY2B0Vl_IUyEHgssBRjazjLCRNgcp6pjKsMU2wEZJyl0ogR66PT7u7S19-tDY0ui5Ba56CydRs0FWREMMMRXnYw9XUI3uZ66YsS_EoTrNeh6D-hRH2yOQshBZd7qNIibFck5ZILGlnSsSI09mc7Bv-lR5JJoeevb_pWyQ82nz7ru-jPOg9p0Iu69VXM5t8HfgFH4Hut</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>25161030</pqid></control><display><type>article</type><title>Curable, thermally stable poly(enaminonitriles)</title><source>American Chemical Society Journals</source><creator>Moore, J. A ; Robello, Douglas R</creator><creatorcontrib>Moore, J. A ; Robello, Douglas R</creatorcontrib><description>Three new bis(1-chloro-2,2-dicyanovinyl) aromatic monomers have been synthesized. Vinylic nucleophilic substitution polymerization with 4,4'-diaminodiphenyl ether led to moderately high molecular weight poly(enaminonitriles) (0.39 &lt; ( eta ) &lt; 0.84 dL/g, measured in dimethylformamide at 25 deg C). The polymers exhibited excellent thermal stability, retaining 100% of their mass up to 400 deg C under nitrogen. Evidence is presented for an intramolecular cyclization reaction occurring &gt; 300 deg C to form poly(4-aminoquinoline) repeat units. The cyclization reaction occurs without the emission of volatile byproducts, which is a drawback in the curing of polyimides. The dielectric constant of a representative polymer of this class was found to be approximately eight before heat treatment and five afterward. 21 ref.--AA</description><identifier>ISSN: 0024-9297</identifier><identifier>EISSN: 1520-5835</identifier><identifier>DOI: 10.1021/ma00193a015</identifier><identifier>CODEN: MAMOBX</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Applied sciences ; Exact sciences and technology ; Organic polymers ; Physicochemistry of polymers ; Polymers with particular properties ; Preparation, kinetics, thermodynamics, mechanism and catalysts</subject><ispartof>Macromolecules, 1989-03, Vol.22 (3), p.1084-1092</ispartof><rights>1989 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a427t-cb4a29d5bbefefa92752023a50850758eb43f135abf4d9d49d020b5ad43c7b563</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ma00193a015$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ma00193a015$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2763,27075,27923,27924,56737,56787</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&amp;idt=7247452$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Moore, J. A</creatorcontrib><creatorcontrib>Robello, Douglas R</creatorcontrib><title>Curable, thermally stable poly(enaminonitriles)</title><title>Macromolecules</title><addtitle>Macromolecules</addtitle><description>Three new bis(1-chloro-2,2-dicyanovinyl) aromatic monomers have been synthesized. Vinylic nucleophilic substitution polymerization with 4,4'-diaminodiphenyl ether led to moderately high molecular weight poly(enaminonitriles) (0.39 &lt; ( eta ) &lt; 0.84 dL/g, measured in dimethylformamide at 25 deg C). The polymers exhibited excellent thermal stability, retaining 100% of their mass up to 400 deg C under nitrogen. Evidence is presented for an intramolecular cyclization reaction occurring &gt; 300 deg C to form poly(4-aminoquinoline) repeat units. The cyclization reaction occurs without the emission of volatile byproducts, which is a drawback in the curing of polyimides. The dielectric constant of a representative polymer of this class was found to be approximately eight before heat treatment and five afterward. 21 ref.--AA</description><subject>Applied sciences</subject><subject>Exact sciences and technology</subject><subject>Organic polymers</subject><subject>Physicochemistry of polymers</subject><subject>Polymers with particular properties</subject><subject>Preparation, kinetics, thermodynamics, mechanism and catalysts</subject><issn>0024-9297</issn><issn>1520-5835</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1989</creationdate><recordtype>article</recordtype><recordid>eNpt0EtLAzEQB_AgCtbqyS_Qg_hA1-bZNEetjwoVBSt4C5PdLG7N7tZkF-y3N2VL8eBpYOY3w_BH6Jjga4IpGZaAMVEMMBE7qEcExYkYM7GLehhTniiq5D46CGERGRGc9dBw0nowzl4Nmk_rS3BuNQjNujNY1m51bisoi6quisYXzoaLQ7SXgwv2aFP76P3hfj6ZJrOXx6fJzSwBTmWTpIYDVZkwxuY2B0Vl_IUyEHgssBRjazjLCRNgcp6pjKsMU2wEZJyl0ogR66PT7u7S19-tDY0ui5Ba56CydRs0FWREMMMRXnYw9XUI3uZ66YsS_EoTrNeh6D-hRH2yOQshBZd7qNIibFck5ZILGlnSsSI09mc7Bv-lR5JJoeevb_pWyQ82nz7ru-jPOg9p0Iu69VXM5t8HfgFH4Hut</recordid><startdate>19890301</startdate><enddate>19890301</enddate><creator>Moore, J. A</creator><creator>Robello, Douglas R</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>19890301</creationdate><title>Curable, thermally stable poly(enaminonitriles)</title><author>Moore, J. A ; Robello, Douglas R</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a427t-cb4a29d5bbefefa92752023a50850758eb43f135abf4d9d49d020b5ad43c7b563</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1989</creationdate><topic>Applied sciences</topic><topic>Exact sciences and technology</topic><topic>Organic polymers</topic><topic>Physicochemistry of polymers</topic><topic>Polymers with particular properties</topic><topic>Preparation, kinetics, thermodynamics, mechanism and catalysts</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Moore, J. A</creatorcontrib><creatorcontrib>Robello, Douglas R</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><jtitle>Macromolecules</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Moore, J. A</au><au>Robello, Douglas R</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Curable, thermally stable poly(enaminonitriles)</atitle><jtitle>Macromolecules</jtitle><addtitle>Macromolecules</addtitle><date>1989-03-01</date><risdate>1989</risdate><volume>22</volume><issue>3</issue><spage>1084</spage><epage>1092</epage><pages>1084-1092</pages><issn>0024-9297</issn><eissn>1520-5835</eissn><coden>MAMOBX</coden><abstract>Three new bis(1-chloro-2,2-dicyanovinyl) aromatic monomers have been synthesized. Vinylic nucleophilic substitution polymerization with 4,4'-diaminodiphenyl ether led to moderately high molecular weight poly(enaminonitriles) (0.39 &lt; ( eta ) &lt; 0.84 dL/g, measured in dimethylformamide at 25 deg C). The polymers exhibited excellent thermal stability, retaining 100% of their mass up to 400 deg C under nitrogen. Evidence is presented for an intramolecular cyclization reaction occurring &gt; 300 deg C to form poly(4-aminoquinoline) repeat units. The cyclization reaction occurs without the emission of volatile byproducts, which is a drawback in the curing of polyimides. The dielectric constant of a representative polymer of this class was found to be approximately eight before heat treatment and five afterward. 21 ref.--AA</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><doi>10.1021/ma00193a015</doi><tpages>9</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0024-9297
ispartof Macromolecules, 1989-03, Vol.22 (3), p.1084-1092
issn 0024-9297
1520-5835
language eng
recordid cdi_proquest_miscellaneous_25161030
source American Chemical Society Journals
subjects Applied sciences
Exact sciences and technology
Organic polymers
Physicochemistry of polymers
Polymers with particular properties
Preparation, kinetics, thermodynamics, mechanism and catalysts
title Curable, thermally stable poly(enaminonitriles)
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-10T22%3A34%3A47IST&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=Curable,%20thermally%20stable%20poly(enaminonitriles)&rft.jtitle=Macromolecules&rft.au=Moore,%20J.%20A&rft.date=1989-03-01&rft.volume=22&rft.issue=3&rft.spage=1084&rft.epage=1092&rft.pages=1084-1092&rft.issn=0024-9297&rft.eissn=1520-5835&rft.coden=MAMOBX&rft_id=info:doi/10.1021/ma00193a015&rft_dat=%3Cproquest_cross%3E25161030%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=25161030&rft_id=info:pmid/&rfr_iscdi=true