| Revision as of 18:05, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 424756212 of page 4,4'-Oxydianiline for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 15:18, 26 April 2022 edit Sybren93 (talk | contribs)167 editsNo edit summary |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 413270432 |
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| ImageFile = 4,4'-ODA.png|thumb |
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| verifiedrevid = 477220684 |
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| Name = 4,4′-Oxydianiline |
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| ImageFile = 4,4'-ODA.png |
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| ImageSize = |
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| ImageSize = |
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| IUPACName = 4,4'-oxydianiline |
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| PIN = 4,4′-Oxydianiline |
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| OtherNames = 4,4'-diaminodiphenyl ether; 4-aminophenyl ether; 4,4'-oxybisbenzenamine; bis(4-aminophenyl) ether; 4,4'-ODA |
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| OtherNames = 4,4′-Diaminodiphenyl ether; 4-Aminophenyl ether; 4,4′-Oxybisbenzenamine; Bis(4-aminophenyl) ether; 4,4′-ODA |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 7298 |
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| ChemSpiderID = 7298 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 354663 |
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| ChEMBL = 354663 |
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| ChEBI = 34384 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C12H12N2O/c13-9-1-5-11(6-2-9)15-12-7-3-10(14)4-8-12/h1-8H,13-14H2 |
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| StdInChI = 1S/C12H12N2O/c13-9-1-5-11(6-2-9)15-12-7-3-10(14)4-8-12/h1-8H,13-14H2 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = HLBLWEWZXPIGSM-UHFFFAOYSA-N |
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| StdInChIKey = HLBLWEWZXPIGSM-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 101-80-4 |
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| CASNo = 101-80-4 |
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| PubChem = 7579 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII = 28DLB4Z70T |
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| EC_number = 202-977-0 |
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| UNNumber = 3077 |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>12</sub>H<sub>12</sub>N<sub>2</sub>O |
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| Formula = C<sub>12</sub>H<sub>12</sub>N<sub>2</sub>O |
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| MolarMass = 200.24 g/mol |
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| MolarMass = 200.24 g/mol |
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| Appearance = Colorless crystalline solid |
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| Appearance = Colorless crystalline solid |
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| MeltingPt = 188-192 °C (461.15-465.15 K) |
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| MeltingPtC = 188 to 192 |
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| MeltingPt_notes = |
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| BoilingPt = 219 °C (492.15 K) |
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| BoilingPtC = 219 |
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| Solubility = Insoluble |
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| Solubility = Insoluble |
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| Section7 = {{Chembox Hazards |
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| GHSPictograms = {{GHS06}}{{GHS08}}{{GHS09}} |
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| NFPA-H = 2 |
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| NFPA-F = |
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| GHSSignalWord = Danger |
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| HPhrases = {{H-phrases|301|311|331|340|350|361f|411}} |
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| NFPA-R = |
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| PPhrases = {{P-phrases|201|202|261|264|270|271|273|280|281|301+310|302+352|304+340|308+313|311|312|321|322|330|361|363|391|403+233|405|501}} |
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| NFPA-O = |
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| NFPA-H = 2 |
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| FlashPt = 219 °C (492.15 K) |
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| FlashPtC = 219 |
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'''4,4′-Oxydianiline''' (ODA) is an ] with the ] ](]<sub>6</sub>]<sub>4</sub>]H<sub>2</sub>)<sub>2</sub>. It is an ] derivative of ]. This colourless solid is a useful monomer and ] for ]s, especially the ]s, such as ]. |
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== Uses == |
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4,4′-Oxydianiline is used in the production of a wide variety of polymer resins. The primary use lies in the production of polyimide and poly(ester)imide resins. These resins are used for their temperature-resistant properties and are utilized in products including wire enamels, coatings, film, adhesives, insulating varnishes, coated fabrics, flame-retardant fibers, oil sealants and retainers, insulation for cables and ], and ]s and composite for aerospace vehicles. |
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Other applications of 4,4′-oxydianiline include the production of poly(amide)imide resins (which are used in the manufacture of heat-resistant wire enamels and coatings), as an intermediate in the manufacture of epoxy resins and adhesives, and in the production of aromatic polyether imides.<ref>{{Cite web |url=https://ntp.niehs.nih.gov/ntp/roc/content/profiles/oxydianiline.pdf |title=11th ROC: 4,4'-Oxydianiline<!-- Bot generated title --> |access-date=2008-02-28 |archive-url=https://web.archive.org/web/20090131033756/http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s141oxyd.pdf |archive-date=2009-01-31 |url-status=live }}</ref> Its use in the production of polyimine ] has also been proposed.<ref>{{Cite journal| last = Schoustra| first = Sybren K.| author2 = Dijksman, Joshua A.| author3= Zuilhof, Han| author4 = Smulders, Maarten M. J.| title = Molecular control over vitrimer-like mechanics – tuneable dynamic motifs based on the Hammett equation in polyimine materials | journal = Chemical Science |year=2021 | volume = 12 | issue = 1| pages = 293–302 | doi = 10.1039/d0sc05458e |issn=2041-6520 | pmid = 34163597| pmc = 8178953}}</ref> |
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A specific reaction involving industrial use of 4,4′-oxydianiline is in the production of thermostable poly(amideurea) acids, which can be prepared from 4,4′-oxydianiline, pyromellitic dianhydride, and diisocyanates. These poly(amideurea) acids can be used as intermediates in the syntheses of poly(imideurea)s:<ref>{{cite journal |
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| author = Chiria, C.I |
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| author2 = Tanasã, F. |
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| title = Polyureas |
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| journal = Ullmann's Encyclopedia of Industrial Chemistry |
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| volume = |
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| issue = |
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| pages = |
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| year = 2000 |
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| publisher = Wiley-VCH Verlag GmbH & Co. KGaA |
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| location = Weinheim |
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| doi = 10.1002/14356007.d21_d01 | isbn = 3527306730 |
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}}</ref> |
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] |
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==Related compounds== |
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* ] |
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* ] |
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* ] |
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==References== |
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{{reflist}} |
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== External links == |
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* Material Safety Data Sheet provided by Sigma-Aldrich. |
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{{DEFAULTSORT:Oxydianiline, 4,4'-}} |
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] |