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Synthesis of polyamides from rigid and sterically hindered dicarboxylic acids and diamines under mild conditions

dc.contributor.authorOverberger, Charles Gilberten_US
dc.contributor.authorSøebenda, Janen_US
dc.date.accessioned2006-04-28T18:14:40Z
dc.date.available2006-04-28T18:14:40Z
dc.date.issued1969-10en_US
dc.identifier.citationOverberger, Charles G.; SØebenda, Jan (1969)."Synthesis of polyamides from rigid and sterically hindered dicarboxylic acids and diamines under mild conditions." Journal of Polymer Science Part A-1: Polymer Chemistry 7(10): 2875-2887. <http://hdl.handle.net/2027.42/38752>en_US
dc.identifier.issn0449-296Xen_US
dc.identifier.issn1542-9350en_US
dc.identifier.urihttps://hdl.handle.net/2027.42/38752
dc.description.abstractThe rate of polycondensation of piperazine with the 2,4-dinitrophenyl, succinimido, phthalimido, and 4-nitrophenyl esters of bicyclo[2.2.2]octane- trans -2,3-dicarboxylic acid was measured and found to decrease in this sequence. In the reaction of two moles of piperazine with one mole of diester, the reactivity of both ester groups was equal. In equimolar mixtures, the second ester group reacts with the second group about ten times slower because of steric hindrance. In the reaction of the esters with N , N ′-dimethylethylenediamine no such effects were observed. The aminolysis of the N -hydroxyphthalimido ester stops at low conversions unless a very large excess of triethylamine is added. The catalytic effect of 1,2,4-triazole on the aminolysis was proportional to the triazole concentration. From the rate of ester consumption in the presence of pure triethylamine, the extent of possible racemization of the optically active dicarboxylic acid was estimated. In view of the rate data, the extent of polycondensation, and side reactions, only 2,4-dinitrophenyl and N -hydroxysuccinimido diesters are suitable for the synthesis of polyamides derived from rigid and sterically hindered dicarboxylic acids.en_US
dc.format.extent689696 bytes
dc.format.extent3118 bytes
dc.format.mimetypeapplication/pdf
dc.format.mimetypetext/plain
dc.language.isoen_US
dc.publisherJohn Wiley & Sons, Inc.en_US
dc.subject.otherPhysicsen_US
dc.subject.otherPolymer and Materials Scienceen_US
dc.titleSynthesis of polyamides from rigid and sterically hindered dicarboxylic acids and diamines under mild conditionsen_US
dc.typeArticleen_US
dc.rights.robotsIndexNoFollowen_US
dc.subject.hlbsecondlevelMaterials Science and Engineeringen_US
dc.subject.hlbtoplevelEngineeringen_US
dc.description.peerreviewedPeer Revieweden_US
dc.contributor.affiliationumDepartment of Chemistry, University of Michigan, Ann Arbor, Michigan 48104en_US
dc.contributor.affiliationumDepartment of Chemistry, University of Michigan, Ann Arbor, Michigan 48104 ; Visiting Research Associate (1967–1968), from the Institute of Macromolecular Chemistry, Czechoslovak Academy of Sciences, Prague, Czechoslovakia.en_US
dc.description.bitstreamurlhttp://deepblue.lib.umich.edu/bitstream/2027.42/38752/1/150071011_ftp.pdfen_US
dc.identifier.doihttp://dx.doi.org/10.1002/pol.1969.150071011en_US
dc.identifier.sourceJournal of Polymer Science Part A-1: Polymer Chemistryen_US
dc.owningcollnameInterdisciplinary and Peer-Reviewed


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