Accession Number : ADA188591

Title :   Synthesis and Characterization of 1,2-Cyclobutenedicarboxamides: Thermally Generated Polymers and Diels-Alder Adducts.

Descriptive Note : Technical rept.,

Corporate Author : UNIVERSITY OF SOUTHERN MISSISSIPPI HATTIESBURG DEPT OF POLYMER SCIENCE

Personal Author(s) : Powell, Douglas G ; Mathias, Lon J

PDF Url : ADA188591

Report Date : 10 Dec 1987

Pagination or Media Count : 22

Abstract : A series of model diamides were synthesized from mono- and disinstituted amines with the diacid chloride of cyclobutene-1,2-dicarboxylic acid. Yields ranged from 30 to 70%. Melting points of the purified diamides ranged from less than 23 C for N alkyl and N,N dialkyl species to 204 C for the N-phenyl model. Relative rates of thermolysis (by DSC) with maxima from 208-224 C at 10 C/min. were dependent on the number and type of substituents, and on intramolecular hydrogen bonding. Thermolysis products were Diels-Alder dimers for N-mono-substituted materials and for bulky tetrasubstituted models with at least one methyl group on each nitrogen. Thermal imidization of cyclo adducts was possible in some cases with concomitant oxidation to tetrasubstituted aromatic bisimides.

Descriptors :   *ALKYL RADICALS, *AMINES, *DIMERS, *METHYL RADICALS, *POLYMERS, *AMIDES, *BUTENES, ACIDS, CHLORIDES, HEAT, HYDROGEN BONDS, MELTING POINT, MOLECULE MOLECULE INTERACTIONS, NITROGEN, OXIDATION, SYNTHESIS(CHEMISTRY)

Subject Categories : Polymer Chemistry
      Organic Chemistry

Distribution Statement : APPROVED FOR PUBLIC RELEASE