Accession Number : ADA188974

Title :   Synthesis and Characterization of 1,2-Disubstituted Cyclobutene Amides: Polymers and Cycloadducts.

Descriptive Note : Technical rept.,

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

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

PDF Url : ADA188974

Report Date : 01 Dec 1987

Pagination or Media Count : 4

Abstract : A series of model diamides were synthesized from mono- and disubstituted 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 23C for N-alkyl and N,N-dialkyl species to 204 C for the N-phenyl model. Relative rates of thermolysis (by DSC) wit maxima from 208-224 C at 10 C/min. were dependent on the number and type of substituents, and intramolecular hydrogen bondings. Thermolysis products were Diels Alder dimers (for N-mono-substituted materials and for bulky tetrasubstituted models) while polymers formed spontaneously for two tetrasubstituted models with at least one methyl group on each nitrogen. Thermal imidization of cycloadducts was possible in some cases with concomitant oxidation to tetrasubstituted aromatic bisimides.

Descriptors :   *AMINES, *POLYMERS, *AMIDES, *CYCLIC COMPOUNDS, *BUTENES, ACIDS, CHLORIDES, HYDROGEN BONDS, MELTING POINT, METHYL RADICALS, MOLECULE MOLECULE INTERACTIONS, NITROGEN, OXIDATION

Subject Categories : Polymer Chemistry
      Organic Chemistry

Distribution Statement : APPROVED FOR PUBLIC RELEASE