Approaches to Ladder Structures. VII. Polycondensation of Aromatic Diamino Dicarboxylic Acids with Dimethylformamide and Phosphorus Pentoxide
Technical rept. Oct 1967-Jan 1970
AIR FORCE MATERIALS LAB WRIGHT-PATTERSON AFB OH
Pagination or Media Count:
It has been found that a new compound, 6-dimethylamino-carbonyl- dibenzo-b,f 1,5-diazocine-12, 11H-one, is produced when either anthranilic acid or dibenzo-b,f 1,5-diazocine-6,12, 5H, 11H-dione is heated at 50 to 80C in solution in dimethylformamide in the presence of a suspension of phosphorus pentoxide. A mechanism involving self condensation of anthranilic acid to dibenzo-b,f 1,5-diazocine-6, 12 5H, 11H-dione followed by reaction with dimethylformamide is proposed. Polycondensation of ortho substituted diamino aromatic dicarboxylic acids such as 2,5-diaminoterephthalic acid, or benzidine-3,3-dicarboxylic acid accurs in a similar fashion resulting in formation of double strand or ladder polymers of high molecular weight which can be extruded into fibers. These new ladder polymers have a high degree of thermal stability and contain at least one dimethylaminocarbonyl group for each unit in the polymer chain. The polymers appear to be hydroscopic.
- Organic Chemistry
- Polymer Chemistry