Approaches to Ladder Structures. VII. Polycondensation of Aromatic Diamino Dicarboxylic Acids with Dimethylformamide and Phosphorus Pentoxide
Abstract
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.
Document Details
- Document Type
- Technical Report
- Publication Date
- Feb 01, 1972
- Accession Number
- AD0893342
Entities
People
- Gerald A. Loughran
Organizations
- Air Force Research Laboratory