Model Polymers for Black Orlon with Anthyridine and Penthyridine Units.
Abstract
The high thermal stability of 'black orlon'--composed of a linearly annelated sequence of partially oxygenated 1,8-naphthyridine units--prompted the authors to investigate the synthesis of well-characterized model systems for this material. The introduction of the anthyridine or 1,8-naphthyridine heterocyclic systems in fully aromatic polymers would provide model polymers for pyrolyzed poly(acrylonitrile). The research described in this report details a new and extremely versatile reaction sequence leading to the 1,8-naphthyridine system that can be adapted to polymer synthesis in linear as well as ladder systems. Ring formation or annelation is achieved via the Friedlander condensation of compounds containing the o-amino aldehyde functional groups and ketomethylenes. The key step in this new approach to monomer synthesis is the base-catalyzed condensation of 4-aminopyrimidine-5-carboxaldehyde (readily available from malononitrile and formamidine acetate) and ketones, followed by acid hydrolysis of the intermediate pyrido(2,3-d)pyrimidine system, resulting in the formation of compounds containing a new o-amino aldehyde functional group.
Document Details
- Document Type
- Technical Report
- Publication Date
- Aug 15, 1975
- Accession Number
- ADA015199
Entities
People
- M. Szwarc
- Paul Caluwe
Organizations
- State University of New York