Heat Stable Polymers: Polyphenylene and Other Aromatic Polymers.
Abstract
The Diels-Alder reaction of cyclopentadienones with acetylenic dienophiles provides a unique synthesis of polyphenylenes. High molecular weight (60 - 100,000) phenylated polyphenylenes are amorphous and soluble in common organic solvents. Isomer studies on model compounds indicate that about 50% of the new linkages in the phenylated polyphenylene are meta catenated which may account in part for their good solubility. A new phenylated polyphenylated polyphenylene containing fewer pendant phenyls per repeating unit has been synthesized. Its thermal and solubility properties are similar to previous phenylated polyphenylenes. A new synthetic route to p-bis-2-pyrone has been developed allowing larger quantities of monomer to be prepared. The Diels-Alder reaction of the bis-2-pyrone with p-diethynylbenzene provides an unequivocal synthesis of poly(p-phenylene). The model reaction of 3,4-diphenylthiophene dioxide with phenylacetylene demonstrated that this reaction is not a suitable polymer forming reaction since dimerization of the sulfone competes with acetylene addition. Model reactions leading to poly(p-phenylene) containing removable chromium tricarbonyl arene complexes to improve solubility during polymer formation were studied. (Modified author abstract)
Document Details
- Document Type
- Technical Report
- Publication Date
- Jun 01, 1974
- Accession Number
- AD0781546
Entities
People
- John K. Stille
- Robert G. Nelb
Organizations
- University of Iowa