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New thermally stable polymer with a graphite‐type structure

1972; Inderscience Publishers; Volume: 10; Issue: 4 Linguagem: Inglês

10.1002/pol.1972.150100427

1542-9350

Samuel A. Hurley, Prabir K. Dutt, C. S. Marvel,

Synthetic Organic Chemistry Methods

Abstract A new thermally stable polymer with a structure resembling that of graphite has been synthesized by the condensation of 1,4,5,8‐tetraaminoanthraquinone and 1,3,6,8‐tetraketo‐1,2,3,6,7,8‐hexahydropyrene (naphthalene‐1,8,4,5‐diindandione). Prepolymers, with an open structure, were soluble to some extent in concentrated sulfuric acid but were more completely solubilized by methanesulfonic acid. The final polymer with a closed‐ring structure, which was obtained by heating the prepolymer having an inherent viscosity of 0.4, was completely insoluble in these acids. Elemental analysis indicated that a high degree of cyclization was achieved, and the final polymer showed good thermal stability. Prepolymers with inherent viscosities in the range 0.11–1.58 have been obtained but, usually, a high viscosity was accompanied by a low acid solubility. Prepolymers with an inherent viscosity of 0.4, which were very soluble (>90%) in strong acids, were solubilized to a high degree by reduction with sodium dithionite in alkaline, aqueous dimethylacetamide. The highest molecular weight prepolymer (inherent viscosity of 1.30–1.58) was solubilized to a greater extent in this base mixture than in methanesulfonic acid. However, it was not completely soluble, under the conditions employed. The propolymers of higher molecular weight showed some fiber‐ and film‐forming properties.