Approaches to Ladder Structures. VI. Condensation Polymerization of Some Difunctional Derivatives Related to (4H), 3, 1-Benzoxazine-4-One with Certain Aromatic Diamino Dicarboxylic Acids, Esters or Aromatic Tetraamines
Abstract
The compounds 2,7-dimethyl-(4H,9H),3,1,8,6-benzobisoxazine-4,9-dione, and 6,6'-bis-(2-methyl-(4H),3,1-benzoxazine-4-one) condense on heating at 300C either in the melt or in solution in sulfolane or molten benzophenone to give insoluble highly condensed cross-linked polymers. High molecular weight or cross-linked materials were obtained when 2,7-bis-(trifluoro-methyl)-(4H,9H),3, 1,8,6-benzobisoxazine-4,9-dione, and 6,6'-bis-(2-trifluoromethyl-(4H),3,1- benzoxazine-4-one) were similarly treated. 2-methyl-(4H),3,1benzoxazine-4-one reacted with methyl anthranilate in refluxing xylene to give 3-methyl-3-(o- carboxymethyl)-phenylquinazoline-4-one. Polyquinazolinones in the medium molecular weight range were obtained when 2,7-dimethyl-(4H,9H),3,1,8,6- benzobisoxazine-4,9-dione was reacted with either 2,5-diamino-terephthalic acid or its diethyl ester in sulfolane or diphenylether up to 300C. 2,7-dimethyl-(4H, 9H),3,1,8,6-benzobisoxazine-4,9-dione and 3,3'diamino-benzidine were reacted in dimethylformamide, diethyl cellosolve, and trimethylene glycol dimethyl ether to give a soluble low molecular weight linear polyamide expected to use as a prepolymer for subsequent conversion to the corresponding quinazoline and benzimidazo-(1,2c)-quinazoline polymers.
Document Details
- Document Type
- Technical Report
- Publication Date
- Feb 01, 1971
- Accession Number
- AD0882089
Entities
People
- Gerard A. Loughran
Organizations
- Air Force Research Laboratory