Polybenzimidazoles via aromatic nucleophilic displacement

US5412059A · kind A · utility

Assignee

• The United States of America as represented by the Administrator of the National Aeronautics and Space Administration · US

Inventors

• John W. Connell · Newport News, US
• Paul M. Hergenrother · Yorktown, US
• Joseph G. Smith, Jr. · Smithfield, US

Key dates

• Filing date: Apr 5, 1993
• Grant date: May 2, 1995
• Expiry date: Apr 5, 2013

Classification

• Technology area (CPC Y): Emerging Cross-Sectional Technologies
• CPC primary: Y10T428/31504
• WIPO field: Macromolecular chemistry, polymers
• WIPO sector: Chemistry

Abstract

Novel molecular weight controlled and endcapped polybenzimidazoles (PBI) are prepared by the aromatic nucleophilic displacement reaction of di(hydroxyphenylbenzimidazole) monomers with activated aromatic dihalides or activated aromatic dinitro compounds. The PBI are endcapped with mono(hydroxyphenyl)benzimidazoles. The polymerizations are carried out in polar aprotic solvents such as N-methyl-2-pyrrolidinone or N,N-dimethylacetamide using alkali metal bases such as potassium carbonate at elevated temperatures under nitrogen. Mono(hydroxyphenyl)benzimidazoles are synthesized by reacting phenyl-4-hydroxybenzoate with aromatic (o-diamine)s in diphenylsulfone. Molecular weight controlled and endcapped PBI of new chemical structures are prepared that exhibit a favorable combination of physical and mechanical properties.