Synthesis and characterization of polyimides from 4-(diphenyl phosphine oxide)phenyl pyrromellitic dianhydride

• Published in: Journal of applied polymer science Vol. 123; no. 6; pp. 3298 - 3308
• Main Authors: Bae, Yeon-Ung, Yoon, Tae-Ho
• Format: Journal Article
• Language: English
• Published: Hoboken Wiley Subscription Services, Inc., A Wiley Company 15.03.2012; Wiley; Wiley Subscription Services, Inc
• Subjects: adhesive property; Adhesives; Applied sciences; CTE; Diamines; dianhydride; Dianhydrides; Exact sciences and technology; Materials science; Monomers; Organic polymers; Phosphine oxide; Phosphines; Physicochemistry of polymers; Polycondensation; polyimide; Polyimide resins; Polymers; Preparation, kinetics, thermodynamics, mechanism and catalysts; Synthesis; Polyimide; Adhesivity; Molecular structure; adhesive property; dianhydride; Intrinsic viscosity; Aromatic polymer; Condensation polymerization; Experimental study; Thermal stability; Phosphorus polymer; Suzuki coupling; Thermal properties; Pyromellitimide polymer; Tertiary phosphine oxide; Imidation; CTE; Preparation; Surface properties; Organo non metallic polymer; phosphine oxide; Rheological properties
• ISSN: 0021-8995; 1097-4628
• DOI: 10.1002/app.34934

A novel rigid‐rod type dianhydride monomer with phosphine oxide moiety, 4‐(diphenyl phosphine oxide)phenyl pyrromellitic dianhydride (POPPMDA), was synthesized via the Suzuki coupling reaction of 4‐(diphenyl phosphine oxide)phenyl boronic acid (POBB) and 1‐bromo‐2,3,5,6‐tetramethyl benzene (B4MB), followed by oxidation and cyclodehydration. The monomer was characterized by FTIR, NMR, EA, and melting point analyzer and utilized to synthesize polyimides with diamines such as bis(3‐aminophenyl)phenyl phosphine oxide (mDAPPO) and p‐phenylene diamine (pPDA) by varying their ratio. The polyimides were prepared via a conventional two‐step synthesis: preparation of poly(amic‐acid), followed by solution imidization. The polyimides were characterized by FTIR, NMR, DSC, TGA, and TMA, and their solubility, intrinsic viscosity, and adhesive properties were also evaluated. The polyimides exhibited high Tg (342–362°C), good thermal stability (>500°C), excellent adhesive property (134–107 g/mm), and low CTE (28–17 ppm/°C). © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2012