Synthesis and characterization of polyimides from novel 1-(3′,5′-bis(trifluoromethyl)benzene) pyromelliticdianhydride (6FPPMDA)

Abstract

Mono-substituted dianhydride monomer, 1-(3′,5′-bis(trifluoromethyl)phenyl) pyromellitic dianhydride (6FPPMDA), was prepared via the Suzuki cross coupling reaction followed by oxidation and cyclodehydration. The monomer was characterized by FT-IR, NMR, elemental analyzer (EA) and melting point apparatus. For comparison, 1-(4′-trifluoromethylphenyl)pyromellitic dianhydride (3FPPMDA) and 1-phenyl pyromellitic dianhydride (PPMDA) were also utilized. The dianhydrides were used to prepare polyimides with aromatic diamines such as bis(3-aminophenyl) 3,4-bis(trifluoromethyl)phenyl phosphine oxide ( mDA6FPPO), bis(3-aminophenyl) 4-(trifluoromethyl)phenyl phosphine oxide ( mDA3FPPO), bis(3-aminophenyl) phenyl phosphine oxide ( mDAPPO) and 1,1-bis(4-aminophenyl)-1-phenyl-2,2,2-trifluoroethane ( p3FDAm). The polyimides were synthesized via a two-step process; preparation of poly(amic-acid) in p-chlorophenol with isoquinoline, followed by solution imidization at the reflux temperature for 12 h. Polymer characterization was carried out by FT-IR, NMR, GPC, DSC and TGA, and their solubility, solution viscosity, water absorption, CTE, dielectric constant and refractive index were also evaluated.