Synthesis and characterization of novel highly soluble and optical transparent polyimides containing tert-butyl and morpholinyl moieties

Abstract

A series of novel organo-soluble and optical transparent polyimides were synthesized via conventional one-step polycondensation from a novel diamine, 3,3′-diterbutyl-4,4′-diaminodiphenyl-4″-morpholinophenylmethane (TAMPM) and various commercial aromatic dianhydrides. The structures of monomer and polymers were confirmed by FT-IR and NMR. The solubility, thermal stability, optical transparency, dielectric and hydrophobic properties of polyimides were investigated. The results showed polymers presented excellent solubility in common organic solvents, such as N,Ndimethylformamide (DMF), N,N-dimethyl acetamide (DMAc), dimethyl sulfoxide (DMSO), N-methyl-2-pyrrolidone (NMP), chloroform (CHCl 3 ), tetrahydrofuran (THF) and dichloromethane (CH 2 Cl 2 ). The polymers exhibited prominent thermal stability and high optical transparency with the glass transition temperature (T g ) in the range of 311-355°C, and the cutoff wavelengths in the range of 287-344 nm. Furthermore, all of the polymers also presented low dielectric constants in the range of 2.85-3.16 at 1 MHz, and outstanding hydrophobic properties with the contact angle in the rang of 85.1-94.2 o .

Recent Trends on Transparent Colorless Polyimides with Balanced Thermal and Optical Properties: Design and Synthesis

“…Another diamine monomer with bulky substituents, namely, 3,3 ′ ‐di(tert‐butyl)‐4,4 ′ ‐diaminodiphenyl‐4 ″ ‐morpholinophenylmethane (TAMPM) was synthesized by the condensation reaction of 2‐ tert ‐butylaniline with 4‐morpholinobenzaldenhyde in the presence of hydrochloric acid as a catalyst ( Scheme ) . The λ 0 of TAMPM based PI films was in the range of 287–344 nm while the average transmittance of films was above 78% in the wavelength range of 400–700 nm.…”

Synthesis and properties of novel colorless and thermostable polyimides containing cross‐linkable bulky tetrafluorostyrol pendant group and organosoluble triphenylmethane backbone structure

“…Common methods include the introduction of alicyclic structures, fluorine atoms, bulky substituents, twisted asymmetric structures and flexible links, and so forth, which could depress the close packing of polymer chains and disrupt the conjugation between the molecular chains to reduce the formation of CTC, and thereby increasing the light transmittance of the film. [10][11][12][13][14][15][16][17][18][19][20][21][22][23] However, the molecular structure designs that are in favor of optical transparency usually impair the thermal performance of the materials to some extent. For example, Zhou et al synthesized a novel monomer trans-1,4-bis (2,3-dicarboxyphenoxy) cyclohexane dianhydride with alicyclic structure, which reacted with a variety of diamines to prepare a series of PIs.…”

High performance polyimides with good solubility and optical transparency formed by the introduction of alkyl and naphthalene groups into diamine monomers

“…It is therefore anticipated that this synthetic route to diamines containing side groups could be extremely useful in the development of high performance PIs of low-cost. Sarojadevi, 13 Huang 14 and Li groups 15 have previously used this reaction to prepare various diamines, discovering that most of the resulting PIs were soluble in common organic solvents. However, some PIs were found to still exhibit deep color.…”