Soluble polyimides based on a novel pyridine-containing diamine <Emphasis Type="Italic">m</Emphasis>,<Emphasis Type="Italic">p</Emphasis>-PAPP and various aromatic dianhydrides |
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Authors: | Shanyin Yan Wenqiu Chen Xiaojin Yang Chuan Chen Mingfu Huang Zushun Xu Kelvin W K Yeung Changfeng Yi |
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Affiliation: | (1) Ministry-of-Education Key Laboratory for the Green Preparation and Application of Functional Materials, Hubei University, Wuhan, China;(2) Division of Spine Surgery, Department of Orthopaedics and Traumatology, The University of Hong Kong, Pokfulam, Hong Kong, China; |
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Abstract: | A novel pyridine-containing aromatic diamine monomer, 4-phenyl-2,6-bis3-(4-aminophenoxy)phenyl]pyridine (m,p-PAPP), was successfully synthesized by a modified Chichibabin reaction of benzaldehyde and a substituted acetophenone, 3-(4-nitrophenoxy)acetophenone
(m,p-NPAP), followed by a reduction of the resulting dinitro compound 4-phenyl-2,6-bis3-(4-nitrophenoxy)phenyl]pyridine (m,p-PNPP) with Pd/C and hydrazine monohydrate. The aromatic diamine was employed to synthesize a series of pyridine-containing
polyimides (PIs) by polycondensation with various aromatic dianhydrides in N,N-dimethylformamide (DMF) via the conventional two-step method, and further thermal or chemical imidization forming PIs. The
inherent viscosities of the resulting poly(amic acid)s and PIs were 0.59–0.73 and 0.56–0.68 dL/g; most of the PIs obtained
by chemical imidization were readily soluble in common organic solvents such as DMF, N,N-dimethylacetamide (DMAc), N-methyl-2-pyrrolidone (NMP), tetrahydrofuran (THF), etc. Meanwhile, strong and flexible PI films were obtained, which had
good thermal stability, with the glass transition temperature (T
g) of 204.5–237.4 °C and the temperature at 10% weight loss of 527.7–552.0 °C in nitrogen atmosphere, as well as outstanding
mechanical properties with tensile strengths of 88.6–90.4 MPa, a tensile moduli of 1.04–1.56 GPa, and elongations at break
of 7.2–8.7%. The PI films also were found to possess low water uptake of 0.89–0.98%. |
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