New route to poly (2, 6–diimidaazo (4,5-b: 4’,5-e) pyridinelene-1,4 (2,5-dihydroxy)-phenylene) (PIPD) and high modulus fiber on it basis
Abstract
A novel entry toward poly( 2,6-diimidazo(4,5-b: 4’,5’-e)pyridinylene-1,4(2,5-dihydroxy)-phenylene) (PIPD) has been elaborated. A strategy based on a new route to monomers: a sequential nitration of 2,6-diaminopyridine with KNO3/H2SO4 gives 2,6-diamino- 3,5-dinitro pyridine (DNDAP) in moderate yield and its hydrogenation with Raney nickel as catalyst leads to 2,3,5,6-tetraaminopyridine (TAP) in high yield. The second monomer 2,5-dihydroxyterephthalate (DHTA) was synthesized in high yield as product of sulfur-mediated aromatization of dimethyl succinoyl succinate with subsequent base hydrolysis. PIPD was synthesized by step-by-step heating in polyphosphoric acid with molecular weights of 19 – 25 kilodaltons. The macromolecule of PIPD can be seen as lap-join chain form nano-sized rigid fragment. The as-polymerized liquid crystalline PIPD solution was used for fiber spinning. The tensile strength of PIPD fibers were 1.28 – 1.99 GPa and depended on the molecular weight of the polymer used for spinning.
Keywords
Supporting agencies: The research reported in this paper was partly supported by RFBR-NNSFC grant No. 14- 03-91152-a, by National Natural Science Foundation of China (NNSFC) (grant No. 51203034), Research Fund for the Doctoral Program of Higher Education of China (grant No. 20122302120038), Special Foundation of China Postdoctoral Science (grant No. 2013T60379), Supported by China Postdoctoral Science Foundation (grant No. 2013M541392)
About the Authors
Jun Li
Harbin Institute of Technology
China
China
Jun Li
State Key Laboratory of Urban Water Resource and Environment; School of Chemical Engineering and Technology
150001; Harbin
Zhen Hu
Harbin Institute of Technology
China
China
Zhen Hu
State Key Laboratory of Urban Water Resource and Environment; School of Chemical Engineering and Technology
150001; Harbin
Yuanjun Song
Harbin Institute of Technology
China
China
Yuanjun Song
State Key Laboratory of Urban Water Resource and Environment; School of Chemical Engineering and Technology
150001; Harbin
Yudong Huang
Harbin Institute of Technology
China
China
Yudong Huang
State Key Laboratory of Urban Water Resource and Environment; School of Chemical Engineering and Technology
150001; Harbin
V. V. Zuev
ITMO University; Institute of Macromolecular Compounds of the Russian Academy of Sciences
Russian Federation
Russian Federation
197101; Kronverkskiy pr. 49; 199004; Bolshoi pr. 31; Saint Petersburg
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Review
For citations:
Li J., Hu Zh., Song Yu., Huang Yu., Zuev V.V. New route to poly (2, 6–diimidaazo (4,5-b: 4’,5-e) pyridinelene-1,4 (2,5-dihydroxy)-phenylene) (PIPD) and high modulus fiber on it basis. Nanosystems: Physics, Chemistry, Mathematics. 2014;5(6):829-835.
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