Abstract—
A novel monomer for the synthesis of polyimides, 5-methyl-1,3-phenylene-bis-4-oxyphthalic acid dianhydride was developed. The synthesis was carried out in three stages: the reaction of nucleophilic nitro substitution of 4-nitrophthalonitrile with 5‑methylresorcinol (orcinol) potassium salt and subsequent hydrolysis of the nitrile groups have afforded 5‑methyl-1,3-phenylene-bis-4-oxyphthalic acid, dehydration of which has given the corresponding dianhydride. A series of new thermoplastic high molecular weight polyetherimides based on 5-methyl-1,3-phenylene-bis-4-oxyphthalic acid dianhydride and several aromatic diamines of various structures were synthesized by the method of one-stage catalytic polycondensation in a benzoic acid melt. Inherent viscosity and weight-average molecular mass of the polyetherimides have been of 0.28‒1.20 dL/g and (33‒114) × 103, respectively. The polyetherimides have been soluble in chloroform, THF, DMF, DMAA, N-methylpyrrolidone, and DMSO and have revealed film-forming properties. According to the DSC and wide-angle X-ray scattering data, the polyetherimides have been found completely amorphous, the glass transition temperature being in the 185–307°C range.
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ACKNOWLEDGMENTS
Registration of the IR and NMR spectra and thermal studies was made using the equipment of the Collaborative Access Center “Center for Polymer Research” of ISPM RAS.
Funding
This study was partially financial supported by the Russian Foundation for Basic Research (project code 19-03-00820) and performed in the scope of the State Task no. 0086-2019-0007. Registration of the IR and NMR spectra and thermal studies were supported by the Ministry of Science and Higher Education of Russian Federation.
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Translated by E. Karpushkin
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Orlova, A.M., Tsegelskaya, A.Y., Kolesnikov, T.I. et al. Novel Polyetherimides Based on 5-Methyl-1,3-phenylene-bis-4-oxyphthalic Acid Dianhydride: Synthesis and Physicochemical Properties. Polym. Sci. Ser. B 64, 17–25 (2022). https://doi.org/10.1134/S1560090422010031
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DOI: https://doi.org/10.1134/S1560090422010031