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Preparation and characterization of aromatic polyimides derived from 4,4′-oxydiphthalic anhydride and 4,4′-diaminodiphenylmethane with different alkyl substituents

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Abstract

New soluble polyimides were synthesized from different 4,4′-diaminodiphenylmethane monomers with different alkyl substituents [4′4′-diamino-3,3′-dimethyl-diphenyl-methane, DDMDPM; 4,4′-methylene -bis(2-ethyl-6-methylaniline), MBEMA; and 4,4′-methylene-bis(2,6-diethylaniline), MBDEA] in one-step with the poly(amic acid)s prepared from the polyaddition of 4,4′-oxydiphthalic anhydride (ODPA). The structures of the synthesized polyimides were confirmed by Fourier transform infrared (FTIR) and nuclear magnetic resonance (NMR) spectroscopy measurements. The sizes and numbers of alkyl substituents affected the thermal properties, dielectric constants, and solubilities of the polyimides. The obtained polyimides were soluble in various solvents, such as N-methyl-2-pyrrolidone (NMP), N,N-dimethylacetamide (DMAc), N,N-dimethylformamide (DMF), tetrahydrofuran (THF), dichloromethane (DCM), and chloroform (CClH3). These polyimides exhibited excellent thermal stability with a decomposition temperature (Td) greater than 500 °C and relatively low coefficients of thermal expansion and dielectric constants. The resulting properties make these new polyimides attractive for practical applications.

Typical mechanism for the synthesis of polyimides from 4,4′-diamino-diphenyl-methane monomers and 4,4′-Oxydiphthalic anhydride

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Acknowledgments

The authors gratefully acknowledge the support for this research by the Ministry of Economic Affairs in Taiwan under the grant numbers 101-EC-17-A-08-S1-205 and Kaohsiung Medical University in Taiwan under the grant numbers KMU-TP103B03, respectively.

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    Authors and Affiliations

    1. Institute of Polymer Science and Engineering, College of Engineering, National Taiwan University, No. 1, Sec. 4, Roosevelt Road, Taipei City, 10617, Taiwan

      Wei-Yao Chang, Szu-Hsien Chen, Cheng-Han Yang, Ching-Nan Chuang & Kuo-Huang Hsieh

    2. Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, No. 100, Shih-Chuan 1st Road, Kaohsiung, 80708, Taiwan

      Chih-Kuang Wang

    3. Orthopaedic Research Center, Kaohsiung Medical University, No. 100, Shih-Chuan 1st Road, Kaohsiung, 80708, Taiwan

      Chih-Kuang Wang

    4. Department of Chemical Engineering, College of Engineering, National Taiwan University, No. 1, Sec. 4, Roosevelt Road, Taipei City, 10617, Taiwan

      Kuo-Huang Hsieh

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    1. Wei-Yao Chang
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    2. Szu-Hsien Chen
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    Correspondence to Chih-Kuang Wang or Kuo-Huang Hsieh.

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    Wei-Yao Chang and Szu-Hsien Chen contributed equally to this work.

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    Chang, WY., Chen, SH., Yang, CH. et al. Preparation and characterization of aromatic polyimides derived from 4,4′-oxydiphthalic anhydride and 4,4′-diaminodiphenylmethane with different alkyl substituents. J Polym Res 22, 38 (2015). https://doi.org/10.1007/s10965-015-0679-5

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