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Preparation and characterization of diamine-functional bisphthalonitrile resins with self-promoted cure behavior

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Abstract

The sluggish polymerization is one of the major problems of the high-performance phthalonitrile-based resins that needs to be solved urgently. In the present study, two types of new bisphthalonitrile resins 3,3'-((propane-2,2-diylbis(2-amino-4,1-phenylene))bis(oxy))diphthalonitrile (PN-m) and 4,4'-((propane-2,2-diylbis(2-amino-4,1-phenylene))bis(oxy))diphthalonitrile (PN-p) containing diamino groups were synthesized from 2,2'-bis(3-amino-4-hydroxylphenyl)propane and 3-nitrophthalonitrile/4-nitrophthalonitrile by nucleophilic substitution. Fourier-transform infrared (FTIR), nuclear magnetic resonance (1HNMR and 13CNMR), and time of flight mass spectroscopy (TOF–MS) were used to identify the chemical structures of new bisphthalonitrile resins. The different self-catalyzed curing behavior, owing to different positions of cyano groups on the benzene ring were confirmed by differential scanning calorimetry (DSC) and FTIR techniques. The thermal stability of the cured diamine-functional bisphthalonitriles was determined by thermogravimetric analysis (TGA) under a nitrogen atmosphere. The 5% mass-loss temperatures (T5%) and 10% mass-loss temperatures (T10%) of PN-p polymers were observed to be 413–498 °C and 486–562 °C, respectively, which were higher than those of the PN-m polymers (i.e., 408–497 °C and 477–559 °C, respectively). The char yields at 800 °C for PN-m and PN-p under a nitrogen flow were 73.58–78.76% and 74.22–79.14%, respectively. After the thermal treatment at 375 °C, the glass transition temperature (Tg) above 400 °C has been observed for both polymers. Regarding the adhesive qualities, PN-p showed a comparatively high lap shear strength of more than 15 MPa at 300 °C. Therefore, these diamine-functional bisphthalonitriles are suitable as resin matrices for structural metal-bonding applications.

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Authors and Affiliations

  1. College of Materials Science and Chemical Engineering, Harbin Engineering University, No.145 Nantong Street, Nangang District, Harbin City, 150001, Heilongjiang, People’s Republic of China

    Caizhao Liu & Bin Zhang

  2. Institute of Petrochemistry, Heilongjiang Academy of Sciences, Harbin, 150040, Heilongjiang, People’s Republic of China

    Caizhao Liu, Bin Zhang, Mingming Sun & Xugang Zhang

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  1. Caizhao Liu
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Correspondence to Bin Zhang.

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Liu, C., Zhang, B., Sun, M. et al. Preparation and characterization of diamine-functional bisphthalonitrile resins with self-promoted cure behavior. Iran Polym J 32, 177–186 (2023). https://doi.org/10.1007/s13726-022-01118-9

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