Synthesis of multifunctional copolyamides with both cyclobutane ring and conjugated double bond in the main chain

Authors

  • Tadatomi Nishikubo,

    Corresponding author
    1. Department of Applied Chemistry, Faculty of Engineering, Kanagawa University, Rokkakubashi, Kanagawa-ku, Yokohama, 221 Japan
    • Department of Applied Chemistry, Faculty of Engineering, Kanagawa University, Rokkakubashi, Kanagawa-ku, Yokohama, 221 Japan
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  • Takashi Iizawa,

    1. Department of Applied Chemistry, Faculty of Engineering, Kanagawa University, Rokkakubashi, Kanagawa-ku, Yokohama, 221 Japan
    Current affiliation:
    1. Department of Chemical Engineering, Faculty of Engineering, Hiroshima University
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  • Yasunori Shiozaki,

    1. Department of Applied Chemistry, Faculty of Engineering, Kanagawa University, Rokkakubashi, Kanagawa-ku, Yokohama, 221 Japan
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  • Tsutomu Koito

    1. Department of Applied Chemistry, Faculty of Engineering, Kanagawa University, Rokkakubashi, Kanagawa-ku, Yokohama, 221 Japan
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Abstract

Copolyamides 1,9, and 10 containing both cyclobutane rings and conjugated double bonds in the main chain were synthesized by polycondensation of 1,3-di(4-piperidyl)propane (DPP) with β-truxinate (β-BNPT), with di(p-nitrophenyl) p-phenylenebis(acrylate) (p-NPDA), with di(p-nitrophenyl) p-phenylenebis (α-cyanoacrylate) (p-NPDC), and with di(p-nitrophenyl) p-phenylenebis (α-cyanobutadienecarboxylate) (p-NPDCB) in aprotic polar solvents at room temperature, respectively. Reduced viscosity of copolyamide 1 was strongly affected by the reaction process, the molar ratio of two ester monomers, and reaction time. The copolyamide 1 with the highest viscosity was prepared by the reaction of DPP with 70–50 mol % of β-BNPT for 24 h followed by the polycondensation of the resulting precursor with 30–50 mol % of p-NPDA for 24–96 h. Although copolyamide 9 with high viscosity was not obtained by the polycondensation with β-BNPT and p-NPDC, copolyamide 10 with relatively high viscosity was obtained by the reaction with β-BNPT and p-NPDCB under the same conditions applied for the synthesis of copolyamide 1. The solubility of copolyamides 1,9, and 10 decreased gradually with increasing p-NPDA, p-NPDC, and p-NPDCB units in the copolymers. Furthermore, it was found that copolyamides 1,9, and 10 crosslinked upon irradiation with 313 or 365 nm light, and these copolyamides also decomposed upon irradiation with 254 nm light. That is, the photochemical property of these copolyamides can be controlled by the selection of wavelength of the photoirradiation.

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