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Synthesis of polyesters and polyurethanes using telechelic oligobenzimidazoles as macromonomers

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Abstract

The organocatalytic reaction of telechelic oligobenzimidazoles with hydroxyl groups at the both ends, OBI(n)s (n denotes degree of oligomerization), with suberic acid (SA) and isophthalic acid (IA) yielded polyesters PE(OBI(n)-co-SA) and PE(OBI(n)-co-IA), respectively. The reaction of OBI(n)s with hexamethylene diisocyanate (HDI) and tolylene-2,4-diisocyanate (TDI) yielded polyurethanes that were partly cross-linked by 1,6-hexanediamide and 1-methyl-2,4-phenylenediamide units, PU(OBI(n)-co-HDI) and PU(OBI(n)-co-TDI), respectively. A model polyester and ester were synthesized by the organocatalytic reactions of 4,4′-biphenyldimethanol (BPDM) with SA and of OBI(3) with hexanoic acid, respectively. The polyesters were soluble in polar organic solvents, whereas the polyurethanes were insoluble in the solvents due to their cross-linked structures. The absorption maxima and emission wavelengths of PE(OBI(n)-co-SA) and PE(OBI(n)-co-IA) were essentially the same as those of OBI(n)s in solution. PE(OBI(n)-co-SA), PE(OBI(n)-co-IA), and PU(OBI(n)-co-HDI) showed higher thermal stability than the corresponding OBI(n) because of their higher molecular weights and cross-linked structures.

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Funding

This work was performed under the Cooperative Research Program of “Network Joint Research Center for Materials and Devices” (No. 20181163). The authors thank to Mr. T. Deguchi of Shimane Institute for Industrial Technology for his help in thermal analysis.

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  1. Department of Chemistry, Shimane University, 1060 Nishikawatsu, Matsue, 690-8504, Japan

    Kohei Imoto, Isao Yamaguchi & Aohan Wang

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  1. Kohei Imoto
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  2. Isao Yamaguchi
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  3. Aohan Wang
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Correspondence to Isao Yamaguchi.

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Imoto, K., Yamaguchi, I. & Wang, A. Synthesis of polyesters and polyurethanes using telechelic oligobenzimidazoles as macromonomers. Polym. Bull. 77, 4789–4803 (2020). https://doi.org/10.1007/s00289-019-02986-7

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  • DOI: https://doi.org/10.1007/s00289-019-02986-7

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