Skip to main content
SpringerLink
Log in

Synthesis of 1,2-bis(2-oxazolinyl-2)ethane and its application as chain extender for poly(ethylene terephthalate)

  • Published:
Polymer Bulletin Aims and scope Submit manuscript

Summary

The reaction of ethanolamine (EA) with nitriles is a general route to prepare oxazolines. However, in case of vicinal nitrile groups, cyclic imidines are formed. It is shown, that succinonitrile gives with EA mainly 1-(hydroxyethyl)-2,5-bis-(hydroxyethylimine) azacyclopentane (= triol). The corresponding 1,2 bis-(2-oxazolinyl-2) ethane (BOXE) is formed by heating the triol. BOXE can be used as chain extender of poly(ethylene terephthalate) (PET). If PET is heated with BOXE at 270 °C the viscosity increases first. However, on prolonged heating the viscosity decreases again, which can not be ascribed to the normal degradation processes. Therefore, a mechanism is proposed in which the chain scission takes place in the newly formed bridge.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. R.Andreasch, Monatsch. Chem., 5, 33, (1884).

    Article  Google Scholar 

  2. J.A.Frump, Chem. Reviews, 71, no 5, 483–505, (1971).

    CAS  Google Scholar 

  3. T.Saegusa et. al., Polymer Journal, 3, no 1, 35–39, 176–180, (1972), 4, no 1, 87–92, (1973); Macromolecular Science, 8, 153–190, (1975), Butterworths Publishers, Ltd, London; J.Macromol. Sci. chem., A21 (8&9), 1021–1034 (1984).

    CAS  Google Scholar 

  4. T.Kagiya, J. of Polym. Sci., Polym. Lett. 4, 257–260, (1966)

    CAS  Google Scholar 

  5. T.Nishikubo, J. Polym. Sci., Polym. Lett. Ed. 18, 761–764, (1980).

    Article  CAS  Google Scholar 

  6. Ashland, US 4,430,491, (1984).

  7. B.Rivas, Polymer Bulletin, 19, 123–128, (1988).

    CAS  Google Scholar 

  8. G.Odian, Macromolecules, 17, no. 7, 1297–1307, (1984).

    Article  CAS  Google Scholar 

  9. K.Lee, Polym. Prep. 31, no 2, 466–467, 1990.

    CAS  Google Scholar 

  10. T.Saegusa, Macromolecules, 5, 354, (1972).

    CAS  Google Scholar 

  11. W.Seelinger, Justus Liebig Ann. Chem., 698, 167–173, (1966).

    Google Scholar 

  12. H.Inata et. al., J. of Appl. Polym. Sci., 30, no 8, 3325–3337 (1985); id. 32, 5193–5202, (1986); id, 32, 4581–4594, (1986); id. 33, 3069–3079, (1987); id. 34, 2609–2617, (1987) and id. 34, 2769–2776, (1987).

    CAS  Google Scholar 

  13. W.Seelinger, Liebigs Ann. Chem., (1974), 996–1009

  14. Sheremeteave, Bull. of the Ac. of Sci. USSR, 7, 1404–1408, (1969).

    Google Scholar 

  15. Z.Wicks, J. Org. Chem. 44, 1244–1247, (1979).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. DSM Research, P.O. Box 18, 6160 MD, Geleen, The Netherlands

    Ton Loontjens, Wil Belt, Dirk Stanssens & Pierre Weerts

Authors
  1. Ton Loontjens
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Wil Belt
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Dirk Stanssens
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Pierre Weerts
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Loontjens, T., Belt, W., Stanssens, D. et al. Synthesis of 1,2-bis(2-oxazolinyl-2)ethane and its application as chain extender for poly(ethylene terephthalate). Polymer Bulletin 30, 13–18 (1993). https://doi.org/10.1007/BF00296228

Download citation

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00296228

Keywords

Search

Navigation