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Polymer Bulletin

, Volume 35, Issue 6, pp 671–676 | Cite as

Cyclopolymerization of cinnamate ester derivatives of alkyl α-(hydroxymethyl) acrylates

  • Duygu Avci
  • Lon J. Mathias
Article

Summary

Three new monomers for cyclopolymerization were synthesized using phase transfer catalysis of ethyl α-(chloromethyl) acrylate (ECMA), t-butyl α-(bromomethyl) acrylate (TBBMA) and isobornyl α-(bromomethyl)acrylate (IBBMA) with cinnamic acid sodium salt. Bulk and solution polymerization at 70–80°C using AIBN gave soluble cyclopolymers with Mn=13650 and Mw=36540 for the ethyl ester, Mn=47700 and Mw=86900 for the t-butyl ester and Mn=3500 and Mw=4650 for the isobornyl ester monomer. The ester polymerizabilities decreased with increasing substituent bulkiness. FTIR spectra showed ca 30 to 93% cyclic units depending on the concentration of the monomer used in polymerizations. DSC thermograms showed that alkyl group size had little effect on Tg's, with values of 151°C, 156°C, and 164°C for the ethyl, t-butyl and isobornyl esters, respectively.

Keywords

Acrylate Ethyl Ester AIBN Cinnamic Acid Sodium Salt 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    Butler GB (1992) Cyclopolymerization and Cyclocopolymerization. p. 129–162, Marcel Dekker, New York, USAGoogle Scholar
  2. 2.
    Butler GB (1986) Encyclopedia of Polym. Sci. and Eng. Vol. 4, pp. 556 Kroschwitz JI (ed), Wiley, New York, USAGoogle Scholar
  3. 3.
    Roovers J, Smets G (1963) Makromol. Chem. 60: 89Google Scholar
  4. 4.
    Paesschen GV, Janssen R, Hart R (1960) Makromol. Chem. 37: 46Google Scholar
  5. 5.
    Mathias LJ, Kusefoglu SH, Kress AO (1987) Macromolecules 20: 2326Google Scholar
  6. 6.
    Mathias LJ, Warren RM, Huang S (1991) Macromolecules 24: 2036Google Scholar
  7. 7.
    Knochel P, Chou T, Jubert C, Rajagopal D (1993) J. Org. Chem. 58: 588Google Scholar
  8. 8.
    Avci D, Kusefoglu SH, Thompson RD, Mathias LJ (1994) J. Polym. Sci.: Part A: Polym. Chem. 32: 2937Google Scholar
  9. 9.
    Thompson RD, Jarrett WL, Mathias LJ (1992) Macromolecules 25: 6455Google Scholar

Copyright information

© Springer-Verlag 1995

Authors and Affiliations

  • Duygu Avci
    • 1
  • Lon J. Mathias
    • 2
  1. 1.Department of ChemistryBogazici UniversityIstanbulTurkey
  2. 2.Department of Polymer ScienceUniversity of Southern MississippiHattiesburgUSA

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