Skip to main content
SpringerLink
Log in

Synthesis, characterization and side chains crystallization of comb-like poly(p-n-alkylstyrene)s

  • Original Paper
  • Published:
Polymer Bulletin Aims and scope Submit manuscript

Abstract

A series of comb like poly(p-n-alkylstyrene)s with linear alkyl groups, containing even numbers of carbon atoms from 12 up to 22 were synthesized by radical polymerization and characterized by FTIR, 1H NMR, TGA, TVA DSC, and WAXS. All polymers were obtained in good yields and were soluble in organic solvents as chloroform, dichloromethane or tetrahydrofuran and insoluble in methanol; they are stable up to temperatures near 300 °C. On the other hand, the alkylic side chains of all series are able to crystallize in a paraffinic phase in which the melting temperature and enthalpy increase with the methylene number of the n-alkyl chain.

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

Scheme 1
Scheme 2
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  1. Sulzsbacher M, Bergmann E (1948) Synthesis of p-alkylstyrenes. J Org Chem 13:30

    Google Scholar 

  2. Overberger CG, Frazier C, Mandelman J, Smith HF (1953) The preparation and polymerization of p-alkylstyrenes.1 Effect of structure on the transition temperatures of the polymers. J Am Chem Soc 75:3326

    Article  CAS  Google Scholar 

  3. Quirk RP, Ok M-A (2004) Syndiospecific synthesis of longer p-n-alkyl-substituted polystyrenes using monocyclopentadienyl-type titanium catalysts. Macromolecules 37:3976

    Article  CAS  Google Scholar 

  4. Giammanco G, Dávila J, Díaz A, Bahsas A, Lopez-Carrasquero F (2008) Síntesis y Polimerización de Algunos Derivados Alquílicos del Estireno. Revista Iberoamericana de Polímeros 9:228

    Google Scholar 

  5. Gisser H, Mertwoy H (1969) Polymerization of α-n-alkylstyrenes. I. Preparation of the α-n-alkylstyrenes. Macromolecules 2:461

    Article  CAS  Google Scholar 

  6. Overberger CG, Tanner D (1958) Ionic polymeryzation. Copolymerization of nuclear and sidechain alkyl-substituted styrene monomers. J Am Chem Soc 80:4566–4568

    Article  CAS  Google Scholar 

  7. Rabagliati FM, Pérez M, Soto M, Martínez de Ilarduya A, Muñoz Guerra S (2001) Copolymerization of styrene by diphenylzinc-additive systems. I. Copolymerization of styrene/p-tert-butylstyrene by Ph2Zn-metallocene-MAO. Eur Polym J 37:1001

    Article  Google Scholar 

  8. Rabagliati FM, Pérez M, Cancino CA, Soto M, Rodríguez FJ, León AG, Ayal J, Quijada R (2001) Polymerization and copolimerization of styrene by Ph2Zn-metallocene-MAO initiator systems. Macromol Symp 168:31

    Article  CAS  Google Scholar 

  9. Rabagliati FM, Caro CJ, Pérez M (2002) Copolymerization of styrene by diphenylzinc-additive systems. Part III. Copolymerization of styrene/para-methylstyrene using CpTiCl3-MAO and Ph2Zn-CpTiCl3-MAO initiator systems. Bol Soc Chil Quim 47:137

    CAS  Google Scholar 

  10. Díaz A (2007) Licenciature Thesis. Los Andes University, Mérida

    Google Scholar 

  11. Grassie N, Scott G (1985) Polymer degradation and stabilization. University Press, Cambridge, pp 25–29

  12. Shibaev LA, Stepanov NG, Zuev VV, Solovkaya NA, Sazanov YN (1991) Odd-even effect and thermal stability in the series of vinyl polymers. I, Poly-4-n-alkylstyrenes odd-even effect and thermal stability in the series of vinyl polymers. Thermochim Acta 186:19

    Article  CAS  Google Scholar 

  13. Espenschied B, Schulz RC (1983) N-alkylated polyamides. A new type of comb-like polymers. Macromol Chem Rapid Commun 4:663

    Article  Google Scholar 

  14. López-Carrasquero F, Monserrat S, Martínez de Ilarduya A, Muñoz-Guerra S (1995) Structure and thermal properties of new comb-like polyamides: helical poly(β-l-aspartate)s containing linear alkyl side chain. Macromolecules 28:5535

    Article  Google Scholar 

  15. López-Carrasquero F, Martínez de Ilarduya A, Cárdenas M, Carrillo M, Arnal ML, Laredo E, Torres C, Méndez B, Müller A (2003) New comb-like poly(n-alkyl itaconate)s with crystallizable side chains. Polymer 44:4969

    Article  Google Scholar 

  16. Jordan EF Jr, Feldeisen DW, Wrigley AN (1971) Side-chain crystallinity. I. Heats of fusion and melting transitions on selected homopolymers having long side chains. J Polym Sci Part A-1 9:1835

    Google Scholar 

Download references

Acknowledgements

This work has been supported by CDCHT-ULA (grants C-1517-07-08-A and C1522-07-08-F) and by DID-USB (DID-G15). The authors also thank to Laboratorio Nacional de RMN Nodo ULA (Mérida Venezuela) for NMR facilities.

Author information

Authors and Affiliations

  1. Grupo de Polímeros ULA, Departamento de Química, Facultad de Ciencias, Universidad de los Andes, Mérida, 5101A, Venezuela

    Francisco López-Carrasquero, Giuseppe Giammanco, Angélica Díaz, Johanna Dávila & Carlos Torres

  2. Grupo FIMAC, Departamento de Física, Universidad Simón Bolívar, Caracas, 1080A, Venezuela

    Estrella Laredo

Authors
  1. Francisco López-Carrasquero
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Giuseppe Giammanco
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Angélica Díaz
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Johanna Dávila
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Carlos Torres
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Estrella Laredo
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Francisco López-Carrasquero.

Rights and permissions

Reprints and permissions

About this article

Cite this article

López-Carrasquero, F., Giammanco, G., Díaz, A. et al. Synthesis, characterization and side chains crystallization of comb-like poly(p-n-alkylstyrene)s. Polym. Bull. 63, 69–78 (2009). https://doi.org/10.1007/s00289-009-0071-x

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00289-009-0071-x

Keywords

Search

Navigation