Skip to main content
SpringerLink
Log in

Simple process for preparation of optically active methacrylates polymer with controlled molecular weight

  • Published:
Polymer Bulletin Aims and scope Submit manuscript

Abstract

Novel optically active methacrylates polymer with controlled molecular weight have been prepared simply by opening ring reaction of poly(glycidyl methacrylate) and S-(−)-α-methylbenzylamine. The structure of the novel optically active methacrylates polymer was characterized by FT-IR, and chiroptical properties of the polymer were characterized by polarimeter and circular dichroism spectrum. Thermogravimetry analysis and differential scanning calorimetry were employed to examine the thermal properties of the polymer. This preparation process was simple and the racemization of optically active monomers in preparation can be avoided. The molecular weight of optically active methacrylates polymer could be controlled by molecular weight of poly(glycidyl methacrylate) prepared by atom transfer radical polymerization.

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
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. Gohsh S, Krishnamurti N (2000) Use of glycidyl methacrylate monomers for developing crosslinkable pressure sensitive adhesives. Eur Polym J 36:2125–2131

    Article  Google Scholar 

  2. Coessens V, Pintauer Y, Matyjaszewski K (2001) Functional polymer by atom transfer radical polymerization. Prog Polym Sci 26:337–377

    Article  CAS  Google Scholar 

  3. Coessens V, Pyun J, Miller PJ, Gaynor SG, Matyjaszewski K (2000) Functionalization of polymers prepared by ATRP using radical addition reactions. Macromol Rapid Commun 21:103–109

    Article  CAS  Google Scholar 

  4. Li G, Zhu X, Zhu J, Cheng Z, Zhang W (2005) Homogeneous reverse atom transfer radical polymerization of glycidyl methacrylate and ring-opening reaction of the pendant oxirane ring. Polymer 46:12716–12721

    Article  CAS  Google Scholar 

  5. Loyens W, Groeninckx G (2003) Rubber toughened semicrystalline PET: influence of the matrix properties and test temperature. Polymer 44:123–136

    Article  CAS  Google Scholar 

  6. Sanda F, Nakamura M, Endo T (1994) Synthesis of novel optically active polymethacrylamide having l-leucine structure in the side chain. Macromolecules 27:7928–7929

    Article  CAS  Google Scholar 

  7. Nakano T (2001) Optically active synthetic polymers as chiral stationary phases in HPLC. J Chromatogr A 906:205–225

    Article  CAS  Google Scholar 

  8. Angiolini L, Caretti D, Giorgini L, Salatelli E, Altomare A, Carlini C, Solaro R (2000) Optically active polymethacrylates with side-chain l-lactic acid residues connected to push–pull azobenzene chromophores. Polymer 41:4767–4780

    Article  CAS  Google Scholar 

  9. Angiolini L, Caretti D, Giorgini L, Salatelli E (2000) Optically active methacrylic polymers bearing side-chain conjugated azoaromatic chromophores. Synth Met 115:235–239

    Article  CAS  Google Scholar 

  10. Bush SM, North M (1996) Synthesis of homochiral addition polymers derived from N-trityl-(S)-serine. Polymer 37:4649–4752

    Article  CAS  Google Scholar 

  11. Angiolini L, Giorgini L, Li H, Golemme A, Mauriello F, Termine R (2010) Synthesis, characterization and photoconductive properties of optically active methacrylic polymers bearing side-chain 9-phenylcarbazole moieties. Polymer 51:368–377

    Article  CAS  Google Scholar 

  12. Angiolini L, Caretti D, Giorgini L, Salatelli E (2001) Methacrylic polymers bearing side-chain permanent dipole azobenzene chromophores spaced from the main chain by chiral moieties: synthesis and characterization. Polymer 42:4005–4016

    Article  CAS  Google Scholar 

  13. Mallakpour S, Habibi S (2003) Microwave-promoted synthesis of new optically active poly(ester-imide)s derived from N, N′-(pyromellitoyl)-bis-l-leucine diacid chloride and aromatic diols. Eur Polym J 39:1823–1829

    Article  CAS  Google Scholar 

  14. Mallakpour S, Sepehri S (2008) Polycondensation of new optically active diacid with diisocyanates in the presence of tetrabutylammonium bromide as a green media under microwave heating. React Funct Polym 68:1459–1466

    Article  CAS  Google Scholar 

  15. Mallakpour S, Kolahdoozan M (2007) Synthesis and properties of thermally stable and optically active novel wholly aromatic polyesters containing a chiral pendent group. Eur Polym J 43:3344–3354

    Article  CAS  Google Scholar 

  16. Krishnan R, Srinivasan KSV (2003) Controlled/“living” radical polymerization of glycidyl methacrylate at ambient temperature. Macromolecules 36:1769–1771

    Article  CAS  Google Scholar 

  17. Krishnan R, Srinivasan KSV (2004) Room temperature atom transfer radical polymerization of glycidyl methacrylate mediated by copper(I)/N-alkyl-2-pyridylmethanimine complexes. Macromolecules 37:3614–3622

    Article  CAS  Google Scholar 

  18. Haddleton DM, Jasieczek CB, Hannon MJ, Shooter AJ (1997) Atom transfer radical polymerization of methyl methacrylate initiated by alkyl bromide and 2-pyridinecarbaldehyde imine copper(I) complexes. Macromolecules 30:2190–2193

    Article  CAS  Google Scholar 

  19. Haddleton DM, Kukulj D, Duncalf DJ, Heming AM, Shooter AJ (1998) Low-temperature living “radical” polymerization (atom transfer polymerization) of methyl methacrylate mediated by copper(I) N-alkyl-2-pyridylmethanimine complexes. Macromolecules 31:5201–5205

    Article  CAS  Google Scholar 

  20. Çaykaraa T, Alaslana ŞŞ, Gürü M, Bodugöz H, Güven O (2007) Preparation and characterization of poly(isobutyl methacrylate) microbeads with grafted amidoxime groups. Radiat Phys chem 76:1569–1576

    Article  Google Scholar 

  21. Çelik SÜ, Bozkurt A (2008) Preparation and proton conductivity of acid-doped 5-aminotetrazole functional poly(glycidyl methacrylate). Eur Polym J 44:213–218

    Article  Google Scholar 

  22. Nanjundan S, Unnithan CS, Selvamalar CSJ, Penlidis A (2005) Homopolymer of 4-benzoylphenyl methacrylate and its copolymers with glycidyl methacrylate: synthesis, characterization, monomer reactivity ratios and application as adhesives. React Funct Polym 62:11–24

    Article  Google Scholar 

  23. Aslan A, Çelik SÜ, Bozkurt A (2009) Proton-conducting properties of the membranes based on poly(vinyl phosphonic acid) grafted poly(glycidyl methacrylate). Solid State Ionics 180:1240–1245

    Article  CAS  Google Scholar 

Download references

Acknowledgment

We would like to gratitude for the financial support from the Central Universities Foundation of Harbin Engineering University, China (HEUCFT1009).

Author information

Authors and Affiliations

  1. College of Material Science and Chemical Engineering, Harbin Engineering University, Harbin, China

    Xing Juan Chen, Min Zhao & Shan Shan Gu

Authors
  1. Xing Juan Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Min Zhao
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Shan Shan Gu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Xing Juan Chen.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Chen, X.J., Zhao, M. & Gu, S.S. Simple process for preparation of optically active methacrylates polymer with controlled molecular weight. Polym. Bull. 68, 1525–1535 (2012). https://doi.org/10.1007/s00289-011-0624-7

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00289-011-0624-7

Keywords

Search

Navigation