Skip to main content
SpringerLink
Log in

Synthesis and characterization of novel antibacterial poly(imidosulfide)/Ag nanocomposite

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

Abstract

Novel poly(imidosulfide) containing acidic pendent group has been synthesized by Michael addition reaction between dithiol and new synthesized bismalimide (BMI) monomer which was synthesized from 3,5-diaminobenzoic acid and 4-maleimidobenzoyl chloride. This new BMI that characterized completely with FT-IR, 1H-NMR, 13C-NMR spectroscopy and elemental analysis, copolymerized with glycol bis(mercaptoacetate) in N,N-dimethylacetamide in presence of p-toluenesulfonic acid as catalyst. The resulting polymer with carboxylic acid pendent group is soluble in polar solvents such as NMP, DMF, DMSO and DMAc. Reaction conditions were modified based on the reaction time, yield and viscosity. Synthesized poly(imidosulfide) was characterized by FT-IR, 1H-NMR, elemental analysis, thermogravimetric analysis (TGA) and X-ray diffraction (XRD) techniques. Acidic pendent group of the polymer has potential to form silver carboxylate metal salt. The synthesized poly(imidosulfide) silver complex reduced to form, new antibacterial bionanocomposite. The resulting nanocomposite was characterized by FT-IR, UV/Vis, XRD, TGA, FE-SEM/EDX and TEM. Also antibacterial properties and bacterial degradation of nanocomposite and polymer were investigated.

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
Scheme 3
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12
Fig. 13
Fig. 14

Similar content being viewed by others

References

  1. Crivello J (1973) Polyaspartimides: condensation of aromatic diamines and bismaleimide compounds. J Polym Sci Polym Chem Ed 11:1185–1200

    Article  CAS  Google Scholar 

  2. Liu Y, Liu Y, Jeng R, Chiu Y (2001) Triphenylphosphine oxide-based bismaleimide and poly(bismaleimide): synthesis, characterization, and properties. J Polym Sci Part A Polym Chem 39:1716–1725

    Article  CAS  Google Scholar 

  3. Dinakaran K, Alagar M (2003) Studies on thermal and morphological properties of 1,1-bis(3-methyl-4-cyanatophenyl)cyclohexane-epoxy-bismaleimide matrices. Polym adv Tech 14:544–556

    Article  CAS  Google Scholar 

  4. Mijovic J, Andjelic S (1996) Study of the mechanism and rate of bismaleimide cure by remote in situ real time fiber optic near-infrared spectroscopy. Macromolecules 29:239–246

    Article  CAS  Google Scholar 

  5. Yamabe S, Okumoto S (2000) A theoretical study of curing reactions of maleimide resins through michael additions of amines. J Org Chem 65:1544–1548

    Article  Google Scholar 

  6. White J (1986) Synthesis and properties of high-molecular-weight step-growth polymers from bismaleimides. Ind Eng Chem Prod Res Develop 25:395–400

    Article  CAS  Google Scholar 

  7. Wang C-S, Leu T-S, Hsu K-R (1998) Novel bismaleimide with naphthalene side group. 1. From 1-naphthaldehyde and 2,6-dimethylaniline. Polymer 39:2921–2927

    Article  CAS  Google Scholar 

  8. Liaw D, Liu D, Liaw B, Ho T (1999) Synthesis and characterization of novel polyaspartimides derived from 2,2′-dimethyl-4,4′-bis(4-maleimidophenoxy)biphenyl and various diamines. J Appl Polym Sci 73:279–286

    Article  CAS  Google Scholar 

  9. Gherasim M, Zugravescu I (1978) Polydisuccinimides: polyaddition reactions of aliphatic and aromatic diamines to N, N′-bismaleimide. Eur Polym J 14:985–990

    Article  CAS  Google Scholar 

  10. Liu Y, Tsai S, Wu C, Jeng R (2004) Preparation and characterization of hyperbranched polyaspartimides from bismaleimides and triamines. J Polym Sci Part A Polym Chem 42:5921–5928

    Article  CAS  Google Scholar 

  11. Hill D, Hopewell J, George G (2000) Quantitative analysis of bismaleimide-diamine thermosets using near infra red spectroscopy. Polymer 41:8221–8229

    Article  Google Scholar 

  12. Dix LR, Ebdon JR, Hodge P (1995) Chain extension and crosslinking of telechelic oligomers—II. Michael additions of bisthiols to bismaleimides, bismaleates and bis(acetylene ketone)s to give linear and crosslinked polymers. Eur Polym J 31:653–658

    Article  CAS  Google Scholar 

  13. Gaina V, Gaina C (2004) Synthesis and characterization of some new polyimidothioethers with ester groups in the backbone. Polym Plast Technol 43:539–553

    Article  CAS  Google Scholar 

  14. Ghatge ND, Murthy RAN (1981) Polyimidothioether polymers. Polymer 22:1250–1256

    Article  CAS  Google Scholar 

  15. White J, Scaia M (1984) Synthesis and properties of some new polyimidosulfides with highly mobile backbones. J Polym Sci Polym Chem Ed 22:589–595

    Article  CAS  Google Scholar 

  16. Crivello J (1976) Polyimidothioethers. Polym Sci Polym Chem Ed 14:159–182

    Article  CAS  Google Scholar 

  17. Frechet J (2005) Functional polymers: from plastic electronics to polymer-assisted therapeutics. Prog Polym Sci 30:844–857

    Article  CAS  Google Scholar 

  18. Avasthi D, Mishra Y, Kabiraj D, Lalla N, Pivin J (2007) Synthesis of metal–polymer nanocomposite for optical applications. Nanotechnology 18:1–4

    Article  Google Scholar 

  19. Corbierre MK, Cameron NS, Sutton M, Laaziri K, Lennox RB (2005) Gold nanoparticle/polymer nanocomposites: dispersion of nanoparticles as a function of capping agent molecular weight and grafting density. Langmuir 21:6063–6072

    Article  CAS  Google Scholar 

  20. Schurmann U, Takele H, Zaporojtchenko V, Faupel F (2006) Optical and electrical properties of polymer metal nanocomposites prepared by magnetron co-sputtering. Thin Solid Films 515:801–804

    Article  Google Scholar 

  21. Balan L, Burget D (2006) Synthesis of metal/polymer nanocomposite by UV-radiation curing. Eur Polym J 42:3180–3189

    Article  CAS  Google Scholar 

  22. Sangermano M, Yagci Y, Rizza G (2007) In situ synthesis of silver–epoxy nanocomposites by photoinduced electron transfer and cationic polymerization processes. Macromolecules 40:8827–8829

    Article  CAS  Google Scholar 

  23. Russell AD, Hugo WB (1994) Antimicrobial activity and action of silver. Prog Med Chem 31:351–370

    Article  CAS  Google Scholar 

  24. Silver S (2003) Bacterial silver resistance: molecular biology and uses and misuses of silver compounds. FEMS Microbiol Rev 27:341–353

    Article  CAS  Google Scholar 

  25. Klasen HJ (2000) A historical review of the use of silver in the treatment of burns. II. Renewed interest for silver. Burns 26:131–138

    Article  CAS  Google Scholar 

  26. Vu-Khanh T, Sanschagrin B, Fisa B (1985) Fracture of mica-reinforced polypropylene: mica concentration effect. Polym Compos 6:249–260

    Article  CAS  Google Scholar 

  27. Singh N, Khanna PK (2007) In situ synthesis of silver nano-particles in polymethylmethacrylate. Mater Chem Phys 104:367–372

    Article  CAS  Google Scholar 

  28. Wang C, Lin C (1999) Synthesis and properties of phosphorus containing copoly(bismaleimide). Polymer 40:5665–5673

    Article  CAS  Google Scholar 

  29. Esumi K, Suzuki A, Aihara N, Usui K, Torigoe K (1998) Preparation of gold colloids with UV irradiation using dendrimers as stabilizer. Langmuir 14:3157–3159

    Article  CAS  Google Scholar 

  30. Cheng D, Zhou X, Xia H, Chan HSO (2005) Novel method for the preparation of polymeric hollow nanospheres containing silver cores with different sizes. Chem Mater 17:3578–3581

    Article  CAS  Google Scholar 

  31. Lu Y, Yu M, Drechsler M, Ballauff M (2007) Ag nanocomposite particles: preparation, characterization and application. Macromole Symp 254:97–102

    Article  CAS  Google Scholar 

  32. Mallakpour S, Tirgir F, Sabzalian MR (2011) Synthesis and structural characterization of novel biologically active and thermally stable poly(ester-imide)s containing different natural amino acids linkages. J Polym Res 18:373–384

    Article  CAS  Google Scholar 

  33. Kong H, Jang J (2008) Antibacterial properties of novel poly(methyl methacrylate) nanofiber containing silver nanoparticles. Langmuir 24:2051–2056

    Article  CAS  Google Scholar 

  34. Liao Y, Wang Y, Feng X, Wang W, Xu F, Zhang L (2010) Antibacterial surfaces through dopamine functionalization and silver nanoparticle immobilization. Mater Chem Phys 121:534–540

    Article  CAS  Google Scholar 

  35. Tankhiwale R, Bajpai SK (2010) Silver-nanoparticle-loaded chitosan lactate films with fair antibacterial properties. J Appl polym Sci 115:1894–1900

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Isfahan University of Technology, Isfahan, 84156-83111, Islamic Republic of Iran

    Amir Abdolmaleki & Elahe Sorvand

  2. Nanotechnology and Advanced Materials Institute, Isfahan University of Technology, Isfahan, 84156-83111, Islamic Republic of Iran

    Amir Abdolmaleki

  3. Department of Agronomy and Plant Breeding, College of Agriculture, Isfahan University of Technology, Isfahan, 84156-83111, Islamic Republic of Iran

    Mohammad R. Sabzalian

Authors
  1. Amir Abdolmaleki
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Elahe Sorvand
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Mohammad R. Sabzalian
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Amir Abdolmaleki.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Abdolmaleki, A., Sorvand, E. & Sabzalian, M.R. Synthesis and characterization of novel antibacterial poly(imidosulfide)/Ag nanocomposite. Polym. Bull. 72, 1007–1023 (2015). https://doi.org/10.1007/s00289-015-1317-4

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00289-015-1317-4

Keywords

Search

Navigation