Skip to main content
Log in

A Novel Bola-Type Rosin-Based Functional Surfactant and Its Synergistic Effect with Natural Surfactant Saponin

  • Original Article
  • Published:
Journal of Surfactants and Detergents

Abstract

A novel bola-type acrylic-modified rosin ester tertiary ammonium salt surfactant (AETAS) with two hydrophilic groups and a rigid hydrophobic group was synthesized through a simple method from rosin acid, which is a natural raw material. The chemical structure of the synthesized surfactant was confirmed by infrared spectroscopy and nuclear magnetic resonance spectroscopy (1H NMR and 13C NMR). The critical micelle concentration (CMC) of the AETAS was 0.44 g/L, and the surface tension at the CMC (γ cmc) was 45.02 mN/m. Self-assembly behavior of the AETAS in aqueous solution was characterized by transmission electron microscopy. The micelle diameter of the AETAS was about 150 nm in aqueous solution. We also explored the synergy of the AETAS and soapnut saponin. The binary surfactant compound systems of the AETAS and soapnut saponin had obvious synergistic effect in enhancing surface activity when the mass ratio of AETAS/soapnut saponin was 1:1. The γ cmc of soapnut saponin was 47.70 mN/m when the concentration reached 0.46 g/L, but the γ cmc of mixtures decreased to 44.26 mN/m at 0.30 g/L. The emulsification ability of the mixtures was significantly improved and the emulsion performance increased from 245 to 595 s when the mass ratio of AETAS/soapnut saponin was 1:1.

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

Access this article

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

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7

Similar content being viewed by others

References

  1. Takahashi M, Haraguchi N, Itsuno S. Preparation of a polymer-supported chiral 1,2-diamine and its application to the asymmetric hydrogenation of aromatic ketones. ChemInform. 2008;39:60–6.

    Google Scholar 

  2. Mileti N, Rohandi R, Vukvoi Z. Surface modification of macroporous poly (glycidyl methacrylate-co-ethylene glycol dimethacrylate) resins for improved Candida antarctica, lipase B immobilization. React Funct Polym. 2009;69:68–75.

    Article  Google Scholar 

  3. Bonaduce I, Cito M, Colombini MP. The development of a gas chromatographic–mass spectrometric analytical procedure for the determination of lipids, proteins and resins in the same paint micro-sample avoiding interferences from inorganic media. J Chromatogr A. 2009;1216:5931–9.

    Article  CAS  Google Scholar 

  4. Deng WX, Zhang YC, Zhong YW. Synthesis and thermodynamic properties of rosin-based gemini surfactants. J Surfactants Deterg. 2014;17:453–8.

    Article  CAS  Google Scholar 

  5. Satturwar PM, Mandaogade PM, Darwhekar GN, et al. Biodegradation studies of rosin-based polymers. Drug Dev Ind Pharm. 2012;29:669–77.

    Article  Google Scholar 

  6. Wang J, Chen YP, Yao K, et al. Robust antimicrobial compounds and polymers derived from natural resin acids. Chem Commun. 2011;48:916–8.

    Article  Google Scholar 

  7. Liu X, Xin W, Zhang J, et al. Rosin-derived imide-diacids as epoxy curing agents for enhanced performance. Bioresour Technol. 2010;101:2520–4.

    Article  CAS  Google Scholar 

  8. Han SY, Song ZQ, Fang GZ, et al. Synthesis and analysis of rosin-based quaternary ammonium Gemini surfactant. For Sci Technol. 2009;29:110–2.

    CAS  Google Scholar 

  9. Tan WX, Lin ZT, Bu HT, et al. Nanomicelles based on a rosin derivative as potent sorbents and sinking agents with high absorption capabilities for the removal of metal ions. RSC Adv. 2012;2:7279–89.

    Article  CAS  Google Scholar 

  10. Han CR, Zhu LW, Liu LJ, et al. Controlled synthesis of Ni(OH)2 materials with rosin-based surfactant by microwave solvothermal method. Chem Ind For Prod. 2009;29:149–53.

    CAS  Google Scholar 

  11. Li YJ, Li PX, Dong CC, et al. Aggregation properties of cationic Gemini surfactants with partially fluorinated spacers in aqueous solution. Langmuir ACS J Surf Colloid. 2006;22:42–5.

    Article  Google Scholar 

  12. Chen LY, Fang GZ, Liu K, et al. Sulfonated dehydroabietic based dual structure characterization and properties of quaternary ammonium salt cationic surfactant. Chem Ind For Prod. 2007;27:66–70.

    Google Scholar 

  13. Wang J, Wang D, Shang SB, et al. The synthesis and performance of rosin-based quaternary ammonium salt heterogemini surfactants. Chem Ind For Prod. 2014;34:111–6.

    CAS  Google Scholar 

  14. Lu H, Wang L, Huang Z. Unusual pH-responsive fluid based on a simple tertiary amine surfactant: the formation of vesicles and wormlike micelles. RSC Adv. 2014;4:51519–27.

    Article  CAS  Google Scholar 

  15. Lu H, Xue M, Wang B, et al. pH-regulated surface property and pH-reversible micelle transition of a tertiary amine-based Gemini surfactant in aqueous solution. Soft Matter. 2016;11:9135–43.

    Article  Google Scholar 

  16. Gao XH, Zhou C, Liu HR, et al. Tertiary amine derivatives of chlorochalcone as acetylcholinesterase (AChE) and buthylcholinesterase (BuChE) inhibitors: the influence of chlorine, alkyl amine side chain and α, β-unsaturated ketone group. J Enzyme Inhib Med Chem. 2016;32(1):146–52. doi:10.1080/14756366.2016.1243534

    Article  Google Scholar 

  17. Syam S, Abdelwahab SI, Al-Mamary MA, et al. Synthesis of chalcones with anticancer activities. Molecules. 2012;17:6179–95.

    Article  CAS  Google Scholar 

  18. Rosen MJ. Surfactants and interfacial phenomena, 3rd edn. 2004. Wiley, New York.

  19. Gubitosi M, Travaglini L, Gregorio M-C, et al. Tailoring supramolecular nanotubes by bile salt based surfactant mixtures. Angew Chem Int Ed. 2015;127:7124–7.

    Article  Google Scholar 

  20. Li W, Yang Y, Liu L, et al. Dual stimuli-responsive self-assembly transition in zwitterionic/anionic surfactant systems. Soft Matter. 2015;11:4283–9.

    Article  CAS  Google Scholar 

  21. Shi L, Chen F, Sun N, et al. Gemini supra-amphiphiles with finely-controlled self-assemblies. Soft Matter. 2015;11:4075–80.

    Article  CAS  Google Scholar 

  22. Feng Y, Chu Z. pH-Tunable wormlike micelles based on an ultra-long-chain “pseudo” Gemini surfactant. Soft Matter. 2015;11:4614–20.

    Article  CAS  Google Scholar 

  23. Shi L, Sun N, Zheng L. Controlled topologies and self-assembly behaviors of oligomeric supra-amphiphiles. Chem Commun. 2015;51:15700–3.

    Article  CAS  Google Scholar 

  24. Sun N, Shi L, Lu F, et al. Spontaneous vesicle phase formation by linear pseudo-oligomeric surfactant in aqueous solutions. Langmuir ACS J Surf Colloid. 2015;31:2281–7.

    Article  CAS  Google Scholar 

  25. Berhow MA, Wagner ED, Vaughn SF. Characterization and antimutagenic activity of soybean saponins. Mutat Res Fundam Mol Mech Mutagen. 2000;448:11–22.

    Article  CAS  Google Scholar 

  26. Wang RR, Wang Y, Liu Q. The synthesis of BOLA rosin modified surfactant. Fine Chem Intermed. 2007;37:56–9.

    CAS  Google Scholar 

  27. Cao Y. The synthesis of poly acrylic modified rosin acid ethylenediamine. Chem Eng Equip. 2009;7:4–9.

    Google Scholar 

  28. Fan H, Li B, Yan Y. Phase behavior and microstructures in a mixture of anionic Gemini and surfactants. Soft Matter. 2014;10:4506–12.

    Article  CAS  Google Scholar 

  29. Rosen MJ. Surface concentration and molecular interactions in binary mixtures of surfactants. J Colloid Interface Sci. 1982;86:164–72.

    Article  CAS  Google Scholar 

  30. Qi F, Cai ZS, Zhu XM, et al. Synthesis, characterization, and performance of a novel polymeric surfactant based on low molecular weight chitosan and 3-chloro-2-hydroxypropyl dimethyl dehydroabietyl ammonium chloride (CHPDMDHA). J Surfactants Deterg. 2015;18:463–70.

    Article  CAS  Google Scholar 

  31. Emad B, Basalious N. Novel self-assembled nano-tubular mixed micelles of Pluronics P123, Pluronic F127 and phosphatidylcholine for oral delivery of nimodipine: in vitro characterization, ex vivo transport and in vivo pharmacokinetic studies. Int J Pharm. 2015;493:347–56.

    Article  Google Scholar 

  32. Fan D, Xia X, Ma H, et al. Honeycomb-patterned fluorescent films fabricated by self-assembly of surfactant-assisted porphyrin/polymer composites. Colloid Interface Sci. 2013;402:146–50.

    Article  CAS  Google Scholar 

  33. Piispanen B, Hedman TS. Synthesis and characterization of dehydroabietic acid derivatives suitable for surfactant synthesis. Colloid Interface Sci. 2002;5:165–8.

    CAS  Google Scholar 

  34. Lidia FT, Evelyn MC, Mary CS, et al. Quatsomes: vesicles formed by self-assembly of sterols and quaternary ammonium surfactants. Langmuir ACS J Surf Colloid. 2013;29:6519–28.

    Article  Google Scholar 

Download references

Acknowledgements

This work was supported by the China Ministry of Science and Technology (2016YFD0600803), Fundamental Research Funds for the Central Universities (2016ZCQ01), National Natural Science Foundation of China (30901139), and Special Fund for Beijing Common Construction Project.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Chun-rui Han.

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Lin, Hx., Yang, Ms., Li, J. et al. A Novel Bola-Type Rosin-Based Functional Surfactant and Its Synergistic Effect with Natural Surfactant Saponin. J Surfact Deterg 20, 1205–1212 (2017). https://doi.org/10.1007/s11743-017-1994-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11743-017-1994-0

Keywords

Navigation