Skip to main content

Advertisement

SpringerLink
Log in

Alkyl 2-furoates obtained by green chemistry procedures as suitable new antifoulants for marine protective coatings

  • Published:
Journal of Coatings Technology and Research Aims and scope Submit manuscript

Abstract

In search of new sustainable alternatives to reduce the use of metallic antifouling pigments in marine paints, three n-alkyl 2-furoates were synthesized by safe procedures framed within the green chemistry concepts. These compounds were characterized by current organic analysis, and their antifouling properties were first evaluated on Artemia salina nauplii in the laboratory. Then, antifouling paints formulated with these compounds were assayed in a marine environment. Both laboratory and field tests indicate that n-alkyl 2-furoates have strong antifouling activity and are safe chemicals for marine paints.

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

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

Similar content being viewed by others

References

  1. Amara, I, Miled, W, Slama, R, Ladhari, N, “Antifouling Processes and Toxicity Effects of Antifouling Paints on Marine Environment. A Review.” Environ Toxicol Pharmacol, 57 115–130 (2018)

    Article  Google Scholar 

  2. Schwindt, E, Lopez Gappa, J, Raffo, M, Tatian, M, Bortolus, A, Orensanz, J, Alonso, G, Diez, M, Doti, B, Genzano, G, Lagger, C, Lovrich, G, Piriz, P, Mendez, M, Savoya, V, Sueiro, M, “Marine Fouling Invasions in Ports of Patagonia (Argentina) with Implications for Legislation and Monitoring Programs.” Mar Environ Res, 99 60–68 (2014)

    Article  Google Scholar 

  3. Thomas, K, Fileman, T, Readman, J, Waldock, M, “Antifouling Paint Booster Biocides in the UK Coastal Environment and Potential Risks of Biological Effects.” Mar Pollut Bull, 42 (8) 677–688 (2001)

    Article  Google Scholar 

  4. Ytreberg, E, Bighiu, M, Lundgren, L, Eklund, B, “XRF Measurements of Tin, Copper and Zinc in Antifouling Paints Coated on Leisure Boats.” Environ Pollut, 213 594–599 (2016)

    Article  Google Scholar 

  5. Qi, S, Zhang, S, Qian, P, Xiao, Z, Li, M, “Ten New Antifouling Briarane Diterpenoids from the South China Sea Gorgonian Juncella juncea.” Tetrahedron, 62 (39) 9123–9130 (2006)

    Article  Google Scholar 

  6. Santos-Acevedo, M, Puentes, C, Carreño, K, Gómez-León, J, Stupak, M, García, M, Pérez, M, Blustein, G, “Antifouling Paints Based on Marine Natural Products from Colombian Caribbean.” Int Biodeterior Biodegrad, 83 97–104 (2013)

    Article  Google Scholar 

  7. Fusetani, N, “Antifouling Marine Natural Products.” Nat Prod Rep, 28 (2) 400–410 (2011)

    Article  Google Scholar 

  8. Stewart, M, Miles, W, Depree, C, “Antifouling Activity of Synthetic γ-Hydroxybutenolides.” Int Biodeterior Biodegrad, 88 1–9 (2013)

    Google Scholar 

  9. de Nys, R, Givskov, M, Kumar, N, Kjelleberg, S, Steinberg, P, “Furanones.” Prog Mol Subcell Biol, 42 55–86 (2006)

    Google Scholar 

  10. Li, Y, Wu, H, Xu, Y, Shao, C, Wang, C, Qian, P, “Antifouling Activity of Secondary Metabolites Isolated from Chinese Marine Organisms.” Mar Biotechnol, 15 (5) 552–558 (2013)

    Article  Google Scholar 

  11. Stewart, M, Depree, C, Thompson, K, “Antifouling Sesterterpenes from the New Zealand Marine Sponge Semitaspongia bactriana.” Nat Prod Commun, 4 (3) 1–6 (2009)

    Google Scholar 

  12. Raveendran, T, Limna Mol, V, Parameswaran, P, “Natural Product Antifoulants from the Octocorals of Indian Waters.” Int Biodeterior Biodegrad, 65 265–268 (2011)

    Article  Google Scholar 

  13. FAO, Specifications for Flavourings. http://www.fao.org/food/food-safety-quality/scientific-advice/jecfa/jecfa-flav/details/en/c/715/ (2016)

  14. Corma, A, Iborra, S, Velty, A, “Chemical Routes for the Transformation of Biomass into Chemicals.” Chem Rev, 107 (6) 2411–2502 (2007)

    Article  Google Scholar 

  15. Okada, M, Tachikawa, K, Aoi, K, “Biodegradable Polymers Based on Renewable Resources. II. Synthesis and Biodegradability of Polyesters Containing Furan Rings.” J Polym Sci A Polym Chem, 35 (13) 2729–2737 (1997)

    Article  Google Scholar 

  16. Escobar, A, Ruiz, D, Autino, J, Romanelli, P, “Single-Step Synthesis of 4-phenyl and 3,4-dihydro-4-phenyl Coumarins Using a Recyclable Preyssler Heteropolyacid Catalyst Under Solvent-Free Reaction Conditions.” Res Chem Intermed, 41 10109–10123 (2015)

    Article  Google Scholar 

  17. Persoone, G, Castritsi-Catharios, J, “A Simple Bioassay with Artemia Larvae to Determine the Acute Toxicity of Antifouling Paints.” Water Res, 23 (7) 893–897 (1989)

    Article  Google Scholar 

  18. Foster, M, Harrold, C, Hardin, D, “Points Versus Photo Quadrat Estimates of the Cover of Sessile Marine Organisms.” J Exp Mar Biol Ecol, 146 (2) 193–203 (1991)

    Article  Google Scholar 

  19. Sánchez, L, Pasquale, G, Sathicq, A, Ruiz, D, Jios, J, Ferreira de Souza, A, Romanelli, G, “Simple and Ecofriendly Synthesis of Dihydropyrimidinones (thiones), Dihydropyridines, and Pyridines Using 3-formylchromones as Substrates Assisted by a Recyclable Preyssler Heteropolyacid.” Heteroat Chem, 27 (5) 295–305 (2016)

    Article  Google Scholar 

  20. Escobar, A, Sathicq, A, Pizzio, L, Blanco, M, Romanelli, G, “Biomass Valorization Derivatives: Clean Esterification of 2-Furoic Acid Using Tungstophosphoric Acid/Zirconia Composites as Recyclable Catalyst.” Process Saf Environ Prot, 98 176–186 (2015)

    Article  Google Scholar 

  21. Castritsi-Catharios, J, Bourdaniotis, N, Persoone, G, “A New Simple Method with High Precision for Determining the Toxicity of Antifouling Paints on Brine Shrimp Larvae (Artemia): First Results.” Chemosphere, 67 (6) 1127–1132 (2007)

    Article  Google Scholar 

  22. Klostergaard, H, “Notes—Esterification with Trapping Phase.” J Org Chem, 23 (1) 108–110 (1958)

    Article  Google Scholar 

  23. Pérez, M, García, M, Sánchez, M, Stupak, M, Mazzuca, M, Palermo, J, Blustein, G, “Effect of Secochiliolide Acid Isolated from the Patagonian Shrub Nardophyllum bryoides as Active Component in Antifouling Paints.” Int Biodeterior Biodegrad, 89 37–44 (2014)

    Article  Google Scholar 

  24. Shao, C, Wu, H, Wang, C, Liu, Q, Xu, Y, Wei, M, Qian, P, Gu, Y, Zheng, C, She, Z, Lin, Y, “Potent Antifouling Resorcylic Acid Lactones from the Gorgonian-Derived Fungus Cochliobolus lunatus.” J Nat Prod, 74 (4) 629–633 (2011)

    Article  Google Scholar 

  25. Lowery, C, Abe, T, Park, J, Eubanks, L, Sawada, D, Kaufmann, G, Janda, K, “Revisiting AI-2 Quorum Sensing Inhibitors: Direct Comparison of Alkyl-DPD Analogues and a Natural Product Fimbrolide.” J Am Chem Soc, 131 (43) 15584–15585 (2009)

    Article  Google Scholar 

  26. Badireddy, A, Hernández Delgadillo, R, Sánchez-Nájera, S, Chellam, S, Cabral-Romero, C, “Synthesis and Characterization of Lipophilic Bismuth Dimercaptopropanol Nanoparticles and Their Effects on Oral Microorganisms Growth and Biofilm Formation.” J Nanopart Res, 16 2456 (2014)

    Article  Google Scholar 

  27. Cahill, P, Heasman, K, Jeffs, A, Kuhajek, J, “Laboratory Assessment of the Antifouling Potential of a Soluble-Matrix Paint Laced With the Natural Compound Polygodial.” Biofouling, 30 (9) 967–975 (2014)

    Article  Google Scholar 

  28. Moodie, L, Trepos, R, Cervin, G, Larsen, L, Larsen, D, Pavia, H, Hellio, C, Cahill, P, Svenson, J, “Probing the Structure-Activity Relationship of the Natural Antifouling Agent Polygodial Against both Micro and Macrofoulers by Semisynthetic Modification.” J Nat Prod, 80 (2) 515–525 (2017)

    Article  Google Scholar 

  29. Grandic, M, Zovko, A, Frangež, R, Turk, T, Sepcic, K, “Binding and Permeabilization of Lipid Bilayers by Natural and Synthetic 3-Alkylpyridinium Polymers.” Bioorganic Med Chem, 20 (5) 1659–1664 (2012)

    Article  Google Scholar 

  30. Jung, J, Pandit, S, Jeon, J, “Identification of Linoleic Acid, a Main Component of the n-Hexane Fraction from Dryopteris crassirhizoma, as an Anti-Streptococcus mutans Biofilm Agent.” Biofouling, 30 (7) 789–798 (2014)

    Article  Google Scholar 

  31. Pérez, M, García, M, Blustein, G, “Evaluation of Low Copper Content Antifouling Paints Containing Natural Phenolic Compounds as Bioactive Additives.” Mar Environ Res, 109 177–184 (2015)

    Article  Google Scholar 

  32. Carteau, D, Vallée-Réhel, K, Linossier, I, Quiniou, F, Davy, R, Compère, C, Delbury, M, Faÿ, F, “Development of Environmentally Friendly Antifouling Paints Using Biodegradable Polymer and Lower Toxic Substances.” Prog Org Coat, 77 (2) 485–493 (2014)

    Article  Google Scholar 

  33. Viju, N, Satheesh, S, Vincent, S, “Antibiofilm Activity of Coconut (Cocos nucifera Linn.) Husk Fibre Extract.” Saudi J Biol Sci, 20 (1) 85–91 (2013)

    Article  Google Scholar 

  34. Al-Naamani, L, Dobretsov, S, Dutta, J, Burgess, J, “Chitosan-Zinc Oxide Nanocomposite Coatings for the Prevention of Marine Biofouling.” Chemosphere, 168 408–417 (2017)

    Article  Google Scholar 

  35. Myan, F, Walker, J, Odette Paramo, O, “The Interaction of Marine Fouling Organisms with Topography of Varied Scale and Geometry: A Review.” Biointerphases, 8 (30) 1–13 (2013)

    Google Scholar 

Download references

Acknowledgments

We thank CONICET (PIP 003), ANPCyT (PICT 0409), ANPCYT (Project: ERANET-LAC), Universidad Nacional de La Plata and CICPBA for their financial support. We also wish to thank the Club de Motonáutica of Mar del Plata for permission to use their marine testing site.

Author information

Authors and Affiliations

  1. Centro de Investigación y Desarrollo en Ciencias Aplicadas (CINDECA), Departamento de Química, Facultad de Ciencias Exactas, UNLP-CCT-CONICET, Calle 47 N 257, 1900, La Plata, Argentina

    Angélica Escobar, Ángel Sathicq & Gustavo Romanelli

  2. Facultad de Ciencias Naturales y Museo, Universidad Nacional de La Plata, Calle 60 y 122, 1900, La Plata, Argentina

    Míriam Pérez & Analia Paola

  3. Centro de Investigación y Desarrollo en Tecnología de Pinturas (CIDEPINT), CICPBA-CONICET, Calle 52 e/121 y 122, 1900, La Plata, Argentina

    Míriam Pérez, Mónica García, Analia Paola & Guillermo Blustein

  4. Centro de Investigación en Sanidad Vegetal (CISaV), Facultad de Ciencias Agrarias y Forestales, Universidad Nacional de La Plata, Calle 60 y 119, 1900, La Plata, Argentina

    Gustavo Romanelli & Guillermo Blustein

Authors
  1. Angélica Escobar
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Míriam Pérez
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ángel Sathicq
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Mónica García
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Analia Paola
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Gustavo Romanelli
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Guillermo Blustein
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Guillermo Blustein.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Escobar, A., Pérez, M., Sathicq, Á. et al. Alkyl 2-furoates obtained by green chemistry procedures as suitable new antifoulants for marine protective coatings. J Coat Technol Res 16, 159–166 (2019). https://doi.org/10.1007/s11998-018-0110-3

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11998-018-0110-3

Keywords

Search

Navigation