Abstract
Antifouling based on biocides is the most important method preventing biofoulings in modern maritime industries and boating communities. Most antifouling paints, such as the famous but already banned organotin containing self-polishing coatings, belong to this category. Decades of development of the technology has resulted in a variety of biocides, organic matrixes, and paint systems. However, with increasing environmental concerns, the most challenging for these coatings is preventing fouling settlement effectively and meanwhile fulfilling regulations imposed by the International Marine Organization (IMO) to stop environmental damages. More and more efforts, including developing nontoxic or green biocides, new organic matrixes and advanced embedding and encapsulating technologies, and learning from nature, have been addressing the challenge. This chapter seeks to combine all these topics: the biocides from toxic to green, the organic matrix and paint system, the antifouling effects and the environmental impacts, and to draw a developing trend map for biofouling based on biocides.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Yebra DM, Kiil S, Dam-Johansen K (2004) Antifouling technology-past, present and future steps towards efficient and environmentally friendly antifouling coatings. Prog Org Coat 50:75–104
Evans SM, Leksono T, Mckinnell PD (1995) Tributyltin pollution: a diminishing problem following legislation limiting the use of TBT-based anti-fouling paints. Mar Pollut Bull 30:14–21
Ruiz JM, Bachelet G, Caumette P, Donard OFX (1996) Three decades of tributyltin in the coastal environment with emphasis on arcachon bay. Environ Pollut 93:195–203
Champ MA (2000) A review of organotin regulatory strategies, pending actions, related costs and benefit. Sci Total Environ 258:21–71
Xu Y, He HP, Schulz S, Liu X, Fusetani N, Xiong HR, Xiao X, Qian PY (2010) Potent antifouling compounds produced by marine Streptomyces. Bioresour Technol 101:1331–1336
Evans SM (1999) TBT or not TBT? That is the question. Biofouling 14:117–129
Sousa A, G´enio L, Mendo S, Barrosoi C (2005) Comparison of the acute toxicity of tributyltin and copper to veliger larvae of Nassarius reticulatus (L.). Appl Organometal Chem 19:324–328
Mailhot G, Brand N, Astruc M, Bolte M (2002) Photoinduced degradation by iron (III): removal of triphenyltin chloride from water. Appl Organometal Chem 16:27–33
Konstantinou IK (2006) Antifouling paint biocides. In: Omae I (ed) Chemistry and fate of organotin antifouling biocides in the environment, 2nd edn. Springer, Berlin, p 17–50
Gadd GM (2000) Microbial interactions with tributyltin compounds: detoxification, accumulation, and environmental fate. Sci Total Environ 258:119–127
Huggett RJ, Unger MA, Seligman PF, Valkirs AO (1992) Assessing and managing the environmental risks. Environ Sci Technol 26:232–237
Qian PY, Chen LG, Xu Y (2013) Mini-review: molecular mechanisms of antifouling compounds. Biofouling 29:381–400
Dowson PH, Bubb JM, Lester JN (1993) Temporal distribution of organotins in the aquatic environment: five years after the 1987 UK retail ban on TBT based antifouling paints. Mar Pollut Bull 26:487–494
Minchin D, Oehlmann J, Duggan CB, Stroben E, Keatinge M (1995) Marine TBT antifouling contamination in Ireland, following legislation in 1987. Mar Pollut Bull 30:633–639
Sapozhnikova Y, Wirth E, Schiff K, Fuiton M (2013) Antifouling biocides in water and sediments from California marinas. Mar Pollut Bull 69:189–194
Voulvoulis N, Scrimshaw MD, Lester JN (1999) Alternative antifouling biocides. Appl Organometal Chem 13:135–143
Omae I (2003) General aspects of tin-free antifouling paints. Chem Rev 103:3431–3448
Almeidaa E, Diamantino TC, Sousa O (2007) Marine paints: the particular case of antifouling paints. Prog Org Coat 59:2–20
Thomas KV, Brooks S (2010) The environmental fate and effects of antifouling paint biocides. Biofouling 26:73–88
Yonehara Y, Yamashita H, Kawamura C, Itoh K (2001) A new antifouling paint based on a zinc acrylate copolymer. Prog Org Coat 42:150–158
Bellas J (2005) Toxicity assessment of the antifouling compound zinc pyrithione using early developmental stages of the ascidian Ciona intestinalis. Biofouling 21:289–296
Bellas J, Granmo A, Beiras R (2005) Embryotoxicity of the antifouling biocide zinc pyrithione to sea urchin (Paracentrotus lividus) and mussel (Mytilus edulis). Mar Pollut Bull 50:1382–1385
Bellotti N, Deya C, Amo B, Romagnoli R (2010) Antifouling paints with zinc “Tannate”. Ind Eng Chem Res 49:3386–3390
Mohr S, Berghahn R, Mailahn W, Schmeiediche R, Feibicke M, Schmidt R (2009) Toxic and accumulative potential of the antifouling biocide and TBT successor Irgarol on freshwater macrophytes: a pond mesocosm study. Environ Sci Technol 43:6838–6843
Schoknecht U, Gruycheva J, Mathies H, Bergmann H, Burkhardt M (2009) Leaching of biocides used in facade coatings under laboratory test conditions. Environ Sci Technol 43:9321–9328
Morones JR, Elechiguerra JL, Camacho A, Holt K, Kouri JB, Ram´ırez JT, Yacaman MJ (2005) The bactericidal effect of silver nanoparticles. Nanotechnology 16:2346–2353
Qu F, Xu HY, Xiong YH, Lai WH, Wei H (2010) Research progress in bactericidal mechanisms of nano-silver. Food Sci 31:420–424
Lee SY, Kim HJ, Patel R, Im SJ, Kim JH, Min BR (2007) Silver nanoparticles immobilized on thin film composite polyamide membrane: characterization, nanofiltration, antifouling properties. Polym Advan Technol 18:562–568
Dai JH, Bruening ML (2002) Catalytic nanoparticles formed by reduction of metal ions in multilayered polyelectrolyte films. Nano Lett 2:497–501
Silver S (2003) Bacterial silver resistance: molecular biology and uses and misuses of silver compounds. FEMS Microbiol Rev 27:341–353
Wang RM, Wang BY, He YF, Lv WH, Wang JF (2009) Preparation of composited nano-TiO2 and its application on antimicrobial and self-cleaning coatings. Polym Advan Technol 21:331–336
Fu GF, Vary PS, Lin CT (2005) Anatase TiO2 nanocomposites for antimicrobial coatings. J Phys Chem B 109:8889–8898
Banerjee I, Pangule RC, Kane RS (2010) Antifouling coatings: recent developments in the design of surfaces that prevent fouling by proteins, bacteria, and marine organisms. Adv Mater 23:690–718
Cao ZQ, Jiang SY (2012) Super-hydrophilic zwitterionic poly(carboxybetaine) and amphiphilic non-ionic poly(ethylene glycol) for stealth nanoparticles. Nano Today 7:404–413
Hucknall A, Rangarajan S, Chilkoti A (2009) In pursuit of zero: polymer brushes that resist the adsorption of proteins. Adv Mater 21:2441–2446
Jeon SI, Lee JH, Andrade JD, Gennes PG (1990) Protein-surface interactions in the presence of polyethylene oxide. J Colloid Interf Sci 142:149–158
Kim HS, Ham HO, Son YJ, Messersmith PB, Yoo HS (2013) Electrospun catechol-modified poly(ethyleneglycol) nanofibrous mesh for anti-fouling properties. J Phys Chem B 1:3940–3949
Gon S, Kumar KN, NuÌsslein K, Santore MM (2012) How bacteria adhere to brushy PEG surfaces: clinging to flaws and compressing the brush. Macromolecules 45:8373–8381
Zhou F, Liang YM, Liu WM (2009) Ionic liquid lubricants: designed chemistry for engineering applications. Chem Soc Rev 38:2590–2599
Hallett JP, Welton T (2011) Room-temperature ionic liquids: solvents for synthesis and catalysis. 2. Chem Rev 111:3508–3576
Dobbs W, Heinrich B, Bourgogne C, Donnio B, Terazzi E, Bonnet ME, Stock F, Erbacher P, Bolcato-Bellemin AL, Douce L (2009) Mesomorphic imidazolium salts: new vectors for efficient siRNA transfection. J Am Chem Soc 131:13338–13346
Ye Q, Gao TT, Wan F, Yu B, Pei XW, Zhou F, Xue QJ (2012) Grafting poly(ionic liquid) brushes for anti-bacterial and anti-biofouling applications. J Mater Chem 22:13123–13128
Manna U, Carter MCD, Lynn DM (2013) “Shrink-to-fit” superhydrophobicity: thermally-induced microscale wrinkling of thin hydrophobic multilayers fabricated on flexible shrink-wrap substrates. Adv Mater 25:3085–3089
Latała A, Nedzi M, Stepnowski P (2009) Toxicity of imidazolium and pyridinium based ionic liquids towards algae. Chlorella vulgaris, Oocystis submarina (green algae) and Cyclotella meneghiniana, Skeletonema marinoi (diatoms). Green Chem 11:580–588
Zhang Z, Chen SF, Jiang SY (2006) Dual-functional biomimetic materials: nonfouling poly(carboxybetaine) with active functional groups for protein immobilization. Biomacromolecules 7:3311–3315
Zhang Z, Chen SF, Chang Y, Jiang SY (2006) Surface grafted sulfobetaine polymers via atom transfer radical polymerization as superlow fouling coatings. J Phys Chem B 110:10799–10804
Callow JA, Callow ME (2011) Trends in the development of environmentally friendly fouling-resistant marine coatings. Nat Commun 2:244–253
West SL, Salvage JP, Lobb EJ, Armes SP, Billingham NC, Lewis AL, Hanlon GW, Lloyd AW (2004) The biocompatibility of crosslinkable copolymer coatings containing sulfobetaines and phosphobetaines. Biomaterials 25:1195–1204
Jiang SY, Cao ZQ (2010) Ultralow-fouling, functionalizable, and hydrolyzable zwitterionic materials and their derivatives for biological applications. Adv Mater 22:920–932
Yin HY, Akasaki T, Sun TL, Nakajima T, Kurokawa T, Nonoyama T, Taira T, Saruwatarie Y, Gong JP (2013) Double network hydrogels from polyzwitterions: high mechanical strength and excellent anti-biofouling properties. J Mater Chem B 1:3685–3693
Aldred N, Li GZ, Gao Y, Clare AS, Jiang SY (2010) Modulation of barnacle (Balanus amphitrite Darwin) cyprid settlement behavior by sulfobetaine and carboxybetaine methacrylate polymer coatings. Biofouling 26:673–683
Gui AL, Luais E, Peterson JR, Gooding JJ (2013) Zwitterionic phenyl layers: finally, stable, anti-biofouling coatings that do not passivate electrodes. ACS Appl Mater Interfaces 5:4827–4835
Liu YW, Leng C, Chisholm B, Stafslien S, Majumdar P, Chen Z (2013) Surface structures of PDMS incorporated with quaternary ammonium salts designed for antibiofouling and fouling release applications. Langmuir 29:2897–2905
Chang Y, Liao SC, Higuchi A, Ruaan RC, Chu CW, Chen WY (2008) A highly stable nonbiofouling surface with well-packed grafted zwitterionic polysulfobetaine for plasma protein repulsion. Langmuir 24:5453–5458
Fusetani N (2004) Biofouling and antifouling. Nat Prod Rep 21: 94–104
Qian PY, Xu Y, Fusetani N (2010) Natural products as antifouling compounds: recent progress and future perspectives. Biofouling 26:223–234
Feng XQ, Li XF, Yang S, Wang TP (2009) Current research on anti-microbial mechanisms related influencing factors and applications of chitosan. China Brewing 202:19–23
Kim JY, Kim SK (2006) Chitosan derivatives killed bacteria by disrupting the outer. J Agric Food Chem 54:6629–6633
Kumar R, Isloor AM, Ismail AF, Rashid SA, Matsuura T (2013) Polysulfone-chitosan blend ultrafiltration membranes: preparation, characterization, permeation and antifouling properties. Rsc Adv 3:7855–7861
Angarano MB, McMahon RF, Hawkins DL, Schetz JA (2007) Exploration of structure-antifouling relationships of capsaicin-like compounds that inhibit zebra mussel (Dreissena polymorpha) macrofouling. Biofouling 23:295–305
Peng BX, Wang JL, Peng ZH, Zhou SZ, Wang FQ, Ji YL, Ye ZJ, Zhou XF, Lin T, Zhang XB (2011) Studies on the synthesis, pungency and anti-biofouling performance of capsaicin analogues. Sci China Chem 55:435–442
Cope WG, Bartsch MR, Marking LL (1997) Efficacy of candidate chemicals for preventing attachment of zebra mussels (Dreissena polymorpha). Environ Toxicol Chem 16:1930–1934
Olsen SM, Pedersen LT, Laursen MH, Kiil S, Dam-Johansen K (2007) Enzyme-based antifouling coatings: a review. Biofouling 23:369–383
Lejars M, Margaillan A, Bressy C (2012) Fouling release coatings: a nontoxic alternative to biocidal antifouling coatings. Chem Rev 112:4347–4390
Zhou XJ, Zhang Z, Xu Y, Jin CL, He HP, Hao XJ, Qian PY (2009) Flavone and isoflavone derivatives of terrestrial plants as larval settlement inhibitors of the barnacle Balanus amphitrite. Biofouling 25:69–76
Kato T, Shizuri Y, Izumida H, Yokoyama A, Endo M (1995) Styloguanidines, new chitinase inhibitors from the marine sponge stylotella aurantium. Tetrahedron Lett 36:2133–2136
Zhang YF, Zhang HM, He LS, Liu CD, Xu Y, Qian PY (2012) Butenolide inhibits marine fouling by altering the primary metabolism of three target organisms. ACS Chem Biol 7:1049–1058
Novick SJ, Dordick JS (2002) Protein-containing hydrophobic coatings and film. Biomaterials 23:441–448
Xu Y, Li HL, Li XC, Xiao X, Qian PY (2009) Inhibitory effects of a branched-chain fatty acid on larval settlement of the polychaete Hydroides elegans. Mar Biotechnol 11:495–504
Yang LH, Lee OO, Jin T, Li XC, Qian PY (2006) Antifouling properties of 10β-formamidokalihinol-A and kalihinol A isolated from the marine sponge Acanthella cavernosa. Biofouling 22:23–32
Gui TJ, Yu XY (2010) Existing state and development trend of binder resin for marine antifouling coatings. China Coatings 10:7–11
Railkin AT (2004) Marine biofouling: colonization processes and defenses. In: Railkin AT (ed) Protection of man-made structures against biofouling, 9th edn. Chemical Rubber Company (CRC), London, p 179–194
Yan DZ, Jia CG (2002) Technology development and application of antifouling coating. Chem Technol Mark 25(12):21–24
Yebra DM, Kiil S, Weinell CE, Dam-Johansen K (2006) Presence and effects of marine microbial biofilms on biocide-based antifouling paints. Biofouling 22:33–41
Monfared H, Sharif F, Kasiriha SM (2008) Simulation and development of tin-free antifouling self-polishing coatings. Macromol Symp 274:109–115
Thouvenin M, Peron JJ, Charreteur C, Guerin P, Langlois JY, Vallee-Rehel K (2002) A study of the biocide release from antifouling paints. Prog Org Coat 44:75–83
Cima F, Ballarin L (2008) Effects of anitfouling paints alternative to organotin-based ones on macrofouling biocoenosis of hard substrates in the Lagoon of Venice. Fresen Environ Bull 17:1901–1908
Xiao DS, Yuan YC, Rong MZ, Zhang MQ (2009) Self-healing epoxy based on cationic chain polymerization. Polymer 50:2967–2975
Fluri DA, Kemmer C, Daoud-El Baba M, Fussenegger M (2008) A novel system for trigger-controlled drug release from polymer capsules. J Control Release 131:211–219
Kooiman K, Bohmer MR, Emmer M, Vos HJ, Chlon C, Shi WT, Hall CS, de Winter SH, Schroen K, Versluis M, de Jong N, van Wamel A (2009) Oil-filled polymer microcapsules for ultrasound-mediated delivery of lipophilic drugs. J Control Release 133:109–118
Mao Z, Ma L, Gao C, Shen J (2005) Preformed microcapsules for loading and sustained release of ciprofloxacin hydrochloride. J Control Release 104:193–202
Cui J, Yan Y, Such GK, Liang K, Ochs CJ, Postma A, Caruso F (2012) Immobilization and intracellular delivery of an anticancer drug using mussel-inspired polydopamine capsules. Biomacromolecules 13:2225–2228
Liu QZ, Yu B, Ye W, Zhou F (2011) Highly selective uptake and release of charged molecules by pH-responsive polydopamine microcapsules. Macromol Biosci 11:1227–1234
Zheng JN, Xie HG, Yu WT, Tan MQ, Gong FQ, Liu XD, Wang F, Lv GJ, Liu WF, Zheng GH, Yang Y, Xie WY, Ma XJ (2012) Enhancement of surface graft density of MPEG on alginate/chitosan hydrogel microcapsules for protein repellency. Langmuir 28:13261–13273
Liu T, Song X, Guo Z, Dong Y, Guo N, Chang X (2014) Prolonged antibacterial effect of silver nanocomposites with different structures. Colloid Surface B 116:793–796
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2015 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Zhao, W., Wang, X. (2015). Antifouling Based on Biocides: From Toxic to Green. In: Zhou, F. (eds) Antifouling Surfaces and Materials. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-45204-2_5
Download citation
DOI: https://doi.org/10.1007/978-3-662-45204-2_5
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-662-45203-5
Online ISBN: 978-3-662-45204-2
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)