Modified tannin extracted from black wattle tree as an environmentally friendly antifouling pigment

Industrial Crops and Products

Volumn 65, Issue , 2015, Pages 506-514

  Peres, Rafael S ^a   Armelin, Elaine ^b   Alemán, Carlos ^b   Ferreira, Carlos A ^a  

^a FEDERAL UNIVERSITY OF RIO GRANDE DO SUL   (Brazil)

^b UNIVERSITAT POLITÈCNICA DE CATALUNYA   (Spain)

Author keywords

Antifouling; Black wattle; Coatings; Environmentally friendly; Tannin

Indexed keywords

ACTIVATED CARBON; ANTIFOULING PAINT; BLACK COATINGS; COATINGS; FLAVONOIDS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PAINT;

ANTIFOULING; ANTIFOULING COATING; BLACK WATTLE; ENVIRONMENTALLY FRIENDLY; HYDROPHILIC CHARACTERISTICS; INTERFLAVONOID BONDS; MARINE ENVIRONMENT; WATER CONTACT ANGLE;

TANNINS;

ACTIVATED CARBON; ADSORPTION; ANTIFOULING AGENT; COATING; MARINE ENVIRONMENT; PESTICIDE; RESIN; TANNIN;

MEDITERRANEAN SEA;

EID: 84945175594     PISSN: 09266690     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.indcrop.2014.10.033     Document Type: Article

References (72)

1. Alzieu C. Environmental impact of TBT: the French experience. Sci. Total Environ. 2000, 258:99-102.
2. Amarowicz R. Tannins: the new natural antioxidants?. Eur. J. Lipid Sci. Technol. 2007, 109:549-551.
3. Anil C., Chiba A., Okamoto K., Kurokura H. Influence of temperature and salinity on larval development of Balanus amphitrite: implications in fouling ecology. Mar. Ecol. Prog. Ser. 1995, 118:159-166.
4. Arai T., Harino H., Ohji M., Langston W.J. Ecotoxicology of Antifouling Biocides 2009, Springer. first ed.
5. ASTM D3623-78a Standard Test Method for Testing Antifouling Panels in Shallow Submergence 2004.
6. ASTM D6990-05 Standard Practice for Evaluating Biofouling Resistance and Physical Performance of Marine Coating Systems 2011.
7. Azémard C., Vieillescazes C., Ménager M. Effect of photodegradation on the identification of natural varnishes by FT-IR spectroscopy. Microchem. J. 2014, 112:137-149.
8. Bate-Smith E., Swain T. Flavonoid compounds. Comp. Biochem. 1962, 3:705-809.
9. Bellotti N., del Amo B., Romagnoli R. Tara tannin a natural product with antifouling coating application. Prog. Org. Coat. 2012, 74:411-417.
10. Bellotti N., Deyá C., del Amo B., Romagnoli R. Quebracho tannin derivative and boosters biocides for new antifouling formulations. J. Coat. Technol. Res. 2012, 9:551-559.
11. Callow M.E., Callow J.A. Marine biofouling: a sticky problem. Biologist 2002, 49:1-5.
12. Castillo-Muñoz N., Gómez-Alonso S., García-Romero E., Gómez M.V., Velders A.H., Hermosín-Gutiérrez I. Flavonol 3-O-glycosides series of Vitis vinifera Cv Petit Verdot red wine grapes. J. Agric. Food Chem. 2008, 57:209-219.
13. Chai W.-M., Shi Y., Feng H.-L., Qiu L., Zhou H.-C., Deng Z.-W., Yan C.-L., Chen Q.-X. NMR HPLC-ESI-MS, and MALDI-TOF MS analysis of condensed tannins from Delonix regia (Bojer ex Hook.) Raf. and their bioactivities. J. Agric. Food Chem. 2012, 60:5013-5022.
14. Chesworth J., Donkin M., Brown M. The interactive effects of the antifouling herbicides Irgarol 1051 and Diuron on the seagrass Zostera marina (L). Aquat. Toxicol. 2004, 66:293-305.
15. Chet I., Asketh P., Mitchell R. Repulsion of bacteria from marine surfaces. Appl. Microbiol. 1975, 30:1043-1045.
16. Chiu J.M.Y., Thiyagarajan V., Tsoi M.M.Y., Qian P.Y. Qualitative and quantitative changes in marine biofilms as a function of temperature and salinity in summer and winter. Biofilms 2005, 2:183-195.
17. Chung K.-T., Lu Z., Chou M.W. Mechanism of inhibition of tannic acid and related compounds on the growth of intestinal bacteria. Food Chem. Toxicol. 1998, 36:1053-1060.
18. 13C NMR. Tetrahedron Lett. 2002, 43:4545-4549.
19. Czochanska Z., Foo L.Y., Newman R.H., Porter L.J. Polymeric proanthocyanidins. Stereochemistry, structural units, and molecular weight. J. Chem. Soc., Perkin Trans. 1980, 1:2278-2286.
20. 13C NMR assignments of some green tea polyphenols. Magn. Reson. Chem. 1996, 34:887-890.
21. Devilla R.A., Brown M.T., Donkin M., Readman J.W. The effects of a PSII inhibitor on phytoplankton community structure as assessed by HPLC pigment analyses, microscopy and flow cytometry. Aquat. Toxicol. 2005, 71:25-38.
22. Etoh H., Kondoh T., Noda R., Singh I.P., Sekiwa Y., Morimitsu K., Kubota K. Shogaols from Zingiber officinale as promising antifouling agents. Biosci. Biotechnol. Biochem. 2002, 66:1748-1763.
23. Etoh H., Kondoh T., Yoshioka N., Sugiyama K., Ishikawa H., Tanaka H. 9-Oxo-neoprocurcumenol from Curcuma aromatica (Zingiberaceae) as an attachment inhibitor against the blue mussel, Mytilus edulis galloprovincialis. Biosci. Biotechnol. Biochem. 2003, 67:911-913.
24. Flemming C., Trevors J. Copper toxicity and chemistry in the environment: a review. Water Air Soil Pollut. 1989, 44:143-158.
25. Font J., Salvadó N., Butí S., Enrich J. Fourier transform infrared spectroscopy as a suitable technique in the study of the materials used in waterproofing of archaeological amphorae. Anal. Chim. Acta 2007, 598:119-127.
26. Goldberg E.D. TBT: an environmental dilemma environment. Sci. Policy Sustain. Dev. 1986, 28:17-44.
27. Hagerman A., Robbins C. Implications of soluble tannin-protein complexes for tannin analysis and plant defense mechanisms. J. Chem. Ecol. 1987, 13:1243-1259.
28. Hagerman Ann E., Zhao Y., Johnson S. Methods for determination of condensed and hydrolyzable tannins antinutrients and phytochemicals in food. Am. Chem. Soc. 1997, 209-222.
29. Hemingway R.W., McGraw G.W. Kinetics of acid-catalyzed cleavage of procyanidins. J. Wood Chem. Technol. 1983, 3:421-435.
30. Hernes P.J., Benner R., Cowie G.L., Goñi M.A., Bergamaschi B.A., Hedges J.I. Tannin diagenesis in mangrove leaves from a tropical estuary: a novel molecular approach. Geochim. Cosmochim. Acta 2001, 65:3109-3122.
31. Hillis W.E. Tannin chemistry. Black Wattle and its Utilisation 1997, 106-121. Rural Industries Research and Development Corporation, Barton. first ed. A.G. Brown, H.C. Ko (Eds.).
32. His E., Robert R. Developpement des veligeres de Crassostrea gigas dans le bassin d'Arcachon Etudes sur les mortalites larvaires. Revue des Travaux de l'Institut des Pêches Maritimes 1983, 47:63-88.
33. Hussein M.Z.b.Ghotbi M.Y., Yahaya A.H., Abd Rahman M.Z. Synthesis and characterization of (zinc-layered-gallate) nanohybrid using structural memory effect. Mater. Chem. Phys. 2009, 113:491-496.
34. IMO International Maritime Organization (IMO) - International Convention on the Control of Harmful Anti-fouling Systems on Ships 2001.
35. Jensen J.S., Egebo M., Meyer A.S. Identification of spectral regions for the quantification of red wine tannins with Fourier transform mid-infrared spectroscopy. J. Agric. Food Chem. 2008, 56:3493-3499.
36. Kennedy J.A., Jones G.P. Analysis of proanthocyanidin cleavage products following acid-catalysis in the presence of excess phloroglucinol. J. Agric. Food Chem. 2001, 49:1740-1746.
37. Lau S.C.K., Qian P.Y. Inhibitory effect of phenolic compounds and marine bacteria on larval settlement of the barnacle Balanus amphitrite amphitrite darwin. Biofouling 2000, 16:47-58.
38. Lewandowski Z., Beyenal H. Mechanisms of microbially influenced corrosion. Marine and Industrial Biofouling 2009, 35-64. Springer, Berlin. H.-C. Flemming, P.S. Murthy, R. Venkatesan, K. Cooksey, J.W. Costerton (Eds.).
39. Matamala G., Smeltzer W., Droguett G. Comparison of steel anticorrosive protection formulated with natural tannins extracted from acacia and from pine bark. Corros. Sci. 2000, 42:1351-1362.
40. 13C NMR characterization of maritime pine industrial tannin extract. Ind. Crop. Prod. 2010, 32:105-110.
41. Onem E., Gulumser G., Akay S., Yesil-Celiktas O. Optimization of tannin isolation from acorn and application in leather processing. Ind. Crop. Prod. 2014, 53:16-22.
42. Peres R.S., Cassel E., Ferreira C.A., Azambuja D.S. Black wattle tannin as a zinc phosphating coating sealer. Surf. Interface Anal. 2014, 46:1-6.
43. Peres R.S., Cassel E., Ferreira C.A., Azambuja D.S. Grain refiner effect of black wattle tannin in iron and zinc phosphate coatings. Ind. Eng. Chem. Res. 2014, 53:2706-2712.
44. Pérez M., Blustein G., García M., del Amo B., Stupak M. Cupric tannate: a low copper content antifouling pigment. Prog. Org. Coat. 2006, 55:311-315.
45. Pérez M., Garcia M., Blustein G., Stupak M. Tannin and tannate from the quebracho tree: an eco-friendly alternative for controlling marine biofouling. Biofouling 2007, 23:151-159.
46. Pizzi A. Condensed tannins for adhesives. Ind. Eng. Chem. Prod. Res. Dev. 1982, 21:359-369.
47. 13C NMR study of polyflavonoid tannin extracts for phenolic polycondensates. J. Appl. Polym. Sci. 1993, 50:2105-2113.
48. Pizzi A. Advanced Wood Adhesives Technology 1994, Marcel Dekker. first ed.
49. Porter L.J., Hrstich L.N., Chan B.G. The conversion of procyanidins and prodelphinidins to cyanidin and delphinidin. Phytochemistry 1985, 25:223-230.
50. Qian P.-Y., Xu Y., Fusetani N. Natural products as antifouling compounds: recent progress and future perspectives. Biofouling 2010, 26:223-234.
51. Rahim A.A., Kassim J. Recent development of vegetal tannins in corrosion protection of iron and steel. Rec. Pat. Mater. Sci. 2008, 1:223-231.
52. Rahim A.A., Rocca E., Steinmetz J., Jain Kassim M. Inhibitive action of mangrove tannins and phosphoric acid on pre-rusted steel via electrochemical methods. Corros. Sci. 2008, 50:1546-1550.
53. Rahim A.A., Rocca E., Steinmetz J., Kassim M., Adnan R., Sani Ibrahim M. Mangrove tannins and their flavanoid monomers as alternative steel corrosion inhibitors in acidic medium. Corros. Sci. 2007, 49:402-417.
54. Readman J.W. Development occurrence and regulation of antifouling paint biocides: historical review and future trends. Antifouling Paint Biocides 2006, 1-16. Springer, Berlin. I.K. Konstantinou (Ed.).
55. Redfield A.C., Hutchins L.W. Problems of fouling. Marine Fouling and its Prevention 1952, George Banta Publishing Co., Menasha. A.C. Redfield, B.H. Ketchum (Eds.).
56. Schmidt B.M., Howell A.B., McEniry B., Knight C.T., Seigler D., Erdman J.W., Lila M.A. Effective separation of potent antiproliferation and antiadhesion components from wild blueberry (Vaccinium angustifolium Ait) fruits. J. Agric. Food Chem. 2004, 52:6433-6442.
57. Senda T. International trends in regulatory aspects. Ecotoxicology of Antifouling Biocides 2009, 23-38. Springer, Tokyo. T. Arai, H. Harino (Eds.).
58. Sieburth J.M., Conover J.T. Sargassum tannin, an antibiotic which retards fouling. Nature 1965, 208:52-53.
59. Slabbert N. Complexation of condensed tannins with metal ions. Plant Polyphenols 1992, 421-436. Springer, USA. R. Hemingway, P. Laks (Eds.).
60. Soto R., Freer J., Baeza J. Evidence of chemical reactions between di- and poly-glycidyl ether resins and tannins isolated from Pinus radiata D. Don bark. Bioresour. Technol. 2005, 96:95-101.
61. Stupak M.E., García M.T., Pérez M.C. Non-toxic alternative compounds for marine antifouling paints. Int. Biodeterior. Biodegrad. 2003, 52:49-52.
62. Swain T., Hillis W. The phenolic constituents of Prunus domestica I. - the quantitative analysis of phenolic constituents. J. Sci. Food Agric. 1959, 10:63-68.
63. Szczurek A., Fierro V., Pizzi A., Stauber M., Celzard A. A new method for preparing tannin-based foams. Ind. Crop. Prod. 2014, 54:40-53.
64. 13C NMR. Ind. Crop. Prod. 2013, 49:697-704.
65. Wahl M. Marine epibiosis. I. Fouling and antifouling: some basic aspects. Mar. Ecol. Prog. Ser. 1989, 58:175-189.
66. Watanabe M. Catechins as antioxidants from buckwheat (Fagopyrum esculentum Moench) Groats. J. Agric. Food Chem. 1998, 46:839-845.
67. Watts, J.L., 1995. Anti-fouling coating composition containing capsaicin. US Patent US5397385 A.
68. Wawer I., Wolniak M., Paradowska K. Solid state NMR study of dietary fiber powders from aronia, bilberry, black currant and apple. Solid State Nucl. Magn. Reson. 2006, 30:106-113.
69. Yebra D.M., Kiil S., Dam-Johansen K., Weinell C. Reaction rate estimation of controlled-release antifouling paint binders: Rosin-based systems. Prog. Org. Coat. 2005, 53:256-275.
70. Yuan Y., Lee T.R. Contact angle and wetting properties. Surface Science Techniques 2013, 3-34. Springer, Berlin, Heidelberg. G. Bracco, B. Holst (Eds.).
71. Zhang L.-L., Lin Y.-M., Zhou H.-C., Wei S.-D., Chen J.-H. Condensed tannins from mangrove species Kandelia candel and Rhizophora mangle and their antioxidant activity. Molecules 2010, 15:420-431.
72. Zhao Y., Yan N., Feng M.W. Biobased phenol formaldehyde resins derived from beetle-infested pine barks-structure and composition. ACS Sustain. Chem. Eng. 2012, 1:91-101.