AZO GRUPLARI İÇEREN SUDA ÇÖZÜNÜR ÇİNKO FTALOSİYANİN İLE BOYANAN PAMUKLU KUMAŞIN HASLIK VE ANTİBAKTERİYEL ÖZELLİKLERİNİN İNCELENMESİ

Year 2016, Volume: 26 Issue: 1, 92 - 99, 01.06.2016

Pınar Saral Özdemir Arif Taner Özgüney Günay Kaya Kantar Selami Şaşmaz Necdet Seventekin

Abstract

Araştırmanın temel amacı, azo grupları içeren suda çözünebilen çinko ftalosiyanin (Azo-ZnPc) ile boyanmış pamuklu kumaşın boyanma özelliklerini, renk haslık değerlerini (ışık, su, ter, klorlanmış su, sürtme, yıkama) ve antibakteriyel aktivitesini incelemektir. Bir ftalosiyanin (Pc) yapısında aynı anda bulunan çinko metal iyonu ve azo gruplarının pamuklu kumaş üzerinde antibakteriyel etki sağlayabileceği düşünülmüştür. Literatür araştırması, bu Azo-ZnPc yapısının tekstil renklendirilmesinde bir boyarmadde olarak önceden kullanılmadığını göstermektedir. Bu sebeple, bu boyanın sentezi ve bazı özelliklerinin incelenmesi değerli olabilir. Bu çalışmada ilk olarak, Azo-ZnPc sentezi gerçekleştirilmiş ve yapısı; FT-IR, UV/vis, kütle spektrumları ve 1H-NMR, 13C-NMR çalışmaları ile doğrulanmıştır. Daha sonra, bir katyonik yardımcı madde ile modifiye edilmiş pamuklu kumaş, çektirme prosesiyle sodyum karbonat varlığında Azo-ZnPc ile boyanmıştır. Son olarak, renk haslık değerleri ISO standartlarına göre belirlenmiş ve renk verimi (K/S değerleri), L, a*, b*, C*, h* değerlerinin ölçümleri elde edilmiştir. Homojen biçimde yeşil renge boyanan kumaşın antibakteriyel özellikleri AATCC 100 standartlarına göre incelenmiştir. Staphylococcus aureus (S. aureus) ve Klebsiella pneumoniae (K. pneumoniae) bakterilerinde, sırasıyla %99.99, %99.74 gibi, önemli derecede azalma gözlenmiştir

Keywords

Antibakteriyel, pamuk, ftalosiyanin, azo grubu, çinko

AN INVESTIGATION OF FASTNESS AND ANTIBACTERIAL PROPERTIES OF COTTON FABRIC COLOURED WITH WATER-SOLUBLE ZINC PHTHALOCYANINE CONTAINING AZO GROUPS

Abstract

Main purpose of this research is to investigate dyeing properties, colour fastness values (light, water, perspiration, chlorinated water, rubbing, washing) and antibacterial activity of cotton fiber fabric dyed with water-soluble zinc phthalocyanine containing azo groups (Azo-ZnPc). It is expected that zinc metal ion and azo groups present simultaneously in one phthalocyanine (Pc) structure can ensure antibacterial effect on cotton fabric. Literature survey shows that this Azo-ZnPc structure was not used before as a dyestuff in textile colouration. Therefore, synthesis and investigation some properties of this dye could be worthwhile. In this study firstly, the AzoZnPc was synthesized and the structure was verified with FT-IR, UV/vis, mass spectra and 1H-NMR, 13C-NMR studies. Afterwards, the cotton fabric modified with a cationic auxiliary was dyed with the Azo-ZnPc in the presence of sodium carbonate via exhaustion process. Finally, the colour fastness values were determined according to ISO standards and color strength (K/S values), L, a*, b*, C*, h* values measurements were performed. Antibacterial properties of the uniformly green coloured fabric were examined according to AATCC 100 standard. Significant reduction of Staphylococcus aureus (S. aureus) and Klebsiella pneumoniae (K. pneumoniae) bacteria, rated as 99.99 %, 99.74 %, respectively, were observed on cotton fiber fabric

Keywords

Antibacterial, cotton, phthalocyanine, azo group, zinc

References

• 1. Garcia J., Gonzalez A., Gouloumis A., 1998,“Phthalocyanines and Related Compounds: Subunits for the Preparation of Molecular Materials”, Tr. J. Of Chemistry, 1998: 22 (1), p:23-31.
• 2. “Copper Phthalocyanines”, http://www.pcimag.com/articles/copper-phthalocyanines, ( Access date: 21 February 2014 ) 3. Han K-J., Kay K-Y., 2005, ‘‘Synthesis and Photoresponsive Properties of Cu – Phthalocyanine With Azobenzene Groups’’, Bull. Korean Chem. Soc., 2005: 26(8), p: 1274 – 1276.
• 4. Kumar G. A., Thomas J., George N., 2000, ‘‘Physical And Optical Properties Of Phthalocyanine Doped İnorganic Glasses’’, Journal Of Materials Science, 2000: 35, p: 2539 – 2542.
• 5. Hamuryudan E., Akkurt B., 2008, “Enhancement Of Solubility Via Esterification: Synthesis and Characterization Of Octakis (Ester)-Substituted Phthalocyanines”, Dyes and Pigments, 2008: 79, p:153-158.
• 6. Christie R. M., 2001, ‘‘Chapter 5: Phthalocyanines’’, Colour Chemistry, The Royal Society Of Chemistry, p: 1-201, ISBN 0-85404-573-2
• 7. Wöhrle D., Schnurpfeil G., Makarov S. G., 2012, ‘‘Practical Applications Of Phthalocyanines – From Dyes And Pigments To Materials For Optical, Electronic And Photo – Electronic Devices’’, Macroheterocycles, 2012: 5(3), p: 191 – 202, DOI: 10.6060/mhc2012.120990w
• 8. Bamfield P., Hutchings M G, 2010, ‘‘Chapter 2: Phenomena Involving The Absorption And Reflectance Of Light’’, Chromic Phenomena: Technological Applications Of Colour Chemistry, Royal Society of Chemistry, 2nd Edition, UK, p:185, ISBN: 978-1-84755-868-8.
• 9. Joshi M., Ali S. W., Purwar R., 2009, ‘‘Ecofriendly Antimicrobial Finishing Of Textiles Using Bioactive Agents Based On Natural Products’’, Indian Journal Of Fibre & Textile Research, 2009: 34, p: 295 – 304.
• 10. Yasuyuki M., Kunihiro K., Kurissery S., 2010, “Antibacterial Properties Of Nine Pure Metals: A Laboratory Study Using Staphylococcus Aureus and Escherichia Coli”, Biofouling: The Journal Of Bioadhesion and Biofilm Research, 2010: 26(7), p:851-858, DOI: 10.1080/08927014.2010.527000
• 11. Rizzotto M., 2012, “Chapter 5: Metal Complexes As Antimicrobial Agents”, A Search For Antibacterial Agents, Bobbarala V. (Ed.), InTech, p:73, ISBN : 978-953-51-0724-8, DOI: 10.5772/45651, http://www.intechopen.com/books/a-search-for-antibacterial-agents/metal-complexes-as-antimicrobial-agents , (Access date: 02 September 2014)
• 12. Chang E. L., Simmers C., Knight D. A., 2010, “Cobalt Complexes As Antiviral And Antibacterial Agents”, Pharmaceuticals, 2010:3, p:1711-1728, DOI: 10.3390/ph3061711
• 13. Landage S. M., Wasif A. I., 2012, “Nanosilver-An Efective Antimicrobial Agent For Finishing Of Textiles”, International Journal of Engineering Sciences & Emerging Technologies, 2012: 4(1), p:66-78, ISSN: 2231 -6604
• 14. Rajendran R., Balakumar C., Ahammed H. A. M., 2010, ‘‘Use Of Zinc Oxide Nano Particles For Production Of Antimicrobial Textiles’’, International Journal Of Engineering, Science and Technology, 2010: 2(1), p:202 -208.
• 15. Ryskova L., Buchta V., Karaskova M., 2013, “In Vitro Antimicrobial Activity of Light-Activated Phthalocyanines”, Central European Journal of Biology, 2013:8(2), pp168-177.
• 16. Polony R, Reinert G, Hölzle G, 1985, United States Patent, Patent Number: 4,530,924
• 17. Hölzle G, Reinert G, Polony R, 1984, United States Patent, Patent Number:4, 456,452
• 18. Polony R, Reinert G, Hölzle G, 1982, United States Patent, Patent Number: 4,318,883
• 19. Minnock A., Vernon D. I., Schofield J., 1996, “Photoinactivation of bacteria. Use of a Cationic Water-Soluble Zinc Phthalocyanine to Photoinactivate both Gram-negative and Gram-positive Bacteria”, Journal of Photochemistry and Photobiology B: Biology, 1996:32(3) , pp159-164.
• 20. Minnock A., Vernon D. I., Schofield J., 2000, “Mechanism of Uptake of a Cationic Water-Soluble Pyridinium Zinc Phthalocyanine across the Outer Membrane of Escherichia coli”, Antimicrobial Agents and Chemotherapy, 2000:44 (3),pp 522-527.
• 21. Özgüney A., Kantar C., Saral P., 2013, ‘‘Investigation Of Fastness Properties And Antibacterial Effect Of Metallophthalocyanine ( M : Zn ) Containing Eugenol Printed On Cotton Fabric’’, Tekstil ve Konfeksiyon, 2013 : 23(2), p: 261 – 266.
• 22. Hamid H. M., Zeinab N. M., Istabraq M. A., 2011, ‘‘Synthesis And Studies The Biological Activity Of New Azo Compounds’’, Journal Of Kerbala University, 2011: 9(3), p:75 -83.
• 23. Mkpenie V., Ebong G., Obot I. B., 2008, ‘‘Evaluation Of The Effect Of Azo Group On The Biological Activity Of 1-(4-Methylphenylazo)-2-naphthol’’, E – Journal Of Chemistry, 2008: 5(3), p: 431 – 434, ISSN : 0973 – 4945
• 24. Kantar C., Atacı E., Şaşmaz S., 2014, “Water Soluble Phthalocyanines Containing Azo Dye; Microwave Assisted Synthesis And Photochemical Properties Of ZnPcs”, Turkish Journal of Chemistry, DOI: 10.3906/kim-1404-35.
• 25. Li Y-F., Li S-L., Jiang K. J., 2004, “Synthesis and Spectral Property of Novel Phthalocyanines Substituted with Four Azo Group Moieties on Periphery of Phthalocyanine Ring”, Chemistry Letters, 2004: 33, pp:1450-1451.
• 26. Yazıcı A., Ateş D., Bekaroğlu Ö., 2006, “Synthesis and Charecterization of Novel Azo-bridged Zn(II) and Co (II) Bisphthalocyanines”, Journal of Porphyrins and Phthalocyanines, 2006: 10(9), p1140.
• 27. Şaşmaz S., Kaya Kantar G., Hacıalioğlu E., 2014, “Synthesis and Properties of Phthalocyanines Containing A New Triazol-5-one Moieties, El-Cezerî Journal of Science and Engineering, 2014:1(11), p:1-6.
• 28. Àlvarez Micó X., Vagin S. I., Subramanian L. R.,2005, “New Unsymmetrical Zinc-Phthalocyanine Conjugated with One Azo-Dye Moiety: Synthesis via Opening the Fused Triazole Ring and Spectral Properties” European Journal of Organic Chemistry, 2005: 2005 (20), p:4328-4337, DOI: 10.1002/ejoc.200500237.
• 29. Young J. G., Onyebuagu W., 1990, “Synthesis and Characterization of Di-disubstituted Phthalocyanines”, J. Org. Chem., 1990:55(7), p:2155-2159.
• 30. Ojala W. H., Sudbeck E. A., Lu L. K., 1996, “Complexes of Lysine, Histidine, and Arginine with Sulfonated Azo Dyes: Model Systems for Understanding the Biomolecular Recognition of Glycosaminoglycans by Proteins”, J. Am. Chem. Soc., 1996: 118 (9), p: 2131-2142.
• 31. ‘‘Staphylococcus Aureus Infection’’ http://emedicine.medscape.com/article/971358-overview, (Access Date: 26 February 2014).
• 32. ‘‘Klebsiella Pneumoniae in Healthcare Settings’’, http://www.cdc.gov/HAI/organisms/klebsiella/klebsiella.html, (Access Date: 26 February 201