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Ftalosiyanin esaslı boyarmaddelerin kimyasal yapıları ve fonksiyonel tekstillerin üretilmesinde kullanımı

Year 2017, Volume: 23 Issue: 7, 809 - 817, 27.12.2017

Abstract

Ftalosiyaninler
keskin mavi-yeşil renkli, oldukça sağlam, iki boyutlu 18 π-elektron konjuge
sistemine sahip aromatik makrosiklik bileşiklerdir. Makrohalka yapının merkezi
koordinasyon boşluğuna periodik tablonun birçok elementinin; aromatik yapının
periferal ve non-periferal konumlarına ise çeşitli fonksiyonel sübstitüentlerin
bağlanmasıyla ftalosiyaninlere katalitik, elektrokromik, elektriksel iletkenlik,
fotovoltaik, fotoiletkenlik, ışık absorbsiyonu, foto uyarıcı gibi çeşitli
özellikler kazandırmak mümkündür. Geleneksel bakır ftalosiyanin pigmenti
dışında farklı ftalosiyanin türevlerinin de tekstil materyallerinin
renklendirilmesinde kullanılmasıyla; farklı fonksiyonel özellikli (güç tutuşur,
antibakteriyel…vs) teknik tekstillerin elde edilebileceği düşünülmektedir. Bu
sebeple bu araştırmada ftalosiyaninler hakkında genel bilgi verilip, tekstil
materyallerinin renklendirilmesi ve antibakteriyel özellik kazandırılması üzerine
yapılmış bazı çalışmalar anlatılmıştır.

References

  • Şen BN. Terminal Alkinil Sübstitüe Simetrik ve Asimetrik Ftalosiyaninler. Yüksek Lisans Tezi, İstanbul Teknik Üniversitesi, İstanbul, Türkiye, 2013.
  • Akkuş F. Nonperiferal Grup Taşıyan Benzopirrolik Bileşiklerin Sentezi, Karakterizasyonu ve Kompleks Oluşumlarının İncelenmesi. Yüksek Lisans Tezi, Pamukkale Üniversitesi, Denizli, Türkiye, 2011.
  • Kantar C. Fenol ve Türevlerini İçeren Ftalosiyaninlerin Sentezi ve Spektroskopik Özelliklerinin İncelenmesi. Yüksek Lisans Tezi, Ondokuz Mayıs Üniversitesi, Samsun, Türkiye, 2004.
  • Garcia J, Gonzalez A, Gouloumis A, Maya EM, Perez MD, Rey BD, Vazquez P, Torres T. “Phthalocyanines and related compounds: subunits for the preparation of molecular materials”. Turkish Journal of Chemistry, 22, 23-31, 1998.
  • Hart MM. Cationic Exchange Reactions Involving Dilithium Phthalocyanine. MSc Thesis, Wright State University, Dayton, USA, 2009.
  • Mert F. Azo Grubu İçeren Ftalosiyaninlerin Mikrodalga Yardımlı Sentezi ve Karakterizasyonu. Yüksek Lisans Tezi, Recep Tayyip Erdoğan Üniversitesi, Rize, Türkiye, 2011.
  • İlgün C. Karboksilik Asit Sübstitüentleri İçeren Ftalosiyaninler. Yüksek Lisans Tezi, İstanbul Teknik Üniversitesi, İstanbul, Türkiye, 2009.
  • Namlı M. Bazı İzokinolin İçeren Ftalosiyaninlerin Mikrodalga Yardımlı Sentezi, Karakterizasyonu ve Fotosensitizer Özelliklerinin İncelenmesi. Yüksek Lisans Tezi, Recep Tayyip Erdoğan Üniversitesi, Rize, Türkiye, 2013.
  • Harikumar PS. Electrochemical Studies on Metal Phthalocyanines. PhD Thesis, Cochin Universty of Science and Technology, Cochin, India, 1990.
  • Yang J. Synthesis of Novel Red-Shifted Phthalocyanines. PhD Thesis, Dublin City University, Dublin, Ireland, 2006.
  • Sakamoto K, Ohno-Okumura E. “Syntheses and functional properties of phthalocyanines”. Materials, 2, 1127-1179, 2009.
  • Hiroaki I. Optical Spectra of Phthalocyanines and Related Compounds, A Guide for Beginners. Japan, Springer Tokyo, 2015.
  • Kadish KM, Smith KM, Guilard R. The Porphyrin Handbook: Applications of Phthalocyanines. Volume 19, California, USA, Academic Press, Elsevier, 2003.
  • Jiang J. Functional Phthalocyanine Molecular Materials. Series Editor: Mingos DMP. Structure and Bonding (Book 135), Heidelberg, Berlin, Germany, Springer Verlag, 2010.
  • Keen IM. “The platinum metal phthalocyanines: The preparation and characteristics of the pure compounds”. Platinum Metals Review, 8(4), 143-144, 1964.
  • Wöhrle D, Schnurpfeil G, Makarov SG, Kazarin A, Suvorova ON. “Practical Applications of Phthalocyanines-from Dyes and Pigments to Materials for Optical, Electronic and Photo-electronic Devices”. Macroheterocycles, 5(3), 191-202, 2012.
  • Bamfield P, Hutchings MG. Chromic Phenomena: Technological Applications of Colour Chemistry. 2nd ed. UK, The Royal Society of Chemistry, 2010.
  • Yalçınkaya H. Tiyofen Grupları İçeren Ftalosiyaninlerin Sentezi. Yüksek Lisans Tezi, İstanbul Teknik Üniversitesi İstanbul, Türkiye, 2010.
  • Paint Coating Industry (PCI). “Copper Phthalocyanines”. http://www.pcimag.com/articles/83452-copper-phthalocyanines , (Erişim tarihi: 22.11.2014).
  • Narayan Group of Industries. http://www.narayan-pigments.com/pigment_blue_153.html .(Erişim tarihi: 28. 11.2014).
  • Hao L, Wang R, Liu J, Cai Y, Liu R. “Investigating the adsoption performance of nanoscale pigment on cationized cotton substrate”. Powder Technology, 222, 176-181, 2012.
  • Pal L, Fleming III PD. “The study of ınk pigment dispersion parameters”. The Hilltop Review, 2, 61-70, 2006.
  • Yano H, Sugihara Y, Shirai H, Wagatsuma Y, Kusada O, Matsuda T, Kuroda S, Higaki S. “Phthalocyanine-dyed fibers adsorb allergenic proteins”. Amino Acids, 30, 303-305, 2006.
  • Kobayashi Y, Kosaka K, Nakanishi T. “Deodorizing and antibacterial abilities of knitted cotton fabrics mordant dyed with reactive dyes and copper (ıı) sulfate”. Textile Research Journal, 80(3), 271-278, 2010.
  • Gül A, Sevim AM, Ilgün C. “Preparation of heterogeneous phthalocyanine catalysts by cotton fabric dyeing”. Dyes and Pigments, 89, 162-168, 2011.
  • Özgüney AT, Kantar C, Saral Özdemir P, Seventekin N, Şaşmaz S. “Investigation of fastness properties and antibacterial effect of metallophthalocyanine (M:Zn) Containing Eugenol Printed on Cotton Fabric”. Tekstil ve Konfeksiyon, 23(2), 261-266, 2013.
  • Özdemir Saral P, Özgüney AT, Kaya Kantar G, Şaşmaz S, Seventekin N. “An ınvestigation of fastness and antibacterial properties of cotton fabric coloured with water-soluble zinc phthalocyanine containing azo groups”. Tekstil ve Konfeksiyon, 26(1), 92-99, 2016.
  • Ryskova L, Buchta V, Karaskova M, Rakusan J, Cerny J, Slezak R. “In vitro antimicrobial activity of light-activated phthalocyanines”. Central European Journal of Biology, 8(2), 168-177, 2013.
  • Polony R, Reinert G, Hölzle G, Pugin A, Vonderwahl R. Phthalocyanine Compounds and Anti-microbial Use. United States Patent, 1985, Patent Number: 4, 530, 924.
  • Hölzle G, Reinert G, Polony R. Process For Bleaching Textiles And For Combating Microorganisms With Sulphonated Phthalocyanine Carring Halogen Or Pseudohalogen Substituents As Photoactivator. United States Patent, 1984, Patent Number:4, 456, 452.
  • Polony R, Reinert G, Hölzle G, Pugin A, Vonderwahl R. Process For Combating Micro-organisms, And Novel Phthalocyanine Compounds. United States Patent, 1982, Patent Number: 4, 318, 883.
  • Minnock A, Vernon DI, Schofield J, Griffiths J, Parish JH, Brown SB. “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, 32(3), 159-164,1996.
  • Minnock A, Vernon DI, Schofield J, Griffiths J, Parish JH, Brown SB. “Mechanism of uptake of a cationic water-soluble pyridinium zinc phthalocyanine across the outer membrane of escherichia coli”. Antimicrobial Agents and Chemotherapy, 44(3), 522-527, 2000.
  • Ağar E, Karaoğlu AŞ, Şaşmaz S. “Antimicrobial activities of some phthalocyanine derivatives”. Journal of Faculty of Pharmacy of Gazi University, 20(2), 79-86, 2003.
  • Moinuddin Khan MH, Venugopala Reddy KR, Keshavayya J. Chapter 15 : Synthesis, Spectral, Magnetic, Thermal and Antimicrobial Studies on Symmetrically Substituted 2, 9, 16, 23-tetraphenyliminophthalocyanine complexes. Editor: Bobbarala V. A Search For Antibacterial Agents, InTech, 305-318, 2012.
  • Crutchley RJ, DeRosa MC. “photosensitized singlet oxygen and ıts applications”. Coordination Chemistry Reviews, 233-234, 351-371, 2002.
  • Özdemir Saral P. Bazı Farklı Sübstitüe Gruplar İçeren Çinko Ftalosiyanin Boyarmaddelerinin Sentezi ve Tekstil Materyallerinin Renklendirilmesi. Doktora Tezi, Ege Üniversitesi, İzmir, Türkiye, 2015.
  • Staicu A, Pascu A, Nuta A, Sorescu A, Raditoiu V, Pascu ML. “Studies about phthalocyanine photosensitizers to be used in photodynamic therapy”. Romanian Reports in Physics, 65(3), 1032-1051, 2013.
  • Kalhotka L, Hrdinova Z, Korinkova R, Prichastalova J, Konecna M, Kubac L, Lev J. “Test of phthalocyanines antimicrobial activity”. 2012 Nanocon, Brno, Czech Republic, EU, 23-25.10.2012.

Chemical structures of phthalocyanine based dyestuffs and their useage in production of functional textiles

Year 2017, Volume: 23 Issue: 7, 809 - 817, 27.12.2017

Abstract

Phthalocyanines
are intensely blue-green-coloured, quite stable aromatic macrocyclic compounds
having a two-dimensional 18-π electron conjugated system. Phthalocyanines are
acquired various properties such as catalytic, electrochromic, electrical
conductivity, photovoltaic, photo-conductivity, photo-absorbtion,
photosensitizer by bonding most elements of the periodic table to central
coordination cavity of macrocylic structure and by linking various functional
substituents to peripheral or non-peripheral position of aromatic structure. It
is thought that technical textiles having different functional properties,
e.g.; antibacterial, fire retardant, can be obtained by also using various
phthalocyanine derivatives except traditional copper phthalocyanine pigment in
colouration of textile materials. For this reason, in this research general
knowledge about phthalocyanines were given then some studies about their usage
in textile material colouration and being achieved antibacterial
properties   were told.

References

  • Şen BN. Terminal Alkinil Sübstitüe Simetrik ve Asimetrik Ftalosiyaninler. Yüksek Lisans Tezi, İstanbul Teknik Üniversitesi, İstanbul, Türkiye, 2013.
  • Akkuş F. Nonperiferal Grup Taşıyan Benzopirrolik Bileşiklerin Sentezi, Karakterizasyonu ve Kompleks Oluşumlarının İncelenmesi. Yüksek Lisans Tezi, Pamukkale Üniversitesi, Denizli, Türkiye, 2011.
  • Kantar C. Fenol ve Türevlerini İçeren Ftalosiyaninlerin Sentezi ve Spektroskopik Özelliklerinin İncelenmesi. Yüksek Lisans Tezi, Ondokuz Mayıs Üniversitesi, Samsun, Türkiye, 2004.
  • Garcia J, Gonzalez A, Gouloumis A, Maya EM, Perez MD, Rey BD, Vazquez P, Torres T. “Phthalocyanines and related compounds: subunits for the preparation of molecular materials”. Turkish Journal of Chemistry, 22, 23-31, 1998.
  • Hart MM. Cationic Exchange Reactions Involving Dilithium Phthalocyanine. MSc Thesis, Wright State University, Dayton, USA, 2009.
  • Mert F. Azo Grubu İçeren Ftalosiyaninlerin Mikrodalga Yardımlı Sentezi ve Karakterizasyonu. Yüksek Lisans Tezi, Recep Tayyip Erdoğan Üniversitesi, Rize, Türkiye, 2011.
  • İlgün C. Karboksilik Asit Sübstitüentleri İçeren Ftalosiyaninler. Yüksek Lisans Tezi, İstanbul Teknik Üniversitesi, İstanbul, Türkiye, 2009.
  • Namlı M. Bazı İzokinolin İçeren Ftalosiyaninlerin Mikrodalga Yardımlı Sentezi, Karakterizasyonu ve Fotosensitizer Özelliklerinin İncelenmesi. Yüksek Lisans Tezi, Recep Tayyip Erdoğan Üniversitesi, Rize, Türkiye, 2013.
  • Harikumar PS. Electrochemical Studies on Metal Phthalocyanines. PhD Thesis, Cochin Universty of Science and Technology, Cochin, India, 1990.
  • Yang J. Synthesis of Novel Red-Shifted Phthalocyanines. PhD Thesis, Dublin City University, Dublin, Ireland, 2006.
  • Sakamoto K, Ohno-Okumura E. “Syntheses and functional properties of phthalocyanines”. Materials, 2, 1127-1179, 2009.
  • Hiroaki I. Optical Spectra of Phthalocyanines and Related Compounds, A Guide for Beginners. Japan, Springer Tokyo, 2015.
  • Kadish KM, Smith KM, Guilard R. The Porphyrin Handbook: Applications of Phthalocyanines. Volume 19, California, USA, Academic Press, Elsevier, 2003.
  • Jiang J. Functional Phthalocyanine Molecular Materials. Series Editor: Mingos DMP. Structure and Bonding (Book 135), Heidelberg, Berlin, Germany, Springer Verlag, 2010.
  • Keen IM. “The platinum metal phthalocyanines: The preparation and characteristics of the pure compounds”. Platinum Metals Review, 8(4), 143-144, 1964.
  • Wöhrle D, Schnurpfeil G, Makarov SG, Kazarin A, Suvorova ON. “Practical Applications of Phthalocyanines-from Dyes and Pigments to Materials for Optical, Electronic and Photo-electronic Devices”. Macroheterocycles, 5(3), 191-202, 2012.
  • Bamfield P, Hutchings MG. Chromic Phenomena: Technological Applications of Colour Chemistry. 2nd ed. UK, The Royal Society of Chemistry, 2010.
  • Yalçınkaya H. Tiyofen Grupları İçeren Ftalosiyaninlerin Sentezi. Yüksek Lisans Tezi, İstanbul Teknik Üniversitesi İstanbul, Türkiye, 2010.
  • Paint Coating Industry (PCI). “Copper Phthalocyanines”. http://www.pcimag.com/articles/83452-copper-phthalocyanines , (Erişim tarihi: 22.11.2014).
  • Narayan Group of Industries. http://www.narayan-pigments.com/pigment_blue_153.html .(Erişim tarihi: 28. 11.2014).
  • Hao L, Wang R, Liu J, Cai Y, Liu R. “Investigating the adsoption performance of nanoscale pigment on cationized cotton substrate”. Powder Technology, 222, 176-181, 2012.
  • Pal L, Fleming III PD. “The study of ınk pigment dispersion parameters”. The Hilltop Review, 2, 61-70, 2006.
  • Yano H, Sugihara Y, Shirai H, Wagatsuma Y, Kusada O, Matsuda T, Kuroda S, Higaki S. “Phthalocyanine-dyed fibers adsorb allergenic proteins”. Amino Acids, 30, 303-305, 2006.
  • Kobayashi Y, Kosaka K, Nakanishi T. “Deodorizing and antibacterial abilities of knitted cotton fabrics mordant dyed with reactive dyes and copper (ıı) sulfate”. Textile Research Journal, 80(3), 271-278, 2010.
  • Gül A, Sevim AM, Ilgün C. “Preparation of heterogeneous phthalocyanine catalysts by cotton fabric dyeing”. Dyes and Pigments, 89, 162-168, 2011.
  • Özgüney AT, Kantar C, Saral Özdemir P, Seventekin N, Şaşmaz S. “Investigation of fastness properties and antibacterial effect of metallophthalocyanine (M:Zn) Containing Eugenol Printed on Cotton Fabric”. Tekstil ve Konfeksiyon, 23(2), 261-266, 2013.
  • Özdemir Saral P, Özgüney AT, Kaya Kantar G, Şaşmaz S, Seventekin N. “An ınvestigation of fastness and antibacterial properties of cotton fabric coloured with water-soluble zinc phthalocyanine containing azo groups”. Tekstil ve Konfeksiyon, 26(1), 92-99, 2016.
  • Ryskova L, Buchta V, Karaskova M, Rakusan J, Cerny J, Slezak R. “In vitro antimicrobial activity of light-activated phthalocyanines”. Central European Journal of Biology, 8(2), 168-177, 2013.
  • Polony R, Reinert G, Hölzle G, Pugin A, Vonderwahl R. Phthalocyanine Compounds and Anti-microbial Use. United States Patent, 1985, Patent Number: 4, 530, 924.
  • Hölzle G, Reinert G, Polony R. Process For Bleaching Textiles And For Combating Microorganisms With Sulphonated Phthalocyanine Carring Halogen Or Pseudohalogen Substituents As Photoactivator. United States Patent, 1984, Patent Number:4, 456, 452.
  • Polony R, Reinert G, Hölzle G, Pugin A, Vonderwahl R. Process For Combating Micro-organisms, And Novel Phthalocyanine Compounds. United States Patent, 1982, Patent Number: 4, 318, 883.
  • Minnock A, Vernon DI, Schofield J, Griffiths J, Parish JH, Brown SB. “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, 32(3), 159-164,1996.
  • Minnock A, Vernon DI, Schofield J, Griffiths J, Parish JH, Brown SB. “Mechanism of uptake of a cationic water-soluble pyridinium zinc phthalocyanine across the outer membrane of escherichia coli”. Antimicrobial Agents and Chemotherapy, 44(3), 522-527, 2000.
  • Ağar E, Karaoğlu AŞ, Şaşmaz S. “Antimicrobial activities of some phthalocyanine derivatives”. Journal of Faculty of Pharmacy of Gazi University, 20(2), 79-86, 2003.
  • Moinuddin Khan MH, Venugopala Reddy KR, Keshavayya J. Chapter 15 : Synthesis, Spectral, Magnetic, Thermal and Antimicrobial Studies on Symmetrically Substituted 2, 9, 16, 23-tetraphenyliminophthalocyanine complexes. Editor: Bobbarala V. A Search For Antibacterial Agents, InTech, 305-318, 2012.
  • Crutchley RJ, DeRosa MC. “photosensitized singlet oxygen and ıts applications”. Coordination Chemistry Reviews, 233-234, 351-371, 2002.
  • Özdemir Saral P. Bazı Farklı Sübstitüe Gruplar İçeren Çinko Ftalosiyanin Boyarmaddelerinin Sentezi ve Tekstil Materyallerinin Renklendirilmesi. Doktora Tezi, Ege Üniversitesi, İzmir, Türkiye, 2015.
  • Staicu A, Pascu A, Nuta A, Sorescu A, Raditoiu V, Pascu ML. “Studies about phthalocyanine photosensitizers to be used in photodynamic therapy”. Romanian Reports in Physics, 65(3), 1032-1051, 2013.
  • Kalhotka L, Hrdinova Z, Korinkova R, Prichastalova J, Konecna M, Kubac L, Lev J. “Test of phthalocyanines antimicrobial activity”. 2012 Nanocon, Brno, Czech Republic, EU, 23-25.10.2012.
There are 39 citations in total.

Details

Subjects Engineering
Journal Section Research Article
Authors

Pınar Saral Özdemir 0000-0002-7503-4075

Arif Taner Özgüney 0000-0003-3936-615X

Publication Date December 27, 2017
Published in Issue Year 2017 Volume: 23 Issue: 7

Cite

APA Saral Özdemir, P., & Özgüney, A. T. (2017). Ftalosiyanin esaslı boyarmaddelerin kimyasal yapıları ve fonksiyonel tekstillerin üretilmesinde kullanımı. Pamukkale Üniversitesi Mühendislik Bilimleri Dergisi, 23(7), 809-817.
AMA Saral Özdemir P, Özgüney AT. Ftalosiyanin esaslı boyarmaddelerin kimyasal yapıları ve fonksiyonel tekstillerin üretilmesinde kullanımı. Pamukkale Üniversitesi Mühendislik Bilimleri Dergisi. December 2017;23(7):809-817.
Chicago Saral Özdemir, Pınar, and Arif Taner Özgüney. “Ftalosiyanin Esaslı Boyarmaddelerin Kimyasal yapıları Ve Fonksiyonel Tekstillerin üretilmesinde kullanımı”. Pamukkale Üniversitesi Mühendislik Bilimleri Dergisi 23, no. 7 (December 2017): 809-17.
EndNote Saral Özdemir P, Özgüney AT (December 1, 2017) Ftalosiyanin esaslı boyarmaddelerin kimyasal yapıları ve fonksiyonel tekstillerin üretilmesinde kullanımı. Pamukkale Üniversitesi Mühendislik Bilimleri Dergisi 23 7 809–817.
IEEE P. Saral Özdemir and A. T. Özgüney, “Ftalosiyanin esaslı boyarmaddelerin kimyasal yapıları ve fonksiyonel tekstillerin üretilmesinde kullanımı”, Pamukkale Üniversitesi Mühendislik Bilimleri Dergisi, vol. 23, no. 7, pp. 809–817, 2017.
ISNAD Saral Özdemir, Pınar - Özgüney, Arif Taner. “Ftalosiyanin Esaslı Boyarmaddelerin Kimyasal yapıları Ve Fonksiyonel Tekstillerin üretilmesinde kullanımı”. Pamukkale Üniversitesi Mühendislik Bilimleri Dergisi 23/7 (December 2017), 809-817.
JAMA Saral Özdemir P, Özgüney AT. Ftalosiyanin esaslı boyarmaddelerin kimyasal yapıları ve fonksiyonel tekstillerin üretilmesinde kullanımı. Pamukkale Üniversitesi Mühendislik Bilimleri Dergisi. 2017;23:809–817.
MLA Saral Özdemir, Pınar and Arif Taner Özgüney. “Ftalosiyanin Esaslı Boyarmaddelerin Kimyasal yapıları Ve Fonksiyonel Tekstillerin üretilmesinde kullanımı”. Pamukkale Üniversitesi Mühendislik Bilimleri Dergisi, vol. 23, no. 7, 2017, pp. 809-17.
Vancouver Saral Özdemir P, Özgüney AT. Ftalosiyanin esaslı boyarmaddelerin kimyasal yapıları ve fonksiyonel tekstillerin üretilmesinde kullanımı. Pamukkale Üniversitesi Mühendislik Bilimleri Dergisi. 2017;23(7):809-17.

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