Abstract
Phthalocyanines (Pcs)
are structurally similar to macro-cyclicporphyrin-derived compounds.
Phthalocyanines generally have at least two crystal modifications that are distinct
from each other in terms of solubility, color intensity and stability. The
strongest derivatives in terms of color intensity (pigment property) are
copper, cobalt and nickel phthalocyanines. The only phthalocyanine having
commercial value as pigment is copper phthalocyanine. Copper phthalocyanines
are also used in printing inks, textiles, paper, rubber and plastics, and even
in the production of construction and industrial paint thanks to their
outstanding properties. In this study, production, characterization and
experimentation on industrial applications of the phthalocyanine-derived, PB15:
1 coded pigment (In this study, HNS 15: 1 code is given to the synthesized
pigment) which is not produced but widely used in our country, have been
successfully implemented. In the synthesis of the pigment, suitable starting
materials were mixed in an oil-heated reactor and the crude product was
obtained. The crude product from the reaction was washed, filtered and dried.
The obtained pigment was characterized by spectroscopic techniques such as
UV-vis., FTIR, MS, and elemental analysis. Industrial compatibility tests of
pigment are made in the masterbatch, artificial leather and pigment pastry
sectors.
Keywords
References
- Aravindakshan A 2005. Copperphthalocyanines, Paint and Coatings Industry, 29: 686-692.
- Bhoge YE, Deshpande TD, Patil VJ, Badgujar NP, Chaudhari RA, Kulkarni RD 2014. Synthesis of Copper Phthalocyanine Blue Pigment: Comparative Evaluations of Fusion, Solvent and Microwave Techniques, International Journal of Applied Engineering Research, 9: 1271-1278.
- Borker P, Salker AV 2006. Synthesis, characterization and photocatalytic studies of some metal phthalocyanines”, Indian Journal of Chemical Technology, 13: 341-346.
- Chunyu M, Guotong D, Yong C, Yu S, Cheng C, Jiang W, Chang Y, Wang X, Cong F, Yu H 2007. Synthesis and electrochemistry of a substituted phthalocyaninatozinc, Dyes Pigments, 72: 267-270.
- Durmuş M, Nyokong T 2007. Synthesis, photophysical and photochemical properties of aryloxy tetra-substituted gallium and indium phthalocyanine Derivatives, Tetrahedron, 63: 1385-1394.
- Gregory P 2000. Industrial applications of phthalocyanines, J. Porphyrines and Phthalocyanines, 4:432–437.
- Lomax SQ 2005. Phthalocyanine and quinacridone pigments: their history, properties and use, Studies in Conservation, 50: 19-29.
- Mack J, Kobayashi N 2011. Low Symmetry Phthalocyanines and Their Analogues, Chem. Rev., 111: 281–321.
- Ozer M, Ozkaya AR, Bulut M, Bekaroglu O 2006. Synthesis characterization and some properties of novel bis pentafluorophenyl methoxyl substituted metal free and metallophthalocyanines, Polyhedron, 25: 3593–3602.
- Özdemir L, Yılmaz Y, Sönmez M, Akkurt M, Tahir MN 2016. Synthesis and Crystal Structure of a New Phthalonitrile and Its Phthalocyanines Bearing Diamagnetic Metals. Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 46: 110–117.
- Reddy KRV, Keshavayya J 2002. Synthesis of symmmetrically substituted octabromopht halocyanine pigments and their characterization, Dyes and Pigments, 53: 187–194.
- Rapulenyane N, Antunes E, Masilela N, Nyokong T 2012. Synthesis and photophysicochemical properties of novel zinc phthalocyanines mono substituted with carboxyl containing functional groups, Journal of Photochemistry and Photobiology A: Chemistry, 250: 18–24.
- Robertson JM 1936. Quantitative structure determination of the metal- free compound, Journal of the Chemical Society, 1: 1195-1209.
- Sakamoto K, Ohno E 1997. Synthesisandelectron transfer property of phthalocyanine Derivatives, Progress in Organic Coatings, 31: 139-145.
- The British ColourMakers’ Association 1981. Phthalocyaninepigments, Polymers Paint ColourJournal, 171: 252–255.
- Wanser CC 1985. Physical and chemical considerations on copper phthalocyanine, Journal of Coatings Technology, 57: 57–62.
- Yıldız SZ, Kucukislamoğlu M, Tuna M 2009. Synthesis and characterization of novel flavonoid-substituted phthalocyanines using naringenin, Journal of Organometallic Chemistry, 694: 4152–4161.
- Yılmaz Y, Erdoğmuş A, Şener MK 2014. Diphenylethoxy-substituted metal-free and metallo phthalocyanines as potential photosensitizer for photodynamic therapy: synthesis and photophysical and photochemical properties, Turk J Chem., 38: 1083-1093.
- Yılmaz Y, Zengin H, Sönmez M 2015. Synthesis and Photoluminescence Properties of Saccharide Conjugated Copper Phthalocyanine via Click Reaction, Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 45: 337–341.
- Ziaefar N, Arjomandirad F, Mehrabad JT, Shaaba B 2011. Analyzing and Synthesis of copper, cobalt, manganese and zinc phthalocyanines and a study on their pigments, Archives of Applied Science Research, 3: 542-547.
Abstract
Ftalosiyaninler (Pc’ler) yapısal olarak makro
halkalı porfirin türevli bileşiklere benzemektedirler. Ftalosiyaninlerin
genellikle farklı çözünürlük, renk şiddeti ve kararlılık açısından birbirinden
ayrı en az iki kristal modifikasyonu bulunmaktadır. Renk şiddeti (pigment özelliği)
en kuvvetli olan türevleri bakır, kobalt ve nikel ftalosiyaninlerdir. Pigment
olarak ticari öneme sahip tek ftalosiyanin bakır ftalosiyaninlerdir. Bakır
ftalosiyaninler (CuPc, PB15), sayılan bu üstün özellikleri nedeniyle, baskı
mürekkepleri, tekstil, kâğıt, kauçuk ve plastiklerin renklendirilmesinde ve
hatta inşaat ve endüstriyel boya üretiminde kullanılmaktadır. Bu çalışmada,
ülkemizde üretilmeyen ancak ithal edilip yaygın bir şekilde kullanılan
ftalosiyanin türevli, PB15:1 kodlu (bu kapsamda sentezlenen pigmente HNS 15:1
kodu verilmiştir) pigmentin sentezi, karakterizasyonu ve endüstriyel uygulama
örnekleri yapılmıştır. Pigmentin sentezinde uygun başlangıç maddeleri yağ
ısıtmalı bir reaktörde karıştırılmış ve ham ürün elde edilmiştir. Reaksiyondan
elde edilen ham ürün yıkanmış, filtre edilmiş ve kurutulmuştur. Elde edien
pigment UV-vis., FTIR, MS gibi spektroskopik teknikler ve elementel analiz ile
karakterize edilmiştir. Pigmentin endüstriyel uygunluk denemeleri masterbatch,
suni deri ve pigment pasta sektörlerinde yapılmıştır.
Keywords
References
- Aravindakshan A 2005. Copperphthalocyanines, Paint and Coatings Industry, 29: 686-692.
- Bhoge YE, Deshpande TD, Patil VJ, Badgujar NP, Chaudhari RA, Kulkarni RD 2014. Synthesis of Copper Phthalocyanine Blue Pigment: Comparative Evaluations of Fusion, Solvent and Microwave Techniques, International Journal of Applied Engineering Research, 9: 1271-1278.
- Borker P, Salker AV 2006. Synthesis, characterization and photocatalytic studies of some metal phthalocyanines”, Indian Journal of Chemical Technology, 13: 341-346.
- Chunyu M, Guotong D, Yong C, Yu S, Cheng C, Jiang W, Chang Y, Wang X, Cong F, Yu H 2007. Synthesis and electrochemistry of a substituted phthalocyaninatozinc, Dyes Pigments, 72: 267-270.
- Durmuş M, Nyokong T 2007. Synthesis, photophysical and photochemical properties of aryloxy tetra-substituted gallium and indium phthalocyanine Derivatives, Tetrahedron, 63: 1385-1394.
- Gregory P 2000. Industrial applications of phthalocyanines, J. Porphyrines and Phthalocyanines, 4:432–437.
- Lomax SQ 2005. Phthalocyanine and quinacridone pigments: their history, properties and use, Studies in Conservation, 50: 19-29.
- Mack J, Kobayashi N 2011. Low Symmetry Phthalocyanines and Their Analogues, Chem. Rev., 111: 281–321.
- Ozer M, Ozkaya AR, Bulut M, Bekaroglu O 2006. Synthesis characterization and some properties of novel bis pentafluorophenyl methoxyl substituted metal free and metallophthalocyanines, Polyhedron, 25: 3593–3602.
- Özdemir L, Yılmaz Y, Sönmez M, Akkurt M, Tahir MN 2016. Synthesis and Crystal Structure of a New Phthalonitrile and Its Phthalocyanines Bearing Diamagnetic Metals. Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 46: 110–117.
- Reddy KRV, Keshavayya J 2002. Synthesis of symmmetrically substituted octabromopht halocyanine pigments and their characterization, Dyes and Pigments, 53: 187–194.
- Rapulenyane N, Antunes E, Masilela N, Nyokong T 2012. Synthesis and photophysicochemical properties of novel zinc phthalocyanines mono substituted with carboxyl containing functional groups, Journal of Photochemistry and Photobiology A: Chemistry, 250: 18–24.
- Robertson JM 1936. Quantitative structure determination of the metal- free compound, Journal of the Chemical Society, 1: 1195-1209.
- Sakamoto K, Ohno E 1997. Synthesisandelectron transfer property of phthalocyanine Derivatives, Progress in Organic Coatings, 31: 139-145.
- The British ColourMakers’ Association 1981. Phthalocyaninepigments, Polymers Paint ColourJournal, 171: 252–255.
- Wanser CC 1985. Physical and chemical considerations on copper phthalocyanine, Journal of Coatings Technology, 57: 57–62.
- Yıldız SZ, Kucukislamoğlu M, Tuna M 2009. Synthesis and characterization of novel flavonoid-substituted phthalocyanines using naringenin, Journal of Organometallic Chemistry, 694: 4152–4161.
- Yılmaz Y, Erdoğmuş A, Şener MK 2014. Diphenylethoxy-substituted metal-free and metallo phthalocyanines as potential photosensitizer for photodynamic therapy: synthesis and photophysical and photochemical properties, Turk J Chem., 38: 1083-1093.
- Yılmaz Y, Zengin H, Sönmez M 2015. Synthesis and Photoluminescence Properties of Saccharide Conjugated Copper Phthalocyanine via Click Reaction, Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 45: 337–341.
- Ziaefar N, Arjomandirad F, Mehrabad JT, Shaaba B 2011. Analyzing and Synthesis of copper, cobalt, manganese and zinc phthalocyanines and a study on their pigments, Archives of Applied Science Research, 3: 542-547.
Details
| Primary Language | Turkish |
|---|---|
| Journal Section | RESEARCH ARTICLE |
| Authors | |
| Publication Date | June 30, 2019 |
| Submission Date | December 15, 2018 |
| Acceptance Date | January 31, 2019 |
| Published in Issue | Year 2019Volume: 22 Issue: 3 |
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KSU Journal of Agriculture and Nature
e-ISSN: 2619-9149