Application of some novel pyrazole disperse dyes to synthetic fabrics

Year 2022, , 78 - 94, 30.12.2022

Emine Bakan , Fikret Karcı

https://doi.org/10.47137/uujes.1095062

Abstract

In this study, 8 novel pyrazole disperse dyes which were synthesized in our previous work [1] were applied to polyethylene terephthalate (PET), poly (lactic acid) (PLA) and polyamide 6.6 (PA 6.6) fiber fabrics and their colorimetric and fastness properties were evaluated. The measured a*, b* and hue angle (ho) values of all dyed fabrics exhibited yellow, orange and red colour shades. Quite high colour strength values (K/S) were measured particularly for dyes containing substitute groups; p-OCH3 and o-OCH3. Shade changes of all fabrics after standard washing and sublimation tests were in the commercially adequate range. All dyed PET, PLA and PA 6.6 fabrics exhibited commercially acceptable fastness staining performances with very good to excellent levels. Synthesized novel disperse dyestuffs led to moderate to high light fastness levels particularly in the case of PLA and PET fabrics.

Keywords

Pyrazole, disperse dye, PLA, Poly (lactic acid), colour, fastness, PET, Polyamide.

Supporting Institution

Pamukkale University Scientific Research Project Coordination Unit

Project Number

2012FBE035

Thanks

The authors wish to thank to PAUBAP for supporting this project.

References

• Referans1 Karcı F, Bakan E. 2015. New disazo pyrazole disperse dyes:Synthesis, spectroscopic studies and tautomeric structures. Journal of Molecular Liquids.206, 309-315.
• Referans2 Ghanavatkar C. W., Mishra V. R., Sekar N. 2020. Benzothiazole-pyridone and benzothiazole-pyrazole clubbed emissive azo dyes and dyeing application on polyester fabric: UPF, biological, photophysical and fastness properties with correlative computational assessments. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 118064.
• Referans3 Sreenath M. C., Joe I. H., Rastogi V. K. 2018. Experimental and theoretical investigation of third-order nonlinear optical properties of azo dye 1-(2, 5-Dimethoxy-phenylazo)-naphthalen-2-ol by Z-scan technique and quantum chemical computations. Dyes and Pigments, 157, 163-178.
• Referans4 Fang S., Feng G., Guo Y., Chen W., Qian H. 2020. Synthesis and application of urethane-containing azo disperse dyes on polyamide fabrics. Dyes and Pigments, 108225.
• Referans5 Al-Etaibi A. M., El-Apasery M. A. 2019. Dyeing performance of disperse dyes on polyester fabrics using eco-friendly carrier and their antioxidant and anticancer activities. International Journal of Environmental Research and Public Health, 16(23), 4603.
• Referans6 Ansari A., Ali A., Asif M. 2017. Biologically active pyrazole derivatives. New Journal of Chemistry, 41(1), 16-41.
• Referans7 Karrouchi K., Radi S., Ramli Y., Taoufik J., Mabkhot Y. N., Al-aizari F. A. 2018. Synthesis and pharmacological activities of pyrazole derivatives: a review. Molecules, 23(1), 134.
• Referans8 Şener N, Erişkin S, Yavuz S, Şener I. 2017. Synthesis, characterization, solvatochromic properties and antimicrobial‐radical scavenging activities of new diazo dyes derived from pyrazolo [1, 5‐a] pyrimidine. Journal of Heterocyclic Chemistry. 54(6), 3538-3548.
• Referans9 Ciçen G, Atay ÇK, Tilki T. 2017. Disazo dyes containing pyrazole and benzothiazole moieties: synthesis, characterization, absorption characteristics and tautomeric structures. Research on Chemical Intermediates. 43(12), 6803-6816.
• Referans10 El-Borai MA, Rizk HF, El- Hefnawy GB, Ibrahim SA, Aser SS, El-Sayed HF. 2016. Synthesis and spectral characterization of novel azomethine disperse dyes derived from pyrazolone moiety and their dyeing performance on polyester fabrics. Fibers and Polymers. 17(5), 729-737.
• Referans11 Rizk HF, İbrahim SA, El-Borai MA. 2015. Synthesis, fastness properties, colour assessment and antimicrobial activity of some azo reactive dyes having pyrazole moiety. Dyes and Pigments. 112, 86-92.
• Referans12 Karabacak Ç, Tilki T, Tuncer BÖ, Cengiz M. 2015. Antimicrobial pyrazole dyes: synthesis, characterization, and absorption characteristics. Research on Chemical Intermediates. 41(4), 1985-1999.
• Referans13 Sayed GH, Azab ME, Anwer KE, Raouf MA, Negm NA. 2018. Pyrazole, pyrazolone and enaminonitrile pyrazole derivatives: Synthesis, characterization and potential in corrosion inhibition and antimicrobial applications. Journal of Molecular Liquids, 252, 329-338.
• Referans14 Malladi S, Isloor AM, Isloor S, Akhila DS, Fun HK. 2013. Synthesis, characterization and antibacterial activity of some new pyrazole based Schiff bases. Arabian Journal of Chemistry, 6(3), 335-340. Referans15 Xu Z, Gao C, Ren QC, Song XF, Feng LS., Lv ZS. 2017. Recent advances of pyrazole-containing derivatives as anti-tubercular agents. European journal of medicinal chemistry, 139, 429-440.
• Referans16 Das A, Ishitani H, Kobayashi S. 2019. Toward Continuous‐Flow Synthesis of Biologically Interesting Pyrazole Derivatives. Advanced Synthesis & Catalysis, 361(22), 5127-5132.
• Referans17 Turkan F, Cetin A, Taslimi P, Karaman M, Gulçin İ. 2019. Synthesis, biological evaluation and molecular docking of novel pyrazole derivatives as potent carbonic anhydrase and acetylcholinesterase inhibitors. Bioorganic chemistry, 86, 420-427.
• Referans18 Erten G, Karcı F, Demirçalı A, Söyleyici S. 2020. 1H-Pyrazole-Azomethine Based Novel Diazo Derivative Chemosensor For The Detection Of Ni2+. Journal of Molecular Structure, 127713.
• Referans19 Şener N, Bayrakdar A, Kart HH, Şener İ. 2017. A combined experimental and DFT investigation of disazo dye having pyrazole skeleton. Journal of Molecular Structure, 1129, 222-230.
• Referans20 Yıldız B, Güzel E, Akyüz D, Arslan BS, Koca A, Şener MK. 2019. Unsymmetrically pyrazole-3-carboxylic acid substituted phthalocyanine-based photoanodes for use in water splitting photoelectrochemical and dye-sensitized solar cells. Solar Energy, 191, 654-662.
• Referans21 Gudmundsson KS, Johns BA, Wang Z, Turner EM, Allen SH, Freeman GA, Boyd FL, Sexton CJ, Selleseth DW, Moniri KR, Creech KL. 2005. Synthesis of novel substituted 2-phenylpyrazolopyridines with potent activity against herpesviruses. Bioorganic & Medicinal Chemistry. 13(18), 5346-5361.
• Referans22 Belal A, Abdelgawad MA. 2017. New benzothiazole/benzoxazole-pyrazole hybrids with potential as COX inhibitors: design, synthesis and anticancer activity evaluation. Research on Chemical Intermediates. 43(7), 3859-3872.
• Referans23 Shaki H, Gharanjig K, Khosravi A. 2015. Synthesis and investigation of antimicrobial activity and spectrophotometric and dyeing properties of some novel azo disperse dyes based on naphthalimides. Biotechnology Progress. 31(4), 1086-1095.
• Referans24 Deeb AA, El-Hossami MB, AbdelGawad AA. 2014. Pyridazine derivatives and its related compounds. Part 31. Synthesis of some disperse dyes derived from 3-amino-1H-pyrzolo [3, 4-c] pyridazine and their colour assessment on polyester fabrics. European Journal of Chemistry. 5(4), 639-643.
• Referans25 Mohamed F, Youssef YA. 2012. Synthesis and application of bifunctional reactive dyes pyrazolo[1,2‐a] pyrazole 3‐ carboxylic acid. Pigment & Resin Technology. 41(1),49-54.
• Referans26 Bagdatli E, Ocal N. 2012. Synthesis, spectroscopic and dyeing properties of new azo and bisazo dyes derived from 5-pyrozolones. Journal of Heterocyclic Chemistry. 49(5), 1179-1186.
• Referans27 Al-Etaibi AM, Al-Awadi NA, El-Apasery MA, Ibrahim MR. 2011. Synthesis of some novel pyrazolo [1, 5-a] pyrimidine derivatives and their application as disperse dyes. Molecules. 16(6), 5182-5193.
• Referans28 Rizk HF, El-Badawi MA, Ibrahim SA, El-Borai MA. 2010. Synthesis, fastness and spectral properties of some new azo pyrazole and pyrazolotriazole derivatives. Journal of Korean Chemical Society. 54(6), 737-743.
• Referans29 Shams HZ, Youssef YA, Mohamed FA, El-Zawahry MM, Helal MH, El-Kharadly EA. 2009. Synthesis and application of novel disazo pyrazolo[1,2‐a]pyrazole reactive dyes. Pigment & Resin Technology. 38(6), 372-379.
• Referans30 Helal MH, Elgemeie GH, Masoud DM. 2008. Synthesis of a new series of polyfunctionally substituted thiazole azo dye systems for dyeing of synthetic fibers. Pigment & Resin Technology. 37(6), 402-409.
• Referans31 Kamel MM, Youssef YA, Ali NF, Abd El Megiede SA. 2014. Synthesis and application of novel bifunctional pyrazole[1,5-a]pyrimidine reactive dyes. International Journal of Current Microbiology and Applied Sciences. 3(10), 519-530.
• Referans32 Bakan E, Karcı F, Avinc O. 2018. Synthetic fiber dyeing with new pyrazole disperse dyes and their colorimetric and fastness properties. Fibers and Polymers. 19(3), 670-681.
• Referans33 Karst D, Yang Y. 2005. Using the solubility parameter to explain disperse dye sorption on polylactide. Journal of Applied Polymer Science. 96(2), 416-422.
• Referans34 DyStar Textilfarben GmbH & Co. Deutschland KG. IngeoTM Fiber Colouration Pack. DyStar plc. (2004).
• Referans35 Avinc O, Owens H, Bone J, Wilding M, Phillips D, Farrington D. 2011. A colorimetric quantification of softened polylactic acid and polyester filament knitted fabrics to ‘Water-spotting’. Fibers and Polymers. 12(7), 893-903.
• Referans36 Avinc O, Wilding M, Bone J, Phillips D, Farrington D. 2010. Colour fastness properties of dyed, reduction cleared and softened poly(lactic acid) fabrics. AATCC Review. 10(5)I, 2-58.
• Referans37 Avinc O, Wilding M, Bone J, Phillips D, Farrington D. 2010. Evaluation of colour fastness and thermal migration in softened polylactic acid fabrics dyed with disperse dyes of differing hydrophobicity. Colouration Technology. 126(6), 353-364.
• Referans38 Tungtriratanakul S, Setthayanond J, Avinc O, Suwanruji P, Sae-Bae P. 2016. Investigation of UV Protection, Self-Cleaning and Dyeing Properties of Nano TiO^ sub 2^-Treated Poly (lactic acid) Fabric. Asian Journal of Chemistry. 28(11), 2398.
• Referans39 Avinc O, Bone J, Owens H, Phillips D, Wilding M. 2006. Preferred alkaline reduction‐clearing conditions for use with dyed Ingeo poly (lactic acid) fibers. Colouration Technology. 122(3), 157-161.
• Referans40 Avinc O. 2011. Clearing of dyed poly (lactic acid) fabrics under acidic and alkaline conditions. Textile Research Journal, 81(10), 1049-1074.
• Referans41 Avinc O. 2011. Maximizing the wash fastness of dyed poly (lactic acid) fabrics by adjusting the amount of air during conventional reduction clearing. Textile research journal, 81(11), 1158-1170.
• Referans42 Khoddami A, Avinc O, Mallakpour S. 2010. A novel durable hydrophobic surface coating of poly (lactic acid) fabric by pulsed plasma polymerization. Progress in Organic Coatings, 67(3), 311-316.
• Referans43 Deopura BL, Alagirusamy R, Joshi M, Gupta B. 2008. Polyesters and Polyamides, Woodhead Publishing Series in Textiles. Elsevier.
• Referans44 Avinc O, Phillips D, Wilding M. 2009. Influence of different finishing conditions on the wet fastness of selected disperse dyes on polylactic acid fabrics. Colouration Technology. 125(5), 288-295.
• Referans45 Avinc O, Day R, Carr C, Wilding M. 2012. Effect of combined flame retardant, liquid repellent and softener finishes on poly (lactic acid)(PLA) fabric performance. Textile Research Journal. 82(10), 975-984.
• Referans46 Avinc O, Khoddami A. 2010. Overview of poly (lactic acid) (PLA) fiber. Fiber Chemistry. 42(1), 68-78.
• Referans47 Nakamura T, Ishii K, Kubokawa H, Mogi K, Bommu RR. 2001. AATCC International Conference and Exhibition.