Citation: Meng-Juan Li, Yan-Hong Huang, An-Qi Ju, Tian-Shi Yu, Ming-Qiao Ge. Synthesis and characterization of azo dyestuff based on bis(2-hydroxyethyl) terephthalate derived from depolymerized waste poly(ethylene terephthalate) fibers[J]. Chinese Chemical Letters, ;2014, 25(12): 1550-1554. doi: 10.1016/j.cclet.2014.09.022 shu

Synthesis and characterization of azo dyestuff based on bis(2-hydroxyethyl) terephthalate derived from depolymerized waste poly(ethylene terephthalate) fibers

Meng-Juan Li ^a,b,, ,
Yan-Hong Huang ^b ,
An-Qi Ju ^b ,
Tian-Shi Yu ^b ,
Ming-Qiao Ge ^a,b,,

a.
a. Key Laboratory of Eco-Textiles (Jiangnan University), Ministry of Education, Wuxi 214122, China;
b.
b. College of Textile & Clothing, Jiangnan University, Wuxi 214122, China

Corresponding author: Meng-Juan Li, Ming-Qiao Ge,
Received Date: 24 May 2014
Available Online: 18 September 2014
Fund Project: This work was financially supported by the National High-tech R&D Program of China (863 Program, No. 2012AA030313) (863 Program, No. 2012AA030313) the Open Project Program of Key Laboratory of Eco-Textiles (Jiangnan University) (Jiangnan University) Ministry of Education, China (No. KLET1115) (No. KLET1115) the Fundamental Research Funds for the Central Universities (No. JUSRP11201) (No. JUSRP11201)

This work aimed at effectively utilizing the chemically depolymerized waste poly(ethylene terephthalate) (PET) fibers into useful products for the textile industry. PET fibers were glycolytically degraded by excess ethylene glycol as depolymerizing agent and zinc acetate dihydrate as catalyst. The glycolysis product, bis(2-hydroxyethyl) terephthalate (BHET), was purified through repeated crystallization to get an average yield above 80%. Then, BHET was nitrated, reduced, and azotized to get diazonium salt. Finally, the produced diazonium salt was coupled with 1-(4-sulfophenyl)-3-methyl-5-pyrazolone to get azo dyestuff. The structures of BHET and azo dyestuff were identified by FTIR and 1H NMR spectra and elemental analysis. Nylon filaments dyed by the synthesized azo dyestuff with the dye bath pH from 4.14 to 5.88 showed bright yellow color. The performances of the dyestuff were described with dye uptake, color fastness, K/S, L^*, a^*, b^*, and ΔE^* values.
- Waste PET fibers,
- Depolymerization,
- Bis(2-hydroxyethyl) terephthalate,
- Azo dyestuff
1. [1]
  [1] D.E. Nikles, M.S. Farahat, New motivation for the depolymerization products derived from poly(ethylene terephthalate) (PET) waste: a review, Macromol. Mater. Eng. 290 (2005) 13-30.
2. [2]
  [2] A. Oromiehie, A. Mamizadeh, Recycling PET beverage bottles and improving properties, J. Polym. Int. 53 (2004) 728-732.
3. [3]
  [3] L. Bartolome, M. Imran, B.G. Cho, A.A.M. Waheed, H.K. Do, Recent developments in the chemical recycling of PET, in: D.S. Achilias (Ed.), Material Recycling -Trends and Perspectives, Intech, Croatia, 2012, pp. 65-84.
4. [4]
  [4] S. Sivaram, in: Proceedings of National Seminar on Recycling and Plastics Waste Management, India, (1997), pp. 283-288.
5. [5]
  [5] H.J. Koo, G.S. Chang, S.H. Kim, W.G. Hahm, S.Y. Park, Effects of recycling processes on physical, mechanical and degradation properties of PET yarns, Fibers Polym. 14 (2013) 2083-2087.
6. [6]
  [6] A. Aguado, L. Martínez, L. Becerra, et al., Chemical depolymerisation of PET complex waste: hydrolysis vs. glycolysis, J. Mater. Cycles Waste Manag. 16 (2014) 201-210.
7. [7]
  [7] D. Carta, G. Cao, C. D'Angeli, Chemical recycling of poly(ethylene terephthalate) (PET) by hydrolysis and glycolysis, J. Environ. Sci. Pollut. Res. 10 (2003) 390-394.
8. [8]
  [8] L.R. Zhang, J. Gao, J.Z. Zou, F.P. Yi, Hydrolysis of poly (ethylene terephthalate) waste bottles in the presence of dual functional phase transfer catalysts, J. Appl. Polym. Sci. 130 (2013) 2790-2795.
9. [9]
  [9] M. Imran, D.H. Kim, W.A. Al-Masry, et al., Manganese-, cobalt-, and zinc-based mixed-oxide spinels as novel catalysts for the chemical recycling of poly(ethylene terephthalate) via glycolysis, Polym. Degrad. Stabil. 98 (2013) 904-915.
10. [10]
  [10] N.D. Pingale, S.R. Shukla, Microwave-assisted aminolytic depolymerization of PET waste, Eur. Polym. J. 45 (2009) 2695-2700.
11. [11]
  [11] R. Shamsi, M. Abdouss, G.M.M. Sadeghi, F.A. Taromi, Synthesis and characterization of novel polyurethanes based on aminolysis of poly(ethylene terephthalate) wastes, and evaluation of their thermal and mechanical properties, J. Polym. Int. 58 (2009) 22-30.
12. [12]
  [12] Y. Yang, Y.J. Lu, H.W. Xiang, Y.Y. Xu, Y.W. Li, Study on methanolytic depolymerization of PET with supercritical methanol for chemical recycling, Polym. Degrad. Stabil. 75 (2002) 185-191.
13. [13]
  [13] P.K. Roy, R. Mathur, D. Kumar, C. Rajagopal, Tertiary recycling of poly(ethylene terephthalate) wastes for production of polyurethane-polyisocyanurate foams, J. Environ. Chem. Eng. 1 (2013) 1062-1069.
14. [14]
  [14] M.J. Li, J. Luo, Y.H. Huang, et al. Recycling of waste poly(ethylene terephthalate) into flame-retardant rigid polyurethane foams, J. Polym. Appl. Sci. 131 (2014), http://dx.doi.org/10.1002/AP.P.40857.
15. [15]
  [15] I. Duque-Ingunza, R. Ló pez-Fonseca, B. de Rivas, J.I. Gutié rrez-Ortiz, Synthesis of unsaturated polyester resin from glycolysed postconsumer PET wastes, J. Mater. Cycles Waste Manag. 15 (2013) 256-263.
16. [16]
  [16] A.M. Atta, W. Brostow, T. Datashvili, et al., Porous polyurethane foams based on recycled poly(ethylene terephthalate) for oil sorption, Polym. Int. 62 (2013) 116-126.
17. [17]
  [17] S.R. Shukla, A.M. Harad, L.S. Jawale, Chemical recycling of PET waste into hydrophobic textile dyestuffs, Polym. Degrad. Stabil. 94 (2009) 604-609.
18. [18]
  [18] V.S. Palekar, N.D. Pingale, S.R. Shukla, Synthesis, spectral properties and application of novel disazo disperse dyes derived from polyester waste, Color Technol. 126 (2010) 86-91.
19. [19]
  [19] J. Choi, H. Lee, A.D. Towns, Dyeing properties of novel azo disperse dyes derived from phthalimide and color fastness on poly (lactic acid) fiber, Fibers Polym. 11 (2010) 199-204.
20. [20]
  [20] M. Ghaemy, H. Mighani, Synthesis and identification of dinitro-and diaminoterephthalic acid, Chin. Chem. Lett. 20 (2009) 800-804.
21. [21]
  [21] W. Ma, M. Meng, X. Jiang, B.T. Tang, S.F. Zhang, Synthesis of a water-soluble macromolecular light stabilizer containing hindered amine structures, Chin. Chem. Lett. 24 (2013) 153-155.
22. [22]
  [22] R. McDonald, Colour Physics for Industry, 2nd ed., Society of Dyers and Colourists, Bradford, 1997.
23. [23]
  [23] J.D. Wang, S.M. Han, D.D. Ke, Synthesis and white-light emission character of CdS magic-sized nanocrystals, Chin. Chem. Lett. 23 (2012) 1407-1410.
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