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
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