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The Modification and Application of Curcumin

Author: ZhangZuo
Tutor: LuoYan
School: Donghua University
Course: Applied Chemistry
Keywords: curcumin esterification compound light fastness dyeing performance
CLC: TQ611.3
Type: Master's thesis
Year: 2014
Downloads: 15
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Abstract


Compared with synthetic dyes, natural dyes are non-carcinogenic and hypo-Allergenic to skin. Moreover, they have the advantages of biodegradability and environmental compatibility. However, the stability of natural dyes is relatively poor and their color is easily changed because of the environmental factors such as light, heat and metal ions, which hinders the application of natural dyes. With the structure of1,3-dione, curcumin has excellent dyeing performance, simple dyeing process and high dyeing rate. However, due to the high electron cloud density in chemistry structure, the light fastness of curcumin is relatively poor, which limits its application in fabric dyeing.In view of this, this paper improves the light fastness of curcumin on fabric in two ways. The first way is that two kinds of acylated curcumin were prepared by curcumin reacting with different anhydride to introduce the acyl group, which is benefit for reducing the electron density of conjugated chromophore system. The structure of acylates was characterized by UV spectrophotometry, FT-IR, melting point apparatus and1H-NMR. Then, the fabrics were dyed with curcumin and acylated curcumin respectively. The dyeing properties of dyed samples, such as light fastness, soaping fastness, rubbing fastness and levelness were investigated in detail. The second way is to compound the curcumin with antioxidants such as butylated hydroxyanisole (BHA), ascorbic acid, propyl gallate and quercetin. The selected compounds have wide range of applications, and are relatively cheap. They easy to get to block the chain reaction of free radical by reducing the free radical in the chain initiation stage of the oxidation of curcumin or capturing the free radical in the chain reaction stage of the oxidation of curcumin. The fabrics were dyed with curcumin and compound curcumin respectively. The dyeing properties of dyed samples, such as light fastness, soaping fastness, rubbing fastness and levelness were investigated in detail and the dyeing conditions were optimized.The main results are summarized as following:(1) The optimal approach for ethyl curcumin is that curcumin reacts with acetic anhydride (5mL/g curcumin) and concentrated sulfuric acid (0.05mL/g curcumin) at60℃for6h with the yield of65%. The optimal approach for butyl curcumin is that curcumin reacts with butyric anhydride (2g/g curcumin) and benzene sulfonic acid (0.02g/g curcumin) at60℃for7h with the yield of38%.(2) Compared with fabrics dyed by curcumin, the light fastness of wool samples dyed by acylated curcumin is improved but the fastness of acrylic, polyester, nylon, cotton, acetate samples shows little improvement. The light fastness of wool samples dyed by acylated curcumin exhibits1-2level higher under auxiliary-free condition and2-3level higher under auxiliary condition than the unmodified one. The light fastness of wool samples dyed by butyl curcumin reveals1level higher under auxiliary-free condition and1-2level higher under auxiliary condition than the unmodified one. Moreover, compared with wool fabrics dyed by curcumin under auxiliary-free condition and auxiliary condition, the soaping fastness, rubbing and levelness of samples dyed by acylated curcumin are all improved, and these dyeing performances can get more improvements under the auxiliary condition.(3) The K/S value of samples dyed by compound curcumin is lower than the fabrics dyed by curcumin except the wool samples. The light fastness of acrylic, polyester, nylon, cotton, acetate samples dyed by compound curcumin exhibits0.5-1level higher, and the light fastness of wool samples dyed by compound curcumin exhibits0.5-2level higher than that of fabrics dyed by curcumin. While compared with wool fabrics dyed with curcumin, the light fastness of wool samples dyed by curcumin compound with propyl gallate and quercetin improves2degree.(4) Compared with wool samples dyed by curcumin compound with propyl gallate and quercetin under auxiliary-free condition, the K/S value and the levelness of samples dyed under auxiliary condition are all improved, however, the light fastness shows no improvement. The K/S value of wool samples dyed by compound curcumin under mordant of Al3+、Cu2+、Zn2+dyeing condition is higher and the levelness is lower than that of samples dyed by compound curcumin with non-mordant. The levelness of wool samples dyed by compound curcumin with mordant of Cu2+is the best, while the fastness and soaping fastness of that show half level higher than the samples dyed with non-mordant. Compared with the wool samples dyed with non-mordant, the light fastness of wool samples dyed with Al3+or Zn2+shows no improvement and the soaping fastness reduces a little.(5) The wool samples dyed by the curcumin compound with propyl gallate and quercetin can achieve high light fastness with mordant of Cu2+under auxiliary condition.

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CLC: > Industrial Technology > Chemical Industry > Dyes and intermediates industry > Natural dyes > Turmeric Department
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