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Chemical structure modification-based water-soluble curcumin dye, and preparation method and application thereof

A technology of chemical structure and curcumin, applied in the direction of chemical instruments and methods, dyeing methods, azo dyes, etc., can solve the problems of difficult industrial production, high preparation cost, poor color fastness, etc., to achieve improved color fastness, no Effect of heavy metal residue and high dyeing rate

Inactive Publication Date: 2014-07-30
嘉兴君宏光学有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] However, in the above-mentioned dye preparation process, toxic or strongly acidic reagents such as sodium nitrite or concentrated hydrochloric acid need to be used, the preparation cost is high, and it is not easy for industrial production.
At the same time, when the dye is actually used, there are still problems such as low dyeing rate and poor color fastness.

Method used

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  • Chemical structure modification-based water-soluble curcumin dye, and preparation method and application thereof
  • Chemical structure modification-based water-soluble curcumin dye, and preparation method and application thereof
  • Chemical structure modification-based water-soluble curcumin dye, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Example 1: Synthesis of Curcumin Bis(2-Bromoethyl) Ether Intermediate 1

[0051] Curcumin powder (1 g, 2.72 mmol), potassium carbonate (0.94 g, 6.8 mmol) and tetrabutylammonium bromide (0.043 g, 0.126 mmol) were placed in a chamber containing 1,2-dibromoethane (12 mL). In a round-bottomed flask, the mixture was heated at 90 °C for 24 h and cooled to room temperature. The unreacted 1,2-dibromoethane was collected by distillation under reduced pressure, the residue was washed several times with an appropriate amount of n-hexane, and the obtained orange-yellow solid powder (1.38g) was naturally dried, which is curcumin bis(2-bromoethane) ethyl) ether intermediate in 87% yield.

[0052] m.p.137.5-139.3℃;

[0053] FT-IR(KBr)ν2923,1626,1587,1508,1257,1136,1021,971cm-1; as Figure 9 shown.

[0054] 1 H NMR (400MHz, CDCl 3 )δ3.68(t,J=7.8Hz,4H),3.92(s,6H),4.37(t,J=7.8Hz,4H),5.82(s,1H),6.50(d,J=16Hz,2H ), 6.89 (d, J=8Hz, 2H), 7.11 (m, 4H), 7.59 (d, J=16Hz, 2H), 15.94 (br, ...

Embodiment 2

[0057] Example 2: Synthesis of water-soluble curcumin dye 2

[0058] Curcumin bis(2-bromoethyl) ether (1 g, 1.72 mmol) was placed in a round-bottomed flask containing triethylamine (12 mL), wrapped with thick tin foil to protect from light and passed through a stream of nitrogen, and the mixture was heated at 90°C After 48 hours of reaction, it was cooled to room temperature. The unreacted triethylamine was collected by distillation under reduced pressure, and the residue was washed several times with an appropriate amount of acetone. The obtained orange-red solid powder (1.23 g) was dried in a vacuum drying oven at 60°C and stored in a desiccator. The obtained product is water-soluble curcumin dye with a yield of 91%.

[0059] m.p.>360℃;

[0060] FT-IR (KBr) ν3388 (water peak due to moisture absorption), 2938, 2675, 1624, 1592, 1511, 1262, 1139, 1030, 808cm -1 ;like Figure 13 shown.

[0061] 1 H NMR (400MHz, CDCl 3 )δ1.43(t,J=7.2Hz,18H),3.11(q,J=7.2Hz,12H),3.69(t,J=6....

Embodiment 3

[0077] Example 3: Dyeing of cotton fabric with water-soluble curcumin dyes

[0078]The water-soluble curcumin dye was dissolved in an aqueous solution of acetic acid with a pH value of 5 to a concentration of 2% (o.w.f.). Take a piece of boiled and bleached cotton grey cloth (about 5×10cm 2 ), put it in the conical flask containing the above dye solution, and the liquor ratio is 1:30. The conical flask was placed in a constant temperature water bath shaker at 70°C and kept for 1.5h. Take out the cotton cloth, squeeze the dye liquid, rinse it with water, and hang it to dry naturally.

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Abstract

The invention discloses a chemical structure modification-based water-soluble curcumin dye. The invention also discloses a preparation method of the chemical structure modification-based water-soluble curcumin dye. The preparation method comprises the following steps: reacting curcumin with 1,2-dibromoethane, and reacting the above obtained product with triethylamine to obtain the chemical structure modification-based water-soluble curcumin dye. The invention also discloses an application method of the chemical structure modification-based water-soluble curcumin dye. The dye can be directly used for dyeing unmodified cotton fabrics without a dyeing accelerant, a dye leveler or a dye mordant, so the environmental protection property of a dyeing process and the safety of the fabric are improved. All dyeing indexes, especially the indexes comprising the washing color fastness and the like of the water-soluble dye are obviously better than that of natural curcumin for direct dyeing, wherein the washing color fastness reaches 3 level, the staining fastness reaches 5 level, and each of the dry crock fastness and the wet crock fastness reaches 5 level.

Description

technical field [0001] The invention belongs to the field of dye preparation, in particular to a water-soluble curcumin dye based on chemical structure modification, a preparation method and an application. Background technique [0002] The use of vegetable dyes to dye fabrics has a long history. Vegetable dyes were the main dyeing raw materials for the production and processing of colored fabrics before the 19th century. Most of the vegetable dyes have good biocompatibility and pharmacological activity. Gradually, and with a growing focus on one's own health, they are again being valued. [0003] Curcumin is a powder obtained by drying the rhizomes of Herbaceae herbs, extracted by organic solvents and concentrated and purified. Formula 1), among which curcumin has the most content, and the chemical and physical properties of the three components are very similar. It is a relatively rare natural pigment with β-diketone structure existing in nature. In addition, curcumin al...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B57/00D06P1/00D06P3/60
Inventor 夏敏姚起超
Owner 嘉兴君宏光学有限公司
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