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Functional active dye complexing with zinc ions and preparation method and application thereof

A reactive dye and functional technology, applied in reactive dyes, dyeing methods, azo dyes, etc., can solve the problems of low reuse rate, less functional research, single detection, etc. good use effect

Inactive Publication Date: 2014-09-24
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Chinese patent 201220053802X "near-infrared fluorescent probe for detecting zinc ions in water phase and its preparation and application", the current fluorescent probes are all small molecules, and they are only used for single detection, and the reuse rate is low, while for them Less used for functional studies

Method used

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  • Functional active dye complexing with zinc ions and preparation method and application thereof
  • Functional active dye complexing with zinc ions and preparation method and application thereof
  • Functional active dye complexing with zinc ions and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039]Dissolve 2g (13.2mmol) of methyl p-aminobenzoate in 20ml of absolute ethanol, slowly add 1ml (19.8mmol) of 98% hydrazine hydrate dropwise, reflux reaction for 3-4h, perform rotary evaporation on a rotary evaporator, and dissolve the solvent and excess Hydrazine hydrate was evaporated to obtain crude white solid p-aminobenzoic hydrazide, 1.6g (10.5mmol) p-aminobenzoic hydrazide was dissolved in absolute ethanol, and 1.3ml (11mmol) 98% salicylaldehyde was slowly added dropwise Put it into a three-necked bottle, heat and reflux for 1-2h, cool to obtain the crude product of salicylaldehyde-4-aminobenzoylhydrazine hydrazone, obtain the pure product through multiple recrystallizations from ethanol, filter to obtain golden yellow flaky crystals, and the yield 86%. FTIR(KBr):ν=3440cm -1 (-OH); 3041cm -1 (=CH)1720cm -1 (-C=O); 1625cm -1 (-C=N); 1289cm -1 (–C-N); 3041cm -1 (=CH); 1604cm -1 ,1571cm -1 Ar-H). 1 HNMR(400MHz,DMSO,δ / ppm),5.76(2H,s),6.96-7.03(2H,m),7.40-7.48(1H...

Embodiment 2

[0041] Dissolve salicylaldehyde-4-aminobenzoylhydrazide in acetone, make the temperature of the solution reach 0-5°C in an ice-water bath, then dissolve 99% cyanuric chloride with acetone, pour it into the dropping funnel and Slowly added dropwise to the three-necked flask. After the dropwise addition, stir for 1-2h, the same method NaHCO 3 The solution was added dropwise to prevent the solution from becoming acidic. The mixture was stirred at 0-5°C and reacted for 2-3h. After filtering, the product was washed several times with a small amount of acetone to obtain a functional reactive dye with a yield of 72.3%. FTIR(KBr):ν=3284cm -1 (-OH); 3199cm -1 (-NH-); 3055 (=CH); 1612cm -1 ,1538cm -1 (AR-H); 1514cm -1 ,1453cm -1 ,1388cm -1 (triazine);

[0042] 1 HNMR (400MHz, DMSO, δ / ppm): 5.75 (2H, s), 7.76-7.80 (4H, m), 7.94-8.01 (4H, m), 10.94 (1H, s), 11.32 (1H, s).

Embodiment 3

[0044] Dissolve 98% aminofluorene in 5 mL of THF and stir with a magnetic stirrer to dissolve it. And heated to 40-45°C in an oil bath, dissolved the condensed product with 15mL of THF, poured it into a dropping funnel, and slowly added it dropwise into a three-necked flask. After the dropwise addition, stir for 1h, the same method NaHCO 3 Add dropwise. After reacting for 3 hours, filter with suction to remove part of the solvent, and slowly drop the filtrate into 120 mL of petroleum ether for precipitation. A white solid was obtained. Put it into a vacuum drying oven at 50° C. to dry to obtain a dicondensed reactive functional dye. Yield 69%. mp: 237-238°C. FTIR (KBr) ν=3420cm -1 (-OH); 3304cm-1(-NH-); 3059cm -1 (=CH); 2955cm -1 (-CH2); 1707cm -1 (C=O); 1611cm-1, 1552cm -1 (Ar-H); 1516cm -1 ,1441cm -1 ,1417cm -1 (triazine).

[0045] 1H NMR (400MHz, DMSO, δ / ppm): 3.84 (2H, s), 3.91 (2H, br), 7.31-7.27 (2H, t, J = 15.01Hz), 7.40-7.36 (2H, t, J = 14.74 Hz), 7.58-7...

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Abstract

The invention relates to a functional active dye complexing with zinc ions and a preparation method and an application thereof. The structural formula of the functional active dye is shown in the specification. The preparation method comprises the following steps: (1) dissolving methyl p-aminobenzoate in anhydrous ethanol, dropping hydrazine hydrate, carrying out a reflux reaction and rotatably steaming to obtain p-aminobenzoyl hydrazide; then, dissolving the p-aminobenzoyl hydrazide in anhydrous ethanol, adding salicylaldehyde, heating reflux, cooling, recrystallizing and filtering to obtain salicylaldehyde-4-aminobenzoyl hydrazide; and (2) dissolving the product in acetone, heating the solution in an ice-water bath to 0-5 DEG C, then, dissolving cyanuric chloride by acetone, adding into the solution and then adding a NaHCO3 solution and stirring to react; and filtering and washing the product to obtain the functional active dye. The functional active dye provided by the invention is of good selectivity to zinc ions, is convenient and has a good using effect in sewage treatment application.

Description

technical field [0001] The invention belongs to the field of functional reactive dyes, in particular to a functional reactive dye complexed with zinc ions and its preparation method and application. Background technique [0002] Zinc ions are the second most abundant transition metals in organisms after iron. At present, more than 300 kinds of enzymes have been identified in animals, plants and microorganisms to function normally without the participation of zinc. In biological systems, the concentration of zinc ions varies widely. In the cytoplasm, the concentration of zinc is about 10 -9 mol.L -1 range, and in some vesicles, the concentration of zinc can reach 10 -3 mol.L -1 above. Disorders of zinc ion metabolism can cause many diseases, such as Alzheimer's disease, amyotrophic (spinal cord) lateral sclerosis, epilepsy, and Parkinson's disease. Zinc ion fluorescent sensor is currently researched to measure intracellular Zn 2+ very important research method. [00...

Claims

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Application Information

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IPC IPC(8): C09B62/78C09K11/06G01N21/64B01J20/22D06P1/382D06P3/04
Inventor 光善仪徐洪耀陈浩张发荫
Owner DONGHUA UNIV
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