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Double ether-containing triazinyl stilbene fluorescent whitening agent, its synthesis method and application

A technology of triazine-based stilbene and fluorescent whitening agent, which is applied in the direction of styrene-based dyes, detergent compositions, chemical instruments and methods, etc., and can solve the problems of strong acid resistance, poor light fastness, and easy precipitation

Inactive Publication Date: 2013-08-28
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, most triazine-DSD acid fluorescent whitening agents have the disadvantages of strong acid resistance and light fastness, and are easy to precipitate under acidic conditions.

Method used

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  • Double ether-containing triazinyl stilbene fluorescent whitening agent, its synthesis method and application
  • Double ether-containing triazinyl stilbene fluorescent whitening agent, its synthesis method and application
  • Double ether-containing triazinyl stilbene fluorescent whitening agent, its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] In a 500mL three-neck flask (ice-water bath), add 250mL of water, then add 9.8g of cyanuric chloride and 9.82g of DSD acid, stir vigorously to disperse evenly, keep it at 0-3°C, and react for 2.5h; raise the temperature to 50°C, add 9.18 g p-aminobenzenesulfonic acid, adjust the pH value to 5.0, and react for 3 hours; adjust the pH value to 10, heat and reflux for 20 hours, add 1.83g benzyl bromide, react for 3 hours, cool to room temperature, adjust the pH value to 3 with 4mol / L hydrochloric acid, reduce Suction filtration and drying to obtain a solid product, the product, with a yield of 85.6%.

[0026] Structural formula:

[0027]

[0028] Proton NMR data, spectrogram see figure 1

[0029] (300MHz; DMSO-d6, δ): 4.49(s, 4H, CH 2 ), 6.56-7.36 (m, 10H, ArH), 7.77 (d, 2H, CH=CH), 8.10-7.30 (m, 14H, ArH), 10.77 (s, 8H, NH and OH)

[0030] Infrared spectrum see figure 2

Embodiment 2

[0032] In a 500mL three-neck flask (ice-water bath), add 250mL of water, then add 9.8g of cyanuric chloride and 9.82g of DSD acid, stir vigorously to disperse evenly, maintain the temperature at 0-4°C, adjust the pH at about 2.5, react for 2.5h, and then Raise to 45°C, add 9.18g p-aminobenzenesulfonic acid, adjust the pH value to 4.5, react for 2.5h, adjust the pH value to 11, raise the temperature and reflux for 20h, then add 4.47g bromoethane, react for 3.0h, and dry to obtain a solid product It is the product, and the yield is 87.2%.

[0033] Proton NMR data:

[0034] (300MHz; DMSO-d6, δ): 1.09(t, 6H, CH 3 ), 3.33(q, 4H, CH 2 ), 6.56-7.36 (m, 10H, ArH), 7.77 (d, 2H, CH=CH), 8.10-7.30 (m, 14H, ArH), 10.77 (s, 8H, NH and OH)

Embodiment 3

[0036] In a 500mL three-neck flask (ice-water bath), add 250mL of water, then add 9.8g of cyanuric chloride and 9.82g of DSD acid, stir vigorously to disperse evenly, maintain the temperature at 0-3°C, adjust the pH at about 2.0, react for 2.5h, and then Raise to 45°C, add 9.18g p-aminobenzenesulfonic acid, adjust the pH value to 4.2, react for 2.5h, adjust the pH value to 11, raise the temperature and reflux for 20h, then add 4.6g chloropropene, adjust the pH value to 8.0, and react for 3.0h , The solid product obtained by drying is the product, and the yield is 85.8%.

[0037] Proton NMR data:

[0038] (300MHz; DMSO-d6, δ): 3.39(d, 4H, CH 2 ), 4.32(t, 4H, CH 2 ), 4.54 (t, 2H, CH), 6.56-7.36 (m, 10H, ArH), 7.77 (d, 2H, CH=CH), 8.10-7.30 (m, 14H, ArH), 10.77 (s, 8H, NH and OH)

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PUM

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Abstract

The invention relates to a double ether-containing triazinyl stilbene fluorescent whitening agent, its synthesis method and application. The synthesis method comprises the steps of: conducting first condensation to cyanuric chloride and DSD acid (4, 4'-Diaminostilbene-2, 2'-disulfonic acid), then subjecting the product of the first condensation and sulfanilic acid or para aminobenzoic acid to second condensation, carrying out pyrohydrolysis under an alkaline condition, and finally subjecting the product of the second condensation and a halohydrocarbon compound to a nucleophilic substitution reaction for synthesizing the target product. By utilizing the hydrophilicity of sulfanilic acid or para aminobenzoic acid, the fluorescent whitening agent of the invention has enhanced water solubility and reduced toxicity, and can be widely applied in biomedicine and other fields, thus having substantially improved practicality.

Description

technical field [0001] The invention relates to the technical field of fine chemicals, and provides a series of bisethers-containing triazine-stilbene-type fluorescent whitening agents and their synthesis methods and applications. Background technique [0002] Triazine-DSD acid fluorescent whitening agent, that is, triazine aminostilbene fluorescent whitening agent, is widely used in papermaking, textile, coating, detergent and other industries because of its high cost performance, and has become a research topic at home and abroad. And one of the most produced fluorescent whitening agents. Traditional triazine-DSD acid fluorescent whitening agents are limited in many fields due to the toxicity of aromatic amine groups. The fluorescent whitening agent with amino acid groups has the characteristics of low toxicity and environmental protection. Therefore, the synthesis of low-toxicity and environmental protection fluorescent whitening agents containing amino acid groups has a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B23/14C09K11/06C09D7/12D21H21/30C11D3/42C11D9/32
Inventor 曹成波陈锦钊万茂生王名扬郭敬兰孙书安
Owner SHANDONG UNIV