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Stilbene fluorescent whitening agent, and preparation method and application thereof

A technology of fluorescent whitening agent and stilbene, which is applied in the direction of styrene-based dyes, chemical instruments and methods, and addition of luminescent/fluorescent substances. Advanced problems, to achieve the effect of strong fluorescence intensity

Inactive Publication Date: 2014-01-01
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] At present, the synthesis process of stilbene-type fluorescent whitening agent is relatively complicated, and the yield is average. A large amount of acid is used in the production process, causing environmental pollution, and the synthetic fluorescent whitening agent has low fluorescence intensity and low whiteness.

Method used

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  • Stilbene fluorescent whitening agent, and preparation method and application thereof
  • Stilbene fluorescent whitening agent, and preparation method and application thereof
  • Stilbene fluorescent whitening agent, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 11

[0024] Synthesis of embodiment 11,3,4-oxadiazole stilbene fluorescent whitening agent (I)

[0025]

[0026] (1) Dissolve 0.0088mol 2-naphthyl-5-(4-(bromomethyl)phenyl)-1,3,4-oxadiazole in 0.0132mol triethyl phosphite, heat to 130°C and stir Refluxing reaction for 5 hours, after decompressing to distill off excess triethyl phosphite in the reaction system, add 5ml of n-hexane with stirring while hot to precipitate a solid product, and then recrystallize with a 1:1 mixture of tetrahydrofuran and n-hexane to obtain 3.32g of 4-( 5-Naphthyl-1,3,4-oxadiazol-2-yl)benzylphosphonate, yield: 89.4%. Melting point: 139-140°C. H NMR structural characterization data: 1 H NMR (400MHz, CDCl 3 )δ9.30(d,J=8.6Hz,1H,naphthalene-H),8.29(d,J=7.2Hz,1H,naphthalene-H),8.18(d,J=7.9Hz,2H,C 6 h 4 ,2,6-H),8.07(d,J=8.2Hz,1H,naphthalene-H),7.97(d,J=8.1Hz,1H,naphthalene-H),7.73(t,J=7.7Hz,1H ,naphthalene-H),7.63(t,J=7.6Hz,2H,naphthalene-H),7.53(d,J=7.9Hz,2H,C 6 h 4 ,3,5-H),4.08(q,J=7.2Hz,4H,CH 2 )...

Embodiment 2

[0029] Synthesis of 1,3,4-oxadiazole stilbene fluorescent whitening agent (I)

[0030] (1) Dissolve 0.0088mol 2-naphthyl-5-(4-(bromomethyl)phenyl)-1,3,4-oxadiazole in 0.0097mol triethyl phosphite, heat to 125°C and stir Reflux the reaction for 3 hours, distill off the excess triethyl phosphite in the reaction system under reduced pressure, add 5ml of n-hexane to precipitate the solid product while stirring while hot, and recrystallize with a 1:4 mixture of tetrahydrofuran and n-hexane to obtain 2.98g of 4-( 5-Naphthyl-1,3,4-oxadiazol-2-yl)benzylphosphonate, yield: 80.2%.

[0031](2) Dissolve 0.0020mol of 4-(5-naphthyl-1,3,4-oxadiazol-2-yl)benzylphosphonate and 0.0020mol of jasmonal in 10ml of N,N-dimethyl Formamide, and then dropwise add 4ml of anhydrous ethanol solution of potassium tert-butoxide with a mass ratio of 15% to the solution, stir and react at 60°C for 5h to obtain a reaction solution, cool and filter, and the volume ratio of the obtained solid is 2: The mixture...

Embodiment 3

[0033] 1. Determination of UV light of 1,3,4-oxadiazole stilbene fluorescent whitening agent

[0034] Compound (I) was mixed with solutions of different polarities (DMSO, THF, CHCl 3 ) to the same concentration of 1×10 -5 mol / L solution, take the wavelength range of 200-500nm to measure the ultraviolet absorption on the ultraviolet-visible spectrophotometer, and obtain its ultraviolet-visible absorption spectrum ( figure 1 ).

[0035] From figure 1 It can be seen from the figure that the maximum ultraviolet absorption wavelengths of fluorescent whitening agents in different polar solutions are 363nm, 358nm and 350nm respectively, and the red shift occurs with the increase of the polarity of the solution and they all fall in the ultraviolet range of 340-380nm. It shows that the fluorescent whitening agent can absorb the ultraviolet light falling in the interval.

[0036] 2. Determination of fluorescence intensity of 1,3,4-oxadiazole stilbene fluorescent whitening agent

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Abstract

The invention discloses a stilbene fluorescent whitening agent, and a preparation method and application thereof. The preparation method of the stilbene fluorescent whitening agent comprises the steps of esterification reaction of triethyl phosphite and Wittig-Horner reaction. The synthesis method has the advantages of mild reaction conditions and high yield, and is easy for separation and suitable for industrialization. The fluorescent whitening agent is a nonionic whitening agent using stilbene as a lightwave converter, has the properties of an optical whitening agent and antimicrobial and bactericidal actions, is green and environment-friendly, and has important application value for developing novel environment-friendly high-efficiency fluorescent whitening agents.

Description

technical field [0001] The invention belongs to the field of fine chemicals, and in particular relates to a preparation method and application of a stilbene fluorescent whitening agent. Background technique [0002] Fluorescent whitening agents are well known now, and are widely used in many fields such as textiles, coatings, plastics, washing and papermaking, and the added fabrics or papers become whiter, brighter and brighter. Among them, papermaking is one of the most important application fields of brighteners, and the continuous development of high-performance optical brighteners suitable for papermaking has become a research hotspot in recent years. [0003] Fluorescent whitening agent is a kind of fluorescent substance that absorbs ultraviolet light and emits blue or purple blue. The national standard GB / T6687-1986 defines it as: Fluorescent whitening agent is a colorless fluorescent dye, which can excite blue and purple light under the irradiation of ultraviolet lig...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/10C09K11/06C09B23/14D21H21/30A01P1/00
CPCC07D413/10C09B23/148C09K11/06C09K2211/1048C09K2211/1088D21H17/07D21H21/30D21H21/36
Inventor 何道航卢辉雄
Owner SOUTH CHINA UNIV OF TECH
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